Are layoffs top of mind for you right now? Brad Pinkston is a returning guest and someone who has experienced multiple layoff events in the tech industry from different seats.

In episode 306, Brad shares the story of getting laid off from a small startup. We’ll dissect how he processed that news and eventually returned to big company life. Then, looking at layoffs from a different lens, we talk about feeling survivor’s guilt. Have you ever felt it? Is it wrong to feel it when you didn’t lose your job?

After deciding to continue as an individual contributor, Brad would later become a member of the team he had once managed. Listen closely to hear about the hardest part of that transition and whether Brad sees himself returning to people management someday.

Original Recording Date: 11-21-2024

Brad Pinkston works in technical pre-sales and is a returning guest. If you missed part 1 of this discussion with Brad, check out Episode 305.

Topics – Once Impacted by a Layoff, Examining Survivor’s Guilt, Staying Individual Contributor, Parting Thoughts

2:29 – Once Impacted by a Layoff

• How did Brad process being laid off from the 2nd startup he joined?
  • Looking back, Brad can logically see that his position really did need to be eliminated.
  • Brad likes to stay on the analytical side of his mind because emotions can easily snowball in situations like these.
  • “The startup was taking a chance on trying to create something. After months of trying to create it, it didn’t work. Maybe a bigger company could have taken me and put me in a different place, but this is startup world…. If we’re abandoning the strategy, we’re abandoning people who were hired to execute the strategy, so that’s the way that I analyzed it mentally.” – Brad Pinkston
  • The emotional processing of this event was not easy. Brad says he was worried about finances and taking care of his family among other things.
  • Brad mentions one of the worst things a manager or leader can say in a layoff situation such as this is how great someone is and that they won’t have any trouble finding a job.
    • “If I’m so great, why did you need to eliminate me as opposed to repurposing me or something like that? …That was the biggest emotional reaction I had to the entire thing…. I think that managers or people that have to deliver that news…they say that thinking that it’s going to help you be more confident, but it is not helpful at all. It is a shot to the gut emotionally, so if you’re ever in a place where you have to deliver that news, don’t say that.” – Brad Pinkston, on telling someone being laid off they won’t have trouble finding a job
  • John highlights the fact that we as humans don’t react emotionally the same way we intellectually think we should.
    • “Our emotional reactions…they just are. Whether or not it makes sense intellectually, it is what happens…. You can do all of the intellectualization that you want. That doesn’t change what the emotional reaction was.” – John White, on how reactions to situations might not make sense
    • We might feel that we have failed again or feel worse by having an emotional reaction that intellectually doesn’t make sense. A person can spiral downward quickly this way.
    • John has learned to try and give himself grace in these situations (when the emotional reaction does not make logical sense).
  • This is the only time Brad has been laid off, and he feels lucky that it’s only happened once.
    • Telling people they are going to be fine might cause an emotional reaction.
    • Looking at this differently, Brad thinks he would have been upset if the layoff had been completely impersonal and fact based. He would have been upset that they didn’t care.
    • “There’s no way to receive or deliver that news in a way that’s going to be positive. You can only control levels of bad in that scenario in my opinion.” – Brad Pinkston
  • John references the movie Up in the Air and George Clooney’s character flying around the county to fire people.
    • The way in which Clooney’s character conducted the firing seemed a little bit like emotional manipulation.
  • Brad says there is an emotional reaction to being laid off that you’re “not good enough.”
    • If you have been laid off, let your professional network know what happened. Cast a wide net, and don’t be afraid of telling people.
    • If you haven’t built a strong set of professional connections, start doing it right now. Your network is there to help if they can in times of need. Hopefully you are also giving to your network consistently.
    • “Don’t be ashamed of being laid off. It is what it is. If you haven’t been laid off or fired, just wait a few years.” – Brad Pinkston
  • John was laid off from Google as part of a reduction in force of over 11,000 people. It was a very humbling situation.
    • John tried to cope with the situation intellectually by telling himself it wasn’t personal and that it didn’t mean John was bad. But it still does not feel good to lose your job.
    • You can hear more details of what happened and how John reacted in Episode 220 – John Got Fired.

10:12 – Examining Survivor’s Guilt

• Sometimes the organization you work for has a round of layoffs, and you are not impacted.
• From where John is sitting, he sees friends working at other organizations getting laid off and feels some survivor’s guilt.
  • “I’m sitting where I’m sitting not because of how amazing I am but because of a roll of the dice, literally a roll of the dice. And that’s a difficult thing to deal with.” – John White
• Brad is very analytical and an engineer at heart. He shares the story of being someone who survived a layoff event.
  • It’s helpful if those who remain at a company after a layoff can understand the reasoning behind an organization’s decision to reduce the workforce (i.e. where the organization was going and why).
• John is seeing really good people being let go in these layoffs we’re seeing in the industry.
  • “We’re all going through seeing good friends who are really good at their jobs that are really valuable being let go from organizations…into a job market where other companies are doing the same thing….” – John White
• Brad tells us the team he was on before a restructuring event was an amazing group of engineers.
  • It’s difficult to figure out why you remain but other talented people were laid off.
  • There’s a lot of survivor’s guilt (the only term we have for it) associated with still being at a company after one of these events. We can be thankful for still having a job but still feel a sense of guilt.
  • Nick highlights how this can create an awkward feeling. What business would someone still employed have to feel bad?
    • We want to maintain relationships with people who have been impacted but might not know what to say to encourage.
• Executives have to make hard decisions for the good of the company. We’re also not saying every one of these deicisions by executives are made in the right way either.
  • Brad knows it isn’t easy for the managers and leaders who have to deliver tough news to people about being laid off.
  • When layoff events start to happen, Brad says people are in limbo, uncertain if they are getting a good call or a bad call. There is a lot of uncertainty.
  • “Even the good call…good for me…that’s not a good or a bad call for the manager calling to deliver that. It’s just another call that they’ve got to deliver, and I feel for the folks that have to deliver that message because a lot of times they’re not even part of the decision on who is going to get a good call or a bad call…. That is in a nutshell more of middle management than people realize. Even at good companies you gotta deliver bad news.” – Brad Pinkston, on not always being able to set the strategy as a middle manager but having to execute it
  • John shares the story of a manager he saw deliver tough news to an employee. In this case it was not in the middle of a layoff. The manager realized the person did not fit within what the team needed but still saw value in the person and reached out to contacts who were willing to give them a serious interview for a job better suited for the person.
  • John mentions the issue with layoffs is not enough slack in people’s networks to account for 1000 people hitting the job market in a specific geography on the same day, for example. There may not 1000 job openings right then.
    • John has tried to give to his network to the degree that he can, being open to talking with people if they need a listening ear.
    • “The is not the end of your career. This is a comma in your career. Your career is a long book, and this is…maybe not even the end of a chapter. It might be in the middle.” – John White, on guidance he would give to others right now
    • The job market is tough right now with so many tech layoffs. John heard someone make an off-handed comment about there being a lot of startups 5 years from now founded by people who were laid off. That doesn’t help anyone looking for a job right now and is yet another thing not to say to someone who has been impacted.
• Do the managers or leaders who have to execute mass layoffs also feel survivor’s guilt?
  • Brad has been lucky in that he’s never had to deliver the layoff news to someone.
  • He’s managed people out of the business and managed people into better roles.
  • Brad thinks the front and second-line managers he’s worked with have definitely felt the survivor’s guilt.
    • If Brad were in the position of needing to deliver the bad news, he feels he would be more heartbroken over having to execute something he doesn’t really want to do. This would be more painful than the eventual survivor’s guilt.
    • An individual contributor on a team that was reduced may be feeling survivor’s guilt, but they didn’t get cussed out like a manager might have after delivering bad news to someone, for example. Likely managers will first need to deal with the execution of laying people off and whatever fallout comes from different people’s reactions to that situation.
    • John says it can’t feel good to tell people you know are good at their jobs that the organization no longer needs them.
    • “That’s what’s happen right now, unfortunately…. And that’s why we’re all talking about survivor’s guilt. These are people that are significantly skilled individuals that are impacted by a decision made that was totally out of their control regardless of how they performed…. We keep going back to the same terminology because there’s nothing any easier…. That feeling…it’s hard to get past.” – Brad Pinkston
  • John doesn’t know that we have an answer for this.
    • John says when he sees announcements on LinkedIn with news of layoffs, he offers a listening ear if that’s what people need.
• While Brad was laid off from the startup, he was fortunate to not be unemployed for a long period of time. Here’s some advice Brad would offer to anyone impacted by a layoff, someone feeling survivor’s guilt, or others feeling bad about what is happening within our industry:
  • Reach out to others, and offer to be a reference if you can. Let people know you respect them and that you know they are talented individuals.
  • It is confidence building when someone reaches out and offers to be a reference / sends you some encouragement. It helps motivate people to keep going and to marshal their resources (their network, etc.).
  • Let people know you’re there to help however you can.
  • Nick says we can send people helpful resources and communicate our intent to help with the caveat that they are free to use them or lose them.
• John mentions our industry goes through swings from it being near impossible to find a job to having extreme difficulty finding people to hire, but those periods could be 2 years apart or more.
  • After being laid off from Google Cloud a couple of years ago, John saw there were many openings for sales engineers across the country.
  • It’s different being laid off at the time of this recording because there are multiple companies doing reductions in force, making it tougher for job candidates.

27:19 – Staying Individual Contributor

• Would Brad go back to people management, or is he enjoying individual contributor life too much after returning to it a few years ago?
  • Brad really enjoys what he is doing and is currently a member of the team he managed 5 years ago.
  • When Brad returned as an individual contributor to the team he had once managed, Brad would be working for someone who had once indirectly reported to him.
  • “That was the hardest thing about the transitioning back…. How do I have these conversations and be helpful with my experience but make sure that he knows that I know that it’s his team and that I respect his leadership and will follow him? That was the hardest thing that I’ve dealt with with the manager to individual contributor transition. When I joined back on the team, I had hired or recruited probably 80% of that team to come on board. So I wanted to make sure that everybody knew I’m here to be one of the team members, and I am not going to step on anybody’s toes.” – Brad Pinkston, on being an individual contributor on a team you once managed
    • Even though it was a challenge to join the same team he had once managed, Brad tells us everything went very well.
  • While Brad is enjoying being an individual contributor, he would definitely go back to people management.
    • Brad feels lucky to be working with a talented team of salespeople and technical SE peers.
    • “I would say that I’m not in a rush by any means, but I do want to go back into people management. I did enjoy it. I think I’ll be much more picky with the role than I was when I transitioned to the startup. I’ll ask a lot more of those inciteful questions, John…. But I do think that the story will come full circle back to that for me…because there’s too many aspects of it that I miss.” – Brad Pinkston, on someday going back to people management
• We’ve heard from other guests that going from manager to individual contributor was about getting closer to the technology. Did Brad find himself missing that aspect of the job too?
  • For Brad, it was more about getting closer to working with customers.
  • Brad enjoyed getting back in front of customers and building customer relationships again.
    • Managers might attend customer meetings with members of their team, but it isn’t the same as when you are the front-line SE supporting the customer and own the relationship.
    • “I do believe that if you’re a good leader and you’re a good manager that you contribute more than just being another sport coat in a meeting.” – Brad Pinkston
    • Brad has loved building customer relationships and influencing customer strategies.
    • Brad can only stand behind technology he wholeheartedly believes will make a customer’s life better.
  • “That’s the thing that kind of holds me back from going into people management because you get away from that. Instead, what you’re doing is you’re investing in the people on your team and making them better. And then you see it pay off. But a lot of times when it pays off, they go on to another team. So, you don’t get to see the long-term engagement there like I’m getting to see now that I’ve been back in the role for 2 years.” – Brad Pinkston, on being an individual contributor
    • John mentions he just had his first person promoted off his team (i.e. a growth opportunity this person wanted that John helped foster). Judging success by the number of people promoted off your team is a badge John will proudly wear. He agrees you don’t get to participate in that person’s success in the long term but rather just be an observer of it.
    • Brad shares the story of someone on his team years ago whose family was relocating. This person took a promotion outside the company rather than a new role internally. It was a bigger and better role for the person career wise, and Brad sees it as a bittersweet moment since the company lost top talent in the process.
    • John’s hope is that we are giving advice that is affecting people positively on this podcast.

34:37 – Parting Thoughts

• Nick tries to sum up the theme of the episode to see if that matches what John would say. What do you think?
  • Brad likes to build things and wants to make an impact. Not being able to make an impact leads to job dissatisfaction. The impact for Brad can be on the customers he serves or the team he serves as a people manager. Brad has worked for a big company, multiple startups, and is now back at a big company. He has demonstrated that someone can be successful regardless of whether they are a people manager or individual contributor at multiple companies.
  • John says even if you’re not a people manager you can still affect people’s careers in a positive way. We can mentor and experience the success of others even if it’s not as their direct manager.
• If Brad, John, and Nick didn’t enjoy the people side of what they do, likely they would not have pursued sales engineering.
  • Satisfaction can come from multiple places like…
    • Being an individual contributor working with customers
    • Mentoring others on your team
    • Impacting the people in your professional network
  • “I used to tell my team we need to impact process, pipeline, and people. Hit all 3 every day, and you’ve had a successful day.” – Brad Pinkston
    • Pipeline can mean merely generating some new interesting conversations.
    • Process means we want to be efficient in what we do.
    • “The people was always the biggest piece to me – whether my team was impacting each other, impacting a customer, or whatever it is…I think at the end of the day that’s the most important piece to me. But I’m impacting it in so many different ways…big companies, small companies, through layoffs (being part of them or being the one being laid off). The people impact is always the most important piece of it to me.” – Brad Pinkston
• If you want to follow up with Brad, you can find him on LinkedIn
  • Right now stay focused on your network. Reach out to your peers. And feel free to reach out to Brad.

Mentioned in the Outro

• If you’re looking for more support on the topic of layoffs, whether you’ve been impacted or it happens to be top of mind, check out our Layoff Resources Page. This is a curated set of our most impactful discussions on the topic of layoffs, each with practical tips for listeners like you.
  • What are we missing on the topic of layoffs that you would like to hear more about? Send us an e-mail with your feedback – [email protected]. We would love to hear from you!
• For Brad it was about impacting the people in whatever role he was in. What is it that you like to impact the most?
  • Brad’s story is a great example of how we can make an impact in an area that’s important to us in multiple different job roles.
  • Maybe you want to impact technology architecture, clean up technical debt, impact strategy, impact a product’s long-term roadmap, or you want to impact people but never want to become a people manager.

Contact the Hosts

• The hosts of Nerd Journey are John White and Nick Korte.
  • E-mail: [email protected]
  • DM us on Twitter/X @NerdJourney
  • Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman
  • Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_
• If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

What exactly is a technical alliance? Technology companies create alliance relationships to support product integration and to increase revenue by creating multiple avenues for selling a product. But as Brad Pinkston knows, alliance relationships between different companies can become quite complex.

This week in episode 305 we’re rejoined by Brad Pinkston to hear his story of pursuing a role at a startup while at the same time making the move from people manager to individual contributor. We’ll define go-to-market strategy and how that related to Brad’s role at the startup, discuss what happens when a new job turns out to be different than what we expected, highlight some thoughts on evaluating startups from a different lens before joining, and listen to Brad reflect on his experience interviewing for a second-line manager.

Original Recording Date: 11-21-2024

Topics – Brad Pinkston Returns, The Allure of Startup Life, Go-to-Market and an Expectations Mismatch, Technical Alliance Relationships, Returning to Individual Contributor, Managers and Interview Expertise, Running Away from Something

2:!7 – Brad Pinkston Returns

• We last spoke with Brad Pinkston back in 2020. What has he been up to since? You can find our previous discussions with Brad here:

  • Episode 83 – The Path to People Management and Early Lessons Learned
  • Episode 84 – Management Interviews and Transitions with Brad Pinkston

• Brad decided to leave a big company and try out life working for a startup while at the same time making a move from people manager to individual contributor. Eventually Brad transitioned out of startup life and has returned to a big company in a technical presales role.

3:21 – The Allure of Startup Life

• What attracted Brad to startup life, and what makes it alluring when you work for a big company?
  • One reason to join a startup is the potential for a very large future payday from stocks.
  • “Fundamentally what I really like to do is I like to build things from the ground up.” – Brad Pinkston
    • Before moving to the startup, Brad was in a first line manager role at a big company. At the time, Brad did not feel he had the amount of control he would have liked over what he was building.
  • Moving to the startup was a chance to go and build an organization. Brad’s role was going to be leading the relationship between his past company (the big company) and the new company (the startup). The startup planned to have an OEM relationship with the company he was leaving.
  • More specifically, Brad was going to…
    • Help the two companies work together
    • Develop sales strategies
    • Teach salespeople at the startup how to work with sellers at the former company
    • Teach sellers at his former company about the startup’s new technology – something much more security and networking focused and out of the area of expertise of his former company
• Nick sees Brad’s move as an adjacency with some good relatable experience. *Brad was a people manager who had built and led teams. He would be building an organizational structure in terms of processes and ways of working together. And he also knew the technology from his former employer. With solutions from the former company being integrated into the startup’s technology, Brad wasn’t starting from nothing. His base of knowledge was very relevant to what he would be doing.
  • “Any time I transition between roles…I’m always up for a new challenge, and that’s why any of us take on new roles. But, I try to make sure that there’s a cornerstone of my skillset that’s going to be translatable…. My thought process was that I understood the tech…and I understood the relationships and go-to-market and the way that this was going to work. And I will say that I was 1 for 2 on the 2 things that I thought were going to be the cornerstones there. I did understand the tech really well, but the way that the relationships were going to work and what my role was really going to be, I was completely wrong about.” – Brad Pinkston, on moving to the startup

7:08 – Go-to-Market and an Expectations Mismatch

• How would Brad define go-to-market?
  • Brad learned from his experience that go-to-market means different things across different companies. Another thing to consider in all of this is the OEM relationship mentioned previously and the natural requirement for two companies to collaborate (the big company / Brad’s former employer and the startup).
  • To Brad, go-to-market at the startup was going to be something like the following. And he admits to being very wrong about what it actually was.
    • Interfacing with sales teams
    • Creating sales strategy
    • Be at the forefront of selling and meeting with at least some customers
    • Developing the target persona to sell to / spend time with
    • Developing the value proposition of the solution
  • “What I actually ended up getting is kind of what I felt I was in before.” – Brad Pinkston, on the experience at a startup not being what he expected
  • Brad did not get to develop the go-to-market strategy at the startup as he had hoped. He was told to execute a strategy someone else had already developed.
  • Brad also thought the startup would have a more collaborative culture than it did. Despite conversations about what he thought the go-to-market should be with many people, his ideas for further developing the strategy were not really considered.
    • Brad spent a lot of time trying to clear up misunderstandings between the two companies (the startup and the big company), but it ultimately was not fruitful.
  • Overall, Brad was not able to make the impact he originally desired.
    • “When you’re kind of a builder / engineer mindset like I think we all are…you want to see that impact. Whether it’s a check or big deal or happy customers or you just feel…a sense of success you’ve gotta have some kind of payoff of impact…and I didn’t feel like I had any at the end of the day.” – Brad Pinkston, on the importance of making an impact
• Nick highlights Brad also lost the ability to do creative solutioning in his work.
• Brad shares some lessons learned on startup life.
  • Thinking of startups brings to mind characteristics like collaborative culture, flat organizational structure, being a jack of all trades / the ability to do a variety of different types of work. You normally hear about a lot of hard work but also a willingness of people to pitch in and help wherever needed.
  • “Not all startups are created equal.” – Brad Pinkston
  • One thing Brad didn’t hear about going into this was the different inflection points of a startup’s life.
    • Brad joined the startup in question from a timing perspective during an inflection point that was somewhat detrimental.
    • When an organization is very small, employees are willing to help out in all kinds of areas even if outside their normal purview to help the company or team achieve its goal. People often work across many areas with an “all hands on deck” mentality.
    • As an organization grows, a good leader will recognize the inefficiencies and transition to having clearly defined job roles and responsibilities for each employee. We might even call this a growing pain of an organization. Brad tells us the startup was in the midst of this transition when he joined, and employees were encouraged to work within their own roles and responsibilities. This stage of the startup was not something Brad expected to encounter and inhibited his ability to impact and execute on a strategy the way he was hoping to.
    • “I thought that was the startup I was joining. But it had hit this inflection point with size and revenue and all that they needed much more definition of roles, and they were still building that when I came on board.” – Brad Pinkston
  • Just like go-to-market can mean many things to many different people, startups can go from 3 people working in a garage or home office to multi-million dollar organizations with hundreds of people on staff. John mentions we’re talking about understanding a startup’s stage of growth before joining and making sure our expectations of impact in a role match what the company expects based on the culture they are building.
    • Brad does not recommend the mess around and find out mentality to learn what he ultimately ended up learning. But he respects the fact that the startup needed clearly defined roles for its employees.
    • Brad thinks perhaps he could have had different expectations going into the role or selected another startup as his employer.
    • Large company can also mean different things to different people.
• John thinks it would have been hard to discover the startup was in this phase of growth during the interview process. Asking someone a very pointed question about this in an interview gives you one person’s honest perspective at a point in time, and it may not reflect the reality you experience when you start working in a particular role because something changed.
  • Brad thinks maybe he didn’t ask as many questions as he should have during the interview process because he really wanted the job. Deeper questions about go-to-market to check for alignment might have been helpful.
  • “Looking back on it I’m going to blame myself more than I’m going to blame them…or anything like that. I’m the one who made the deicision to leave the big company and go to the startup…. To be fair, I don’t think my role ended up the way that my manager expected it to either. And that’s just the turn on a dime of a startup.” – Brad Pinkston
• With Brad’s knowledge of and experience at his previous employer, did taking this to a new employer play out the way he expected or differently?
  • This goes back to the difference between crafting a strategy and executing one made by someone else. In the strategy Brad wanted to build, his relationships from the previous company were going to be extremely valuable because sales teams from each company would be in active collaboration.
  • Brad’s role at the startup ended up being more focused on business development in the background – a mix of engineering, product development, and even product management. While Brad felt he was effective in doing the job, he wasn’t as passionate about it as he would have been if the role had been more of what he was expecting.
  • The relationships Brad was bringing to the startup were not valuable in the end because…
    • It was not his strategy.
    • The relationships he had did not bring value to the strategy he was given by others to execute.

20:11 – Technical Alliance Relationships

• John mentions this sounds like it could have been an ISV (Independent Software Vendor relationship), OEM, or even an alliance partnership between the startup and the big company (Brad’s former employer). How did Brad build up his relationships with these teams at his former employer?
  • The definitions of things like ISV, OEM, and alliances can differ slightly.
  • Some ISVs have a technology that is marketed and sold together hand in hand by different companies. There are also ISVs where we may not realize there is an ISV relationship (i.e. something you can buy through Amazon Marketplace that is software developed by a different software vendor).
  • Brad learned that the nature of ISV relationship and which company is involved in selling a product can vary.
  • Brad was expecting an ISV relationship between the startup and his former employer that made for a better together kind of solution. The startup was selling a version of their own product that was part of a different company’s product.
    • One possible future state was having a solution (part of an ISV relationship) that could be purchased based on a customer’s relationship with either company. This unraveled quickly.
    • Brad thought it would be an ISV relationships where both company’s sales teams would be engaging with customers together / going to market together (making his relationships very valuable).
    • The ISV relationship which ended up happening was merely Brad’s company delivering technology for another company to use as part of their own solution. This did not require engagement of sales teams at the startup.
    • John gives an example of an ISV relationship he encountered while working at Google Cloud.
    • “It gets real complicated and sticky in alliances when you’re talking about OEM or ISV or…how all that happens. I respect the people that have been in alliances their entire career because it can be a spaghetti of things you’re having to deal with….” – Brad Pinkston, on the nature of technology alliances
• This presents another job and category of job that most people don’t understand or know is an area for an entire career.
  • We’re talking about managing relationships between companies that sell complimentary products, co-sell their solutions, or have one company use another company’s technology in their products.
  • John did not know this type of role existed before he started working for a big company.
  • How products are sold, where you can buy them, how products will be marketed, what teams will be involved, etc. are far more complex than we might realize (and not a topic we plan to dig deeper on today).

26:30 – Returning to Individual Contributor

• What made Brad want to go back to being an individual contributor after being a people manager?
  • Brad still misses leading a team and helping people progress their careers, and he felt taking the role was only putting this on pause.
  • Brad thought things would be very successful at the startup, and he would eventually build a team of his own there.
  • We can be leaders without needing to be people managers, and Brad highlights the chance he was given to influence people within the startup even though he did not have direct reports.
  • “I’m going to get to build something. I’ll build relationships, sales strategy, and at some point in time I’ll build a team. So it was just a pause on managing people. That’s what I thought was going to happen….” – Brad Pinkston, on the decision to become an individual contributor
  • When Brad interviewed with the startup, was Brad’s decision to pursue an individual contributor role after previously being a people leader something that came up?
    • Brad says he doesn’t feel it came up this tiem because everyone was focused on the future of what things were going to be.
    • Brad has a lot of respect for the manager he had at the startup. Brad would be someone on the bench of talent who could take a people manager role if something changed.
    • After things started to be less successful than people had expected, Brad had conversations with people to discuss what leading a team of SEs might look like at the startup. It really did not go anywhere. Brad says he might have pursued management at the startup if he had decided to stay.
• Is it hard to get used to being an individual contributor again after having been a people manager?
  • Brad says the transition from manager to individual contributor at a new company was pretty easy.
  • Part of Brad’s role at the startup was to educate account SEs at the company on what the solution being brought to market was.
  • Brad was able to leverage some of the skills he had learned from managing people in the past as an individual contributor at the startup like the ability to make connections inside the organization.
  • At first it was strange to not have 1-1s or career progression conversations. Brad missed the ability to help someone along in their career in the way managers who care can do that.
  • Brad does not miss the “adult babysitting” side of being a manager.
    • Brad built the team he was leading before joining the startup as an individual contributor, so there wasn’t much of this.

31:37 – Managers and Interview Expertise

• John had an interesting thought. After sitting through performance reviews and interviewing incoming job candidates as a hiring manager, he should be a lot better at interviewing for jobs. John would know what the interview questions actually mean. This also allows him to make performance reviews easier for leaders.
• Brad feels like his experiences interviewing people and going through performance reviews have helped him be very direct and drive conversations with his managers over time.
  • “Whether you’re selling to a customer or you’re selling to your manager that you should get a raise or a promotion, you’re always selling.” – Brad Pinkston
• Brad also felt his experience interviewing people would help him interview for other jobs. It did in some cases, but Brad says interviewing for a second-line manager humbled him significantly.
  • “But interviewing for a second-line manager humbled me…significantly. It’s a great example of what got you here won’t get you there…. The thought process and the things that I was asked and how well prepared I was…was not in line with I think what the expectations were.” – Brad Pinkston
  • When Brad interviewed for a second-line manager role, he did not get the promotion. But one of his peers did. There are some universal things Brad learned in this process.
    • Sometimes a first line manager can get a feel for what the greater organization needs, but they might not get a true picture of it at their level.
    • “You kind of have to figure out what your strategy would be and deliver it very confidently. And you might be completely wrong….because you just don’t know what the organization is going through.” – Brad Pinkston, on interviewing for a second-line manager role
    • Brad’s strategy as a second-line manager was focused on sales strategy, expectations of the team and how he would run it, etc.
    • The person who got the job was more focused on how to bring the team together, personal development, etc. It was really important to bring the people together as the organization grew and changed. This person knew bringing people together was the first priority. Brad had this item as a lesser priority.
    • At a second-line manager level you have to present a strategy and share how the front-line managers under you will help carry it out. At a front-line manager level, the tactical things are also very important.
    • “You kind of have to set the strategy at a second-line and hope that your leaders under you are adopting and bought in and part of it as much as you want them to be…that kind of thing.” – Brad Pinkston
  • About a year into his role as a front-line manager, John’s manager left. People at that time encouraged him to apply for the open spot.
    • At first, John thought it was kind of crazy to consider interviewing for the next level of management. But, looking back, he feels like the experience interviewing (even if you don’t get it) might be a nice stepping stone to getting a second-line manager role eventually.
    • Part of this might be understanding the relationships you need to have at a second-line manager level, going in with a plan, and having it picked apart. Someone could go interview for the second-line manager role and come to understand they didn’t really know what the job is.
    • “If I don’t know what that job is, then maybe I shouldn’t be applying for it.” – John White, talking about the role of a second-line people manager
    • Brad says the second-line manager job he referenced and the needs of it would be different than it would have been for the same role on the other side of the US, for example.
    • “That’s why it’s always good to be interviewing. It’s a skill you that need to continue to hone just like your technical chops. I learned so much during that process that will help me the next time that I interview for a second-line manager role….if that’s in my future.” – Brad Pinkston

38:40 – Running Away from Something

• Brad eventually left that startup and went to another startup. He felt burned out, and the reorganization did not work out the way he wanted.
• “And so I went to another startup, which…it was the thing that nobody should ever do. I was running away from something as opposed to running to something.” – Brad Pinkston, on leaving one startup and moving to another
• Brad says this was a much smaller startup, and he was eventually laid off. It was definitely a low moment.

Mentioned in the Outro

• We can’t talk about being a builder without talking about Episode 148 – The Magic of Building with Chris Wahl (1/2). It’s a great episode to go back and reference.
• People who like to build things like creative control over what they are building.
  • In Episode 244 – An Array of Decision Points with Tim Crawford (2/2) we heard about the decision between people leadership and individual contributor being a choice between building people and buidling technology.
  • At the startup Brad was trying to build something related to technology and not necessarily developing people as a manager would, so it aligns with what Tim Crawford shared with us.
• Technical alliances could have a career option for you. We’ve not highlighted these roles on the show before now. Every technology company has these types of roles that work on things like integration, OEM relationships, or ISV relationships.
• If you’re thinking of joining a startup, it makes sense to ask each person in the interview process how clearly defined roles and responsibilities are at the company and how clear each person is on their roles and responsibilities.

Contact the Hosts

• The hosts of Nerd Journey are John White and Nick Korte.
  • E-mail: [email protected]
  • DM us on Twitter/X @NerdJourney
  • Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman
  • Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_
• If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

Are you trying to reach that next level in your career? Why do you want to get to the next level, and what is most important to you in doing that? If next level means next job level in your case, at some point there is no next level. What then?

Duncan Epping would encourage you not to set a goal based on an endpoint. This week in episode 304 we share Duncan’s career progression over time to Chief Technologist, discussing his motivations and goals along the way. You’ll hear about the qualities top level individual contributors in our industry possess. We also talk through the willingness to shift our technical specialty over time and the humility of approaching everything with the intent to learn something regardless of the outcome.

Original Recording Date: 10-29-2024

Duncan Epping is Chief Technologist, a published author, a blogger, and someone who loves to learn. If you missed part 1 of our discussion with Duncan, check out Episode 303.

Topics – A Job Role is not the Goal, Reputation and Reliability, Shifting Your Area of Specialization

2:47 – A Job Role is not the Goal

• We’ve discussed not needing to go into management to progress in our careers and continuing to progress as individual contributors with some of our guests. Sometimes this means moving to another company whose clearly defined job leveling supports this choice (staff level, principal level, distinguished level, and perhaps all the way to Chief Technologist). What does it take to progress along this path?
  • Duncan tells us this is something that is quite difficult to discuss because the way someone can progress can differ greatly across companies. Things which may be important for progression at one company may not be important at others.
  • Though Duncan is a Chief Technologist today, repeating the same steps he took does not guarantee someone will reach the same level or end up in the same situation. Some of this has to do with being in the right place at the right time or being properly positioned to reach the next level.
  • “Even for myself, at some point there is no career progression anymore…. There’s not always a next level. The same applies for the CEO of the company. There is no higher level…. That is also something to consider.” – Duncan Epping
  • We might hear of people wanting to get to the next level and then to the next, but at some point, the progression will stop.
  • “You also need to ask yourself, ‘why do you want to get to that next level? What is most important to you?’ …One of the things that was extremely important to me when I started out in the virtualization space…it wasn’t becoming a Chief Technologist or a CTO or anything like that…. The one thing that was really important to me was to learn as much as I possibly could about this new, cool technology that appeared on the market. That is the one thing that I wanted to do. And that is what set me up for success. I wasn’t constantly chasing new job roles. Those job roles were more or less chasing me…which I know sounds very funny, but that’s the way things really went….” – Duncan Epping
  • Several months after Duncan started blogging, both VMware and EMC reached out to him about job openings (because he had written a lot of content). But Duncan did not write the articles to get a new job. He wrote them to learn something about a technology he was passionate about.
  • After starting in professional services at VMware, Duncan consistently tried to stay on top of the latest technical innovations inside the company, expanding his professional network through discussions with product managers and engineering team members. He was asked to move over to the cloud team that did some of the earliest deployments of vCloud Director.
  • Once the VCDX certification was created, Duncan wanted to figure out how to get it. Through the process of obtaining his VCDX, Duncan further expanded his professional network and was asked to become a Technical Marketing Architect.
  • “It was all a more or less natural evolution in terms of my passion and my interests more than me chasing a particular job.” – Duncan Epping
  • In Duncan’s opinion, a principal or a Chief Technologist does not mean you’re the person who has been working at a company the longest. Someone could be a senior engineer for many years while others could progress to higher job levels in a very short time.
  • “It’s also not always the most technical person that gets to the next level. It’s typically that person that knows how to communicate well both internally and externally but on top of that is also extremely interested in learning new things. And that could be anything. I wanted to say learning new technology, but it isn’t necessarily new technology. It could be anything. And I think being able to convey that passion and helping other people moving forward as well…that is what essentially then sets you up for a job role like a Chief Technologist….” – Duncan Epping
  • Being a Chief Technologist isn’t just about understanding technology. Duncan mentions this is about understanding people, processes, customers, and much more.
  • Duncan highlights being a part of mentoring programs in the past as both a mentor and a mentee. In mentoring conversations people often want to know how to get from one point to another or how to replicate what someone else did in a short amount of time. Duncan says when he takes them through the process, they might say they don’t have the time to put in the work.
    • Duncan chose to continue learning over time because it was a part of his job but also because he loves learning about new technology as well. He didn’t think about the process in terms of time he did or didn’t have.
    • Duncan loves writing about and reading about new technology, watching videos about it, and answering questions about it on community forums / Twitter / Facebook / LinkedIn.
    • Duncan feels it is all of the above things combined that present a person as someone who could take on a role of an internal champion and an external facing technologist for a company (a role like Chief Technologist).
• John restates this as the role is more of an outcome of many actions, and the goal was staying curious, continuing to learn, and building a professional network along the way. The recognition and getting new opportunities seem like a byproduct of the underlying curiosity.
  • “A lot of people when they talk about their career progression and then they start thinking about goals, they tend to talk about that endpoint where they want to get. They tend to set that goal and say ‘I want to become a CTO of X, Y, and Z.’” – Duncan Epping, reflecting back on a career progression talk he gave a couple of years ago
  • When Duncan started working for VMware, the role of Chief Technologist did not even exist, so it certainly was not a goal for him. There was one CTO of the company at that time, and that was it.
  • “My goal was always to learn more about the technology that I wanted to learn more about and help other people to understand the technology better. That was what I was working toward.” – Duncan Epping
    • Notice Duncan’s goal was not a sole focus on pay raises or promotions. Those were byproducts of the work he was doing toward a larger goal.
  • People tend to set huge goals and get disappointed when they do not reach them. Duncan mentions even within huge companies, there are a relatively small number of CTO or Chief Technologist roles.
    • In Duncan’s opinion we should not set a goal to land one of these specific roles because the chances of disappointment are quite high when we don’t get one.

12:58 – Reputation and Reliability

• John speaks to his own philosophy of dreaming in bands and not being laser focused on a single job role or company. Think about the types of people you want to work with, the projects you want to work on, and the things you want to learn (i.e. things that can create more opportunities for you in the future – sometimes in the form of a new role).
  • When Duncan became a Chief Technologist, there was no process for becoming one. The process was created internally because people wanted to promote Duncan to that level.
  • “They knew my skill set. They knew I was passionate about something. They didn’t really have a head count for it, but they ended up creating a head count. And they ended up creating that role because they felt there was a need to have someone like myself to be part of that organization.” – Duncan Epping, on getting chosen for a specific role
  • In most cases, Duncan was asked to take certain roles rather than chasing them.
  • “I think that is something that a lot of people don’t tend to understand…. I didn’t wake up on Monday morning and all of a sudden I was a Chief Technologist. I also started out as a consultant at VMware. I was just a consultant, and then I became a senior consultant. And then after a couple of years I became a principal consultant. And then I went from consultancy into technical marketing. And then, within technical marketing I became a principal. And then I moved between different teams…. It all happened organically, and it isn’t something that I planned for. It is just something that occurred over time.” – Duncan Epping, on progressing through different roles within a company
  • There were many things Duncan had achieved even before he came to VMware.
  • Things we can learn from Duncan’s story and apply to our own career progression are things like emphasizing curiosity, knowledge creation / knowledge publishing (learning in public), building professional networks, and developing a reputation inside and outside your company. It sounds to John like when you’ve built a good reputation both inside and outside your company, the learning and publishing of that knowledge is the important thing and over time has a tendency to bring opportunities your way (almost like becoming a center of mass).
  • Duncan says we also need to be open to new opportunities, even if it means stepping into an unknown area. He would encourage us not to be afraid of new opportunities.
  • “I’ve been part of groups that would create a new product which we didn’t know if it was going to be successful or not. And some people don’t take those opportunities because they may think if it isn’t successful I may end up without a role. But in my opinion if you’ve created a big enough network….” – Duncan Epping
  • We don’t have to be the center of mass / center of attention, but developing a reputation of knowing how to find answers is very helpful. Duncan may not know the answer to every question, but he generally knows where to find the answer when someone asks.
    • Duncan mentions colleagues like William Lam, Frank Denneman, Joe Baguley, Alan Renouf, and others who operate in a similar way – they know how to find answers when something is outside their base of knowledge. They can be relied upon to go and find an answer. Duncan has featured these people and the traits they possess in presentations he’s delivered on career to various audiences.
    • “That is what is most important – that people can rely on you. And they know if I ask him or her a question, something is going to come back. And it may take 5 minutes. It may take an hour. It may take a day. But I know something is going to get back. That is also where the power of that network comes into play because if you don’t have a huge network, then you won’t be able to find the answer.” – Duncan Epping, on being a reliable source for helping others find answers to questions

19:49 – Shifting Your Area of Specialization

• When doing something you love to do (for Duncan, writing to learn) becomes part of your job, do you still love it?
  • At the moment, writing blog posts is not part of Duncan’s role (nor is writing books). He could go months without writing anything if he wanted.
  • When Duncan was in technical marketing, he enjoyed the writing aspect of the role. But what may not be so interesting is writing about the same thing many times. This can lead to getting bored. Duncan has written many articles about vSphere HA admission control and vSAN stretched clusters, for example.
  • “The one thing I’ve always forced myself to do is try to figure out what I can write about something which hasn’t been written before…so try to come up with something new. And that could even be for the same feature, for the exact same functionality but just written differently based on a question that a customer asked. Or, it could be a completely different topic. That’s why in my career you’ve seen me move from being a generalist in terms of virtualization then focusing on vSphere HA, then being responsible for availability and storage within technical marketing. After that I became responsible for the SDDC…. Then I became part of the vSAN team. Now I am also part of the VCF business unit but focused on storage and availability in a broader sense. So I’ve always more or less moved around, which made it a bit more interesting to write about things.” – Duncan Epping, on shifting writing topics over time
  • Lately, Duncan has been writing about running (in Dutch). Because Duncan loves writing so much, he is open to writing about anything. Duncan finds writing about new things interesting, and as a result we may see him shifting topics regularly.
• Duncan touched on being a generalist and becoming more specialized at times. What advice does Duncan have for others as it relates to staying a generalist or becoming more specialized?
  • He’s never been too worried about falling into either category.
  • Duncan started out very broad and was a systems administrator in the 1990s, focusing on Novell, Lotus Domino, Windows, and Linux systems.
  • When Duncan became a virtualization consultant, that was still quite broad since it involved a focus on the servers, the storage, and the virtualization layers. As technology grew and Duncan started working for VMware, more and more systems needed to integrate / hook into the virtualization platform.
  • Duncan has never had an issue diving deep into an area to become a specialist, and he’s willing to swap to a new area when needed to become a specialist there too. He has demonstrated specialty in VMware’s vSphere HA, Site Recovery Manager, and vSAN to take a few examples.
  • A Chief Technologist may need to speak to storage and availability in general and then go deep in vSAN stretched clusters for a customer discussion, for example.
  • “In my opinion, you don’t necessarily pigeonhole yourself. If you have the capability to dive deep into something…while you were a generalist before, I’m pretty sure after you dove into something specific, you can go back up if needed. You’re setting those boundaries yourself. No one else is doing that.” – Duncan Epping
  • Duncan understands why people might be worried about making shifts between generalist and specialist, but he’s seen people make some very big jumps.
    • Duncan shares the example of Cormac Hogan. He was a support engineer for EMC 20 years ago and then started working as a support engineer for VMware. When there were openings in technical marketing, Duncan remembered working with Cormac and suggested they bring Cormac onto the technical marketing team. Cormac was very storage focused for many years, but he would later focus on Kubernetes and is currently focused Data Services Manager.
    • “So he’s been going left to right, up and down, whenever someone asks. And the reason he’s capable of doing that is not because he’s thinking about being a generalist or being a specialist. He just has a passion for technology, and if someone asks him tomorrow, ‘hey, you need to focus on x, y, and z’ he’s going to dive into that and try to figure out what it is, how it works, and how he can help customers moving forward using a solution like that. And that solution could be a tiny little feature that is part of this bigger platform, or it could be that whole platform itself…. People are too worried about those things. If you understand the process of learning new technology, you can apply that to anything.” – Duncan Epping, commenting on Cormac Hogan’s career
    • Right now, Duncan is writing about running just for fun. He even puts a disclaimer on his blog about it.
    • “I’m not a coach. I’m not an influencer in any shape or form. I’m not a specialist even. I’ve been running for 25 years, and I’ve got experience in running. I’m just trying to learn more myself, and the way that I learn things is by writing things down. So that’s why I’m sharing it. And hopefully it’s useful to others, and if it’s not, at least I got to learn something. But if you apply that mindset, it doesn’t really matter if you’re pigeonholed into that particular section and that section of the world all of a sudden stops existing. Because you can learn about some other type of technology next week or the week after. I think it’s just that process that you need to focus on and not the particular thing that you need to learn.” – Duncan Epping
    • John re-emphasizes the title not being the goal but rather the process of curiosity, learning, and building relationships being the goal.
• Duncan leaves us with an important disclaimer.
  • Duncan can write about running as much as he wants, but he’s never going to run a marathon in 2:10.
  • “The role and those promotions may never come…. There’s no guarantee whatsoever. And that’s why I think the focus should be in terms of following your passion and having fun and enjoying it. Because if you’re not enjoying it, it’s for sure not going to happen.” – Duncan Epping
    • Remember, even if those roles never come, we can always keep learning!
• If you want to follow up with Duncan on this discussion, you can find him:
  • On Twitter / X – @DuncanYB
  • On LinkedIn – Duncan Epping
  • On his blog Yellow Bricks

Mentioned in the Outro

• Check out Duncan’s VMUG Keynote – Six Fundamentals for Advancing Your Career and the accompanying blog article.
  • Nick loves that Duncan sets goals based on learning.
  • In this presentation Duncan discusses the idea of having an outcome goal that isn’t focused on a job role or endpoint and a process goal with some quantifiable steps toward the outcome. Setting outcome goals in this way makes them independent of job roles and can help set us up for future opportunities.
• The idea of shifting your specialty was very interesting.
  • This is a willingness to go deep in a new area of technology and changing your focus.
  • To do this well you have to understand how you learn best and continue learning, knowing for a time you will be completely focused on learning the new area while being open to changing that focus in the future.
    • Building deep expertise in an area can help prevent distractions in an industry that changes constantly.
    • Developing expertise in multiple areas makes one very broad in technology.
• One of the qualities of people who have reached some of the highest job levels for individual contributors like a principal engineer or Chief Technologist was being reliable – being someone others knew could and would go find an answer.
  • Are you developing a reputation of being reliable?
• Duncan continued to follow his interests just like Stephanie Wong. Listen to these episodes for more of her story.
  • Episode 177 – Follow the Excitement, Follow the Challenge with Stephanie Wong (1/2)
  • Episode 178 – Being a Great Generalist and Finding Your Voice with Stephanie Wong (2/2)
• There’s a great deal of humility in the way Duncan approaches his writing. Even if no one likes what he wrote, at least he got to learn something.
  • This is a great attitude that we can use for approaching so many situations in life. What can we learn from the situation even if it does not turn out the way we want?
• If you’re looking for more help related to public speaking / presentations, check out
  • Neil Thompson’s Teach the Geek podcast
  • Episode 193 – Communication for Specialists with Neil Thompson (1/2)
  • Episode 194 – Question Askers and Problem Solvers with Neil Thompson (2/2)

Contact the Hosts

• The hosts of Nerd Journey are John White and Nick Korte.
  • E-mail: [email protected]
  • DM us on Twitter/X @NerdJourney
  • Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman
  • Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_
• If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

What would you do if your co-presenter for a breakout session at a large technology conference had to back out a couple of weeks before the event? One option is deliver the presentation yourself. That’s exactly what Duncan Epping did in this situation despite his crippling fear of public speaking at the time.

Duncan Epping is a Chief Technologist, a published author, a blogger, and someone who has given many presentations in different settings throughout his career. In episode 303, we have a focused conversation with Duncan on presentations and public speaking. You’ll hear the story of Duncan’s first public presentation at VMworld and why he decided to continue doing presentations. Duncan shares his learning process, how writing has helped him develop deep technical expertise, and how he’s been able to translate this into presentation slides. We talk through different settings for presentations like customer meetings, small groups, and very large groups and stress the importance of focusing on what the audience wants to know.

Original Recording Date: 10-29-2024

Topics – Meet Duncan Epping, A Focus on Presentations and Public Speaking, Lessons Learned Then and Later, Writing and Distilling Concepts to the Core, Think about the Audience, An Outline for Presentation Building, High and Low Stakes Presentations

2:37 – Meet Duncan Epping

• Duncan Epping is presently a Chief Technologist in the VCF Business Unit at Broadcom. In the past, Duncan worked for VMware and has been part of the storage and availability team, the vSAN team, technical marketing, and even professional services.
  • Duncan lives in the south of The Netherlands in an area called Helmond. This is near the city of Eindhoven, which is known for its association with technology companies like Philips and ASML.
  • In the early days of his exposure to virtualization, Duncan was mainly focused on implementations with vSphere. He later would learn about and focus on Site Recovery Manager (SRM) and vCloud Director (VCD).
  • Duncan is also a blogger and the sole maintainer of Yellow Bricks.

4:17 – A Focus on Presentations and Public Speaking

• Nick mentioned the diversity of Duncan’s experience comes out in his writing and especially in his presentations. Duncan has done a number of public presentations at conferences and user groups. He’s even been the keynote speaker a number of times. We wanted to have a focused conversation with Duncan on presentations through the lens of career progression.
• Nick feels like he heard a story on an older episode of The Geek Whisperers about Duncan’s first public presentation being at a large technology conference with hundreds of people in attendance.
  • This is something Duncan would not recommend others do or repeat. Looking back, it was pretty scary and daunting.
  • Duncan had been blogging about vSphere High Availability (or vSphere HA) and developed a deep expertise in this area. In parallel, he got to know and built relationships with the product management and engineering teams for vSphere HA.
  • A member of the HA team at one point asked Duncan if he would help them create slides or possibly help deliver a presentation on the topic. Duncan agreed to help create slides but refused to do any public speaking.
  • “It’s an interesting thing because when they asked me, I had presented before, but it was probably for a group of like 5 or 6 people, more like a group discussion than a presentation. And it usually was with peers as well. Now, just to paint the picture, even when I needed to do that, I would always get extremely terrified. I had a pretty big fear of public speaking in general….” – Duncan Epping
    • Many times in high school if Duncan had to deliver a presentation on a specific day, he would call in sick that morning. Duncan would get so nervous about the presentation it would make him physically sick.
  • Duncan worked together with one of the lead engineers for HA at the time and contributed slides highlighting best practices. They split the work roughly 50/50.
    • Once the slides were created, the two of them went through and highlighted the talking points. Duncan shared the things he would highlight if he were discussing the topic with a customer.
    • The engineer told Duncan it made more sense for him to deliver the slides he had created on stage during the presentation because he knew them so well. The two of them could be co-presenters.
    • Duncan agreed to think about it but wanted to know how many people would be coming to the session. The engineer estimated about 100 people.
    • “I’ve never done more than 5 people. I wouldn’t even get in front of a classroom with people that I know extremely well, so 100 people for me is insane.” – Duncan Epping, thinking through the chance to present at a conference
  • Somehow Duncan was able to convince himself to co-present with the HA engineer at the VMworld conference in San Francisco.
  • A few weeks before the presentation was scheduled to take place, Duncan’s co-presenter had to back out of coming to the conference. No one else from the HA team could attend the conference, so the only option would be for Duncan to deliver the presentation on his own.
    • At this point, conference attendees had already registered to attend the session. Duncan agreed to go forward as the sole presenter.
  • “I logged in, and I expected to see 100 people, 120 people. But it wasn’t 100 or 120. It ended up being 600+ people that had already signed up. And it got worse because on the day itself the room was actually completely packed. So it was like 750 or 760 people or something like that. You can imagine that if you’re terrified of public speaking and your very first session is at VMworld…and you’re actually in one of the bigger rooms and the room is completely packed that it’s going to be a crazy, crazy experience. So that’s why I said it’s something that I probably would never recommend anyone to do. This is not the order in which you should be doing public speaking in any shape or form, so don’t repeat what I did.” – Duncan Epping
  • Thinking back, Duncan feels like the session was probably below average. Attendees rated it ok. They may have come because they read a blog by Duncan or a book he had written.
  • Duncan says walking off that stage after the presentation felt horrible, but it taught him something.
  • “It was horrible, and I also knew then that if I wanted to do this again, I needed to have first of all a completely different approach. And then secondly, I also knew I would probably need to do this extremely often to get more comfortable at presenting…. It’s not a skill you acquire overnight. That’s for sure.” – Duncan Epping, reflecting on his first public presentation at a conference
• How did Duncan prepare for the presentation once he agreed to do it?
  • One thing that stands out for Duncan is not wanting to make any mistakes during the presentation. When people do this, they tend to over-rehearse.
    • “I literally knew every single dot, comma, period on every single slide. I was so overprepared. It’s not like I learned a full script, but it could have been a full script that I learned. So every single slide I knew what to say, when to say every single sentence, when to pause, when to go to the next part, etc.” – Duncan Epping
    • Duncan’s level of preparedness made him even more terrified while presenting. He was afraid he might start forgetting things.
  • “Of course you need to rehearse things, but you don’t need to do it 26 times. I would encourage you to rehearse it because if you don’t rehearse it, that first session is going to be a rehearsal for sure, and it’s going to come across as a rehearsal. But don’t do it 26 or 27 times because you’re going to drive yourself completely nuts, and you’re going to get extremely scared that you’ll send up forgetting things. And in the end, people don’t know what you’re going to say anyway, so if you forget something, you can always come back to that point if you want to get that point across. And if it doesn’t really matter for the story, you just skip it.” – Duncan Epping, giving advice on preparing for a presentation
  • Duncan put a lot of pressure on himself for this presentation too, feeling it could impact his career positively or negatively based on how it turned out, which only increased the level of anxiety he felt.
    • Many of us might treat presenting at a big conference as a possible career inflection point even while we prepare for it.
    • Duncan shared that around the time of his presentation (12-13 years ago), there were close to 20,000 attendees at the VMworld conference. Being a presenter was a huge deal, and he was invited to present as a subject matter expert.
    • Duncan had been writing a lot of content about HA leading up the event. Material from Duncan’s first book on vSphere HA and some of his blogs on the topic were used to create whitepapers on best practice.
    • “But for me, yeah, it very much felt like if I nail this, if I kill this…and they’re already using my content, for sure they will hire me…. So for me…it felt like that…could be a giant moment for my career. If I nail this and everyone talks about it, I for sure will easily move up the ranks.” – Duncan Epping, on the career impact of delivering a presentation

15:45 – Lessons Learned Then and Later

• How many of the lessons learned were immediately incorporated after the conference, and how many came years later reflecting back on it for Duncan?
  • Duncan likes to reflect back pretty quickly after things happen. He gives the example of running and waiting a couple days after the run to think through what happened.
  • After the conference presentation, Duncan tried to determine what he did (what worked), what he did not do (what did not work), and how he could improve (why did something work / not work). Much of the advice Duncan will give others is a number of things he learned after his first few presentations.
  • When looking back on an event like a presentation, Duncan likes to create something like a best practices guide for refining certain skills moving forward.
  • “For me it was fairly straightforward. I knew I wasn’t good at public speaking. I didn’t like public speaking. I didn’t even like speaking in public, and with speaking in public I don’t mean in front of a group of 700 people. Even during a meeting when you’re in a room with 10 or 12 or 15 people, I normally would not be the person raising my hand and then saying something in front of a group. Even if someone would ask a question, and in the group no one would have the answer, I typically wouldn’t even raise my hand and provide the answer if I knew the answer to that particular question. So I was never really comfortable in terms of doing that. And that was also one of the main reasons I forced myself to get comfortable with it.” – Duncan Epping
  • Working for a larger company often times affords you the chance to answer a question in front of one or more of your leaders. Being able to answer in those moments (when you know the answer) can raise your profile across the organization.
    • Duncan highlights the importance for each of us in being ready to do this to grow both personally and professionally.
    • Duncan says forcing himself to speak up in meetings and also speaking in public helped him tremendously over time.
• John highlights Duncan’s linkage of fear of speaking to large groups to the fear of speaking up in a group setting / business meeting. Facing one of those fears is closely linked to facing the other fear.
  • Duncan had to get used to sharing his ideas in front of a group or audience he didn’t completely know.
  • Duncan mentions he would usually be ok speaking up in a small group of other professional services consultants during his time in that role. He knew the people in the group were all at mostly the same level.
  • “If you’re in front of a group, you have no idea who is in the audience. So you don’t know what they know, and you also don’t know what they don’t know. Those are two different things. And the same applies in a meeting.” – Duncan Epping
    • Duncan gives an example of being in a meeting with an engineer with deep technical knowledge as well as a CTO or CEO. These kinds of settings made it more challenging for him to speak up.
  • The fear in the smaller group was not the same as the fear of public speaking in front of a large group. The latter was about 10 times worse and caused a lot more anxiety according to Duncan.
    • “I just had to force myself to get over the fact that there could be someone in the audience that knows more than you do. And that’s fine. You need to be ok with that. And the other thing that you have to be comfortable with is sometimes saying ‘I don’t know. I’ll get back to you…. I don’t have the answer in this particular scenario, so I’ll get back to you.’” – Duncan Epping
    • This was hard for Duncan to do at the start of his career, but he has no problem with it now. When Duncan does not know, he will be the first one to admit it and is willing to go find the answer to the question someone asked.
  • Nick mentions we often feel like it makes us somehow lesser to admit we don’t know something. But admitting it and going to find the answer helps us learn and also helps the person who asked the question learn.
    • Duncan says admitting we don’t know is much better than trying to make something up in the moment that is not correct.
    • Having served on a number of VCDX panels for prospective candidates, Duncan has seen people try to cover up for not knowing the reasons behind their design decisions. It actually made the situation worse. In these moments it is far better to admit you do not know or forgot to document the reason rather than making up a story that is incorrect.
    • “You may as well say that you don’t know, and that’s fine. And most people are ok with that. I’ve never had a situation when someone said, ‘I don’t accept that answer.’ If you don’t know, you don’t know.” – Duncan Epping

22:49 – Writing and Distilling Concepts to the Core

• John says maybe we skipped a step. The first step is to become a subject matter expert. Once you become a subject matter expert, you have to determine how to present that information effectively. Duncan has been a blogger, podcaster, written books, and given a number of presentations. What process does Duncan use to learn content, write about it, and then write about it authoritatively?
  • The way Duncan learns is by writing things out. He learns how something really works in depth by taking a really long article and trying to condense it into a couple of paragraphs.
  • Duncan says this can be the complete opposite of how other people might learn. Frank Denneman might write 60+ pages about NUMA, for example. Duncan likes to distill things down to the core, while Frank likes to get deep into the weeds because it helps with an understanding of the way things work end to end. Duncan’s learning process is the opposite.
  • Duncan has written books that take technical topics into a very deep level of detail. But for blog articles, he will try to condense things as much as possible.
  • When learning about a new topic, Duncan will try to break things down into smaller parts. A storage system or hypervisor will have multiple components. Duncan would then write down each component and what it does, continuing to break down each component into subcomponents where applicable from there. Once he has all the components, Duncan then tries to put them all together again to describe how the larger system works.
  • Duncan says for a long time he assumed this process was the same in other people’s brains but learned that is not the case. His daughter, for example, needed help through the process of breaking down a big concept into smaller components to make an outline for a school assignment.
  • Duncan likes to follow the same process in his presentations – starting with an introduction, breaking that into smaller chunks, and at the end bring everything back together.
  • “I always feel that especially for a presentation (but the same applies to an article or to a book), you typically have to repeat yourself at least 3 or 4 times before you get the point across. And it has nothing to do with the way you communicate. It’s just the way people process information. That’s what I tend to do in my head anyway, so I may as well use the same outline for a blog post, for a book, or for a presentation.” – Duncan Epping
  • John says this matches the pattern we’ve seen of turning information into knowledge.
    • First, writing is thinking. Information we consume is ephemeral unless we process it by writing it down.
    • John mentions this pattern of learning Duncan has shared seems to match the Zettelkasten method of note taking discussed in How to Take Smart Notes.
    • We originally discussed this concept of “writing is thinking” with Josh Duffney in Episode 156 if you want to learn more.

28:42 – Think about the Audience

• Nick feels like the process of going deep and working to condense a very long article as Duncan does almost writes the presentation for him. Once Duncan has written the couple of paragraphs for a finished article, the content is down to the key points that could be part of a presentation. Did this process naturally happen as a byproduct of the way Duncan writes?
  • Duncan feels it happened naturally, and he had done a lot of writing before he started presenting. The writing helped Duncan craft presentations and to convey a particular story.
  • In fact, Duncan started writing even before he began his blog, Yellow Bricks. He had a community forum / website all revolving around hard core punk music that contained album reviews, interviews with bands, etc.
  • “That writing has always been something that was part of me, and that definitely helps processing information in some shape or form…or think about things in a particular way…and also think about ‘what do people actually want to know about this particular thing?’ Whether that’s a CD / an album or whether that’s a product or a feature doesn’t really matter. You really need to understand what people would like to know….” – Duncan Epping, on writing
  • Duncan approaches content creation by putting himself in the shoes of his audience.
  • “If I would read this myself, what are the 5 things I would like to get out of it? What should I learn at the end of this conversation? And that applies to both writing a blog article but also when you do a presentation.” – Duncan Epping
  • When Duncan is asked to present at an event, the first thing he asks is about the audience for the presentation. It is challenging to present something useful if you do not know the audience.
    • Duncan consistently wants to bring value to an audience if he is presenting, and it’s similar when he is writing.
    • We need to know who our audience is and what we think the audience would be interested in learning.
  • “When you write blogs…and it doesn’t matter what the subject is…you’ll quickly find out if it’s interesting or not because people will be reading it or they will not be reading it. And the same applies to a presentation. You can quickly see if people are interested or not. You see it in their faces. You will notice it after the session as well. People will thank you for the content that you delivered, or if it goes completely silent and no one says anything, it probably wasn’t as good as you thought it would be. So you have that fairly quick feedback loop regardless, I think. I think those things are really important. Try to figure out what customers, readers, or listeners would want to consume.” – Duncan Epping

32:34 – An Outline for Presentation Building

• Does Duncan document and then translate into a presentation or start with slides and filling them out?
  • The first thing Duncan likes to do and would recommend others do is figure out a topic or focus area for the presentation.
  • Then, within the focus area Duncan will try to come up with 5-7 things to discuss the presentation (i.e. subtopics). The exact number of things matters less than having a list of things to cover within your focus area.
  • There will be an overarching theme to the discussion. Duncan gives the example of focusing on vSAN stretched cluster configurations as the broad topic. Within that topic, what would customers be interested in? Some examples might be…
    • The configuration of a stretched cluster
    • Best practices
    • Failure scenarios and how they are handled
  • Once Duncan has done the above (selected a topic and some subtopics), he will create an empty slide deck, give it a title, and create sections that align to the items / subtopics he wrote down.
    • For each item (or subtopic), Duncan will create slides to see if it actually makes sense.
  • Duncan usually does 4-5 rehearsals once he has finished building a new set of slides. During that first rehearsal, one would notice how well some slides or sections of work or don’t work. This is the chance to rearrange and change the flow if needed.
    • When you work for a technology company like VMware / Broadcom, there are many slides made by product team members to chose from when building a presentation. Duncan will use some slides that others have made but also has to create his own slides.
  • Duncan gets asked to do presentations on various topics. It can range from things he’s written about to those he hasn’t.
    • As a Chief Technologist, Duncan is responsible for understanding and shaping the product strategy and roadmap (set of features and functionality)p. Sometimes he needs to create slides for things that don’t yet exist.
    • Duncan mentions creating a slide for a product manager last week based on a feature he requested. In addition to this, Duncan will write the user story for the product teams to better understand how they might implement this feature.
  • “Of course it’s 10 times easier to create a slide deck when you’ve already written an article about it because you exactly know what you want to talk about. If you don’t know what you’re going to talk about it’s slightly more complex. But, when you do this on almost a daily basis, it gets a bit easier…. When it’s a presentation in front of a large audience, you need to make sure that slide deck works end to end. Every single bullet point needs to be spot on. But when it’s a meeting with a customer, then I can grab 20 slides, talk through the slides, and then you get to certain areas where you may not have any content but you still get that discussion going. And as a result, it still works.” – Duncan Epping
    • Duncan has learned to be very flexible in what and how he presents in customer meetings. But what enables this flexibility is having a well-prepared deck and focusing on covering the content he is supposed to be covering during the meeting.

37:42 – High and Low Stakes Presentations

• What if Duncan needs to deliver a presentation to people in different roles or at different technical levels? Does he change the content on the slides, change the way he discusses things and the level of depth, or both?
  • Duncan says it depends on how deep the slide deck is. Sometimes the material is really best suited for an administrator, consultant, or architect. Advanced settings, log files, and deep configuration details are near impossible to discuss at an extremely high level.
  • Some of the content these days is built so one could use it to speak to administrators, consultants, architects but also to people at a manager level or slightly higher.
    • “In that particular case I may remove one or two slides that are too geeky, but I’ll just keep the higher-level slides which then allow me to talk through the story….” – Duncan Epping, on adjusting the content for the audience
• Duncan mentioned customer meetings as a form of presentation. These atmospheres could be very conversational with the audience. Does Duncan feel more comfortable when a presentation has more interaction with the audience / is more conversational?
  • If Duncan is in front of a group of customers and not on a stage, it is much easier. You can sit down, have some coffee, go through a set of slides, and have a conversation. Questions throughout allow you to talk about different areas.
  • “But it’s also because of the setting. It’s much more relaxed, right? It’s much different when you’re up on stage and you’ve got 500 people or 2000 people staring at you…. When you do a keynote, and there’s 500 people sitting there, well, you still need to make sure you know your story end to end. And if you mess up, there’s 500 people stating at you. When you’re in a group of 20 people you can always say, ‘let’s take 5 steps back,’ and then it’s not an issue.” – Duncan Epping
  • Duncan tells us public speaking is not scary any longer, but he still gets nervous from time to time.
  • In having so many discussions over the past 10 years, Duncan is confident he could have a discussion with a customer and feel fully comfortable. This is different than presenting in front of a group.
  • John says this is about the stakes of different situations and how bad figuratively or literally falling on your face would be.

Mentioned in the Outro

• The way Duncan learns by taking a high level concept, breaking it down, and putting it back together isn’t so different than people who decided to take a computer apart to learn how it works as a system.
• Condensing a long article into just a couple of paragraphs can be challenging. It requires summarization and brevity, and it’s really a skill to be able to do this. It is a skill we can use to communicate with people at higher levels within an organization (i.e. our managers and above).
  • We can practice this summarization and brevity in our writing, and it will help us in our verbal communication.
  • If you are someone who does not feel comfortable speaking up in meetings when leadership is present, try changing the way you communicate by using summarization and brevity.
• If writing is thinking, that is a 100% transferrable skill across different areas.
  • You don’t have to write about technology. You can write about anything you are learning. But we can make our writing publicly accessible for recruiters and hiring managers and thus show them how we think.
• If you want to hear more stories about public speaking, check out:
  • Episode 73 – Journey to Presenting at Conventions with Al Rasheed
  • Episode 74 – Feedback and Career Impacts of Convention Presentations with Al Rasheed
  • Consider presenting at a user group or join Toastmasters
    • Check out Episode 230 – A Steward of the Community with Chris Williams (2/3) to get a perspective from a user group leader who encourages people to present.
    • Toastmasters is also an option to become better at public speaking. Check out Episode 254 – Train and Teach: A Mixture of Techniques and Concepts with Larry Roberts (1/3).
    • If you’re a STEM professional looking for help with public speaking, be sure to check out Neil Thompson’s Teach the Geek program.

Contact the Hosts

• The hosts of Nerd Journey are John White and Nick Korte.
  • E-mail: [email protected]
  • DM us on Twitter/X @NerdJourney
  • Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman
  • Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_

How do you know when to stop doing something you love? Amy Lewis would say decisions like these require us to be intentional about putting something down so we can pick up something else.

Amy is an unapologetic marketer working in the tech industry, and she was once a Geek Whisperer. This week in episode 302 we explore the genesis of Amy’s involvement in The Geek Whisperers podcast. You’ll hear how it all began, how it changed over time, the overarching purpose, and why the show eventually ended. Amy speaks to the need for intention in our decision making, shares advice for those in our industry impacted by layoffs, and we learn how Amy progressed into people management. For the prospective or current people leaders out there, listen closely for some great tips.

Original Recording Date: 09-19-2024

Amy Lewis is the director of enterprise marketing at GitHub. If you missed part 1 of our discussion about Amy, check out Episode 301.

Topics – Whispering with Intention, Advice for Those Impacted by a Layoff, Pursuing People Leadership, Parting Thoughts with a Geek Whisperers Twist

2:31 – Whispering with Intention

• As big fans of The Geek Whisperers podcast, Nick and John ask Amy how it all began. Nick remembers finding this podcast in 2016 / 2017 and how he couldn’t stop listening.
  • The hosts of The Geek Whisperers were Amy Lewis, John Mark Troyer, and Matt Broberg.
  • Amy likes to make her own luck and will jump in when she sees certain circumstances. In the case of The Geek Whisperers, Amy feels there was a lot of good fortune.
  • John, Matt, and Amy knew of each other and were running similar programs at different companies.
  • Amy thinks John and Matt had been talking about a podcast idea and knew each other a little better. Amy remembers first meeting Matt at a VMworld conference.
  • The original purpose of Amy, Matt, and John getting together was to talk shop. John had a great editorial vision for what could be a podcast.
  • “Everything just kind of disappeared into a group effort. It was magical…. It was just this amazing synergy. And when we first started we really did talk shop. It was a lot of influence marketing. It was about programs we were running. It was a time where influence marketing in a B2B setting was unheard of…. And then there was a moment where we realized so many people were hungry for hearing stories of career, and we decided to pivot. It’s a passion for all of us, and we started to tell the stories that people kind of couldn’t get another way, ask questions that other people might not be able to ask, share stories that we’d overheard or connections that we’d had…. We did what we hoped to do – create a body of work that we hoped would serve a community we really loved and were proud to be part of.” – Amy Lewis
  • Nick remembers Amy’s mention of listening back to past episodes of The Geek Whisperers to help herself fall asleep.
• How do you decide to lay something down that you really enjoy and is very successful (i.e. The Geek Whisperers)?
  • Amy says they found a natural stopping point in terms of number of episodes and in what year.
  • My re-iterates how difficult it can be to produce weekly content. She remembers heavy travel and doing food blogging while still being part of the podcast.
  • Amy would help on the editorial side of the show, while Matt and John would often do editing and write show notes. Looking back she wonders how the 3 of them kept it going when they were all so busy.
  • “We didn’t want to fade away. We wanted to end strong, and we wanted to do it with intention…. That was a shared agreement with the 3 of us. So we stayed in while we were in, and we all agreed when we were out. And it just kind of speaks I think to the synergy of the group…. We didn’t know what was going to happen day to day. We just really enjoyed talking to each other, and it made sense to record it. Then suddenly it became a thing. And there is some pressure. It was hard. We had hard days and we had days where we were tired and really had to gut it out. And we really kind of found our groove. I don’t know. It just had a natural lifecycle. It would be hard even with retrospect to know. So no, we didn’t know where we were going to end when we started, but we knew when it was time. And I think all of us feel really good about that.” – Amy Lewis, on being part of The Geek Whisperers
    • Amy says they did not know where it would end when they got started, but it is amazing to think about how many people the podcast mattered to.
  • John mentions this idea of retiring something while it’s still good.
    • “It’s ok to put something down because it means you get to pick something up…. I think until you make that commitment to symbolically put something down you don’t make space to pick something else up.” – Amy Lewis
    • Amy highlights mentoring a number of women related to maternity leave and how to bring family into their career lives. Going on maternity leave forces hard decisions because life is different before compared to after. This example works well to help people understand they have to choose to put something down to pick something else up.
    • Intention means laying something down and being ok with it. Amy highlights the importance of being intentional when we think through choices.
• Amy says we often feel things happen to us. And right now our industry is being obliterated with layoffs and career choices being made for people.
  • Amy mentions she has been part of workforce reductions and understands what it is like.
  • “We have to where we can bring intention into our career and life and direction…. It’s important to figure out what you’re going to stop doing so you can start doing something else.” – Amy Lewis
  • Part of intention is setting boundaries and understanding our preferences (likes and dislikes). And intention is needed to put something down to allow for picking something up.
  • We can’t learn a new skill if we’re too exhausted, for example.
• John says doing things that are valuable probably aren’t easy. To increase your value likely means picking up something else that is difficult. It is almost laughable that we can maintain everything in our lives that is also difficult when we try to pick up something new that is difficult.
  • If someone other than you said they were going to do this, you would caution them to reconsider and help that person understand what they are trying to do is not sustainable.
  • Amy gives the analogy of a weight lifter at their max and then adding more weight. It’s going to be an injury.
• Amy highlights the finite nature of publishing. After each book, there was a delineated stopping point. After being in online marketing, she feels more like Sisyphus pushing a rock up a hill
  • “Even if it’s fake, we have to create moments of celebrations and endpoints, and this is the same concept, which…makes tons of sense to us in all other aspects of our lives. But somehow we burn ourselves out in career, particularly in technology…. The joy is there’s always something new, but we’re the ultimate push the rock up the hill. What’s our endpoint? The pixels don’t end. Where is the edge of the internet?” – Amy Lewis
    • Working from home can make it hard to have a defined stopping point.
  • Don’t worry – Amy can feel your pushback as you listen to this.
    • “You have to choose for yourself. I strongly recommend it. It’s good for mental health. It’s good for longevity. It’s good for all the things. Decide where some of your parameters are. Decide what wins look like. Decide what the outside edge looks like. And decide very firmly. Be brave. Be bold. Put something down to pick something up.” – Amy Lewis
  • John has a team member who speaks about only having a finite number of tokens to spend each day on work and other parts of life.
    • “If you’re not making a choice, a choice will be made for you. Sometimes it’s your body that will make the choice for you.” – John White

14:57 – Advice for Those Impacted by a Layoff

• “Our best work doesn’t come under duress. It comes in those quiet moments.” – Amy Lewis
  • The reason we get ideas in the shower is because we stopped thinking about it. This applies to careers too. This definitely applies to those listening who may be in transition and are thinking about what they plan to do next.
  • When a choice is made for you, all you can focus on is what your next choice will be. It could be you want to gain or learn a new skill. Perhaps you want to intentionally take a break.
    • Amy found it very hard to take this advice.
    • In one of her last transitions between roles, Amy negotiated her new job offer so that she had a small gap of intentional time before starting work.
    • You can give something up to get a short break between jobs as part of the negotiation.
    • Amy encourages us to think of things we can control in these types of situations.
• If someone listening has been laid off or lost a job, what are some ways Amy has found to get past the hurt, angst, and shame of such an event?
  • “If you think that other people don’t hurt and that you’re broken because you do hurt, just hear me say, ‘it stinks. It always stinks. It is painful grief.’ Don’t try to power through that. Write it down. Say it out loud. Talk to people. But sometimes just the very act of acknowledging and saying, ‘that is terrible and I feel terrible and that makes me feel terrible’ is one of the first things to kind of get through it.” – Amy Lewis
  • Amy tells the story of being part of a division that was laid off. Even though they knew it was coming, that event happening was terrible. So many people in our industry are going through this.
  • “Know you’re not alone. And know that you’re not weak, bad, or failed. And this is not the end…. Like with any grief process, don’t try to make it be better immediately…. It is going to knock your confidence. It’s going to feel bad. It does feel bad…because at its root, a choice was made that you didn’t get to participate in. And that is terrible.” – Amy Lewis, on advice for those processing a layoff
  • For every story of hurt and awful things like layoffs, Amy sees turnaround stories. She appreciates people telling the stories of life after working at a certain company.
  • John mentions we often discount the effect of our human emotions as technical people, often expecting ourselves to react to facts instead of giving the grace to ourselves to react emotionally. We can think the emotion reaction doesn’t make sense and spiral out of control.
    • We don’t often realize our bodies have to go through the emotional processing of what’s happened. The facts don’t just win out over everything.
    • Amy mentions the fear people have about the rise of AI or generative AI tools. Code may be deterministic, but human language is non-deterministic. We gravitate toward what is safe and predictable (i.e. the beauty of technology is its deterministic nature). It’s very unsettling to have an illogical thing happen.
    • Amy believes our human ability to make rational choices in irrational spaces implies we will be able to use tools like generative AI without being mastered by them.
    • “The thing that makes us more able to compete is also the thing that’s going to make us hurt.” – Amy Lewis, on being human
    • Amy had a friend who once said, “sometimes you just can’t square it.”
    • When we are people who work and live in worlds of logic, we have to admit things do not make sense. It can be freeing to admit something makes no sense, allowing you to do what makes sense for you.
    • Amy sees people re-skilling and applying for jobs differently. She feels like our industry will rebound.
    • New jobs will likely appear in different ways. How work is going to be will change, and the jobs available will change.
    • “I am an optimist, and I don’t think it’s over. I think we have to decide what’s next.” – Amy Lewis, on the golden age of tech and how our industry looks moving forward
    • John reiterates that there is going to be immediate short term pain when you’ve gone through job loss. It can destabilize one’s identity or hurt your self-confidence. John doesn’t think there is an easy way to look at the macro view in that situation.
    • “Sometimes when you’re in a hole, it just takes somebody else to go, ‘the hole is not bottomless. There’s nobody who is making the hole deeper, and here let me help you understand how to get out of the hole.’ Sometimes you just need to lean on an outside perspective…. I need somebody to tell me everything’s going to be ok so I can just trust that. And that will help me keep on going.” – John White
    • Amy hopes the above can be an outcome of this podcast. If you are employed, reach out to someone who needs that encouragement right now. Amy says she had the benefit of someone reaching out to her with encouragement during a difficult time.
    • “So if you’re somebody who’s feeling ok right now, I would just challenge all of us to reach out to someone who you think may not be. Check in on them, and give them that encouragement. Give away something because you’re going to need it someday…. Nobody rides this ride without hitting the whammies at some point.” – Amy Lewis, on encouraging others
    • Amy is Geek Whispering to us during this podcast.

24:34 – Pursuing People Leadership

• What made Amy want to pursue people management, and how has she helped others determine what they want to do next?
  • Amy tells us it feels like people management was inevitable in her career. When we was in publishing, Amy invented an unpaid internship that she later convinced leadership to fund as a role.
  • In total, Amy ended up with 7 or 8 interns, and most of them went into publishing as a career after the internship. She was willing to teach them and help move their career forward. Amy tells us she has stayed connected with these folks over time.
  • “I think that’s where I first got a taste for connecting people with opportunity. These were incredibly bright people, so I in no way, shape, or form get full credit. But I knew how to open a door, and I really always believe in opening a door where I can.” – Amy Lewis
  • Amy became a people manager and a director at the same time and developed a habit of inheriting teams due to various circumstances.
    • She likes managing people and can often see connective tissue where others don’t.
    • Amy shares an anecdote from her time at Solidfire. After coming back from vacation, Amy had been placed in charge of field marketing and was told that her CMO had hired someone new. Though surprising at the time, Amy says it turned out really well.
  • People management is hard and is very different from being an individual contributor.
    • “Quickly, whoever reports to you will be better at their job than you, and that is the way it should be. You should help them be better at their job, but that does not mean necessarily on point expertise. They are going to be better experts because they are putting in 8 hours a day. Their seat time will always exceed yours. So you have to genuinely enjoy the HR side, and the HR side is really hard…. It is a hard job. You have to be ready to support people. You have to be ready to do hard things…. If you do not enjoy people, do not do it.” – Amy Lewis, on people management
    • Managers have to deal with people’s personal trauma. This could mean an employee has a family member with cancer, wants to quit, or needs to be fired. Someone once told Amy one of these things is almost always true when you’re a manager.
    • Amy emphasizes the need for managers to take courses, read books, listen to podcasts, and do HR training to gain greater managerial skills. It’s part of the job.
    • If the hard things don’t sound fun for you, people management is likely not for you. We also do not have to manage people to progress in our career.
  • As a first time people manager, Amy’s comments resonated with John.
    • It might be more difficult for a high achieving individual contributor to step into the role of people manager because of the temptation to encourage people to do what they did.
    • Amy says sometimes people managers end up competing with the people reporting to them! The people manager has to accept that they will no longer be the expert like their people will.
    • John shares a story of being at a sales kickoff and being required to attend a session on becoming a better technical manager rather instead of a session focused on a new innovation.
  • “It is truly putting something down to pick something up.” – Amy Lewis, on people management
    • Amy has had player / coach roles, and these are more like a job and a half with a large team.
    • These kinds of positions require you to make strategic choices about what you will and won’t do. There is no way to do it all.
    • Every company is different, but Amy likes the fact that John’s leadership redirected technical managers to get better at their craft.
    • “We had several of these conversations during the Geek Whisperer days. I applaud folks who tried management and decided they genuinely got more joy in their life from not managing people, and I think that’s ok too. I know plenty of people with successful career trajectories on every single combination of that – people who manage people, people who managed people and stepped out of it, people who never want to manage people and are very open about it. I applaud a world we live in where all those ways of being can be celebrated.” – Amy Lewis
  • When Amy first became a manager she was terrified, admitted it, and went to get help immediately.
    • Amy is thankful people were willing to save her from what she did not know.
    • New managers should seek help in the form of a mentor, reading books, etc. Do many things to get help.
    • The new people manager / leader is going to make mistakes and will have to learn how to forgive themselves for it.
    • “I’ve had the fortune of running a few just incredible teams. Teams that give you grace to fail and grow with them is such a gift. So the number 1 thing you can do is build trust. And say what you know and say what you don’t know.” – Amy Lewis
    • When Amy inherited the team at Solidfire, she had never run field marketing, the people knew more than she did, and she had no budget. Amy showed up to the first meeting with that team and was open and honest about what she had and what she didn’t have. She would elevate their work, remove barriers, and established herself as someone the team could be honest with.
    • “From the flip side, if you decide you do this and you get all in…build trust and tell the truth with that team, and encourage them to trust each other. And if people aren’t ready to be in that boat rowing along with you, then help them find the next opportunity.” – Amy Lewis, to those thinking about becoming people managers
• Did Amy have to learn how to do 1-1 meetings with her employees after becoming a manager, or did it come naturally because of Amy’s previous experience?
  • Amy says she wanted to hide from it, and she has seen new managers ignore the power of the 1-1. Now, Amy is adamant about having 1-1s with her people.
  • Some of the episodes Amy, John, and Matt get asked about the most are the ones with Dom Delfino. Dom is a mentor of Amy’s.
  • “One thing about getting a mentor like Dom or any good mentor…they are going to tell you things you don’t want to hear probably immediately…. I knew I didn’t know field marketing, but I thought that somehow being a good human and having good sense was going to save me…. If you prioritize your 1-1s with your people, other things with take care of themselves. You’ll figure the rest out…. I am a story of what not to do. Do not run from your 1-1s. They will catch you.” – Amy Lewis
  • Dom Delfino told Amy the most important thing a manager can be doing is having regular 1-1 calls with their employees.
  • Amy highly recommends checking out the Manager Tools podcast series for those just getting started.
    • This podcast covers much of the basics and is a great refresher for anyone, regardless of skill level. John says Manager Tools has been extremely valuable to him as well.
    • The same group also runs a show called Career Tools, which has a lot of great content on writing your resume, doing a job search, etc.
    • John mentions one of his teachers encouraging him to do the basics better to really progress. It wasn’t about advanced techniques. It was about doing the basics better.
  • If you are someone who is between things, you can train for the job you want next.
    • “You don’t have to have a team to train for the team you want to manage. Go in there and listen to it and get yourself ready so that when the opportunity finds you, you’re ready.” – Amy Lewis, on the Manager Tools podcast

37:45 – Parting Thoughts with a Geek Whisperers Twist

• It was Amy’s idea to have a little fun and ask her the familiar closing question from The Geek Whisperers. What’s one thing in career Amy would never do again in her career?
  • “I’m such a positive person, but I learn through negative space.” – Amy Lewis
  • Amy says don’t move for the title, whether that means relocate, change companies, or both. Avoid letting the appeal of a title lure you somewhere.
    • Being able to make a move does not mean you should make it.
    • Looking back, Amy feels there were a couple of times where she didn’t look carefully enough before making a change. In other instances, Amy took a necessary pause to truly examine if something sounded too good to be true.
    • “One of the things that’s a cheap and easy sell, particularly in this time where things are so chaotic, can be the lure of a high flying title. And I would say the corollary is probably don’t ignore what may sound like a title that’s ‘beneath you.’ Set that aside and really look at the work you’re doing every day and the people you’re doing it with and the people you’re reporting to. So, if you get glamoured, the title is the easiest thing in the world to change…. You will not be made whole by that title…. Don’t ignore or overlook something that you think is beneath you, and don’t get lured by the glamour of something that sounds amazing.” – Amy Lewis
    • Listen to Amy’s analogy about the Moody Café and how it relates to jobs and job titles.
  • John says this sounds a lot like career progression isn’t the only thing in the world. We should assess if a particular job is something we should do and if we’ve already spent all our tokens.
    • “Progression can mean what you would like it to mean…. You said it beautifully in terms of consider how many tokens you’ve got, and consider what makes you happy and really fulfills you. Look at the work. Look at the people. Look at the management chain. The title is the most fluid thing of all of it.” – Amy Lewis
    • And remember. you may have to lay something down to progress.
• If you want to follow up on this conversation with Amy, you can contact her:
  • On LinkedIn
  • On Threads – @amylewi

Mentioned in the Outro

• Nick thinks “once a Geek Whisperer” might not be an accurate description of Amy Lewis. Maybe it should be more like “still a Geek Whisperer?”
  • Nick recently realized while editing this episode that he still had episodes of The Geek Whisperers downloaded to his phone and was able to listen to them again. Amy, John, and Matt had an amazing chemistry that welcomed you as a listener, making you feel like you were in the discussions with them and learning with them. They were also welcoming to Nick when he was a new member of the same technical community.
• The Geek Whisperers as a body of work led to new opportunities for the hosts (Amy, Matt, and John). What the your body of work that makes you stand out?
  • Maybe it isn’t a podcast, blog, or video series. How are you making an impact inside your company or outside it whether paid to do it or not? How are you serving others in the same way Adam Grant describes in Give and Take (the idea of otherish giving)?
  • Keep documenting your accomplishments, community service, your hobbies, community service, etc. All of these things can help us build a body of work. If at least the documentation of your body of work is publicly accessible it allows people to see a little bit of who you are before they talk to you.
• When working on a project, remember things have an endpoint. Being intentional means you might have to make the choice to put something down due to circumstances in your life so you an pick something else up. Don’t be ashamed or afraid to keep re-evaluating over time.
  • In Episode 286 – Succession Planning: Delegation Skills and Technical Ownership with Max Kanat-Alexander (2/3), Max tells us he thinks about how he will hand off a project before he starts it. Maybe you don’t think about it at the beginning, but you can regularly re-evaluate your involvement as part of being intentional.
  • For another discussion of being intentional, check out Episode 165 – Excel by Being Intentional with Andrew Miller (1/3).
• If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page for an aggregated list of our most impactful conversations on the topic.
• Amy has also recently launched the Unicorns in the Breakroom podcast with Sarah Vela – a podcast to help you figure out corporate life.
  • Unicorns in the Breakroom on Apple Podcasts
  • Unicorns in the Breakroom on Spotify

Contact the Hosts

• The hosts of Nerd Journey are John White and Nick Korte.
  • E-mail: [email protected]
  • DM us on Twitter/X @NerdJourney
  • Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman
• Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_

Who knew leaving publishing might result in a career as a marketer in the tech industry? Amy Lewis was encouraged to pursue a role at Cisco by a career counselor who recognized her unique strengths. Now Amy refers to herself as an unapologetic marketer and a people person. On the soccer field and in her career, she is always a winger. She is focused more on the assist than scoring the goal.

In episode 301, Amy shares her early career transition from publishing to marketing for Cisco. We’ll discuss what storytelling is and how it can be used with individuals or large groups of people and how product marketing is about finding connective tissue. Amy also weighs in on online marketing, why she enjoys it, and how she learned to communicate with executives. Listen closely to learn about the impact of having good mentors throughout a career.

Original Recording Date: 09-19-2024

Topics – An Intentional Career Change, People Person and Unapologetic Marketer, Social Aspects of Marketing and Storytelling, Skills and Personas, Product Marketing as Connective Tissue, Candid Headlines and Communicating with Executives, Becoming the Interviewer

2:03 – An Intentional Career Change

• Amy Lewis is the director of enterprise marketing at GitHub.
  • She is also known as @CommsNinja.
• Amy tells us she majored in English and Political Science in school. After a 10-year career in publishing, she wanted to try a new career and landed in technology.
  • “Greatly oversimplified, it started with a Commodore 64, and then we wound up here.” – Amy Lewis
• Has the background in English and Political Science been an advantage since Amy got into the tech industry (i.e. experience in multiple different types of marketing roles)?
  • Amy says yes and went to a career counselor at the time she wanted to make a career change out of publishing.
  • “You have a really interesting skill set. You’re a storyteller, but you understand technology. You see where the world is going…. Cisco needs people like you. Technology needs people like you, people who can tell stories…. Go get a job there.” – Amy Lewis, feedback she received from a career counselor right before she joined Cisco
  • Amy tells us no one in her family worked in technology, and she had no contacts in technology. But after blind applying, she landed a role at Cisco.
  • Amy leaned into storytelling and making complex things simpler and understandable for others.
  • She did not know certain skills would be so applicable in this kind of career change, but she made the pivot at the suggestion of the career counselor.
  • Thinking back, Amy doesn’t remember how she found the career counselor originally.
• What made Amy want to leave publishing as a career?
  • Amy has been thinking a lot lately about return to office (or RTO as we might call it) because she has been working remotely for many years. She worked in New York at the company headquarters and then would later move away to start a family and work remotely.
    • Amy cites some advice from her mentor Brian Gracely about career limitations when you do not work in the same location as a company’s headquarters.
    • While working remotely for the publishing company, Amy saw a number of people get promoted. She felt at the publisher she would not be able to climb or grow any longer and that a new challenge was needed. It seems like she in many ways was out of new things to learn.
    • During the time Amy worked for the publisher, AWS was still Amazon.
  • At the remote office where Amy worked for the publisher, she was in charge of the server closet. In addition to this, Amy had digitized a number of properties for the publisher.
• Did leveling up mean becoming a manager, increasing salary, becoming a team lead, or just taking on new responsibilities?
  • Amy tells us it was all of these things. She is a competitive person.
  • Amy already had children, knew she did not want to have any more, and felt she could take more chances.
    • Amy needed to be with a stable company that would not fire her while on maternity leave. This is important for any working woman out there, even if left unstated.
    • Amy knew she could get paid more. She also had a director title but could not manage people because she worked remotely.
    • “I was ready to try something new, so I kind of restarted everything…. I’m ten years in. I’ve got a lot of contacts, connections, comfort. I had and raised my kids kind of in that environment, and I chucked it all away and…took a temp to perm contractor role at Cisco to get my foot in the door and try something new.” – Amy Lewis

8:39 – People Person and Unapologetic Marketer

• How was Amy’s previous experience looked at coming into the temp role at Cisco?
  • Amy started working as part of a content syndication program, which was focused on storytelling. At the time she hit all the right keywords for the role and was going to outpace most everyone else because of her experience.
  • After building websites and digital properties at the publishing company, Amy knew the disciplines of content syndication and online marketing well. These areas became her initial focus as part of the role at Cisco.
  • Amy describes herself then as someone “not afraid of the server closet and familiar with content.”
  • John highlights that Amy was the exact combination of things her employer was looking for at the time (what we might call a unicorn).
  • “This is the story of me, but everybody is a unicorn. Everybody’s got a superpower. Everybody’s got something that makes them unique. People say this, and when you forget it, let us all be reminded. Figure out who you are, what you’re good at, what drives you, and best of all, if what drives you is also good for business…and then be unapologetic about it and do it over and over and over again. Because I can either be half as good as somebody else if I’m trying to pretend to be them. Or I can be the very best Amy Lewis in the world.” – Amy Lewis
    • Amy embraced her unique skill set to excel in all of her previous roles and continued to embrace it when she landed at Cisco.
  • “I’m a people person. I call myself an unapologetic marketer…. In a traditional publishing company, it was weird to be a marketer there. And in tech, it can feel weird to be a marketer…” – Amy Lewis
  • In the publishing industry, Amy built the online marketing department and helped with the website. She worked for a small company and had easy access to the business owner.
    • As a storyteller, Amy finds connection in things that on the surface do not seem connected.
    • Even before Twitter, Amy would connect with people using online bulletin boards like phpBB.
  • Amy knows she is uniquely good at watching, listening to people, understanding personas / specific groups of people (i.e. the audience), and turning it into something using her creativity.
    • Amy continues to focus on what she is good at, what she likes, and how it serves the business – the connective tissue.
    • Amy mentioned her company once sold page-a-day calendars to the cat buying audience.
    • “Honestly, a cat lady is as passionate as somebody is about the type of phone they have in their pocket is as passionate about the type of networking gear that they use is as passionate about the software stack they’re engaged with. People are passionate, and it’s about people. I’m a people person.” – Amy Lewis
• Was marketing something Amy learned in school or picked up on the job?
  • Many people who are now in marketing had early interests in cults, serial killers, and other dark things. Amy’s field of study required reading all kinds of books on political movements, etc. (which is really marketing).
  • Amy mentioned marketers naturally seem to want to know what makes people tick. For her, it’s a combination of technology, how the world works, and natural curiosity.
  • John cites recent political cycles that are a merging of political movement and online audience building. Even before the internet, building a social movement was a form of marketing. It was about going to meet people, networking with them, connecting around an idea, and building community.
    • Amy’s example is one of reading about these types of movements and then applying that knowledge in a new area.
  • Amy’s mother was an English teacher

17:02 – Social Aspects of Marketing and Storytelling

• Was Amy interested in conversations with other people from a young age or ensuring she could collaborate with others in her work? What about that social aspect of working in marketing?
  • Amy started as a Chemistry major but realized she didn’t want to be stuck in a lab.
  • “I don’t want that. I want to be front of the house. And I don’t know that I wanted to be on a stage per se, but I knew I didn’t want to be in a lab…just doing lab things.” – Amy Lewis, on the decision to not keep pursuing Chemistry
  • Amy even thought about being a lawyer, especially since she had experience as a debater in high school and college, but that did not seem right.
  • “The other kind of spoiler alert is I’m an introvert. I may seem extraverted, but I think I shine a lot brighter online…. I can decompress. I can be behind my keyboard. I can go read a book afterward….I think there’s a lot of us like that too.” – Amy Lewis
  • Amy remembers a study that claimed more marketers were introverts as opposed to extroverts. Marketers like to observe their surroundings and do pattern recognition from there.
• We may have jumped to the conclusion that storytelling and people a people person necessitates being a 1-1 type of person. Is storytelling more of a broadcast or one to many type of communication?
  • Amy thinks people in sales might do better in the 1-1 communication or extraverted world as she calls it.
  • Marketers need to be able to make you feel like it’s 1-to-1, 1-to-few, and then 1-to-many or 1-to-masses. Amy has operated at each level without realizing it.
  • “I understand how to take people’s interest and passion and connect them with each other into that passion. And that I can apply to a lot of different things.” – Amy Lewis
    • Amy has done this with cake mixes and barbecue to bacon and datacenters.
  • Amy likes to take a lot of 1-to-1 observations and consider how much of it is true for 1-to-many and 1-to-masses. Is it connective tissue on a topic?
  • Amy says the best thing about working in technology is the constant new set of ideas, connecting people to these ideas, and then connecting them to each other.
• Nick says in this way the eyes are on Amy’s content or her ideas and not necessarily on her like she’s on stage.
  • Amy is a late-in-life football player (i.e. soccer), and one of her kids is the goalkeeper. You might think Amy would naturally gravitate to being a striker, but she enjoys being a winger.
  • “But the longer I play, the more I enjoy being a winger. And it’s so much less about how many goals I score than my assists. That’s the count that I keep in my head on the field. And I think that speaks a lot to my personality. To your point, I like the stories to shine. And I talk a lot about the invisible hand and how do you connect people to things? I don’t have to stand in front of it all the time, and I have found the longer I’m in career the more I really enjoy leading teams, setting people up for success, and…setting the idea up for success.” – Amy Lewis

22:49 – Skills and Personas

• Nick thinks we can see some of our own skills but will also need help seeing some of them, just like when Amy went to see the career counselor.
  • “I’ve often said, if you want to know what you’re good at or what your reputation is, turn and ask the person next to you. It is unbelievable how quick it will be. They will know. Just say, ‘what’s one word that you think when you think about me?’ Other people know what we’re known for before we do.” – Amy Lewis
  • Amy has done mentoring throughout her career. She spent 5 years as part of The Geek Whisperers and thinking about careers and has done a lot of mentoring in addition to that.
    • Amy likes to observe people in a setting and offer feedback on their strengths and qualities. She reminds us that this kind of feedback is a gift, and we often forget to ask for it.
    • Going back to the soccer analogy, Amy doesn’t know if the goals will always come, but she can always provide someone else a pass.
  • Does it seem narcissistic to ask someone for this kind of feedback?
    • “I like to catch people being great at something. Because they often don’t know, or if they do, it sure feels good to have somebody see it.” – Amy Lewis
  • Amy describes a project she did with the team at Dick’s Sporting Goods. Amy took this role at Dick’s Sporting Goods during a time when she was trying to choose between going back to working for a company she really loved and trying something completely different.
    • A mentor of Amy’s encouraged her to take the role at Dick’s, and she followed the advice, eventually building out a team.
    • Amy’s team worked within the Office of the CTO, which previously did not exist.
    • After observing and working with her team for a while, Amy built a slide deck and gave everyone a superpower and a superhero name. The gift Amy’s team gave her back was dubbing her the analogizer. This fits Amy’s method of storytelling – using analogies to “feel” the story and make it relatable.
    • John describes one of the best teachers he had in school and that teacher’s ability to restate the lesson he wanted to teach in the language of the hobby or sport based on a person’s interest. John has tried to emulate this style over the course of his career.
• Amy has been thinking a great deal about personas lately.
  • We live in a world where we know social media can feed our confirmation biases.
  • When marketers do their job well, they do it to serve a persona.
  • “It’s treating people with respect. It’s hearing them. It’s seeing them. It’s asking the question…all those tactics to either by observation or by direct question to get to know somebody and then to land what you’re trying to say. And then, to meet them halfway.” – Amy Lewis, on the marketer’s role serving personas
  • We talk about the difference between poor and excellent communicators with excellent communicators coming as far or as close to someone to help close the gap.
    • When communicating with someone and having a disagreement, consider whether you want to be right or you want to stay married. Either choice is a choice.
    • Amy highlights the importance of communication to close gaps and truly understand a persona.
• John highlights internet marketing as being focused on 1-to-masses and can lead to recency bias. Audience categorization can be difficult.
  • Amy says this really takes work, and we need to remember what we see in our social media feeds are likely not the same as what others see.
  • “If we don’t actively seek a difference of opinion, you’ll never figure out how to close the gap. You’ll only know how to close the gap with someone who thinks and looks and sounds just like you. And I think we all have to work at finding many voices and listening and thinking about our own to offset that recency.” – Amy Lewis
  • Amy mentions the emphasis in schools on citation and original content. The education we got is very different than what children are getting now.
  • Amy suggests we are raising a generation that is more critical, a group who is aware they are getting recency bias from being inside “the system.” That makes for an interesting group to market to and with.
  • John shares a story about the perception of typing as a necessary skill and compares it to the necessity presently to be able to use presentation software (PowerPoint, Google Slides) or understand sentiment from groups through social media.

33:15 – Product Marketing as Connective Tissue

• Amy likes to understand where groups can align and the connective tissue between them.
  • “Product marketing in some ways is no more than figuring that out…what your value props are and how they connect…to people’s beliefs and needs. That’s what it is. It’s messaging a positioning and then timing.” – Amy Lewis
• John wonders if product marketing is intentionally filled with jargon to foster the feeling of an in crowd who understands the jargon?
  • Amy says yes and calls it a tool often used. We discuss “othering” and “inning” in relation to this.
  • This likely becomes clearer when looking at commercial marketing where things like toothpaste say something about a personality.
  • A product marketer has a bag of tricks. They want to ensure they use product truth and build the messaging in a way that makes people feel they are smarter, ahead of the curve, etc.
  • “It can be true and work at the same time.” – Amy Lewis, on product marketing
• Does product marketing fit within a product team or in its own marketing funnel within an organization?
  • Amy mentions attending ad speaking at a Product Marketing Alliance conference recently.
  • Someone did a presentation sharing the various titles you can find in product marketing, and it made Amy think about how product marketing can take so many forms. Here’s how she thinks about it:
    • Within technology specifically, there is a broad group that is corporate marketing and a broad group that is product marketing.
    • Product marketing is like a slider bar starting with the product and its specifics and then getting more technical. From there corporate marketing would be more generalized information for the masses such as things that demonstrate thought leadership.
    • Someone passionate about the product and the details may gravitate more toward technical marketing or technical product marketing over general product marketing.
    • Many companies organize based on this principle, and it’s important to have both skill sets. On one end you have deep technical details of a product and working with product management and on the other more thought leadership (and a lot in between).
    • Events marketing, for example, would probably be filed under corporate marketing usually.
    • Corporate marketing has to be somewhat neutral, whereas product marketing will sit inside a business unit or division. Usually field marketing, communications, event marketing, etc. fit within the broader corporate marketing area.
    • In companies with a CMO (Chief Marketing Officer), communications usually will be for both internal and external, which includes public relations.
    • There are probably slight variations on all of the above (i.e. field marketing may be field embedded, etc.).
  • At the conference Amy met so many people across so many industries, and they all had the same complaints and problems.
    • For Amy, it was amazing to meet these people and listen to their stories. This helped to combat some of the confirmation biases we discussed earlier.

40:21 – Candid Headlines and Communicating with Executives

• Our discussion returns back to Amy’s temp to hire role at Cisco.
• Amy talks about this as being a moment in her career. Someone helped turn her badge from red to blue (i.e. full-time).
  • As a contractor, Amy was running a specific program and needed to present at a MBR (monthly business review). This is similar to a QBR (quarterly business review).
  • At the time, Amy was running a program but wasn’t getting the resources needed despite her attempts. Things were not going well.
  • “Either we get resourced and we change this, this, and this…or you should just cu the program. This is not a good use of resources.” – Amy Lewis, reporting the status of a program she was running to stakeholders in an honest and direct way
  • This was Amy’s program and had her name attached to it. She was hired almost on the spot.
  • Some of the other presenters were not sharing the true story of how their programs were going. Amy calls it a bold move, especially since we often want to protect ourselves. She often tells this story when coaching other people.
  • Amy knew at the time this program was not good for the business and wanted to ensure her name was synonymous with understanding what was good and what was not good for the business. *“That’s what a business review should be – whether it’s working, whether it’s…. It showed that I knew what was true and I was unafraid to say what needed to be said.” – Amy Lewis
  • Amy likes to emphasize the right kind of metrics and prevent others from focusing on vanity metrics.
    • “Telling those stories and telling people what to demand out of their metrics is part of my personal brand. People know if I show up with metrics, I’m going to know them. They are going to be true, and I’m going to tell you what it means and not just what’s on the paper.” – Amy Lewis
• Nick calls this the other side of the coin. If we’re going to tell someone what they are good at, why not be honest and tell them what they aren’t good at with an assessment of the situation?
  • Looking back, being honest in that business review and telling the truth when it was very uncomfortable was a form of storytelling.
  • Amy had the business acumen, was curious, could do the work, and proved she could lead a program. This put her back on the path to product marketing.
  • John says this is building a personal brand of telling others when someone is not working.
  • Amy mentions she is a headline person and has made a career on some catchy phrases that stuck. We can speak truth in a way that softens the blow but also in a way that makes it harder for people to ignore.
  • This is marketing at a feedback mechanism. Would you rather be around people who will tell you there’s a problem while you are in the room or talk about it when you are not in the room?
• Amy has mentees that often ask her how to work with executives.
  • She gained access to executives from being on social media in the early days when the playing field was more level. Consistently showing up on social media allows us to engage with anyone.
  • Amy has interviewed a number of executives over the course of her career based on the nature of her role (i.e. she had a lot of access to them).
  • These two things made it very normal for Amy to engage with executives.
  • The person who hired Amy full-time at Cisco gave her a business book that discussed the concept of executive inoculation.
    • One simple example of this is when a president doesn’t know the cost of a gallon of milk because they have lost touch with the people.
    • If a business leader has nothing but “yes” people around them, it can lead to executive inoculation.
    • “When you become disconnected…from your persona, from your audience, your business…that’s a danger. There are always going to be executives that wish to stay inside that bubble….” – Amy Lewis
    • The majority of executives Amy has worked with appreciated honesty. We should be thoughtful in our choice of language, stay true, and “bring the receipts” (or the proof) as Amy says.
    • “You can say hard things if you say them nicely, if you’ve built trust, and if you bring the receipts with you.” – Amy Lewis

48:42 – Becoming the Interviewer

• Was the interviewing something Amy had done previously and something she needed to apply to an executive audience, or did she have to learn interviewing on the job?
  • Amy is thankful for mentors like the person who hired her at Cisco as well as Brian Gracely of TheCloudCast.
  • “Though the story sounds good now, what I didn’t know could fill an ocean.” – Amy Lewis
  • Amy worked a few cubes down from Brian, and he was willing to help her learn many things.
  • Amy came up with the idea of Engineers Unplugged, and it was almost like a gameshow / competition with 2 engineers and a whiteboard.
    • “Once more I come up with a headline, and I write the story around it…. I had zero percent experience on camera before Brian Gracely challenged me to get started. And then I just took natural curiosity / extreme nosiness and put it to work. I thought if I’ve got the microphone, how can I serve the audience? How can I ask the questions that everybody wants to know?” – Amy Lewis
    • Through this exercise, Amy had to get comfortable with being on camera.
  • To this point Amy had not interviewed people but had plenty of practice public speaking. She did debate in high school and college and has given speeches to small audiences and those up to 3000 people.
    • “In some ways it almost felt like interviewing easier because I’m trying to make them successful…. And I’m always a winger on the soccer field…. I’m there holding the microphone to make them look good and feel comfortable.” – Amy Lewis

Mentioned in the Outro

• Being a winger in our careers doesn’t sound so different than being a mentor. Amy talked about seeking mentorship during different times in her career and now mentors others. If you’ve never worked with a mentor and don’t know what to expect or how that relationship should work, go back and listen to these episodes with Dale McKay:
  • Episode 288 – Guardrails for Growth: A Mentor’s Experience with Dale McKay (1/2)
  • Episode 289 – Enhance Your Personal Brand: Feedback as a Catalyst for Change with Dale McKay (2/2)
  • May you be blessed with at least one great mentor in your life!
• Amy has recently launched the Unicorns in the Breakroom podcast with Sarah Vela. You can find a discussion with thoughts on return to office mandates in episode 1 of the show.
  • Unicorns in the Breakroom on Apple Podcasts
  • Unicorns in the Breakroom on Spotify

Contact the Hosts

• The hosts of Nerd Journey are John White and Nick Korte.
  • E-mail: [email protected]
  • DM us on Twitter/X @NerdJourney
  • Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman
  • Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_
• If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

What can you learn from 300 episodes focused on career progression in technology? This week we’ll remind listeners of our show’s mission and share the origin story of the podcast. Listen closely for the lessons we’ve learned, the patterns we have seen in our discussions and guests, the feedback we want to hear from listeners like you, and some recommended episodes if you want to dive deeper in specific areas.

As part of episode 300 we’re also announcing the recent creation of our layoff resources page that you can find at nerd-journey.com/layoffresources. This is a curated list of our most impactful discussions on layoffs with HR professionals, career coaches, burnout experts, entrepreneurs, and technologists like you. It’s been put together in a specific order to help you process layoff events, get practical tips on moving forward, and learn from the experiences of others.

Original Recording Date: 10-26-2024

Topics – Restating Our Thesis, The Origin Story and Motivations, Lessons Learned, Trends and Patterns, Key Ideas and Books, Progressing as an Individual Contributor, Management as a Career, Looking at the Future

1:01 – Restating Our Thesis

• Welcome to episode 300!
• We wanted to start by restating our thesis for the show, especially for anyone who might be a new listener to the show.
  • We (John and Nick) are focused on serving the technology professional with the goal of bringing to light information on career progression and expansion that we did not know when we worked in IT Operations. We’re looking to answer questions like:
    • How do I find a new job if I’ve just been laid off?
    • How do I get better at my job?
    • How do I change job functions within the organization I’m in?
    • How can I change organizations / companies?
    • How do I gain recognition?
    • How do I progress in general in my career?
    • What are the different roles that exist under the technology umbrella that I might be qualified to do?
  • We’re extracting the patterns from stories of technologists not so different than you. Our guests have either worked in technology or have a unique perspective on the industry or trends within it. Releasing our discussions in multiple parts allows us to go deep into details and extract those patterns of the different ways one could go about accomplishing some of the aforementioned goals.
    • We also want to educate listeners on how many roles are possible under the technology umbrella as a whole and how you might be qualified for more jobs than you thought. You’ll hear us discuss relatable experience quite a bit on the show.

3:46 – The Origin Story and Motivations

• Right before Nick started a new job in late 2017 (that John had referred him for), John suggested the two of them start a podcast.
  • At first, Nick wasn’t sure what he would say on a podcast, but he said yes.
  • John says in the beginning neither of them was clear on what the podcast was about yet.
    • Based on his experience at a distributor and a technology vendor after being in IT Operations, John felt there were paths and roles that people did not know about that could result in greater pay. He thought they should publicize it and talk about different ways to accomplish it.
    • They also had other ideas like sharing details of the solutions their employer (a technology vendor) was releasing. John remembers recording several episodes on these topics that were never published. Nick recalls some of their first intros using the words “IT news and opinions based on our points of view.”
    • John and Nick didn’t think they could make an impact by just talking about the technology and promoting it. Many others were doing it.
    • “I think a lot of the career stuff just bubbled up to the forefront. We found the reason later on. It just got to be more and more clear that that part of it was the only thing that we should really focus on.” – John White
    • Nick says we have to talk about technology a little bit, but it wasn’t about the nerdy parts of the tech itself. It was more about how working in technology and focusing on it changed someone’s career, how they progressed, etc.
      • Nick had no idea there were so many different roles one could have when they started the podcast.
    • It seemed important to not only educate people on different technology focused roles but also talk about the process of applying for those types of jobs.
  • Nick and John worked together earlier this year to revise the podcast description. It was kind of right, but over time the theme had crystalized even more so than what was previously written in the description.
    • This is also part of the reason you see “Career Advice for the Technology Professional” in the show’s title now.
    • While we are not paid to give career advice, we sure do love continuing to learn on this topic!
• If you hear ads when you listen to our show, they are NOT from us! We’ve never used ads.
• Our costs for the podcast center more on time spent than money. Hosting costs and other subscriptions isn’t a huge expense. It did not seem realistic to monetize in a way that would offset the cost of our time, so we didn’t do it.
• What is it we hope to get out of the podcast if it isn’t money?
  • For John, the payback is more about exposure to guests, hearing their interesting stories, and knowing listeners are finding the models our guests are presenting valuable. One model is coming from a nontraditional background to work in technology. We’ve figured out that there is no “traditional” background.
  • Nick highlights the fantastic people we’ve met as we’ve heard their stories. For Nick, the podcast helps him in addition to helping other people.
    • We talk to people before and after we interview them and try to keep up with how they are doing.
    • Nick says when you edit the show, you get to listen to the advice given in episodes multiple times.
    • “Selfishly, I like doing it for me…. If it helps me, my hope is that it helps other people too.” – Nick Korte

11:43 – Lessons Learned

• Nick has found that you will make time for the things you like and enjoy. In fact, he and John recorded episodes while he was on vacation in Galveston right before the show launched.
  • Nick recounts editing the podcast on cruise ships, in the passenger seat of a car while on a road trip, in hotel rooms, and of course, at home…all out of an unwillingness to miss a release.
  • John had some major life events happen at different points like buying his first home and having a child which required him to step away from the show. The first time this happened, Nick had to learn how to edit.
  • Nick’s wife and daughter know how much he loves doing the podcast and support him in it. They know that weekends are for podcasting and editing. He is only able to do this because of their support.
  • If you plan to do something like this (start and maintain a podcast), make sure you have the support to do it.
  • A podcast takes time, and when you begin you will not be fast at any of it. Nick feels like he and John have improved in the questions they ask, their prep, and hope the quality of the show has improved over time.
  • Hopefully the findability of the show has improved over time with iterative improvements on the show’s description and metadata. Nick wishes they had done this better as the theme became more crystalized.
    • John thinks maybe we would have been better at this part if either of us had marketing backgrounds.
  • With the experiences being part of technical communities in the past and being in pre-sales for a while, Nick is not shy about asking people to be on the show if they have a great story. Neither is John.
    • It has not been hard to get people to say yes once we do the prep work and share what we’re trying to do.
    • “You don’t know when and where, but somebody’s going to be helped by hearing your story. I think people want to be able to help, so it’s finding people that have that compelling lesson that’s embedded in their story.” – John White

16:02 – Trends and Patterns

• Some things we have seen have changed over time, while some have been timeless.
• The strength of the job market has varied over time.
  • Right now, in late 2024, the job market is difficult, and we are seeing many layoffs in the tech industry. There are many reasons behind this – consolidation, interest rates, etc. There are still jobs open, but it’s a challenge when thousands of people have lost their jobs so close together because it might mean high competition amongst a large candidate pool.
  • In 2021, it was a very hot job market with tons of hiring, making finding candidates difficult.
  • As time goes by, the place we are in the job cycle changes quite a bit. John says it’s been interesting to hear our discussions during both a hot job market and a difficult job market.
  • If you are worried about layoffs or have been impacted, Nick mentions the recent creation of a layoff resources page you can visit at nerd-journey.com/layoffresources. You will see the title of “What Can I Do in Response to a Layoff Event?” This is a curated list of some of our most impactful conversations on the show about layoffs given to you in a specific order to help process the event and understand what you can control.
    • You’ll hear from business psychologists, burnout experts, career coaches, entrepreneurs, and technologists.
• John mentions some discussions we’ve done on the best practices in searching for a job. One example is accepting interviews even when you’re not actively seeking a new role to gain practice. Specifically, this is practice when the stakes are very low.
  • Taking an interview may help you learn about a really interesting opportunity.
  • John encourages listeners to know why they are staying at a particular employer. Staying at your current employer has to be better than making a move for you to stay.
  • We’ve talked about considering the type of company to work for and the role you would like to have, keeping them in generalities instead of specifics.
    • Consider the type of work you would like to be doing, the environment in which you would want to work, the types of co-workers you would want, how all of this might make you feel, etc.
    • The above goes back to concepts we discussed in Episode 19 – Process over Outcomes and Dreaming in Bands
• We have also done past episodes on resume construction. While we do not council people on resume writing for a living, we have written several of our own. Here are some recommended episodes from our foundations series that might help you (each contains links in the show notes to other helpful resources):
  • Episode 203 – Revisiting the Foundations of Resumes
  • Episode 204 – Revisiting the Foundations of the Job Search
  • Episode 205 – Revisiting the Foundations of Job Interviews, Part 1
  • Episode 206 – Revisiting the Foundations of Job Interviews, Part 2
• We’ve discussed interviews and explained the goal of an interview, which John mentions is not always obvious.
  • When John worked for Google he conducted many interviews even though he was an individual contributor. Much of it was to evoke how people think and solve problems.
  • We have also done episodes covering the different types of interviews like those with a recruiter or hiring manager, a technical screen, a vibe interview with a leader, etc.
  • There are also many great interview stories people have shared throughout the years. In the interview, we want to be able to tell our career narrative. This is something Jason Belk shared with us in Episode 284 – Draft Your Narrative: Writing and Building a Technical Portfolio with Jason Belk (2/2). One of the days we build a narrative is documenting our work and showing our work so we can speak about it with others.
    • Telling your narrative is not something a person can do if they haven’t thought about it!
    • How did your experiences change the way you think and solve problems?
    • “You need to think about it ahead of time and then construct it and then practice telling that story. And then revisit that because you’ll change. And then your perspective on the past will change also.” – John White, on career narratives

24:09 – Key Ideas and Books

• We’ve compiled a list of ideas listeners need to consider / think about as they start to focus on career progression (i.e. getting better at your current job, becoming a higher performer, etc.).
  • Proof of Work
    • This goes along with the book Show Your Work by Austin Kleon. This is a short and very digestible read containing stories about the power of documenting your learning, being a beginner, sharing your experience, and how it can help your career.
    • One practical implementation of this is blogging about learning a specific topic.
    • Kleon’s book makes a compelling case for learning in public, which means documenting the learning in some way so you can tell that career narrative we spoke about earlier.
  • Turn Information into Knowledge
    • This came to us via a book recommendation from previous guest Josh Duffney. Josh spoke about what he had learned after reading How to Take Smart Notes by Sonke Ahrens, which is often called Zettelkasten (a knowledge management system).
    • Be sure to check out our full discussion with Josh in Episode 156 – Better Notes, Better You with Josh Duffney (1/2) where you will find links to a book Josh wrote called How to Take Smart Notes in Obsidian.
    • John says this methodology has revolutionized how he works. It’s part of showing your work but also a way to keep track of things you know. We can take notes on what we are learning and then formalize our thoughts into our own words, putting them into a system that allows you to create connections between concepts you have learned. It becomes knowledge once it is in a system that allows retrieving it, taking action on it, and then publishing it.
    • Nick feels he could improve in note taking to make it more like the smart notes methodology.
    • John mentions this is less about full adoption and more about being exposed to the idea and trying to implement it in some way. There is no perfect way to do it!
  • Improve Your Ability to Do Complicated Knowledge Work
    • This point is based on Deep Work by Cal Newport. We recorded a 7-part discussion series on this book starting with Episode 141 – Book Discussion: Deep Work, Part 1 – The Why and ending with Episode 147 – Book Discussion: Deep Work, Part 7 – Become Hard to Reach. Episode 147 contains links in the show notes to all discussions in the series.
    • John feels the series of episodes we did stand out as an example of how to take smart notes as applied to the deep work concept. Even just listening to our first episode in the series will give you an idea of what the book is about and an overview of the concept of deep work.
    • This book is an example of why it’s important to be able to do complicated knowledge work and the things you need to do to be good at it. There are other books Cal Newport has written that Nick and John have also read. Cal Newport also has a podcast that is quite good.
  • Incremental Improvements
    • One of the first books we came across here was Switch: How to Change Things When Change Is Hard by Chip and Dan Heath. Another book many people have recommended in this space is Atomic Habits by James Clear.
    • The idea is making small improvements and building upon those improvements, which includes shaping your environment so you can do it well.
    • These overlap a little with the concepts Cal Newport spoke about in Deep Work.
  • Making Big Bets on Technology Waves
    • While there is no specific book here, it is a corollary to the above ideas. We’ve seen this pattern happen with a number of guests.
    • When Nick thinks of guests who have talked about technology waves he thinks of several episodes – Episode 80 – Certification and Mentoring with Manny Sidhu,Episode 188 – The Surfer of Technology Waves with Joe Houghes (2/3), and Episode 184 – Dive Deeper and Enjoy the Process with Michael Levan (2/2). Also check out Episode 264 – Back to Basics: Technology Bets and Industry Relationships with Brad Christian (2/2) to get Brad Christian’s take on making technology bets.
    • Manny Sidhu was the first one to bring up this idea. He came across virtualization in the early days and decided to go all in. The foresight to do that early on can be powerful in your career, but there may be ways to do it which are not as large of a risk.
    • If someone made a bet on blockchain a few years ago, it hasn’t played out just yet. Think about containerization and generative AI and how they will continue to change over time. Will you place a bet and position yourself within one of these trends?
    • Should we talk to more people about how to evaluate technology waves and the smart way to make a bet on a wave?
    • People often want to know where to place their focus to gain new skills and be valuable in the market. It’s a difficult problem to solve.
    • Making a completely safe bet on a technology wave might mean you are late to place your bet.

34:40 – Progressing as an Individual Contributor

• Another trend we’ve seen is progressing to a high level individual contributor, which we might refer to as becoming a principal engineer. The principal level is one of the highest job levels for individual contributors with things like distinguished one step higher. We’ve spoken to guests about what it takes to achieve the principal title and what it means to have the title in our industry.
  • A typical progression for an individual contributor might be systems engineer to senior systems engineer to staff systems engineer to senior staff systems engineer to principal systems engineer, etc. But this progression may look different inside the organization where you work!
  • This is a leadership track but not a management track. High level individual contributors like principal engineers often work on problems with a broad scope within an organization and sometimes outside the organization. It’s about technical depth and breadth but also developing other people too.
  • John highlights the principal as someone who can bring their knowledge to a project and then hand it off to someone.
  • The discussions about the principal title are some of Nick’s favorite. Recommended episodes for learning more about the principal engineer would be:
    • Episode 286 – Succession Planning: Delegation Skills and Technical Ownership with Max Kanat-Alexander (2/3)
    • Episode 287 – Scope Creep: Evaluating Impact in Career Decisions as a Principal Engineer with Max Kanat-Alexander (3/3)
    • Episode 242 – Modalities of the Staff and Principal Engineer with Ken Collins (2/2)
    • Episode 167 – Pause and Step Outside with Andrew Miller (3/3)
    • Episode 152 – The Theme of Your Career with Scott Lowe (1/2)
    • Episode 153 – Creating a Full Stack Career with Scott Lowe (2/2)
    • Episode 170 – Signal What You Want with Joe Chenevey (1/2)
    • Episode 171 – Coaches as Mindset Curators with Joe Chenevey (2/2)
    • Episode 185 – Make Accommodations for Success with Phil Monk (1/2)
    • Episode 186 – The Unassuming Architect with Phil Monk (2/2)

37:45 – Management as a Career

• This has been a trend we’ve seen. If you want to be a manager, what do you need to prepare yourself for, and what is the job of a manager?
  • We’ve had discussions about the differences between managers and the technical lead of a team.
  • There’s also the concept of the player coach where someone might be partially a people manager and still have individual contributor responsibilities.
  • John has made the transition to people manager from individual contributor. He shares that there is a 30% or so crossover of skills.
    • “Being a manager just is a whole new set of…very technical skills that don’t have anything to do with being that individual contributor.” – John White
    • John says there are companies who have developed philosophies that management can be a skill applied to any team, even if the skills of the team are different than your skills when you were an individual contributor.
  • We have also seen people move from manager back to individual contributor. It’s not necessarily a step down and might be right for you based on specific timing in your life. John says it’s just a different job.
  • If you’re listening to this and are thinking about becoming a people manager, check out these episodes:
    • Episode 244 – An Array of Decision Points with Tim Crawford (2/2)
    • Episode 252 – Management is War with Russell Swinney (1/2)
    • Episode 253 – Building Trust as an Interim Leader with Russell Swinney (2/2)
    • Episode 238 – Managers as Culture Keepers with Leanne Elliott (2/2)
    • Episode 278 – Uncovering Empathy: The Greatest Skill of an Inclusive Leader with Marni Coffey (1/3)
    • Episode 279 – Change Management: The Hardest Leap and Developing People with Marni Coffey (2/3)
    • Episode 280 – Life after Layoff: A Leader’s Sense of Duty and A Series of Good Conversations with Marni Coffey (3/3)
  • For more on the player coach role, check out Episode 231 – It Comes Back Tenfold with Chris Williams (3/3).

41:52 – Looking at the Future

• We would like your feedback on this we should be doing more of and less of. Please send any comments to [email protected].
• Who should we be interviewing?
  • More practitioners / people who don’t work for tech vendors, resellers, or distributors?
  • Are there roles we haven’t covered that we should be like venture capitalist, procurement personnel, or platform engineer?
  • Do you have a recommendation for someone who should be on the show? We will take that and run with it.
  • Do we need to interview people in new, interesting verticals?
  • Are there specific types of companies you want to hear about?
• If you’ve heard one episode that has been valuable to you at any point, please take the time to rate the show 5 stars.
  • What did you find helpful about a show you listened to? Please share that and tag us on social media.

Contact the Hosts

• The hosts of Nerd Journey are John White and Nick Korte.
  • E-mail: [email protected]
  • DM us on Twitter/X @NerdJourney
  • Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman
  • Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_

Recent episodes and tech industry layoff trends made us wonder – is there a connection between layoff events and burnout? And if there is, are there differences in how burnout shows up in people impacted by layoffs, in those who remain, and in leaders?

In episode 299 burnout expert, coach, keynote speaker, and podcaster Cait Donovan returns to help us connect the dots. We start by defining burnout and building up from there. You’ll hear thoughts on chronic stress, emotional processing, burnout risk factors, and burnout protection factors. Cait also reminds us that there is a distinct line between managers and employees that has become very blurry in the workplace.

Original Recording Date: 09-28-2024

Topics – Defining Burnout, Connecting Dots between Layoffs and Burnout, Emotional Toil and Processing, Chronic Stress and Capacity Noticers, Taking Stock of Burnout Risks and Protections, Burnout in Leadership, Boundaries and Closing Thoughts

2:08 – Defining Burnout

• Cait Donovan is a burnout expert, a coach, and a keynote speaker. She is also the host of FRIED: The Burnout Podcast.
  • Cait was a practicing acupuncturist for 15 years and then burned out. She would later pursue a degree in biobehavioral health to understand what stress does to our bodies.
  • Cait spends her days podcasting, keynote speaking, and doing corporate training. She’s also working on a second book. Be sure to check out Cait’s first book, [The Bouncebackability Factor: End Burnout, Gain Resilience, and Change the World].(https://www.amazon.com/Bouncebackability-Factor-Burnout-Resilience-Change/dp/1735194905).
  • If you missed the previous episodes we recorded with Cait, check out:
    • Episode 214 – Across the Patterns of Burnout with Cait Donovan (1/2)
    • Episode 215 – The Beautiful Right Turns with Cait Donovan (2/2)
• What is the definition of burnout?
  • Cait likes to start with the World Health Organization (WHO) definition of burnout. Burnout by their definition is an occupational hazard / phenomenon (neither a mental nor a physical health diagnosis). According to WHO, there are 3 components to burnout that must all be present:
    • Physical and emotional exhaustion
    • Cynicism and detachment
    • Feeling a lack of productivity or lack of impact related to your work
    • The above is a little generic and only deals with the workplace. Cait has found chronic stress is more pervasive than just the workplace and has much to do with how we were taught to interact with the world, which may impact many areas of our lives.
  • Cait’s definition of burnout is “chronic stress that has led to a decline in functioning of your body, mind, soul, spirit…over an extended period of time so slow that you didn’t notice it happening until it was like, ‘where did I get here? What am I doing? What is this life, and why am I so miserable?”

5:00 – Connecting Dots between Layoffs and Burnout

• Many people are looking at the tech industry right now, see the layoffs happening, and they get worried / anxious / scared. After recording other layoff focused episodes with Kat Troyer and Liz Bronson from RealJobTalk, we thought it would be interesting to explore this topic with Cait through the lens of how this trends up or down with burnout.
  • Be sure to check out Episode 290 – Reduction in Force: Navigating Layoff Trends in Tech with Real Job Talk (1/2) and Episode 291 – Layoffs and Job Market Impacts: Experience with RIFs Preferred with Real Job Talk (2/2).
• Think about the person seeing the layoffs from afar (reading about it, knowing people who have been impacted). Can anxiety from seeing this kind of thing be enough to start you down the burnout path?
  • Cait says not on its own, and she highlights Burnout Risk Factors (BRFs) and Burnout Protection Factors (BPFs).
  • Many of the burnout risk factors (BRFs) have nothing to do with a person’s current situation. They can be genetic or epigenetic, from culture, from propaganda, or other things happening to us for large portions of life.
    • We often have very little control over how we might interact with these things unless we have been intentional in our awareness of such risk factors.
    • Genetics represent a more stable risk because they aren’t going to change. Epigenetics is a different story.
  • If someone has a large number of risk factors (BRFs) and a small number of protective factors, a layoff could throw them over the edge. Because burnout is the result of a long period of chronic stress, a layoff event may not be chronic enough at the moment to be a cause of burnout (perhaps a low contributor).
• Consider people who have been impacted by a layoff. Since Cait does a lot of coaching, what does she see happen in this situation? Do people often find a layoff is a realization of being burned out and feel relieved, or can it be the event that triggers burnout in someone?
  • Cait says both of the above are possibilities based on perception and a number of other factors.
  • "…If people already know that they’re burnt out, a layoff is like the best thing that ever happened to you. You’re…so grateful because you were never going to make that choice by yourself…. There are so many reasons we stay in jobs that no longer suit us. But if you are in a job that no longer suits you and you get laid off and you don’t have to be the one to end the relationship, it’s a relief…. Probably for the first time since a free summer when you were like 12 you’ve got 2, 3, maybe even 6 months of paid time off…. So for some people this is a really big relief. " – Cait Donovan
    • In a layoff situation there is normally some kind of compensation or severance package associated with it.
  • Some people might not be aware of being on the edge of burnout. If the layoff happens at the same time as several other stressful events (a family member gets a discouraging health diagnosis, etc.), it can eliminate any sense of stability even with the money one would get in a severance package.
    • “This eliminates a sense of stability that they don’t have enough of right now anyway and can really cause people to stumble.” – Cait Donovan
  • Cait says we need to remember people are holistic systems as we talk through this.
• Nick thinks if we add in a tough job market, maybe the scales tilt toward burnout being a result of the sudden layoff event.
  • Cait has a number of clients who work in technology, and several of them have lost their jobs.
  • Statistics seem clear that long term artificial intelligence will create more jobs than it replaces. If we know this is coming and are given time (because of a layoff), we should consider using that time to make ourselves more attractive to the needs of employers.
  • While there are no guarantees, Cait has seen people approach this in a couple of ways:
    • Learn what is coming next so make yourself more marketable moving forward.
    • Some people lose interest in working in the field entirely. Cait gives the example of one client seeking to become an artist. Perhaps there are other ways to use your skills and your hobbies and continue learning.
    • “So, if you are not already in this crazy situation where the layoff makes you sort of break down, there’s actually a huge amount of possibility for tech workers moving forward…. Tech work over…especially the last 5ish years has been so intense…. It had to pop at some point. So here we are. It’s popping. We knew this was going to happen. It’s now here. And the question is what do you want to do moving forward? …I do believe that there’s a huge amount of opportunity in this world. It’s just different than what it has been.” – Cait Donovan
    • Cait also says if you need to take the time you are given to sit on the couch and rest, take the time. It’s ok. There’s no mandate that says you have to decide what to do right away.

13:14 – Emotional Toil and Processing

• Nick thinks there’s a step before the above to process the emotional toil of a layoff event. How is Cait helping her clients with this?
  • Cait says some people are relieved. Actually, most people are relieved.
  • If someone had this happen and was not relieved, Cait would help them focus on what is under their control.
    • Start with writing a new resume / cv based on what you know. Consider using ChatGPT to help you write a version for a non-technical world / role because it can open your eyes to possibilities you do not immediately see.
    • Take a look at your money and where it’s going to determine if it is serving the life you want. Pull back from spending in areas that are not serving the life you want to remove added pressures. This is a great time to figure out what your actual needs are.
    • Looking at the money you need to live the life you truly desire ends up being less than people think according to Cait.
    • Do the math, and set yourself up on some kind of budget. Cait has used YNAB (You Need a Budget) for her business and finds it really helpful. The tool suggests, for example, that you set aside money monthly to be able to pay for yearly expenses when they arise.
    • “A lot of times that’s a fear and a safety area that we can add some sense of safety in by giving people a little more control. Let’s just look at it.” – Cait Donovan, on taking inventory of your money and where you spend it
    • “You’re emotionally processing while you’re doing this because…when you do a cv you’re starting to see…what are the possibilities? What things are available to me? Instead of thinking, there’s nothing left. I’m never going to be able to do anything…. We’re processing that by flipping the script. We’re processing your sense of safety by letting you know where it is or where it isn’t and what needs to really happen….” – Cait Donovan, on processing the layoff
    • Cait shares the story of having two clients who were spouses do the money map exercise after being really concerned about job loss. Both of them lost their jobs, and both of them were fine as a result of doing the exercise (bills were covered).
    • Starting with practical things can be what shifts our emotional state rather than working through an emotion while the stressor is still there. Cait’s suggestion here is to shift the stressor to work through the emotion.
    • Looking through finances is a great exercise for anyone listening. Do it regularly. Cait suggests doing it quarterly. You don’t need a full day if you’re using budgeting software. It takes a glance at where things are. Looking at how much we’re spending across all areas can help us see, for example, that we have too many subscription services and some could be eliminated.
    • Cait loves to read and pays for Kindle Unlimited. While she could use a library system like Libby, she loves the convenience of Kindle. It would be one of the first things to go if she needed to trim down subscription spend.

19:32 – Chronic Stress and Capacity Noticers

• Perhaps there is a similar impact when we take a baseline of stressors. If we don’t have a baseline, we might not know.
  • In both group and individual coaching, Cait works with clients on something she calls capacity noticers.
    • “They are really different from person to person…really different. But most people have no idea what their mental, emotional, or energetic capacity is…. So we have to figure out, financially and not – what is my capacity? And where am I overriding it regularly?” – Cait Donovan, on capacity noticers
    • It takes time for people to uncover capacity noticers.
  • Cait gives the example of working on a computer and needing to put in eye drops at 11:30 and 3:30.
    • People might think it is just their eyes because they forgot to think of themselves as a holistic system.
    • The above is your body’s cue to rest your eyes a little and take a break. It means your capacity has been crossed.
• Chronic stress impacts you slowly over time, and we make adjustments for it.
  • Cait describes a problem that could start with a sore hamstring.
  • Suppose someone then leans to their other side for a few days to take the pressure off the hurt hamstring. Maybe this leads to right hip pain and back soreness followed by neck pain and migraines over a span of a couple of months.
    • The root cause was not addressing the overworked hamstring, but it might seem to the person like a migraine, for example, came out of nowhere.
  • Cait does not expect people to recognize the small shifts over time, especially for people who burn out.
    • Our bodies are designed to make modifications / work around the small agitations like the pain described above.
    • Cait mentions something called interoception, which is our body’s ability to feel a need a respond to it appropriately. These needs can be conscious and subconscious (eating when we are hungry, using the restroom when we need to, etc. would be the more conscious forms). When emotions show up the body also responds to them.
    • “In those that experience chronic stress…we tend to have lower interoceptive skill and awareness than other people. So not only does your body modify naturally. But if you are someone who, for whatever reason,…it’s been taught out of you to listen to your body (i.e. your brain didn’t develop in a way that allows you to listen), then you won’t hear any of those things until you’re being knocked over.” – Cait Donovan, on interoception and chronic stress
    • Cait says people who are burnt out should cut themselves some slack because it isn’t their fault that they did not notice.

24:34 – Taking Stock of Burnout Risks and Protections

• For those who may be in an environment where layoffs have happened, what can they be paying attention to from a stressor standpoint in order to do something about it faster?
  • “So here’s another thing that we need to talk about. If you are in a situation that for some reason is toxic or sort of impossible to ignore, you can’t meditate your way out of it…. You can meditate all day and all night, but if you are swimming in chemicals they are going to affect your body. If you are in a toxic situation in a workplace where everyone is feeling fear, that is going to enter your body too. So the question here for me is how mindful can you be of what emotions you are bringing with you to the communal work soup? Are you adding to the flavor of the broth, or are you making it impossible to eat? …You can’t totally protect yourself if there’s a pervasive fear in the office. So what you have to know is whether or not there’s a pervasive fear in the office. And if there is a pervasive fear and it’s not going away and leadership is not stepping up to increase trust and to increase psychological safety and to calm this fear…you have got to get moving. You can’t stay in a situation like that…. Sometimes the only answer is to get out…. People don’t want to hear that. People want to hear that they can do enough to take care of themselves to manage the situation. But you are not the situation. The situation is bigger than you. And you can’t manage everybody else’s emotions. And you can’t manage the level of safety. And you can’t manage what your work is going to require and what the stakeholders want. You can’t manage any of that. You have no control over it.” – Cait Donovan
    • Cait says we can measure heart waves up to 8-10 feet outside the body.
    • Cait mentioned her husband was near Chernobyl when it happened and had to take iodine for a while as a result.
    • We can exercise and sleep well and do other things to become more resilient. But that resiliency will only last so long based on the environment you’re in.
• Nick thinks this is hard for people to hear, especially when they see a tough job market.
  • “You have to know that the choice that you’re making is to accept that your body is in a state of chronic stress, which means you need to build up as many burnout protection factors as you possibly can…. You are going to bed and waking up at the same time every day. You are spending time outside during dusk or dawn so that your hormonal cascade is working properly. You are focused on getting the right amount of water and electrolytes and all of those things into your body. You are eating well. You are managing your emotional health…. If you are going to stay in that situation you have got to do ALL of the things to last as long as you can…. If that’s your only option, you have got to up everything else.” – Cait Donovan
    • People need different levels of burnout protection factors to begin with.
    • Cait is going to get sunburned without sunscreen. It’s not a judgement but how she is built. Burnout protection factors are called BPFs for a reason because some of us need more of them than others.
    • If you need a higher level of protection factors already, it’s going to be harder to increase the level of protection by very much. And people also have to reduce risk factors.
    • There are many possible burnout protection factors and burnout risk factors, and it might be challenging to identify all of them without outside help. You need to understand what your needs are for standard, average health to see if you have room to add protection factors. And you also would need to remove / reduce the risk factors.
  • If the biggest risk factor is being in a specific environment, then you would land on getting out. But it might not be the biggest burnout risk factor.
    • Cait gives an example scenario of a stress inducing home situation which might need to be addressed so you can stay at your job.
    • This goes back to addressing the holistic life of a person and thinking of them as a system. We need to take a 360-degree look.
  • "We need to up our burnout protection factors and reduce our burnout risk factors as much as we can if we’re going to stay some place. In order to do that, you’ve got to be aware of what they are. So you have to do inventory. What really fuels me? What really drains me? Those are the basic questions… Draw a line down the middle of a paper. Start making a list…. It’s a phenomenal place to start, and most people, again, just like with finances, never stop to take stock of this. " – Cait Donovan

32:25 – Burnout in Leadership

• Is it more difficult for people managers / people leaders to keep burnout protection factors higher than the stressors and risks because of the nature of their position?
  • Cait says yes and that leaders are having a hard time right now.
  • “Mid-managers have long been known to have the highest stress levels in most companies…every time. Because they are getting slammed from both sides. Their leadership is slamming them, and the employees are slamming them. Everything is their fault. It’s either them or HR…. There’s no getting around that. One of those two groups of people is at fault for everything in an office, which of course is not true. But this is how it’s often displayed.” – Cait Donovan
  • Cait feels mid-level managers should have outside support at almost all times in their role. This support could be therapy, coaching, mentorship, or something else.
    • “I honestly don’t believe that you can make it in that position well, be successful at it, and support people the way that you really want to if you don’t have support yourself…. Get somebody. Get something…. Do anything to have a space that is supportive for you. You absolutely need it.” – Cait Donovan, advice for mid-level managers
  • Nick suggests managers could certainly use support if they have to be the ones to execute a layoff event, especially if they were not prepared to do it.
    • Cait says this is part of the job and that the leader should prepare for it as best they can.
  • Going back to a broader view of leadership in general…
    • Over the last 20 years, leadership has drastically changed, but leaders haven’t changed so much over that period. Some leaders at the top do not mesh well with our current world, and they are getting criticized for it.
    • Some of our current business leaders learned specific management and leadership styles in school that might have been hierarchical and authoritative (methods considered successful at the time).
    • “The demand right now is for leaders to show up more authentically, to have more vulnerability, to show more empathy. I think…we are in the midst of this major shift for leaders, and I think it’s been incredibly hard for them…. If you want to stay in a leadership position, then you need to learn how to shift out of this hierarchical system…. For a lot of corporate America, this is not working anymore.” – Cait Donovan
• Is the mismatch in the needs of employees from their leaders the largest contributor to burnout culture?
  • Cait says it is a big contributor and says one of the top 6 contributors to burnout in the workplace is a values mismatch, which can happen on 3 different levels:
    • A mismatch between a company’s spoken or written values and their values in action is one level. Are they (the company) espousing the values they claim to? When this is off, there is a lack of trust within the company. A lack of trust leads to a lack of safety which leads to stress.
    • The next is a mismatch between a manager / leader and an employee. Having differing values than your immediate boss makes it really hard to feel productive and impactful at your job. Feeling lack of impact and productivity at your job are major burnout factors.
    • There can also be a values mismatch between a person and the company where they work. If you feel the things your company is doing are in opposition to / against how you believe the world should function, that will be a massive burnout factor for you. The other two factors will be factors for the culture of the job, and this one specifically will be an individual burnout factor.
• Can the mid-level manager, with support, prevent their team from burning out if there is a mismatch from mid-level management upward?
  • Cait says no.
  • Cait gives a frequent keynote called “Dismantling Burnout: How Leaders and Teams Can Work Together to Overcome Burnout.”
    • This keynote speaks to the lines of responsibility for both leadership and employees. For example, what is leadership responsible for, and what are they not responsible for?
    • “While it’s important for leadership now to have more vulnerability and empathy and the soft skills are becoming more and more and more important…it’s not your leader’s job to be your therapist. It’s not your leader’s job to understand every single thing that’s going on in your life. It’s not your leader’s job to be the person you cry on their shoulder. It’s not your leader’s job to be your best friend in the workplace. That’s not your leader’s job. Your leader’s job is to create a sense of psychological safety for you as best as they can, and then the rest of the stuff that you bring with you to the workplace is up to you…. A leader can only do so much about your stuff. That’s not a leader’s job. A leader’s job is the workplace not the worker.” – Cait Donovan
    • Cait highlights a podcast episode called The Workplace is a Trauma Recycling Center. Each day we go into work and bring things from the rest of our lives with us.
    • We get triggered by things or annoyed by things that may not affect other people. We bring the rules we were taught over the course of our lives. All of this is creating conflict.
    • It’s hard for first time managers out there, especially right now.
  • Nick references an episode of Cait’s podcast with guest Daisy Auger-Dominguez called [Burnt Out Leaders Lead Burnt Out Teams](Daisy Auger-Dominguez).
    • Cait says it isn’t that leaders should not care about their people. We should understand that leaders are not there to act as therapists.
    • Our leaders can absolutely show us empathy and make accommodations for us.
    • “I have seen the power of leadership when you know that a leader has your back. But what a leader can’t do is go in and solve your problems. They can give you space. They can give understanding. They can create accommodations (as much as they can within the system they work in)…but then you’ve still got to work out your stuff. If you’re granted the time and the space, then your job is to work out the stuff. It’s not their job.” – Cait Donovan
    • Right now, the expectations of workers are changing and demanding much more empathy and emotional intelligence from leaders. Cait feels there will be a time when the pendulum swings back closer toward the middle.
    • Often times people who do their jobs well are promoted to leadership, but doing your job well doesn’t mean you can be an effective leader.
    • Managers and leaders definitely need more training. They need more emotional intelligence just like the rest of us. Cait feels being a leader right now is harder because some of the lines have blurred / are blurrier.
    • “We need to figure out where the lines are, and I think leaders don’t know that right now. I think employees don’t know that right now, and I think everybody wants everybody else to be doing more.” – Cait Donovan

42:29 – Boundaries and Closing Thoughts

• How can we set boundaries in a world where we are being asked to do more?
  • “You can’t make boundaries for things that you don’t have control over. If you decide you’re not going to do something, then you’re also deciding that you’ll deal with the consequences of not doing something. That’s the boundary. You don’t get to decide what the outcome is.” – Cait Donovan
  • Cait mentions internal boundaries are me against me boundaries. An example would be not doing a certain thing or crossing a certain line.
  • “If you’re setting an external boundary, then you can make whatever request you like, which is not the boundary. Please don’t call me after 6 PM is not a boundary. That’s a request. The boundary is what you will do in response to people breaking or respecting your boundary.” – Cait Donovan
  • External boundaries are things we told someone in advance would happen in a specific scenario.
  • If we tell someone we will not answer the phone after 6 PM and then don’t answer when that person calls after 6 PM, that is an external boundary.
  • “You have to understand that once you create those lines in the sand, they sometimes have consequences.” – Cait Donovan
• If you want to hear more from Cait and what she is doing to end burnout culture, check out FRIED: The Burnout Podcast.
  • “I think that it’s wise to remember how much power and autonomy you do have in your life. When you are under chronic stress, we tend to end up under this illusion that we don’t have any control and that we don’t have enough autonomy. And if you’re feeling that way right now, I would challenge you to challenge that. Take some time to figure out what you can influence, where you can influence it, and then start making the shifts that you need to make to increase your own feelings of safety, to increase your own feelings of security so that no matter what happens you’re in a better space.” – Cait Donovan

Mentioned in the Outro

• Cait mentioned mapping out your money as well as writing a new resume as things you can control and a way to process emotions from a difficult situation like a layoff.

  • If you’re looking to uncover more things you can control but may have overlooked, check out Episode 90 – Book Discussion: The Inner Game of Stress by Gallwey, Hanzelik, and Horton.

• Helpful links based on this discussion from Cait:

  • Burnout Protection Factors or BPFs
  • Burnout Protection Factors are Smaller Than You Think
  • Burnout Risk Factors or BRFs
  • Download Cait’s Core Values Worksheet

• For the leaders listening who want to improve empathy, check out Episode 278 – Uncovering Empathy: The Greatest Skill of an Inclusive Leader with Marni Coffey (1/3).

• Recommending listening for stories of burnout:

  • Episode 127 – Countdown to Burnout with Tom Hollingsworth (3/3)
  • Episode 132 – Riding the Burnout Wave with Jonathan F
  • Episode 166 – Management and the Hypergrowth Startup with Andrew Miller (2/3)
  • Episode 167 – Pause and Step Outside with Andrew Miller (3/3)
  • Episode 181 – Crossing the Burnout Fault Line with Bill Kindle (2/3)
  • Episode 47 – You, Your Health, and the Datacenter with Keiran Shelden
  • Episode 58 – The Path to Management and Hard Resume Lessons with Kelly Schroeder
  • Other episodes can be found on Nick’s blog Burned Out for the Holidays.

• If you need support because you’ve been impacted by a layoff situation, we recommend listening to the following episodes:

  • Episode 237 – The Psychological Transition of Layoffs with Leanne Elliott (1/2)
  • Episode 280 – Life after Layoff: A Leader’s Sense of Duty and A Series of Good Conversations with Marni Coffey (3/3)
  • Episode 290 – Reduction in Force: Navigating Layoff Trends in Tech with Real Job Talk (1/2)
  • Episode 291 – Layoffs and Job Market Impacts: Experience with RIFs Preferred with Real Job Talk (2/2)

Contact the Hosts

• The hosts of Nerd Journey are John White and Nick Korte.
  • E-mail: [email protected]
  • DM us on Twitter/X @NerdJourney
  • Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman
  • Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_

Technical managers are responsible for developing great engineers, right? Yes, but that is only part of the job. Technical managers should also be developing leaders on their team. But how exactly do you do that? It starts with delegating some leadership responsibility when you delegate work.

Tad Reeves, our guest in episode 298, returns to share his experience as a blogger, the progression from engineer to architect, and thoughts on being a technical manager. You’ll hear how Tad has made conscious decisions to take on or avoid certain types of job roles (consulting, people management, etc.) over time based on life circumstances outside of work.

Original Recording Date: 09-12-2024

Tad Reeves is a principal architect for Arbory Digital. If you missed part 1 or part 2 of our discussion with Tad, be sure to check out Episode 296 and Episode 297.

Topics – LinkedIn and an Emphasis on Technical Writing, Architects and Interview Questions, The Role of Technical Manager, Developing Leaders and Stepping Away from Leadership, Parting Thoughts

2:56 – LinkedIn and an Emphasis on Technical Writing

• Tad mentions he sees people every so often who question the value of being on LinkedIn. Ever since his job at AARP, all of Tad’s future roles (contract and full-time roles alike) have been a result of passive recruitment through LinkedIn.
  • Tad says his resume is what’s on LinkedIn. This is a great data point for all of us to consider (i.e. whether we are on LinkedIn and have our accomplishments listed).
  • “There’s also a reason to be civil and always present the face that you want other people to see on LinkedIn because you never know. Almost certainly, somebody who’s going to hire you is going to be seeing you. If you have a proclivity for political rantings or something like that you should probably take that somewhere else. There are other, better places that aren’t going to affect your career.” – Tad Reeves
• What was Tad’s motivation for leveraging his writing and presentation skills more as he gained experience?
  • Tad mentions he had been blogging for a while because it was interesting but originally began writing the articles for himself.
  • “Google is better than the Confluence search engine anyway. I’m just going to write it on my own blog, and I’ll find it later.” – Tad Reeves, on getting into blogging
  • Tad did not realize it at the time, but his articles were becoming popular. At Tad’s first Adobe Summit (a yearly conference focused on marketing technology), multiple people recognized him and thanked him for the helpful blog articles.
  • Many of Tad’s articles were about infrastructure, CI / CD pipelines and blue green deployments, and various other technical topics. Some articles even included diagrams Tad designed himself.
  • Tad started to understand the visitors to his site were real people that he could impact in a positive way. And for him, that was fun and exciting. He could impact both direct customers and other engineers, which has also brought Tad new work over time.
  • Many times, the thing that has brought Tad more work is writing “a bunch of helpful stuff.” He stresses the importance of considering the audience we are writing for as well.
  • “Would this help somebody else do something? Is it giving away some of my secret sauce? I don’t know. Maybe. But, is it going to help somebody? Probably.” – Tad Reeves
  • The articles became evidence of technical competence that could lead to more work while also being very fulfilling at the same time.
• When he began writing to share things publicly, did Tad have to get over initial anxiety or nervousness? How can others get past this fear of putting work out in the public spotlight?
  • Tad says he had some things to get over.
  • Being someone who is very passionate about analytics and statistics, Tad got certified in Splunk.
  • Listen to Tad’s story of writing a blog to share his research comparing Splunk to a new emerging competitor after hearing about a customer’s choice to move away from Splunk.
    • The blog article got the attention of the competing product’s sales rep, and Tad was asked by his company to take it down.
    • Tad learned to be a bit more diplomatic in the language he’s using. But he also tells us to be prepared for others to distort what we say. Rather than letting this be a discouragement, keep trying to create helpful content.
• How did the emphasis on writing improve Tad’s communication skills?
  • After doing consulting focused on Adobe Experience Manager, Tad worked for Rackspace in their managed hosting unit.
  • Tad describes the Rackspace headquarters as a location housing about a thousand top-end engineers. There were specialists in DNS, public cloud, load balancing, etc. People with expertise were easy to find if Tad had questions.
  • Tad continued writing to build his own expertise and was offered a job as a technical architect. Others saw Tad as a thought leader, and people continued to reference his work.
    • Tad considered himself just an engineer and didn’t really begin calling himself an architect until after he passed an architect exam.
    • Tad made a list of all of the Adobe Experience Manager (or AEM) installations he had touched, and it was scores of companies. The exercise of self-reflection helped Tad realize the breadth of his experience.
    • “I guess I can draw on that…. I’ve actually touched a lot of stuff. I could make a broad statement and have it not be based on my mind but based on having seen a bunch of stuff. That was the next major career jump…. I don’t have to be embarrassed about having an opinion.” – Tad Reeves

11:20 – Architects and Interview Questions

• What does it mean to be an architect as opposed to an engineer?
  • There are many types of architects in the technology field – enterprise architects, VMware architects, application architects, etc.
  • “Not only do you…know how it works, but have you seen enough implementations done correctly and really horribly wrong to be able to have some valuable opinions on how something should be put together? You’re not just reading the manual and doing what the company says are best practices. You have these things that are based on actual experience.” – Tad Reeves, on what an architect should be
    • An experienced architect could have valuable insights to contribute back to a company or a technology vendor based on their expeirence.
  • “Not only could I sit down and make this thing follow orders…and do it right and solve the problem, but do I know all of the things that this thing can do? Do I know what it’s meant for and what it’s really not meant for?” – Tad Reeves
    • Architects know things at a deeper level than the marketing material. Tad tells us architects can also think on their feet and have lived through some mistakes.
• Tad likes to ask interview questions about mistakes.
  • “Mistake related questions are some of my favorite and most revelatory interview questions…. Tell me the worst outage you’ve personally had, and then what did you learn about it?” – Tad Reeves, giving an example interview question
  • Some people are not able to share a fault in an interview. They seem to dodge taking responsibility.
    • Tad gives us an example of owning up to an outage situation, giving the context surrounding it, and what was learned.
    • Tad would opt to hire the person who can admit their fault and share what they learned in the process.
  • “I would like to know when somebody has recognized a fault or a way that they should have done it better. I would like to know that. Very seldom has somebody led a perfect technical career. I don’t even know that that exists…. If you’re ever in an interview with me, admit the fault.” – Tad Reeves
    • Tad gives an example of an outage situation where there were no health checks for a system to alert someone it was down. As a result of that situation, health checks then became standard for all systems.

14:46 – The Role of Technical Manager

• What made Tad want to pursue people management?
  • Tad says being a “people person” is its own skill. Being a tech leader is a complicated thing, and there might not be one simple set of distinct rules to follow for all situations.
  • Tad references his experience working for the Church of Scientology.
    • There was a large website stack to manage, and the organization also did a high amount of nonprofit outreach activities. One example was sponsoring the largest non-governmental drug education campaign.
    • Tad began working as a systems administrator.
    • “I can make that plan if you want. I don’t know that it’ll be exactly what you want, but I’ll make that plan. And if the plan is good and you’re running that plan, the next thing you know you’re a people person.” – Tad Reeves, on volunteering to build a plan when no one else would and becoming a people leader
    • In being a people leader, Tad says you will have to think about what type of organizations can get work accomplished. There will be a mix of technical expertise amongst the employees within an organization, requiring some different approaches.
    • Tad gives the example of a website launch. This could involve content editors, designers, developers, systems people, e-commerce personnel, etc.
    • “I’ve seen people with various philosophies on how they want to run things. Some people are like ‘it’s totally flat around here. Everyone has a direct line to me.’ I don’t know about that. You kind of have to figure out the right way to run that in terms of delegating responsibility – not just responsibility to get something done but delegating leadership responsibility. And that is I think one of the hardest lessons to learn in management….” – Tad Reeves
    • The manager has to build up engineers and also build up leaders.
    • Some of Tad’s first remote management work was managing a team in Denmark. There was no way for him to physically be there, so he had to choose someone located there who could get work accomplished.
    • Tad highlights fostering open lines of communication as an important aspect of managing remote teams. You want employees who are not afraid to bring problems to you. Tad admits he didn’t get it right at first.
    • “How can I be a better manager, a better leader, just really to the benefit of the project? Really, at the end, you’re just trying to get the project done. You’re not doing it for your own self-aggrandizement…. One way or another this thing’s got to get done.” – Tad Reeves, on the manager’s focus on execution
• Was it easy for Tad to spot leadership qualities in others, or did he have to look intentionally for it?
  • Tad says you can observe how people handle being delegated a specific task that contains some ambiguity. In this case there is clear assignment of the problem to solve / thing to be fixed, but you allow an employee to fill in the gaps on the “how.”
  • “This person doesn’t mind running with it and can actually get it done and can actually realize that he’s responsible for the whole thing…. Some people, they want a ticket. Can you spell it all out in a ticket? …That one’s not a leader. That one doesn’t want to be a leader right now. That one would rather do the ticket. And that’s fine.” – Tad Reeves, on seeing leadership qualities in others
  • The manager is looking for who will rise up and take a little more responsibility.
• What about interview skills? Did Tad already have those when he took on a role as a people leader?
  • Tad didn’t really have the interviewing skills when he took on the role of people manager. He had been mostly an individual contributor to that point.
  • “Sometimes you’re only a person leaving away from all of the sudden realizing you’re in a leadership role…. Sometimes it’s not ‘hey, you’ve been promoted.’ Sometimes it’s a bit more by default you’ve inherited these responsibilities.” – Tad Reeves
  • When the person holding all the things together in an area suddenly leaves the company, it might then be you holding it all together.

18:36 – Developing Leaders and Stepping Away from Leadership

• How did Tad determine if continuing as a people leader was something he wanted to do?
  • “One thing that I…struggled with a bit when I was managing is I knew that there was going to be a point in managing where I simply could not keep up enough with tech….” – Tad Reeves
  • Tad knew when he first started managing if someone on the team burned out or left, he could step in and cover the workload.
  • During Tad’s time as a people leader, he would see new tools come out that he hadn’t touched or didn’t understand well. Tad tells us this creates some decisions on how to proceed or how to juggle the right way.
    • Do you use your spare time to skill up / learn the things you need to understand about the new tool?
    • Do you accept that you can only learn the tech at a certain level as the boss?
    • Do you start doing individual contributor work for a specific amount of time each day?
  • “An effective technical manager knows about the technology they’re implementing. To a degree you’re not going to necessarily be effective.” – Tad Reeves
    • Tad gives the example of running a project that requires heavy Java development. He is not a Java developer. He can help manage the developers but would need a Java lead that could help with code reviews, etc.
    • Tad feels he has found his footing in the juggling act over time, but in the early days he had not.
  • For Tad, the time to step away from leading people was when he and his wife had a baby. He wanted to work during a specific time slot and then stop to spend more time with his family.
    • “That was a very conscious decision. There were people asking me if I wanted a leadership role, and I was saying I do not at this time…. I do need this much time to be dad, and I’m totally going to do that.” – Tad Reeves, on the intentional choice to be a dad and how that impacted career decisions
    • According to Tad, work-life balance is often misused because it implies you need equal parts of something.
    • “So that’s where you make conscious decisions about your career to say…can I follow this crazy, ambitious career at this stage of my life?” – Tad Reeves
    • Technical leadership careers have a composition of elements that one needs to consider according to Tad. It’s not just 9 to 5 when you’re the boss.
• Tad shares his current family situation and how that has impacted recent career decisions.
  • He has 3 kids, each involved in different activities. Tad’s wife provides him the air cover to work more intense hours in consulting.
  • Despite the above, they still block off family time. Weekends are reserved for family time, renovation projects, kid activities, mountain biking, carpentry.

25:47 – Parting Thoughts

• Tad works for Arbory Digital as previously mentioned. You can find Tad’s blog at blog.arborydigital.com and his podcast here with lots of helpful information about Adobe Experience Manager.
• Are there specific technical communities listeners should consider joining if they want to get into Adobe Experience Manager?
  • Tad highly recommends attending Adobe Summit. He attends every year, and it is a great place to get technical content.
  • The big conferences in your area (i.e. Dreamforce, Adobe Summit, etc.) are places where we have the opportunity to meet people who can take our career to the next level.
  • “One other piece of advice that I forgot to give along the way is…going to those conferences and not just being a spectator, going and sitting right up front, and then right afterwards go ask the presenter a bunch of stuff. The next thing you know you know all the people at the company. You know all the lead engineers, and you can get some really amazing stuff done. The sit in the back and be a wallflower thing…that was for grade school. Right now, it’s a good idea to sit in the front.” – Tad Reeves

Mentioned in the Outro

• Tad likes to build things people can use and enjoy, and it’s been highlighted multiple times. Getting positive feedback on his blogs at Adobe Summit was like a next iteration of this and a realization that the content he was creating was useful to others and farther reaching than he thought. Tad had started writing the blogs for himself to use for reference later, and he continued to write once he knew it was helping others.
  • This is a great example of what Andrew Miller described about being intentional with your personal brand in Episode 165 – Excel by Being Intentional with Andrew Miller (1/3).
• There were undertones both this week and in Episode 297 – specific times in our lives may be better suited for working in specific types of roles than others. Tad moved away from consulting at one point and then later back to it. He also moved away from people management at one point due to family circumstances.
  • Recommended listening for careers that might have zigzags:
    • Episode 201 – Generate Depth On-Demand with Yvette Edwards (1/2)
    • Episode 202 – Having Some Career Zigzags with Yvette Edwards (2/2)
    • Episode 68 – When Life Disrupts Your Work-Life Balance
• Most of our guests who have pursued people management in tech have struggled with finding the right level of technical depth after making the move. Some guests have even gone back to individual contributor because they wanted to get technically deeper.
• Technical conferences are great for networking with other people. Please take an active role in meeting and interacting with other attendees. Ask them about what they do. Tell them what you’re trying to do and what you’re interested in learning. You never know who you might meet.
  • Don’t forget about meetup groups in your area or smaller local conferences if you cannot travel or afford to attend a big conference.
  • Many tech vendors may have an online conference that could be free or paid, but these could be a way to get some good training. They may not be as great for networking with other attendees, however. Consider taking part of a day off or a full day off to focus on learning.

Contact the Hosts

• The hosts of Nerd Journey are John White and Nick Korte.
  • E-mail: [email protected]
  • DM us on Twitter/X @NerdJourney
  • Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman
• Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_

How can a technology become our focus area unexpectedly? For Tad Reeves, it started when he said yes to the right opportunity. After doing back-end systems work for hosting providers, working in web design and development, stints in contracting and consulting, and experience with web analytics platforms…content management systems seem like a logical next step in the progression.

Tad Reeves, our guest in episode 297, returns to share his experience doing both consulting and contract work. We will also hear about the genesis of Tad’s exposure to Adobe Experience Manager and content management systems and how placing focus in this area allows for making a big impact that keeps the work purposeful and fulfilling.

Why did Tad continue to incorporate his love of design into his work? Listen below to catch the full story.

Original Recording Date: 09-12-2024

Tad Reeves is a principal architect for Arbory Digital. If you missed part 1 of our discussion with Tad, be sure to check out Episode 296.

Topics – A Flip Back to Design, A Framework for Solutioning, Contract and Full-time Work, Out of Balance, Adobe Experience Manager and Content Management

2:33 – A Flip Back to Design

• “I think flavors and harmonics of that thrill you can find also in debugging – when you have something that is affecting a broad swathe of people and then you fix it and it’s jammin’ now and suddenly it’s all working for everybody. I think every time that I’ve found myself in a job where suddenly I’m doing something that doesn’t really matter, that doesn’t really affect anybody, then suddenly I’m almost like a solder pulled back from the front line…. What am I doing here, guys? Only one person used this app that I’m writing. Do I have to do this?” – Tad Reeves, on making an impact in his work
  • Nick suspects a drop in energy when one feels the work they do is not making an impact.
• Tad worked with other engineers but was overall in charge of some projects for UUNET, often being tagged as the lead.
  • He could pull in other engineers to help rack the gear or help with network cabling as needed and did not have to do it all on his own.
  • This role was more of an implementation engineer and was not within the scope of what we might now call an architect. Tad would be given a specification and new equipment that had been procured. His job was to get it up and running and to pull in others as needed to make that happen (i.e. people from other teams like networking, technology vendor personnel, etc.).
  • Tad highlights this role as fulfilling but also a place to grow from and from which to expand a “sphere of responsibility.”
• What made Tad want to expand his sphere of influence? Was it working on those specific projects and being the lead?
  • Normally one would say yes. Tad had several interests he would bounce between. At his point in time, Tad had not completely given up on the idea of design work. Tad tells us he still likes design work, finds it fulfilling, and he tries to do it when he can.
  • Tad flipped back into web design at one point and worked for a firm that did web development work (HTML, CSS, JavaScript). He used tools like Dreamweaver at this time.
  • Tad tells us he enjoys contract work like this and built a website for the US House of Representatives and the Veterans Affairs Committee. Tad not only built this site but designed it as well.
  • “I look back fondly on a lot of that experience because I enjoy understanding how the whole cycle works. So getting a chance to do design work and that whole end of UX work…it’s a completely different problem. But that doesn’t make it any less fulfilling to solve.” – Tad Reeves, on returning to design work
  • Tad did some web analytics projects at the web development firm based on his Webtrends experience. It was an area he still found very interesting.

7:19 – A Framework for Solutioning

• Tad worked a contract gig for Georgia Pacific focused on selecting a web analytics platform. He was involved in activities like requirements gathering / discovery, research projects, stakeholder interviews, and developing success criteria.
  • At this time web analytics was changing. People wanted to use more than just web server logs to do analytics and started leveraging tracking beacons in JavaScript, for example.
  • Tad had to figure out a framework to use for selecting and recommending the best web analytics solution for this company. He wasn’t given a specification to implement like before. This was architecting a solution based on a problem / problems.
  • “Develop a framework for coming up with requirements from scratch. And then who would you ask? What questions would they have? What would they need? …Come up with that framework and figure out how…you map products against a framework. And then how do you rank those? And how do you then present that back…? …It was completely open ended, and it turned out really well. But, you’re figuring out the entire cycle from one requirement of ‘we need web analytics. Figure out how to tell us that it’s the right one.’” – Tad Reeves
  • Did Tad have the same fear taking on this role as when he first got the systems administration job?
    • Tad thinks it was even more fear inducing in this case. He knew a great deal about the product landscape and would not be starting from scratch.
    • Navigating corporate meetings and talking to stakeholders was a new experience for Tad. It was out of his comfort zone, and he had to figure it out.
    • Tad traveled to Georgia to conduct the stakeholder interviews in person. There was no other member of the team to back him up on this project.
    • “It was just ‘figure it out.’ I think some of those sink or swim moments…necessity can be a driver in some cases.” – Tad Reeves
  • What did Tad have to learn quickly when communicating with these stakeholders? Nick is imagining it was a range of people from the very technical to perhaps high level executives.
    • Tad says he listened to the interview we did with Max Kanat-Alexander in Episode 287 – Scope Creep: Evaluating Impact in Career Decisions as a Principal Engineer with Max Kanat-Alexander (3/3). Really at first the goal is to understand what the problem is, and once you understand, you are essentially 90% of the way there.
    • “I don’t even know what their problem is. All these tools look great, and they all have price tags that make me cry. So I just need to understand what their problem is. And I just started talking to people to understand what their problem was.” – Tad Reeves
    • Tad tells us he didn’t have time to doubt himself or get hit with impostor syndrome. He knew the only way the work would be accomplished was to start talking to people. It was a focus on understanding the problem so he could then find a solution.
  • Was Tad’s approach to understanding the problems the same across the board or different and customized based on a person’s position?
    • Tad feels like it was a unified approach to stakeholder interviews, but he also tells us he did not fear a conversation with any person because of their high-ranking position (i.e. a lack of intimidation due to position).
    • Sometimes not having any thought of a need to be intimidated in speaking to someone removes all pressure and supports a much better conversation.

12:15 – Contract and Full-time Work

• After doing contract work, what made Tad want to move back to being a full-time employee at a company and away from being a contractor?
  • Contract work and full-time work have their pros and cons, and Tad has done plenty of each type of work.
  • Tad says working full-time within a large organization can lend stability in knowing where you sit within the organization and understanding your job responsibilities. Often times people can “stop and cut” at the end of the day without trying to figure out where their next job is going to be.
  • Being a contract worker means you need to complete the work assigned to you, and you need to spend time “hunting” for your next role to prepare for when your contract ends. Some people enjoy that hunt while others seek to avoid it entirely.
  • Tad would tell us there are places in life where both contract work and full-time work could make sense.
• Is one of these choices (contract vs. full-time) safer than the other right now during a time of layoffs across the tech industry?
  • Tad shares a story of learning someone he had worked with for 10 years was laid off.
  • “How do you summarily lose somebody who’s got that much skill, knowledge, and drive and passion for their work? I really feel for folks like that. I don’t know that there’s a formula for never getting laid off because in some cases it’s not under your control. Especially when you’re working for a large company, you can be doing everything brilliantly. You can be at the peak of your career and still be at the adverse end of a layoff.” – Tad Reeves
  • Tad has found security in his ability to get a new job when needed or desired.
    • This can, for example, come down to how we present ourselves publicly.
    • “Do you always have your ear to the rail so to speak on…is the work that you do valuable? Is there lots more work of that around? And if something should happen to your job right now, do you have skills that could be in demand?” – Tad Reeves
    • For a long time Tad would brainstorm or cultivate possible careers based on his skillset. If Tad just learned load balancing, he could go work in networking should something happen to his job, even if that wasn’t his first choice. He still knows server technologies as well.
    • Tad also highlights his willingness to go get a new job. We need that willingness when it is time to take action.
  • Did experience doing contract work make Tad better at job seeking than someone who has not had to look for a new job every few months / years?
    • Tad says it has to a degree.
    • “I’ve had waves of necessity that have driven a lot of the career changes that I’ve made. I would love to say that I’m just an ambitious technologist, but technology isn’t the only ambition that has driven my career changes. It’s been a lot of family and things like that too.” – Tad Reevesp
    • Working at a large company for many years may lull us into a false sense of security and make us think the company resources can never be exhausted. We might even think the work we are doing will not make or break the company. Tad contrasts that with working in consulting or for a small company. He knew in those circumstances doing great work was the only way to get another job. It was the feeling of necessity and the impact he felt he was making.

17:02 – Out of Balance

• Tad spoke about self-awareness earlier. This is something we need to exercise and can help us notice things are out of balance. How has Tad experienced this experience of being out of balance in his career?
  • In 2009 Tad and his wife had their first child. He was working for a software development company at that time. He also did contract work for the State Department (developing in languages such as Cold Fusion).
  • “I was developing full-time for an application that had like 9 users. It was extraordinarily unfulfilling. That was a low point. I’m getting paid. They’re paying me. And I’m doing the work that in a normal company brings value. But what are the results of my actions doing? Even the best work that I can do will now affect just 9 users who will use this once every week. This is out of balance.” – Tad Reeves
  • After the addition of the new baby, Tad was doing JavaScript and user interface (UI) work.
  • “This was my first time…where I wasn’t really working in an office either. I was doing a lot of work from home, and I was doing work that never really stopped.” – Tad Reeves
  • At one point Tad’s wife let him know they were having another baby, and he was trying to figure out how to make that work. They were living close to Washington, D.C. It had a high cost of living even in 2009.
  • “Two things gotta happen right now. I need a lot more money, and I’m not about to go and throw away my whole ‘dadding’ time by working from home all the time and never being present for my kids.” – Tad Reeves
  • Sometimes we might wish something was different, but Tad would advise naming specifically what we want. Consider the type of company you want to work for, whether in an office or remote, the type of work you want to do, the schedule you want, etc. Only when we specify exactly what we want can we know when a new opportunity is the right one for us.
• As a result of being very specific about what he wanted, Tad said yes when someone from AARP recruited him via LinkedIn to do Linux systems administration.
  • The mission of AARP really aligned with Tad’s values. He cared deeply for the web property AARP maintained. They were at this time one of the largest membership organizations in the world.
  • The person with F5 load balancer expertise was leaving the company. Tad decided to lean in and learn F5 to become the new subject matter expert, getting certified to do it.
• Tad wanted a job where he could be finished with work at the end of the day, and he knew that meant he could not be in the consulting realm.
  • “I cannot be in the consulting realm right now. Because in consulting…you’re paid by the job. And it doesn’t matter how long it takes. You gotta do it even if it takes longer than you wanted…. I needed control over my schedule. That was an intentional life change that I made at that point. Do you have any idea how many hikes and walks I got to talk with my kids because of that? It was truly wonderful.” – Tad Reeves
• Nick says people may not know what the possibilities are for jobs and work if they have not seen it or been exposed to it.
  • Tad says if you have not been exposed to something, you may not know what you should be asking for in a new job. You may not know that there can be a different way of living, etc.

24:31 – Adobe Experience Manager and Content Management

• AARP was where Tad got into configuration management tools like Puppet and Chef.
• Tad tells the story of his job interview and being asked about a content management system called Day CQ. Tad had never heard of it, and the interviewer said they could train him.
• Not long after Tad joined the company, this software got purchased by Adobe and would later become Adobe Experience Manager.
  • “Little did I know that would end up basically defining my career from that point until now.” – Tad Reeves, on his first exposure to what became Adobe Experience Manager
• For the role at AARP, Tad had been commuting into downtown Washington, D.C. He tells the story of being cold called by a recruiter about a role focused on Adobe Experience Manager.
  • Tad’s opinion of Adobe Experience Manager was not high, but this recruiter was looking for a systems administrator that knew it well. The position was significantly more pay and allowed him to work remotely.
  • “All remote? I’m in. Even if I have to deal with this thing I think is a pig. I’ll deal with the pig if I can be full remote.” – Tad Reeves
  • Tad has worked remotely for the most part since getting the above role.
• What made Tad fall in love with Adobe Experience Manager? How can people be open to going deep in areas that take them by surprise?
  • This caught Tad by surprise. It was a technology he initially knew nothing about despite working on numerous large website projects which included some form content management.
  • This type of technology is used primarily for very large websites, something Tad highlighted as an interesting aspect.
  • “Even though it had a proclivity for going down all the time, it once again was scratching my itch of…there’s a lot of traffic going on it. And I could watch it go. Blinking lights…here we go. Blinking lights again drawing me in. They even let me go to the datacenter every now and then and do stuff. Alright, you got me.” – Tad Reeves
• What exactly do we mean when we say content management?
  • Think about Chevrolet or the Food Network’s website. The main content for Food Network might be recipes, videos, and things of that nature.
    • Recipes, for example, would be input by non-technical people. People writing recipes or uploading videos would not be developers. Non-technical people will maintain the content.
    • The content needs to be organized so that it is performant and everything can be stored and easily retrieved.
    • A system like this could solve the problem of translating pages into multiple languages or present a photo in multiple different sizes on a website.
  • Content management also gets into digital experience.
    • Every site visitor should not get the same experience upon each visit, for example. Think about a new customer vs. a returning customer (i.e. someone who has made a purchase) or the person who has logged in compared to the one who has not logged in. It’s important to have mechanisms to serve the different types of users.
    • “It gets really complicated, and so as a result you need a system that is complicated. And whenever you have a complicated system there’s a million ways that it can break.” – Tad Reeves
  • Content management systems are particularly interesting to Tad because they are often used for the marketing site or corporate website, which can represent a company’s hope for the future.
    • Tad feels his experience in back-end systems came into play at this point. He tells the story of being an e-mail sysadmin (systems administrator).
    • “The problem with being an e-mail sysadmin is…the very best you can possibly be is to be invisible. And also nobody is going to be attributing the company’s success to what you did…. It doesn’t matter that it’s still a fascinating technical problem to solve and I still love e-mail systems. But they can be unfulfilling as a result in some cases. Whereas, marketing systems have all this hope tied to them….” – Tad Reeves
      • An e-mail systems administrator will get complaints if people get too much spam e-mail and also then get complaints if important e-mails are not getting through as expected.
      • Tad says working with marketing systems allows you to meet interesting people who work in them.
    • Nick says working with and supporting a marketing system makes you feel like you have a greater purpose / part in the company’s success because of the contribution one can make that is NOT invisible.
    • Tad says we can get separated from feedback sometimes when we work in systems. Imagine a new website launch making conversion rates go up by 300%. That kind of feedback gets Tad excited.
  • Tad shares an interesting problem he worked on for Food Network and how their traffic spikes by a factor of 50 around Thanksgiving, Christmas, and during the Super Bowl.
    • There were a lot of things which had to be figured out to support this kind of scale. It involved learning about caching, for example, and this was one of Tad’s first big cloud migrations.
    • “These were intense things to learn, out of the comfort zone stuff to learn, but still, you’re solving a really jazzy problem….” – Tad Reeves
    • Tad got to see the scale of traffic and thought it was very cool. It got him excited.

Mentioned in the Outro

• Part of our show’s mission is to educate listeners on the types of roles they could have in technology based on their experience. If we highlight the differences in contract work compared to consulting…
  • Being a consultant could mean you work for a consulting firm, a firm who does services / consulting work for other companies as part of their business model. If you work for that firm, you are likely a resource who is put to work in a specific area based on the pipeline of projects on which the company has committed to execute for their customers. You would move from project to project over time assuming the company has plenty of work to support its staff.
    • You may or may not have a role responsible for bringing in new sales for the consulting firm. Yes, you can do a good job for customers you work with and build great relationships as a way to help your company increase revenue. But there may be a dedicated sales teams who is working to get new engagements for the firm.
  • Doing contract work means you work for a company for a set amount of time and would not be considered a full-time employee (i.e. a 3-month, a 6-month, or a 9-month contract for example). Likely it’s for a company whose business model is not doing consulting for other companies. But in this position you would need to begin searching for your next job role before your contract ends to avoid a gap in employment.
• Were you surprised by Tad getting into Adobe Experience Manager and content management systems?
  • Nick argues this looks like a logical adjacency based on past experience doing back-end systems for web servers, being a web developer, and work with web analytics using Webtrends and other tools.
  • The focus on content management allowed Tad to continue to make the impact he wanted to make and to get that feedback we all want in knowing we are making a difference in a positive way for our company.

Contact the Hosts

• The hosts of Nerd Journey are John White and Nick Korte.
  • E-mail: [email protected]
  • DM us on Twitter/X @NerdJourney
  • Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman
• Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_

What do you love most about your job? Give that some thought before you answer. Have you forgotten what brought you into this industry in the first place?

Tad Reeves, our guest this week in episode 296, has been consistently reminded of the things he loves about technology throughout his career. Tad originally pursued mechanical engineering but made a change to graphic design. Soon he fell into technology and worked for an internet service provider in the early days of the internet. Tad was driven to learn technological concepts at a deeper level and to nurture his interests, letting these behaviors guide him through different jobs and into large scale environments. In this discussion you’ll hear about how doing phone support made Tad’s troubleshooting and communication skills better and prepared him for later roles, thoughts on the role of the technical lead, and how an impromptu dinner meeting led to a job as a systems administrator.

Original Recording Date: 09-12-2024

Topics – Mechanical Engineering and Graphic Design, Supporting the Early Internet, A Level of Interest Drives Deeper Understanding, The Move to Webtrends, Landing Something Bigger, The Technical Lead, Relocation and a Love for Big Gear

2:09 – Mechanical Engineering and Graphic Design

• Tad Reeves is a principal architect for Arbory Digital. Arbory Digital is a consulting firm which specializes in working with enterprises using content management systems, specifically Adobe Experience Manager.
  • Tad is a technologist at heart but has focused on Adobe Experience Manager in the last 15 years or so.
• Why did Tad decide to study graphic arts in school?
  • When Tad was in high school, he wanted to design cars and refers to his young self as a “complete car nerd.” Tad still has a ton of car knowledge.
  • Tad was on the fence between the art side of design (i.e. visual design) or the engineering side of design. After getting into the mechanical engineering school at Oregon State, Tad started an internship with someone who was a seismic engineer, specializing in doing retrofits for buildings.
    • After helping the seismic engineer with some of his work, Tad came to a harsh realization.
    • “And I saw what being an engineer is day to day…. And I’m looking at these pages of Calculus and all that kind of stuff…I don’t want to do that. That’s not what I want to spend the rest of my life doing…. I’m going to have to tell everybody I know that I’m not going to be an engineer anymore because I don’t want to do that.” – Tad Reeves, on the realization that mechanical engineering wasn’t so interesting
    • Though Tad was initially afraid of his parents being angry with his decision to pursue a different career, they supported his choice to pursue something more interesting.
    • Tad’s mother was a nurse and his dad an electrician.
  • Tad already had an interest in design and would design newsletters, for example. He selected graphic design.
    • “I’ll do graphic design. So I did that for a year in college, but then at the same time, I was spending all my spare time fixing stuff. I was always tinkering with computers and stuff. That wasn’t my original interest, but it was one that drew me.” – Tad Reeves

5:42 – Supporting the Early Internet

• Tad shares the story of getting a job doing technical support for a small, local internet service provider (ISP) with about 1000 subscribers in Tigard, Oregon.
  • “The pay…that’s not what I’m here for, but the problems I was solving were genuinely cool. They had my interest… Having the rush come in and seeing that thing just light up with subscribers, that was my first moment of…making stuff that a bunch of people use…that’s cool. Graphic design is awesome. It’s a lot of fun, but this is really awesome…. That was where I kind of switched gears and said ok, I want a career doing computer stuff.” – Tad Reeves
  • Tad remembers building a modem rack for the ISP using USR 336 modems. These would have been 33.6 Kbps speed modems.
  • The type of work was interesting to Tad, and he recognized the technology was still new, meaning not many people understood this area of technology.
• Was the original choice of mechanical engineering work not making enough impact or not providing enough return on Tad’s efforts?
  • With the right people in his life earlier on, some of his decisions about engineering may have turned out different.
  • In engineering school, there were math and physics classes in which Tad felt out of his depth. When speaking to his professors about this feeling, he was told these were weed out classes used to get rid of anyone who truly didn’t want to pursue that field of study. This did not sit well with Tad.
  • Reflecting back, Tad thinks he might have been happy with a career in mechanical engineering.
• Maybe organizing / designing the layout of the closet isn’t so different than going and working on a car in your spare time?
• Tad says there is the design element and then the presentation aspect.
  • During the time Tad worked for the ISP, the internet was new to many people. They would come to classes Tad taught to learn about it.
  • As part of the experience for potential new subscribers, Tad would give them a tour of the “show closet” containing all the modems. It was something that really impressed people and perhaps a humble beginning to what we now know as datacenter tours.
• How did the phone support impact Tad’s troubleshooting skills?
  • Tad feels like most anyone in technology should take on a support role at some point in their life. Speaking more broadly, Tad thinks almost everyone should experience a customer service job because of the skills we can learn.
    • Working in support / customer service type roles helps us to focus on serving the customer and control our reactions to different situations.
    • “That takes drilling, and as a kid you don’t know how to do that. So there’s a lot of maturing that you do.” – Tad Reeves, on support and customer service roles making us better
    • Tad shares the story of a caller he spoke to once whose power was out and had called him on a cell phone. The person did not realize they needed power to use the internet. Listen to the way Tad handled the conversation.
  • Sometimes Tad would need to drive out to someone’s house to provide support, but it was not extremely often.

10:40 – A Level of Interest Drives Deeper Understanding

• “I should dive into this hard. If I’m going to not have a $6 per hour tech support job, I’m going to need to get good at stuff. I think that was where my career started to change.” – Tad Reeves
  • Tad could not afford much working at the ISP and was living with his dad at the time. Necessity drove him to take action.
  • Tad bought some networking books to help him understand concepts at a deeper level about how the internet worked. He realized putting in the work would allow him to get a job somewhere other than the ISP (somewhere bigger).
• Tad had practical experience with some of the technologies before he began to learn them at a deeper level. Did this order of learning affect his learning process over time or the way he studies for certification exams?
  • Tad says it is more known today that certifications like the CCIE (Cisco Certified Internetwork Expert) are a pathway to get better jobs. During the time Tad started his studies, career paths via certifications were much less known or clear.
  • “Whatever I was supposed to do was not known. What I did know is that I loved the internet, and I didn’t understand how it worked…. I really liked the idea of running a mail server…and Exchange was interesting…. But then I just had to keep backtracking and backtracking until I was just sitting in internet fundamentals.” – Tad Reeves
  • Tad would be troubleshooting and hear terms he didn’t understand. There were fundamental concepts he needed to understand to gain a full understanding of some of the terminology.
  • Tad studied books of material but never went for any kind of certification exam at this time. He wasn’t trying to get a certification but merely trying to understand. At the end of his studies, Tad felt he was a much more effective troubleshooter instead of shooting in the dark like before.
• Nick says we can follow our interests and learn things at a deeper level wherever we are in our career. But it can be difficult to decide where to place that focus with so many technologies.
  • Tad has gone back to his old high school in Oregon a few times to give talks on technology careers to the students.
  • The teenager in high school is looking forward to a career and seeking options for their future. But when you are in a career, you might forget what drew you to your field in the first place until you need to explain it to someone.
    • In IT Operations, there are problems with burnout, and there are prevailing thoughts that it can be drudgery.
    • “You sometimes forget what got you into this in the first place until you go to a school and some innocent kid asks you ‘what do you love the most about your job?’” – Tad Reeves
    • Tad says answering the question above can remind us to be appreciative of what we do.
  • Tad says nurturing and paying attention to our level of interest will ultimately help us get and keep jobs.
    • “I feel like this is a theme that I could probably come back to again and again…. I don’t feel like I’m the most technically superior person in the room a lot of the time, but there’s a lot of times where I’m the most interested and the most willing to communicate about it. And there’s a lot of times there’s somebody who might be technically much more proficient, but they’re bored. They want to go home. Which one of us is going to end up in the lead role? …It’s that level of interest and picking something that you want to be interested in and then really just nurturing that.” – Tad Reeves
  • Nick feels like people notice it when you are the person most interested in a topic. Was Tad’s answer to what he loved most about his job that he gets to follow what is interesting?
    • Tad says his interests have been different at different times. He has worn many hats as it relates to large site work over time.
    • “This one thing that does continue to drive me is this love of making stuff that people use and then watching a bunch of people use it. It must be analogous to the joy that must be felt to somebody who designs a bridge…. It’s that creation for others and then watching it then unfold.” – Tad Reeves

18:56 – The Move to Webtrends

• How did Tad progress from the ISP to bigger environments after taking the time to learn foundational concepts?
  • Tad didn’t quite know how to get a better job. This was before LinkedIn, Careerbuilder, and Monster.com. Tad printed copies of his resume and would walk into businesses in the area to share he was looking for a job.
  • Tad responded to a newspaper article for a role in tech support for Webtrends, headquartered in Portland.
    • Webtrends was a leader in web analytics during this time, and their solution would provide customers insights into web traffic volume.
    • Much of the role was spent doing phone support. Customers would often send Tad log files for analysis. In 1998, e-mail could be used to send 600 MB log files!
    • For local customers, Tad would often make site visits to help. This was his first exposure to enterprise datacenters. During this role he learned about the need for clusters web servers.
    • And Tad’s interests continued to drive him. When he heard about things like Netscape Enterprise Server, for example, he wanted to know what it was and how to set it up.
    • During this time, Tad created his own home lab environment to tinker with made up of old laptops, etc. He even got a dedicated ISDN line at his house to support the lab.
• Did Tad target Webtrends because of the impact they were making, or was that something he benefitted from only later?
  • Tad says statistics and analytics are fascinating to him, and one gets a great deal of exposure to these in IT operations roles. He enjoyed supporting a product many companies were using to gain insight from web logs as well.
  • Also, SEO (Search Engine Optimization) was in its infancy during this time.
  • The role overall was made up of several things Tad really enjoyed.

22:56 – Landing Something Bigger

• How did Tad decide what to do next? “So I didn’t decide. All I knew was for sure I needed something bigger.” – Tad Reeves
  • Tad says he had a travel itch and wanted to get out of his hometown.
  • “This is one of these other ones that I think is a theme that I could probably come back to a few times…of things that changed my career and were more of a factor than other things. It wasn’t just that I was a better developer at this than somebody else or something like that. One of those things is a set of well-honed written and verbal communication skills and a willingness to use them…a willingness to just go and talk to somebody, even if it seems weird…. Just do it.” – Tad Reeves
  • Tad wanted a change but wasn’t sure how. While visiting a friend in Omaha, he ended up connecting with someone who conducted Cisco training that needed a systems administrator.
    • Tad was honest about his skills and interests, but this person wanted to interview Tad in person and said he was teaching a course in Wichita, Kansas. Tad rented a car right after getting off the phone and drove to meet this guy for dinner in Wichita.
    • The dinner meeting went really well, and the person Tad met landed him a job with State Farm Insurance as a Windows NT Systems Administrator.
  • “It was awesome that I landed this job. I was in pure terror…. Basically as soon as I landed this job I went and found somebody who had…a bunch of installation CDs, and I just went crazy hitting the books so that I could arrive at least sounding like I wasn’t a fake. Once again it’s this interest thing. I wanted to solve all the problems. I may not have the answer. I’m totally going to find it.” – Tad Reeves
    • The job was a level 3 systems administrator, and at this time State Farm had the largest Windows NT Server deployment in the world (around 33,000 of them).
    • For several months Tad would go home and study after work until he felt confident and competent enough.
    • “I’m trying harder than everybody else, and nobody else is trying. So I’m actually ok.” – Tad Reeves, on beginning to feel competent in his new role in systems administration
• Tad feels like the telephone tech support for the ISP and at Webtrends prepared him well for what came next. He became confident in being able to figure out most any problem if the need arose.
• The role at Webtrends had exposed Tad to outage type situations that were of a more critical nature. These were businesses calling in for support and not consumers who needed help with their internet. A business could have been losing money due to a system outage / problem.
  • Tad had to deal with escalation / urgent calls in the Webtrends role as well.
• At State Farm there were outages, and Tad and the team he worked on were an escalation point for outages.
  • Tad doesn’t think he had yet gained skill in communication around outages at this point in his career.
  • Later in his career Tad had to deal with some outages and would further hone those communication skills out of necessity and responsibility to deliver. Tad recognized the need for improving in this area and took action.
  • Tad worked on a team of 4 other engineers. In addition to the engineers there was a project manager, Tad’s boss, and a Microsoft representative. Systems administrators / engineers worked together to solve problems but may not individually own a system’s uptime.
    • “A lot of the outages and so forth we had to just explain to our supervisor or to the project manager. We didn’t necessarily have to explain them directly to the customer. …I was in some meetings where things had to be explained…. It must be wild to be in a hot seat like that, but I wasn’t yet in the hot seat. That was to come, but at that particular job I was just focused on technology.” – Tad Reeves

29:30 – The Technical Lead

• Being in the hot seat may mean someone has moved from technical contributor to more of a technical lead / technical owner. How has this played out in the roles Tad has held?
  • “There the concept of responsibility for a job, for an individual unit of work, and then there’s a responsibility for your area, your field, the service itself that you support, the whole system you support, the website you support, and so forth…these spheres of responsibility.” – Tad Reeves
  • An individual contributor is often responsible for completing work given to them and by extension has a shared responsibility for the uptime or performance of a service or system.
  • “As a lead, now the buck is stopping with you. And so now you not only are still contributing as an individual, but you have by extension a responsibility for the products that the people by you are also producing. And what is unacceptable at that point in time is for you to point to them as an excuse for your lack of success…. What’s acceptable is keep the site up. Keep your sphere running…. It’s on you to fix it. It’s on you to do those postmortems or to figure out how an inefficient process needs to be more efficient.” – Tad Reeves
  • The technical lead has to answer for whatever problem which is within their responsibility to solve. The task may be to make something affordable that previously was not, for example.
  • Tad emphasizes he was able to make the transition to technical lead once he was able to excel in his technical role. Then he could feel comfortable taking on responsibility for more than just himself.
• What makes someone want to take on the technical lead role or take on the extra responsibility?
  • Tad has observed people who got into leadership because they like the feeling of superiority or enjoy giving orders. These are not things Tad enjoys.
  • “In any group of people, if you see people going in random directions or you see something that is out of control / that’s not being controlled… either it’s just going to explode and die, or somebody’s going to pick it up and deal with it. Somebody’s going to say…‘I got this. I’m going to handle this.’ And I think that’s the same in any job anywhere. Somebody’s going to say ‘I’ll run this. I’ll make this come right. I’ll turn this around. I’ll deal with this, and I’ll let you know when it’s done.’ Somebody has to take ownership.” – Tad Reeves
  • When someone asks for a plan of action, either there is no plan, or someone will speak up.
  • Tad has found himself in a lead role because he decided to be the one to speak up when no one else would.
    • Volunteering when no one else would is a common theme among our guests.
  • Nick’s opinion is we can take ownership of something, but we may need help from others to solve the problem. It doesn’t have to be just you that applies a fix even if you own a problem.
  • Tad says the effective leader is one who can play to the strengths of others, recognizing who is best suited to complete each type of work.
    • “If you think that you’re going to win because you’re the best at everything and you’re just going to do it and everybody’s going to watch you and cheer or something like that, that’s not leading.” – Tad Reeves

34:31 – Relocation and a Love for Big Gear

• Tad tells the story of moving to Washington, DC. He worked for UUNET in Ashburn, Virginia as part of their enterprise hosting group. At the time UUNET was the world’s largest internet provider in the world and was running all dial-up services for America Online.
  • Tad mentions this was his first time to get very hands on with what he calls “big gear” in supporting environments for very large customers. He learned about purpose-built applications for Windows, load balancers, and various server OEM hardware.
  • “I love big gear. Big gear is so cool. You know, little kids with their Lamborghini posters on the wall and stuff like that? I would have put Sun and SGI posters on my wall. Some of that gear was so cool. I love to watch it go.” – Tad Reeves
  • At State Farm Tad was supporting internal business facing systems mostly. At UUNET, it was all externally facing for different customers (big site launches).
  • Tad was involved in some of his first datacenter moves during this time as well as some of his first website creation and migration projects.
    • Tad was involved in the launch of the PlayStation 2 for which he built a server cluster and Webtrends cluster (part of a greater project team focused on the implementation). He shares the story of everyone being forced to go live when the systems were not yet ready.
    • “After PlayStation went live, that was my first time of a big website go live. And watching the live traffic come into that thing where suddenly we had 10,000 visitors crawling all over that thing…I will remember that moment forever. It was exhilarating. Midnight…I actually got in my car and went over to the datacenter just so I could go and watch those lights…. This is a beautiful thing.” – Tad Reeves, on seeing the PlayStation 2 launch

Mentioned in the Outro

• Do you have a list of the things you like about the work you do?
  • Tad liked to build things that make an impact on others (something people will use), but your list may be different. You might enjoy a system you work with, a programming language you use, the people you work with, etc.
  • If you don’t have a written list of your likes, you might not be as prepared for that next job as you could be.
  • In Episode 290 and Episode 291, we spoke to Kat Troyer and Liz Bronson (the hosts of RealJobTalk) about layoffs in tech. They shared a resource called the Must Have List that helps you determine your ideal job. Many of the questions are about the things you like in your work.
    • If we list out what we like, we can be looking for those things in new opportunities and think through how we can get more of those things in the work we do now.
• If you’re thinking of taking on the role of a technical lead, check out Episode 279 – Change Management: The Hardest Leap and Developing People with Marni Coffey (2/3).
• For other episodes like this one, we would recommend the following:
  • Episode 148 – The Magic of Building with Chris Wahl (1/2)
    • Tad, much like Chris, seems to be a builder.
  • Episode 149 – Find Your Gratitude, Find Your Joy with Chris Wahl (2/2)
    • Making a list of things we enjoy can help us find our gratitude for what we do each day.
  • Episode 177 – Follow the Excitement, Follow the Challenge with Stephanie Wong (1/2)
    • Stephanie Wong let her interests guide her career decisions, much like Tad.
  • Episode 178 – Being a Great Generalist and Finding Your Voice with Stephanie Wong (2/2)
  • Episode 283 – Educate and Advocate: Certifications and Community Responsibility as a Joy with Jason Belk (1/2)
    • Jason Belk shares how each of us has to advocate for this industry by sharing what we do and some of the reasons we continue to do it.

Contact the Hosts

• The hosts of Nerd Journey are John White and Nick Korte.
  • E-mail: [email protected]
  • DM us on Twitter/X @NerdJourney
  • Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman
  • Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_