How can we help recruiters advocate for us in a tough job market?

According to people industry veteran Christy Honeycutt, our guest in episode 353, it starts with being kind and translating your experience into something a recruiter can understand. And even more importantly, it takes practice.

In part 2 of our discussion with Christy, she translates deep experience in talent acquisition and recruitment that gives us insight into the current job market. You’ll hear more details about the nuances of RPOs (recruitment process outsourcers), the difference between job hugging and job abandonment, and the importance of personal branding and differentiation. Stay until the end when Christy shares her reasons for turning down C-suite positions and how clarity on her long-term goals is carrying her forward into what’s next.

Now that you’ve heard someone model it for you, how will you translate your own experience?

If you missed part 1 of our discussion with Christy, check out Episode 352 – People First: Systematizing Go-to-Market for Your Role with Christy Honeycutt (1/2).

Original Recording Date: 09-30-2025

Topics – A Deeper Look at Recruitment Process Outsourcing (RPO), Translating Your Experience with 3 Wins, Bad Actors and Leadership in the People Industry, Today’s Job Market and Life Outside the C-Suite

2:56 – A Deeper Look at Recruitment Process Outsourcing (RPO)

• When it comes to RPO (recruitment process outsourcing), is this a one-size-fits-all approach, or does it show up differently depending on what a company needs?
  • In Christy’s experience, most RPO organizations offer services like executive search, but they may offer full RPO, which usually involves hiring more than 500 people per year.
  • Normally an RPO brings a mix of skills to the table. A client may want the RPO to take only talent acquisition or may want to control offer management, but they may want the RPO to take everything (attracting new talent, offer management, coordinating with HR for new employee onboarding).
    • “If a company wants it a certain way, they can stop it at a certain point…. But most RPOs, full RPOs, is attraction to offer accepted and then it tees over to the HR team.” – Christy Honeycutt
  • John has worked for companies where the recruitment or talent acquisition personnel were marked as contractors in the internal global address book but had company e-mail addresses. Would this mean the personnel are contracting directly with a company or working through an RPO?
    • Christy says it could be either scenario. When she managed an RPO earlier in her career, they were most successful when the client encouraged the RPO to brand as the company.
    • Someone might indicate they do recruitment for a specific company on LinkedIn but be an employee of an RPO.
    • Christy tells us how important it is for the RPO to understand an organization’s mission, vision, benefits, and culture because the RPO is often attracting talent and selling people on why they should apply and interview.
    • “When you think about recruitment and talent acquisition, regardless, it’s a lot of marketing because you’ve got a really cool position and you’ve got to find the perfect fit.” – Christy Honeycutt

5:55 – Translating Your Experience with 3 Wins

• Right now, recruiters and talent acquisition professionals have a distinct challenge. Many resumes look the same because candidates are using AI tools.
  • “What people think is helping set them apart is actually making them look more similar. So now you’ve got recruiters and talent acquisition; they don’t know if these are fake resumes. They don’t know if they’re real. And they’re getting on the call with these people and finding out they are fake; they don’t have any of this requirement.” – Christy Honeycutt
• Christy shares a little secret about learning recruitment. She gives the example of a recruiter needing to recruit for an executive level role in technology.
  • Recruiters are encouraged to seek out and find the C-players to practice asking them questions, understand nuance, and grasp the terminology. This is a training exercise.
  • Following this process, a recruiter would then have more credibility once they speak to the A-players they actually want to hire.
  • “What I would encourage is if you are a C-player, you’re not going to know it. Just be kind and know that the person you’re talking to has never held a technical role (probably, most likely)…and might not understand half the stuff that you guys do. The acronyms aren’t going to be the same. Just be gracious with them because the more you can help them translate your experience, the better you’re going to be positioned to get you over the line…. They don’t want to talk to 10 people to get 1 hire. They want to talk to 3 people to get a hire…. And remember that the TA, HR, recruiters, whatever you want to call them…there’s a pretty good chance that they want to help you and that they’re doing the job because they like people. And I think they get a bad rap.” – Christy Honeycutt
  • Christy tells us about something called a slate (a group of 3-5 individuals who apply for a job that a recruiter will go and interview). Recruiters are using AI to help filter through applications.
  • “The biggest thing I can tell you is be your own person. Be your own, authentic person. Have your stories of how you’ve shown up and shown out…. I tell everybody for every job that you’ve worked at, you need to have 3 wins…. Figure out…your top things that you accomplished at each role and have that and be ready to speak to it. And then…ask questions. Interview them too…. Make sure it’s a culture fit for you.” – Christy Honeycutt
  • Christy says things like the great resignation and quiet quitting are just behaviors that get repeated over time. Right now, there is a fearful state of job hugging.
    • “We’re job hugging. No one is hugging a job. People are trying to stay employed in the market. That’s all it is.” – Christy Honeycutt
    • Christy says if you are staying somewhere because you have a job and are not happy, figure out how to make yourself happy by determining it is not a fit, understanding your passions, and beginning your exit plan.
    • “Companies are not our families. They are going to let us go. It’s going to come down to the business.” – Christy Honeycutt
    • It’s important to keep the human element in mind if we are seeking a new role (the human element on both sides).
  • Christy tells the story of a senior recruiter who called her about a conversation with a job candidate, and Christy knew the person was burned out, bored, and curious.
    • “High performers are always open minded and curious, but if you fall in that category, figure it out sooner than later so you’re not burning yourself out because then you’re in a very dangerous situation. That job hugging is going to be job abandonment. You’re going to get to boot. It’s not going to be the other way around. It’s just kind of level setting with your psyche.” – Christy Honeycutt

11:28 – Bad Actors and Leadership in the People Industry

• Going back to recruiters getting practice and experience from interviewing candidates, Nick looks at this from the lens that everyone needs at bats to gain experience. Though it may be batting practice for a recruiter, it is also practice for the candidate. We don’t practice interviewing very often.
  • Christy agrees it is practice on both sides and emphasizes that kindness is key.
  • She’s had multiple conversations with recruiters who didn’t understand why a hiring manager did not want a specific candidate. We might never know all the effort a recruiter put into promoting us with a hiring manager.
  • Some recruiters, however, should not be in their roles. Christy tells us about a time in her career when she was referred to as “The Kraken.”
    • Christy managed a tight team of talent acquisition professionals who respected and loved her as a boss. They knew she had high expectations of her team. Christy’s team members would have to launch programs for global clients within 30-60 days sometimes, for example.
    • “So, my team had to be kind of like special ops because we managed the globe, and it was high pressure.” – Christy Honeycutt
    • As she progressed in her career, Christy would be given individuals who were not performing on other teams. Before managing someone out of the business, Christy always gave people a chance to redeem themselves because until she met the person and they worked for her, she was only hearing one side of the story.
• Christy recounts being asked to join an RPO to clean it up.
  • She met with each recruiter to understand the key metrics and performance indicators.
  • Christy tells us that for any job opening (or job requisition) a recruiter was carrying at this time, they should be submitting 3-5 candidates for each job, and a manager would expect this within 2 weeks of the job opening. There was a specific recruiter who only submitted 2 candidates per week across 15 job openings, and Christy recounts the performance conversation with this person.
  • “There are some people that are in roles that they shouldn’t be that take advantage and kind of sit back….” – Christy Honeycutt
  • As people gain seniority in talent acquisition and recruitment, sometimes you deal with people’s egos. This is the exception and not the rule.
• John mentions it would probably be difficult to coast based on one’s reputation in talent acquisition. Based on the metrics for success and open job requisitions, it should be obvious who is doing well and who isn’t.
  • Christy says this goes back to leadership. Maybe these individuals never had a boss who would hold them accountable.
  • “If we go back to managers and leaders, most of them aren’t trained, and a lot of them want to be liked.” – Christy Honeycutt
  • Christy is the daughter of a Marine. This means the mission gets accomplished no matter what with the fewest amount of casualties. It’s her job as the leader of a team to keep them focused on the mission and accomplishing it. Removing someone from the team may be the best option to keep the rest of the team on track in accomplishing a mission.
    • “You’re only as strong as your weakest link, so if your weakest link is not holding themselves accountable and respecting their team, then they’re putting everybody else’s jobs at risk. And unfortunately, there are bad actors in every industry, in every role, in every organization…and we’ve all seen them. They are like cancer. They really hurt retention. They hurt elevation. They are usually the ones taking credit, taking too long at lunch, whatever the case may be…we’ve all seen them…. It all comes down to behaviors.” – Christy Honeycutt
  • Christy thinks leaders want to be liked and are afraid of having a complaint filed against them.
    • For example, people might file a complaint because they were not doing their job and their manager held them accountable for not doing it.
    • “It’s weird to be in the people industry for so long because it’s just behaviors. It’s just humans.” – Christy Honeycutt
  • Before someone shows up for work, we have no idea what may be going on in their life outside work. Christy encourages us to meet one another with more grace.
    • “Those of you out there, if you’re lucky enough to have a job and be employed, do the job. Because there’s a lot of people that don’t that will come in and do a better job than you. Honor yourself, honor your employer, and show up. But unfortunately, there’s bad actors.” – Christy Honeycutt
• John directs the conversation back to hiring cycles. He has heard it’s beneficial to apply for a job opening quickly and to be in the first wave of candidates but didn’t really think about the why behind it.
  • Christy tells us this varies based on the position, the job requirements, location, salary, and other factors. In fact, recruiters often have to reset unrealistic expectations from hiring managers (i.e. what a specific role salary should be).
  • “If you think about a client and them opening a position, they probably needed that position 30 days before it was ever approved. So, there’s already a ticking time on the recruiter whether that’s fair or not because in the manager’s mind that role opened the second they thought they needed it. Not when they requested it, not when it got approved, but when they realized in their brain, ‘I need this position filled,’ that’s when the clock starts for them. So, it’s an unfair disadvantage for a recruiter.” – Christy Honeycutt
  • Listen to Christy’s description of a best-in-class 4-week process from job opening to making the right candidate an offer.

20:45 – Today’s Job Market and Life Outside the C-Suite

• If we look at this through the lens of the current job market, how much do recruiters need to sell candidates on roles when there are hundreds of applications to sort through for a single job opening?
  • “Tech is like recruitment, like marketing. It’s always the first to go…until they realize…it went, and we need it. So, it’s a boomerang effect with those industries…always has been, always will be.” – Christy Honeycutt
  • Christy tells the story of being at the HR Tech conference with a young lady who was recently laid off from a tech company. This person walked from booth to booth and began networking with people in search of new roles and was able to leverage Christy to get some introductions. She had 5 interviews over the course of the 3-day event.
  • “In the job market today, with recruiters not able to tell if it’s an AI resume or not, with them being overloaded with a vast amount of resumes…the best thing that anybody can do is make sure that your personal brand is on point. Make sure that whatever it is that you’re doing…you’re sharing, you’re engaging your community, and that you’re seen doing it.” – Christy Honeycutt
  • Christy was part of the same tech startup mentioned above and also lost her job. But she had been working on her personal brand before that happened. Christy was speaking at events, sharing with her community, doing podcasts, and doing many go-to-market things on behalf of her employer.
    • Christy’s heart goes out to others in her field who have been out of work for multiple years.
    • Within 3 days of losing her role, Christy was offered 3 different C-suite positions. She turned them all down.
    • “I’ve had that moment where I’ve realized that where I want to go and where I am are 2 different places…. If I put my focus on something, my energy is going to flow in that direction, and I need to make sure that’s the direction I want to go…. Do I want to go be c-suite and kill myself for the next 4 years? …But the reason that gave me confidence is I’m 3 days without a job. I’ve got several job offers. And I realized, they don’t care how I work with them. They just want to work with me, so why don’t I go out on my own?” – Christy Honeycutt, on the internal discussions she’s having after encountering job loss
  • Christy understands she’s in a gifted place only because she put in the work of giving back to her community before she was in a tough spot.
    • Her efforts include things like hosting Inside the C-Suite and doing free mentoring and coaching for others.
    • “It’s because of all the goodwill I’ve done. My community paid it back tenfold. So set yourself apart in whatever it is that you’re doing…. Where we are today is you have to have a differentiator, or you’re going to be sitting on the shelf for 5 years.” – Christy Honeycutt
• Christy mentioned previously that it’s lonely when someone takes a C-suite role. How did her conversations with executives on Inside the C-Suite together with her experience in talent acquisition and recruitment impact her decision to not take a C-suite role?
  • Christy knows that she doesn’t do anything halfway. If she were to take a C-suite role, she would be working 80 hours per week and traveling nonstop.
  • Christy and her partner want to slow the pace down for their family, take time to travel, and do more purposeful things. She shares a story about Matthew McConaughey wanting to make the shift from romantic comedies to more serous roles to illustrate a shift of priority and focus.
  • “Yeah, it crossed my mind. But it does not align with my long-term goal…. I realized I have a choice. You know, the universe has brought a lot of stuff to me. Is it because it’s meant for me, or is it noise?” – Christy Honeycutt
  • Christy has shown up, given to her community in a visible way, and found her voice. But taking a C-suite role right now is not where she wants to be.
  • Some of the job offers Christy received came from people who had been on her podcast. Christy tells more of the story of being at HR Tech and the reactions people in the industry had to her being on the market. Christy plans to continue conversations with those people about ways they can work together moving forward.
  • “I’m really good at certain things, which you guys have broken down and helped me understand. I repeatedly get asked for those things, and those are the things I like to do. So why not go do that? Why not go be a consultant and do the things that I really like to do for people and not do the things I don’t like to do…? …I can just go do the fun stuff that they need my specialization in.” – Christy Honeycutt
  • Christy wants to stay true to herself and honor the decision to increase bandwidth for her family.
  • Many of the C-level executives Christy speaks to on her podcast love what they do, but they’ve had to learn to put themselves first.
    • “I hear this more often than not. When they first start their organization, it’s business business business. Their health fails. Their family fails. So, the ones that actually made it and recovered through that little spike and actually make it out on the other side very quickly flip to ‘take care of my body (my temple), my soul, my family, then my business. It’s a battle for them.” – Christy Honeycutt
    • At the time of this recording, Christy is thinking of starting her own firm, so she hopes she can take it slow enough to avoid these pitfalls.
• When we decide to slow the pace and do more of what we enjoy, can reflecting on those 3 wins from each previous job help us be confident that we can still get those wins without running at a hectic pace? Did Christy do this when thinking about what she wanted to do?
  • Christy says she did not think about these for herself even though it would be her coaching to others in need of advice.
  • “What I found interesting is that when you’re looking for an answer, if you actually open your eyes, it’s right there. It plays back to you. It plays back to you in conversations you have with people…. You often say what you need and what you want and where you’re at, but you don’t comprehend it. But if you hear someone you love, that you trust, repeat it back to you…it’s almost like it gives you permission to accept it.” – Christy Honeycutt
  • Sometimes instead of giving people advice, we need to act as a mirror and reflect back what they’ve said.
  • Christy didn’t need a C-level title. She doesn’t need to go do something to prove she can do it. She’s already done it. Christy understood she was ready for something different, even if it’s a little bit scary to consider going out on one’s own.
  • “It’s scary to put yourself out there like that, but if you don’t, you’ll never know. I’d rather try and fail and learn than regret and not know.” – Christy Honeycutt
• If you want to follow up with Christy on this conversation, you can find here:
  • On LinkedIn
  • On her website
  • On the podcasts she hosts – Inside the C-Suite and StrategicShift

Mentioned in the Outro

• Do you have 3 wins from each job or at least the past several jobs you’ve held? And do you know the stories that go along with these?

  • There are prerequisites that must be met before we can speak to our wins in an interview. It starts with documenting our accomplishments on a regular basis.
  • Consider what the 3 wins are from your accomplishment list. Maybe you have more than 3 or need to use a different set of 3 based on a job to which you’re applying.
  • Consider writing the story that goes with each win. It could be a resume bullet, but think of it as more detailed and something you can share in an interview.
  • This is part of drafting a career narrative like Jason Belk suggested in Episode 284 – Draft Your Narrative: Writing and Building a Technical Portfolio with Jason Belk (2/2). We should not only write the draft but gain practice sharing the stories verbally in interviews, possibly conversations with our manager, and maybe even in conversations with industry peers at networking events (if and when appropriate). This is an iterative process!
  • We like looking at conversations with recruiters as opportunities to practice telling our win stories.

• In the discussion with Christy, we heard about her experience losing a job.

  • In Christy’s case she had been giving to her network long before this happened in a very visible way.
  • Maybe you are doing this in a less visible way. Consider documenting that work, but make the overall intent to help others and impact people positively. It will pay off later when you need help.

• Christy shared an exercise in finding clarity. She knew a C-suite role would not match the pace that was aligned with what her family wanted. It wasn’t just about personal ambition.

• Remember to check out Christy’s podcasts, Inside the C-Suite and StrategicShift.

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_
  • Leave a Comment on Your Favorite Episode on YouTube
• If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.
• If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

Go-to-market strategy is something we often associate with a company or its products / services, but what if we could apply go-to-market to our job role?

Christy Honeycutt, a talent acquisition veteran and our guest this week in episode 352, has used this mindset as a personal differentiator starting with her first job in the banking industry. We’ll follow Christy as she describes early experience as a people manager, learn why she developed a people first mentality, and recount the events that kickstarted her career in recruitment.

This story helps us understand what is required to systematize the work we do and how difficult it can be for things that seem easy. Christy will also educate you on the importance of developing AI competence and the impact of recruitment process outsourcing on job candidate experience.

Original Recording Date: 09-30-2025

Topics – Meet Christy Honeycutt, A Go-to-Market Perspective, Beginnings in the Banking Industry, Learning to Systematize and Duplicate Yourself, A People First Approach, Getting into Recruitment

2:10 – Meet Christy Honeycutt

• Christy Honeycutt has 20 years of talent acquisition experience, go-to-market experience, and some marketing experience sprinkled throughout.
• Christy is also the host of two different podcasts:
  • On Inside the C-Suite, Christy interviews executive leaders to gain insight from life in these roles.
  • StrategicShift is focused on the future of work, innovation, and AI.

3:17 – A Go-to-Market Perspective

• How would Christy define talent acquisition and recruitment and the differences between them?
  • Recruitment should be thought about as more active. There is a job open with specific requirements which need to be filled based on time constraints.
  • Talent acquisition is more strategic according to Christy. This would include understanding why a role is vacant, the succession plans, cultural initiatives, and workforce planning. Christy refers to this as “engaging passive pipelines for long-term goals.”
  • Personnel in talent acquisition and recruitment are usually in those roles because they want to help people, but these roles may look slightly different across companies of various sizes and in different industries.
• How would Christy define go-to-market? We hear this term quite often but are not confident that everyone truly understands what this means.
  • For context, Christy talks about looking at this with a lens across many different departments / internal organizations – marketing, recruitment, and even sales.
  • “Go-to-market is understanding what is the product and who is the end user…. Am I filling a job? Then I’m going to market for that candidate that fits that job. Am I working for a tech company (which I most recently did)? Then, yes, I need to understand what is our product, who is the end user, who is the buyer…and how can I get this to market for them…to see, to use to buy, and to be delighted in? The go-to-market is really kind of a Frankenstein effect in my opinion. It’s really understanding the value and how it translates and then how you can connect the dots…. Go-to-market for me has just kind of been at my core since I was a kid.” – Christy Honeycutt
  • For recruitment, the go-to-market is usually set based on an organization’s vision, mission, values, and culture.
  • Christy uses the example of negotiating with her father (a former Marine) to get what she wanted when she was younger to illustrate that go-to-market can mean understanding how to sell.

7:01 – Beginnings in the Banking Industry

• Christy was a cheerleader in high school and got a fully paid scholarship to college, but at age 17, she was diagnosed with cancer.
  • As a result of the diagnosis, she was not able to attend college. Christy always wanted to be a mom and did not want to ruin her chance to have children.
  • Christy married her college sweetheart and became a stay-at-home mom of 2 children.
    • She is now heathy, happy, and thankful she was able to have children.
    • Christy’s father owned a nonprofit, and even while she was a stay-at-home mom, Christy was involved in marketing for nonprofits as a result.
    • Christy also was part of the boards of her children’s schools, did volunteer work, and even taught pre-school.
• After moving to a new state, Christy needed to get a job to support her children. After applying at a bank, she landed a manager job.
  • Within 6 months, the bank branch where she worked was the highest producing in the state of Texas.
  • Christy came up with marketing initiatives to get customers to visit the bank. She gives the example of a yearly Halloween contest.
  • At one point, the bank was robbed, and Christy learned to lead in stressful situations through this experience. She also learned that she has a photographic memory.
• Christy tells us her career really began in banking and then transitioned into marketing. Listen to the story about one of her clients who was a mortgage broker.
  • Christy had 2 boys in various sports and was wearing herself out between work at the bank and home life.
  • This mortgage broker sent an e-mail to help Christy get interviews for a role at a different bank.
  • Christy tells the story of interviewing in the mortgage division of another bank (Prime Lending) close to Halloween. She was dressed as Lucille Ball for an event at her employer and ended up going to the interview in costume. The people who interviewed Christy loved it, and she was offered the job on the spot.

11:40 – Learning to Systematize and Duplicate Yourself

• “But the really interesting thing that happened is they said, ‘we want you to hire 3 of you…. What you’re doing is working, so what we’d like you to do is go have a think about how you can multiply that into other branches….’ Can you imagine sitting down and going, ‘what is it that I did today and how did I do it?’ …And, just really creating a job description, a profile, how they’re going to be successful…and then find the people and train the people? So that was my very first…experience with recruitment.” – Christy Honeycutt
• After removing the shock of being told to multiply herself, Christy began a process that she would repeat over and over in her career – thinking outside the box to create something special that she could automate or systematize.
• At that first bank, Christy managed people but had no prior training as a manager. How did she figure out how to manage people, and then how did that translate to the role in which she was asked to create job descriptions and multiply herself?
  • We’ve heard from some guests that most first-time managers do not get training. Christy echoes this sentiment.
  • Large banks will train you on laws and procedures, but Christy tells us she had to train herself on the people side. Mainly, she needed to learn how to manage the people, their schedules, and learn how to encourage them. Despite being the boss, Christy was still friends with the people who worked there.
• In being asked to multiply herself, Christy had to systematize the job she was already doing. She tells us it was a daunting task.
• “When you’re really good at things, what I’ve found is they seem natural to you, and they are not that hard.” – Christy Honeycutt
• When asked to duplicate herself, Christy downplayed her contributions a little bit. She advises all of us to step back and really think about the work we have done because we might not immediately recognize it and may downplay it in a similar way.
  • As humans, we might at first feel like it is bragging to share the factual things we have done.
  • Christy had to think about what she did, simplify it, and figure out how to translate that to the people she needed to hire.
  • Christy was working for the mortgage division at a bank, and they needed to get more loans. She first sought to understand the sentiment of the bank’s customer base and if they had any needs. Step 1 was hosting a customer appreciation event.
    • The customer appreciation event generated direct feedback on the bank’s processes and product offerings.
  • Next, Christy sought to understand the bank’s target market, which was real estate agents. She thought about how to get real estate agents to use this specific mortgage broker. New real estate agents need help with marketing, so Christy got certified and began teaching marketing classes to real estate agents. All of the agents would eventually begin using the bank.
  • “It’s just kind of understanding what’s in it for someone else…. I just…went step by step by step and built the framework….” – Christy Honeycutt
    • The framework Christy mentions above outlined where the opportunities were for the bank (i.e. who might need their services), allowed for dividing up the work across divisions, and provided insight into the key performance indicators (KPIs) for measuring success.
    • In many ways, Christy acted as a liaison between the bank, the real estate agents, and end customers.
  • When seeking to hire people to do the work, Christy looked for empathetic people who were interested in helping others.
  • Another avenue for the bank to increase the number of loans was working with first-time home buyers who might have poor credit. This would help real estate agents who needed home buyers. The bank started doing credit repair seminars to generate new leads.
    • “I was bringing in buyers, delighting previous buyers, and then also going after the vendors that would help participate. Honestly, that model…has kind of been my two step my whole career.” – Christy Honeycutt
• Nick thinks Christy’s process is actually a three-step with the third being supplementing the above with the type of education which will both Christy and the audience she seeks to serve. Nick thinks this pattern will probably be repeated somewhere in her story as well.
  • Christy says it actually does repeat. She recounts getting an AI-focused certification when this technology wave started catching on.
  • “In the next 12-18 months, over 80% of all organizations globally will have adopted AI if they haven’t already. So, if you’re looking for a job, and you don’t understand the basics…AI has a lot of different names. I want you guys to think about that. That’s usually marketing.” – Christy Honeycutt
  • Christy tells us AI agents are mostly marketing and an attempt to make things more consumable and understandable rather than some flashy new invention.
  • Christy recounts talking to executive leaders who have mentioned having AI in one’s toolkit even as a kid is important to be relevant in the future workforce. All of us need to have more than a bare minimum exposure to ChatGPT, for example. We need to play, create, and tinker with AI tooling to develop a point of view that is uniquely ours.
  • Christy feels AI will take jobs but that they will be lower-level things that we probably wanted automated anyway. She gives the example of a communications outage impacting airports in Dallas / Fort Worth and the decision to go get information from an AI agent on the company website rather than call the help desk.
  • For any job you go into, expect to get questions around AI.
  • Christy mentions a recent visit to the HR Tech conference. Every booth was promoting some kind of AI, and Christy shared with executives at the conference that buyers don’t fully understand the difference between products because “everyone is saying the same thing.”
  • Christy reminds us there are ways to get low cost or even free education on the topic of AI so we can develop competence and a point of view.
  • Nick shares his perspective on what he calls the “double check mark,” which is looking to educate yourself or build skills in an area that can help you both at your current employer but also make you marketable and relevant in the greater job market.
    • Something that only helps you with your current role isn’t quite as attractive as something that can help you later as well. Ideally, you span into both categories, but it is not always possible.
    • Christy mentions this is a very tech answer and gives the example of making a suggestion to an executive leader while advising for a tech startup. She only brought suggestions that would be attractive to / helpful to many customers (not just a single customer).
• When Christy did research on what was impacting customer sentiment and spoke about understanding product market fit, was that all natural at the time she did it while working at the bank?
  • Christy says it was natural at the time. As a single mom, she needed to be scrappy.
  • “It’s funny because as I sit back and I think…I realize everything was kind of predestined. And at the moment it just felt like I was reacting and I was doing it, but…as I do my own reflection, I’m realizing that these cycles I’ve been on have always been for a reason, guiding me to where I’m at.” – Christy Honeycutt
  • Reflection is one way to uncover our strengths, and Christy reminds us that just because something is easy for us does not disqualify it from being a strength.
  • John mentions that performing a skill really well is different than being able to teach other people how to do it. When something comes easily to you, it might be difficult to know how to teach someone else to do it. But it sounds like Christy had to learn how to systematize the things she did so she could train others (i.e. it was not natural).
    • Christy says it definitely was not natural. She remembers how she felt when asked to duplicate herself. It seemed like a crazy request at the time.
    • One thing that really helped Christy through this process was looking at job descriptions for roles similar to hers at other companies and analyzing both similarities and differences.
    • “Everything is a learning lesson. I don’t regret any place I’ve ever worked. I don’t regret any situation I’ve ever had because it was all opportunity for me to learn how to manage through a situation (good, bad, or indifferent) and reflect on it and how I would do it differently.” – Christy Honeycutt
• Christy mentioned earlier that no one learns how to be a manager. She is a forthcoming author and was recently signed with Postal Publishing House, and the book will be about leadership.
  • In the book Christy talks about how no one is trained to be a leader and how people often just kind of fall into it. She feels it is a big gap. Even as people get up to the director level and maybe even the VP level, they are still learning.
  • “No one sits you down and says, ‘hey, these really crazy things are going to happen, and you’re going to have to respond to these humans in a particular way. And by the way, you’re human, and you might have a really bad response to what you have to respond to….’ There’s lots of things that you deal with that I don’t think anyone could prepare you to deal with. And so, you learn on the job.” – Christy Honeycutt
• Did the need to create job descriptions and hire people to multiply herself make Christy enjoy management more or question whether she wanted to keep doing it?
  • Christy tells us she questioned whether she wanted to keep doing it. Her responsibilities ended up expanding well beyond the go-to-market work she was doing, and things became more complex.
  • Christy went from being in charge of 1 person to being in charge of 4 people trying to do everything using her methodology but with their own flair.
  • “Frankly, I got kind of bored because I created something, I duplicated myself, multiplied myself…. Ok, I’m ready for the next thing. I can do this, and I’m ready for the next thing…. I’m constantly curious, and I always need something more just to kind of keep my attention. There’s a lot of people in the industry I think are that way, especially in tech…. And those are the people that employers are looking for. They are looking for the curious people. They are looking for the open-minded individuals that want to adapt and want to learn and do more because those are the ones that have the longevity.” – Christy Honeycutt
    • Once we master things as technical people, we often want to move onto what is next (something new to learn, a new certification to chase, etc.).

26:23 – A People First Approach

• Did Christy’s background in cheerleading help her in marketing?
  • Actually, yes.
  • Christy gives the illustration of high school cheerleading and pep squads. These are made up of people who love community and love to empower and cheer on other people.
  • Christy reminds us that cheerleading is a sport. For those in cheer or pep squad, it’s not about wearing cute outfits. There is a commonality among the people who participate: an enjoyment of collaboration, a desire to win, and a belief that there is power in the energy they are giving.
  • Christy likes to look at things from an energy lens.
  • “In every industry you’ve got really good players, and you’ve got bad actors. So not all recruiters, not all talent acquisition people are really kindhearted, love what they are doing, and in it for you…. But the majority of the people in the HR and TA (talent acquisition) space generally joined that type of work because they love people, and they are fearful right now because they think AI is taking their job. And some of them it probably will, but you’re never going to get away from the EI and the EQ piece that is required in the age of AI. We need to be more human now than ever.” – Christy Honeycutt
    • Some people in these roles may hate their job. Some may love you as a candidate but be unable to get anything through.
• At what point did Christy realize that for her it was more about the people?
  • “It’s always been about the people for me. Everything I do has been about people. I’m people first just in everything I do.” – Christy Honeycutt
  • After getting the job where she needed to duplicate herself, Christy wanted to talk to all of the company’s customers as her first task.
  • Christy mentions the concept of go-to-market is the same regardless of the company where we work.
  • “Your customers are your biggest resource because they will either be the loudest complainers or your biggest fans.” – Christy Honeycutt
  • Customers with a positive sentiment toward a company (or its products and services) can offer free insight on how to serve them better. This may come in the form of suggestions for new features and capabilities or advice on overall direction, for example, and provides a perspective that a vendor cannot otherwise see.
  • Christy has been told she is too “client advocate friendly.”
    • When selling a product or service to a customer, if users don’t adopt it, you are only as good as the contract. Christy calls this being a one trick pony.
    • On the other hand, we can sell a product or service and care enough to check in with customers and make pivots to make the product or service more valuable. This creates what Christy refers to as a “client for life.”
    • “And that’s, I think, where my specialty comes from is the human side, the people side. It’s just always remembering what’s in it for somebody else. Because we all have exchanges every day. What’s in it for the other person?” – Christy Honeycutt
    • Christy makes a hypothesis that we do this podcast to help people and because we care, and at some point in our career we probably needed what we are giving. What would you have said is the reason for the podcast based on being a listener?
  • “People are my thing. I get the heart. I get the energy, and I think at the end of the day, we all put our shoes on the same way.” – Christy Honeycutt
    • Christy really enjoys hosting Inside the C-Suite because it demystifies what it is like to be an executive leader.
    • “It’s understanding how you navigate and how your priorities change…what’s now, what’s next, what’s urgent always evolves as you grow in your career.” – Christy Honeycutt

31:52 – Getting into Recruitment

• How did Christy end up getting into talent acquisition and recruitment?
  • Even with her hectic travel schedule hosting events for her employer, Christy never missed a little league baseball game in which her kids were playing. At a specific game, someone asked Christy what she did for a living and if she had ever thought about working in recruitment.
    • The person who made the suggestion helped Christy see the similarities between recruitment and marketing.
    • “Client needs a certain thing, and you go find the certain thing. And however you find it, you find it. That’s a lot like marketing. Exactly.” – Christy Honeycutt, describing an exchange with someone who encouraged her to pursue work as a recruiter
  • Christy went to an interview for a recruiting role and got the job on the spot. The company was bought out by Kenexa(CEO was Rudy Karsan) which was later acquired by IBM (or “big blue” as Christy calls them).
    • Christy did recruitment process outsourcing for this company (or RPO for short) and specialized in this area for many years. She led this at IBM and later at Korn Ferry.
  • She tells us there are so many layers to recruiting that people don’t know.
    • Staffing agencies, for example, often get a bad reputation. These agencies are predominantly focused on high-volume hourly roles or other short-term positions. Quality and candidate experience are not always the best. These recruiters have to move quickly because a successful placement is how they get paid.
    • “And when you do that really, really well the clients think that you’re their internal recruiter…. I think over my career, not me directly but within my teams, I’ve probably placed around 30,000 individuals.” – Christy Honeycutt, on specializing in RPO
    • Listen to Christy talk through an example of mapping through the workforce strategy for a client that wanted to outsource global recruitment on a tight timeline. She emphasizes that when we work with a recruiter, that recruiter might not work for the company where we are interviewing.
    • “When an RPO does a good job, not only does the candidate think that they’re an internal recruiter, but the clients think they are an internal recruiter.” – Christy Honeycutt
    • Christy talks about making a move from being a liaison manager for a client (focused on the client’s technology sales and marketing) to managing an internal team. The client thought she was their employee.
    • Don’t miss the part where Christy mentions she wanted to take a role as a recruiter so she could understand how to be a better manager.
    • “While your…audience is out there looking for jobs, just be mindful that…TA, recruitment, HR…depending on the size of the organization…you may be talking to an agency. You may be talking to an RPO. You may be talking to an internal recruiter. You can ask them. They don’t have to tell you.” – Christy Honeycutt
  • Another challenge for the job seekers out there is the amount of fraud happening. On average, every US citizen has 7 points of fraud directed at them per day.
    • Christy mentions getting multiple text messages from companies claiming to be Randstad, Robert Half, or some other firm about jobs. It’s all fraud. Don’t fall for it!
    • When Christy worked for Korn Ferry and another tech startup, as part of the go-to-market strategy, she created a candidate application analysis tool which informed clients about the candidate’s experience.
      • Some clients didn’t realize, for example, that their site was down and was preventing people from even applying.
      • This tool also informed clients about how they showed up on sites like Glassdoor and what the biggest complaints are. The lowest scores 9 out of 10 times for a company are for leadership. Keep in mind rankings on Glassdoor are from job candidates and people who have worked at a specific company, and most do not take time to write glowing reviews of an employer.
      • “We have to give the employers the benefit of the doubt. So when you know where the sources are coming from and you’re honest with yourself on when you give feedback and how you give feedback…until we can all step up as humans and start giving 2-3 good feedbacks a day, we’re never going to balance out the negative.” – Christy Honeycutt

Mentioned in the Outro

• Christy did a great job emphasizing that we understand what is it for the other people we work with (incentives, metrics, what success looks like for them), and that was part of executing a successful go-to-market strategy in banking and other areas. Here’s how Nick thinks a go-to-market might look for someone working internal IT:
  • Understand the technology landscape at your company (hardware, software, cloud services and subscriptions – the overall vendor landscape)
  • Understand the end user base you support and the capabilities you are providing to them. Think also about the value being delivered through these capabilities to both internal users and external users if applicable.
  • Think about the capabilities you provide like products. Can your products be enhanced based on end user needs and feedback, and are we willing to take the feedback? Christy modeled the importance of understanding customer sentiment that can help us here.
    • Will an enhancement save time, decrease cost, decrease risk, or increase revenue? These are important impact metrics to understand (and document).
  • If you change a hardware / software vendor (i.e. a tooling change), will it disrupt your customer base, or can you still provide the same capabilities? Make sure you understand this!
  • Is there a new capability you could provide that delivers more capability? That’s part of the go-to-market.
  • Are there members of the end user base who need education to get more value from the services and capabilities you’re offering?
• Don’t forget to check out the podcasts Christy hosts –Inside the C-Suite and StrategicShift.
  • Nick feels podcasts such as Inside the C-Suite are great sources to gain perspective on how executive leaders operate.

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_
  • Leave a Comment on Your Favorite Episode on YouTube
• If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.
• If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

Original Recording Date: 11/2/2025

Expect a Change Moving Forward – The Schedule

Hi everyone – thank you for being a listener. This is a brief reminder that episodes from this point forward will be releasing every 2 weeks for the time being. Life circumstances have demanded we make this change to keep producing the show.

Don’t expect any changes to our content. We remain committed to serving the technology professional and helping them accelerate career progression, increase job satisfaction, and be more effective in their existing role.

Thanks for coming along with us on the journey, and it will continue. Expect to hear from us every 2 weeks from this point. See you next week for another action-packed episode!

If you have ideas for a topic we should explore or a guest we need to have on the show, feel free to contact us via any of the channels below.

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_
  • Leave a Comment on Your Favorite Episode on YouTube
• If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.
• If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

What does it mean to become AI native? It’s not about using every AI tool on the market. For Milin Desai, the CEO of Sentry, it’s about becoming familiar with the tools and opting in to use the capabilities that deliver practical value. This mindset was born while Milin was the general manager of a business unit at a software company. In this role, he had to manage a profit and loss statement, learning the art of constrained resource planning and organizational adaptability.

In episode 351, our final installment of the conversation, listen as Milin describes both the gravity and different intensity of the CEO’s role compared to past roles. You’ll get insight into the strategy behind enabling an entire organization to shift and become AI native, how this translates into value for customers and employees, and how the individual contributor can be a better contextual communicator when speaking to busy leaders.

Stick with us until the end to understand how a set of first principles can guide our career progression if we choose to actively participate in it.

Original Recording Date: 09-29-2025

Milin Desai is currently the CEO of Sentry. If you missed parts 1 and 2 of our discussion with Milin, check out Episode 349 – Expand Your Curiosity: Build, Own, and Maintain Relevance with Milin Desai (1/3) and Episode 350 – Scope and Upside: The Importance of Contextual Communication with Milin Desai (2/3).

Topics – Contrasting the Role of General Manager with CEO, Embrace Practicality with New Technology, Junior Personnel and a Return to First Principles, Shifting Organizational Focus to Becoming AI Native, Contextual Communication to Leaders and Parting Thoughts

2:41 – Contrasting the Role of General Manager with CEO

• General managers usually own a profit and loss statement (or PNL statement). How was this different than the things Milin had previously gone through?
  • Milin says you do have to prepare yourself for it, and his experience as part of product teams was very helpful to gain familiarity with many of the elements of the general manager role (i.e. revenue protections, investing resources in specific efforts, etc.).
  • Things get very interesting when you are managing PNL in a constrained environment. Milin gives some insight into annual planning and the behaviors he has observed during these times.
    • “Very rarely do people come back and say, ‘I’ve got the same org. I’m going to reshape the org, move things around, and I’m going to do these new things with the same number of people.’ I think most leaders are not very good with that philosophy.” – Milin Desai
  • In this role Milin tells us he learned how to do planning with specific constraints in mind (i.e. stress testing as if no resources / extra people could be added), and this idea of keeping teams lean taught him about the adaptability of an organization.
  • “I really think every organization should do that, and then, you always have the ability to go add more people…. Structurally say, ‘is this how we still want to operate?’ And we rarely do that…. I knew the numbers, the resources, and everything else. We did a lot of planning. But what I learned I needed to get better at is this constrained planning…” – Milin Desai
  • Milin loved working as a general manager and thinking through how to optimize even if the organization didn’t get everything it wanted.
  • “What is the hardest thing to do? To say no. What is the hardest thing for a product manager to do? Shut down a feature. What is the hardest thing for a VP of engineering to do? To shut down a product…. I’m lucky enough to have a leadership team that…thinks along those lines. We are unconstrained, but we kind of try to make sure…let’s put some artificial constraints and see what we would do different.” – Milin Desai
    • Nick mentions this is analogous to the employee who is no longer a fit and having to say no to that person moving on with the company.
• What is the contrast between being a general manager of a business unit and being the CEO of an entire organization?
  • Milin remembers some of the conversations when he was considering becoming a CEO.
  • “Milin, are you sure you want to do this? And it was not a capability question. It was, ‘do you understand what you are signing up for?’ …It is very different. You are responsible for everything. There is no other person. There is no other excuse. There is no other system I can blame. Something goes wrong at Sentry…I am it. And I have to go to sleep every day thinking about it. I wake up every day thinking about it.” – Milin Desai, quoting a question from former boss John Martin and speaking to the contrast of being CEO compared to general manager
  • You have to know you want to be CEO. Many people think they want to do it until they are doing it and realize how difficult it is.
  • Milin admits being CEO has been difficult, but having a great team has been very helpful.
  • Before taking the role, Milin spoke to his wife about it. He describes the role as “a very different intensity.”
  • Three months into Milin being CEO of Sentry, COVID showed up. That is a challenge he never would have expected.
  • “It’s very different to be a GM versus being a CEO. You’re using your same skills, but it’s a completely different magnitude of responsibility and impact.” – Milin Desai
    • As a general manager of a business unit, Milin could change the trajectory of his business unit. As CEO, mistakes are much more costly. But you cannot do it in fear. In fact, for Milin, the larger impact of his role is exciting.
    • The right partners and team around you as CEO are very important as are taking and applying lessons you previously learned. Milin continues to push himself to improve over time even after reaching the CEO level.

9:22 – Embrace Practicality with New Technology

• John cites technology waves like virtualization, cloud, mobile, and generative AI. With generative AI, many of us get value from it. But many people are unconvinced of the value and are even fearful it will turn into something like Skynet (a reference from the movie Terminator 2). How does Milin approach people with this mindset?
  • Milin is practical with his approach to technology.
  • “The unconstrained view of what AI could do…we have seen it in movies already. So, I think the unconstrained aspect of this is what we can imagine or maybe even worse…. You can almost think about that and worry and not participate and be on the other side if that happens…. Or, just practically, on a day-to-day basis, figure out what aspects you want to opt in. So, I’m more in that camp…. On the AI front, just think about how it could practically help you on a day-to-day basis versus trying to worry too much about all the aspects, some of which you absolutely don’t even control…. I think it will bring productivity in ways that we don’t even know.” – Milin Desai
  • For example, Milin doesn’t have a voice assistant, didn’t find them useful, and did not opt in.
  • If you’re worried about supporting a bigger cause, Milin tells us that bigger cause is going to happen irrespective of us supporting it. Instead, we should think about how to practically use AI tools and become an active voice in it.
  • Milin tells us his wife just started using ChatGPT and loves it. He asked her the value question on whether it was worth paying for it vs. staying on the free tier after she talked about how much it helped. She agreed that it was worth the money.
  • Milin cites the potential for productivity gains we don’t even know or understand yet. For example, imagine a robot doing laundry for you so you can do something else.
    • Milin thinks there will be some significant value points with robotics and AI. He’s excited at the potential for optimizing daily tasks that this could bring.
  • “Just be practical in how you’re using it and how it will bring value to your life, and the ones that you don’t find valuable, don’t do it. I don’t try every AI tool…. But the things I care about, I lean in.” – Milin Desai
  • We don’t control the unconstrained and should not worry about it according to Milin, but we can be a positive participant in this (AI) by participating in communities that serve the greater good in this area.
  • Milin says the idea of an AI bubble bursting will be determined over time, but transformation is happening.
    • There are business use cases in vertical industries for AI (i.e. for medical transcribing). It’s not just people doing personal research at home, for example.
    • The intersection of AI and robots will be an exceptional thing.
    • We have to figure out our place in all of this, which is a harder question.
  • “I fundamentally believe you will still need engineers. You will still need certain things. But certain functions are getting automated…. You’re going to have to figure out where is the new value being created and how…you participate in the new value system.” – Milin Desai
    • This comes back to curiosity, asking good questions, listening, watching for where things are moving, etc. We can apply those same principles to the field of AI.
    • Milin tells us almost every company out there is willing to let you explore and learn when it comes to AI (which means. At Sentry, people are encouraged to use the tools they want to become “AI native.”
    • “Leverage that. Lean into it. Don’t shy away from it.” – Milin Desai, on utilizing your job role and resources to learn AI tooling and the value it can provide

15:07 – Junior Personnel and a Return to First Principles

• Nick wonders how junior technology personnel can develop the expertise of someone who is more senior when the senior folks developed their expertise before AI existed? Can giving a junior employee AI tooling help them gain that same level of expertise?
  • Milin says this is about getting more “at bats.” Someone could read all about running a company or working with top leaders, but until they have done it, they cannot really understand what it is like.
  • For senior personnel, using AI tools will remove some of the tedious tasks and be more of an accelerant.
  • Junior personnel do need to become AI native, but in addition to this, Milin recommends spending your time thinking through failure modes and other fundamentals.
  • “If something breaks, will I be able to debug it? What are the failure modes for a user that is accessing the system? At what point in time will we have to look at scale aspects of the system…both just scaling versus architecturally? And then you start asking those questions and putting those pieces as learning building blocks…. I think you have to think again at first level principles, system level thinking.” – Milin Desai
  • In addition to the above questions, think about the following:
    • Is the user’s experience intact?
    • Does good design documentation exist?
  • Milin says these “first principles of system thinking” develop from writing, deep thinking, thinking through things from a user’s perspective, considering failure and scaling modes, etc.
    • “And so you build those habits, even as a young engineer…. When you get to a point, you will start asking the right questions, and AI or no AI, you’re going to be successful and valued because you’re thinking in first principles. You have to develop that, but you can develop that with AI and with the folks around you.” – Milin Desai

17:47 – Shifting Organizational Focus to Becoming AI Native

• With Milin’s view on AI as not pure hype, how are organizations reorganizing priorities around how products get developed, tested, and shipped?
  • Milin tells us over 150,000 organizations use Sentry from the smallest startups to the largest organizations. The customer base scale is massive, and the feedback is constant, fast, and iterative.
  • “We have basically told the entire company, ‘You must become AI native….’ The number one thing we did was we unconstrained everyone to say, ‘go figure out how to become AI native.’ Whether you’re at Sentry or otherwise, this is a skill you are going to need. So, participate in it.” – Milin Desai
    • Milin says employees were encouraged to initially choose the tools necessary to become AI native, and corporate constraints would come into play a little bit later after personnel had built a skill base.
  • The Sentry team also had a set of people building AI-specific capabilities, but the intention was not to have a single, centralized AI team.
    • “There is a set of people who are experts at fine-tuning…the models and how everything works. But, if you want to be the company of the future, it’s not an AI team. It’s everything in terms of what you’re building has a perspective of participating in an AI native world. It cannot be that…30% of the team that is working on AI stuff, and the others are not….” – Milin Desai
    • AI is a tailwind for Sentry according to Milin. It was a goal to take some of the things the team was already doing (i.e. products they were building) and look for ways to make those products AI native.
    • Milin spoke to some of the work new graduates at Sentry did to build session replay summarization. This was their chance to take a project from 0 to 1.
    • Having an AI-themed “hack week” inside the company created a new energy and air of excitement.
  • “And so where are we right now? We basically are like, ‘what does it mean for Sentry to exploit all the opportunity it is in software?’ …It’s not constrained to a team. It’s organization wide…. Pretty much across the board, every team is going to look at what they do and say, ‘Is it a version that brings the experience forward because we now have LLMs and AI and all this new tech?’ That’s the question you have to answer.” – Milin Desai
    • The individual teams also have to think about where the experience in their product gets enhanced with these new technologies. It might be in the front end, back end, or something invisible to the user entirely.
    • Milin also mentions there is an internal team that owns building the core AI and infrastructure elements separate and apart from their product enhancement focus.
    • While everyone is moving in the same direction now, this shift Milin describes came in phases. It was introduced with a little guidance and happened over a period of 3-4 months.
    • “But you have to bring people along for the ride versus… ‘here’s what you’re going to do.’ That doesn’t work.” – Milin Desai
• John says at first these steps sound like ways to modernize an organization, but in this case, it’s more to keep up with current trends and new ways to provide value. Milin says it is to stay relevant.
  • “It’s to stay relevant. That’s why I made the statement – with or without Sentry, every employee has to become AI native…. What we did was let folks opt in into kind of new areas of the product, and now everybody’s opting in.” – Milin Desai
  • Milin says they did not need to do unnatural things to leverage AI as a tailwind. If you are in a situation where a new trend like AI has come out of nowhere to impact what you do or threaten your relevance, it might require a pause and reset.
• John speaks to the technology adoption lifecycle. There are bleeding edge use cases that apply to only the innovators. Next comes the use cases for innovators and early adopters. John says we can be the late majority to some of the things happening and gives the example of e-mail summaries from AI being an extremely useful of a late majority feature.
  • We can opt into late majority features without opting into everything or opting into the worst possible outcomes of using AI.
  • Milin gives the example of Sentry shipping a grouping feature powered by AI that resulted in big efficiency increases for customers. Most people would not know it’s powered by AI, and it was one of the first capabilities they shipped after implementing some of the internal changes Milin described earlier.
  • Milin says our attention spans are getting shorter and shorter, and some of the capabilities AI can bring are going to help with this.

25:35 – Contextual Communication to Leaders and Parting Thoughts

• We spoke about the importance of contextual communication from management down to employees at lower levels and even about how important this is when using generative AI tools. Where Nick sees a lot of people struggle is when they are an individual contributor trying to be a contextual communicator upward to leaders. How can we do this well when working with busy leaders in a world where attention spans are getting shorter?

  • Milin says we don’t really think about this. We don’t think about the potential for running into a senior leader at a company and what we would do if they asked us a question.
  • “What tends to happen is you run into somebody who is maybe 1 or 2 levels of ownership higher than you. They ask you a question. You are deep in the weeds of solving a problem, and so you’re so lost in that problem that when you speak to that person…you may miss an opportunity to talk about why you’re solving that problem…. Always remember and always ask early on in your career…why are we doing this? How does this help? Who does it help? Just knowing that and starting to believe in that is helpful.” – Milin Desai
  • Milin says he’s had 1-1s with people who have told him something isn’t going to work. He would prefer them to speak up and question why something is being built if it’s not going to work based on those questions above.
  • “What is the job of somebody two levels up? They are just asking the right questions. What do you think? Is it going to solve the problem?” – Milin Desai
    • Knowing the fundamentals as Milin outlined above (why, how / who something helps) allows you to have a conversation with a leader on the topic, and you can bring a point of view. It helps with what he calls “asynchronous communication” where you end up getting those unexpected questions about how things are going.
    • “Just always ask this – ‘why am I doing this? Who am I doing it for? And then as a result you’ll know the value, you’ll know the persona, and how does it fit in. Those questions then contextualize everything. It doesn’t matter level 1 or level N at that point in time.” – Milin Desai

• Milin hopes listeners can parse out the value from this conversation.

  • "Just come back to first principles of all the things we talked about. Be insanely curious. Be insanely active. Participate. And then everything kind of flows from there…. At the end of the day, we are only as good as the people around us. And whether you’re a manager listening, you’re an IC…remember, it’s about the humans…. Those people can only help you if you want to be helped. So, you need to take charge and ask and drive the conversation. And there will be a point where you may not be satisfied. We all are impatient. We all want to reach the summit on the very next day. Sometimes it takes time, so you have to understand what level of patience you have. But you own your path, your narrative, your direction…and you need to make sure that you get the most of an organization. I think people tend to forget that. Organizations sometimes get busy. I am not making excuses for people like me and others, but what I am trying to get at is I didn’t get here by waiting for people to give me what I believe was mine…. I actively participated in that conversation. Of course, I then had great mentors who then helped me with it. It did not come right away. I had to wait, be patient. But I’ll tell you, for the most part if you work hard, you’re an active contributor, you’re curious, you have good people you’re working for…things come along. And that formula is going to work. " – Milin Desai

• We cannot assume an organization is going to do wonders but should be active in the story. Milin is living proof of this.

• To follow up with Milin on this conversation:

  • Follow him on X – @virtualmilin
  • Follow Milin on LinkedIn
  • Follow what is happening with Sentry:
    • Sentry Blog

Mentioned in the Outro

• There are layers of opting in throughout this discussion:
  • Opting in to use and learn about AI tools is one aspect, and opting in to leverage the tools for the use cases that provide value is another.
  • Milin had to opt in when he moved into the CEO role, and he has created an environment at Sentry that has enabled people within his organization to opt in for leveraging AI to provide more value to customers.
• Remember those 3 questions Milin mentioned:
  • Why are we doing this?
  • How does it help?
  • Who does it help?
• Due to life circumstances, our show is moving from a weekly release to releasing every 2 weeks for the time being. We want to make it on a schedule that is sustainable and at the quality we want.
  • When you don’t see a release next Tuesday, it’s because of this change.

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_
  • Leave a Comment on Your Favorite Episode on YouTube
• If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.
• If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

When we use a generative AI tool, providing more context can often lead to better output. What if we could apply this to our communication with other humans? Milin Desai, the CEO of Sentry, says contextualizing communication will change the way you operate.

This week in episode 350, we’ll follow Milin’s story of changing companies and pursuing different levels of leadership. Listen closely to learn about the importance and impact of active listening, how practice with written communication can help us develop a clearer narrative, the skills needed in higher levels of leadership, and how we can evaluate new opportunities through the lens of scope and upside.

Original Recording Date: 09-29-2025

Milin Desai is currently the CEO of Sentry. If you missed part 1 of our discussion with Milin, check out Episode 349 – Expand Your Curiosity: Build, Own, and Maintain Relevance with Milin Desai (1/3).

Topics – Customer Discovery and Active Listening, Contextual Communication and Iterating on a Narrative, Scope and Upside, Necessary Skills at Different Leadership Levels, Enabling Active Participation

2:49 – Customer Discovery and Active Listening

• What Milin said without stating it explicitly was that we need to do a better job of asking people more questions to understand where they are coming from and what they care about. This is what Nick refers to as doing discovery, and it applies to the person working a ticket in IT just as much as the product leader or sales engineer working with a customer.
  • “AI is best when given the best context, so contextualize every conversation. And if you contextualize every conversation, it will change how you operate.” – Milin Desai
  • Milin gives the example of a support technician doing the work to close a ticket for someone but then taking a proactive step to let the submitter know there are other related issues you could help resolve. He classifies this as the “extra step” that some people just do without being asked.
  • Very few people are self-aware and like to rate themselves as the best at different things.
  • “That self-assessment is super important…. That extra juice that people are looking for is that contextualization, that personalization, that dot connecting…that is what will change you. And that comes with being curious, asking the questions, listening…active listening.” – Milin Desai
  • Milin says active listening is difficult for him, but it’s something he has become better at over time.
• John says sometimes the question a person asks is not the question that person wants the answer to. It’s not up to us to just answer the question that was asked. It’s up to us to go the extra mile and ask questions to get more of the context.
  • Milin shares an anecdote for people in customer-facing roles. Validation that a product pitch is resonating with a customer comes from active listening and questions. But there’s even more.
  • “But you forgot to ask a simple question…in the next six months, if you had a dollar to spend, would you spend it on this? We forget to ask the most important question. If I’m going to build it, will you use it? Will you buy it?” – Milin Desai
    • Without asking the above questions, product teams may relay that feedback from a customer was nothing but positive and not understand why product activation numbers are low.
    • We need to figure out why a customer would use a product or feature rather than assuming they will use it when it is pitched / suggested to them. Be intentional about understanding the customer’s priority as well.
• “The same principles apply to development and everything else in our lives too. If you only had an hour a day, what would you do with it? Start thinking that way, and it makes things very, very simple.” – Milin Desai
  • Nick says we could also ask about priority when pitching an internal project idea to management. Would someone approve the project in the next six months? John suggests asking how far out in someone’s priority list a project would be.
  • What if your project idea or the product you are pitching is not on someone’s priority list? Should you just stop there?
    • At this point with time left in a meeting you have options. Asking to tell someone what you are building is a mistake, and so is just ending the meeting.
    • “What if you spend the next 5 minutes asking, ‘what is the most important things you’re thinking through?’ Because yes, it may not be the current thing you are doing, but again, coming back to knowing what other people in the company are doing, it could be connected to another initiative, another project, another product that the team is building. So, coming back to the same curiosity we talked about, and knowing what’s happening around you, you may find something. Or you may just learn…. But you came ahead as a high IQ individual who is saving them time, who cares about them more than they care about selling a product.” – Milin Desai
    • It’s important that we learn to pause in this way to gain understanding. Asking someone what they feel is important or what their priorities are after they’ve said something is not a priority is an acknowledgement that what you brought them isn’t relevant.
    • Learning more about the priorities of your audience may bring about an opportunity for a different group / team if you’re plugged into what is happening in other parts of your organization.
    • One option is nothing comes of it, and you learn something.
  • Nick says once we learn what someone thinks is important, we might get a much better idea than what we originally came to the meeting with.

9:00 – Contextual Communication and Iterating on a Narrative

• John says this goes back to empathizing with the customer and living in their shoes. Part of this job is to collect customer priorities and report it back to your organization. This information might indicate a product a company is building does not solve the right customer problems or doesn’t align with customer priority.
  • From a career perspective, people might think they need to do all of this alone – get on the customer calls, understand what customers want, and synthesize it to relay to other teams.
    • When Milin was a product manager, he started pulling in other team members to be on customer calls with him. This began when Milin was at Riverbed, but Milin tells us he leveraged it much more during his time at VMware.
    • “The interpretation of that conversation can be very different…. After that call is finished, you ask for their interpretation. Did they have happy ears? Did you have happy ears? But more importantly you as a team get on the same page about the opportunity.” – Milin Desai
    • Milin is speaking about promoting collaboration between product managers and engineering teams by ensuring the engineering team members have access to the same set of information. Getting them to hear information straight from a customer helps promote alignment better than receiving feedback only via the product manager who spoke to the customer. Being part of the live conversation is also better than only having access to the recording.
    • Letting other members of your team that you work closely with participate along with you is extremely important according to Milin. You don’t need to do it alone.
• “So, I think that participation is really important, and the second most important thing in any career progression, anything from non-tech or tech, is communication…contextual communication…. Talking to a VP versus an EVP versus a CRO…everyone is different. We as humans don’t spend enough time on contextual communication in our personal or professional lives. And I would say the single biggest thing I see people make a mistake on is not invest in communication, written form communication….” – Milin Desai
  • If communicating to an engineering team, have them feel they were in that conversation. Give them a synthesis of the problems you talked about and what happened as a result.
    • Storytelling and communication are important to provide your perspective on what happened to others.
  • We can write our thoughts down and then iterate on them. When the thoughts are fully formed, we can share them with a group. Spend time writing down your thoughts, and contextualize them for the audience with which you are sharing them.
    • When we write down our thoughts in draft form, Milin says it should feel natural and not take a lot of time. The story arc can be cleaned up as a next pass / next iteration.
• John mentions there is a difference between a transient idea and something you take the time to articulate through writing. The latter is something you can understand and have a conversation with others about. John talks about writing as something that enables fully formed thoughts and the evolution of those thoughts.
  • Milin had the opportunity to work for Marin Casado (founder Nicira), and Martin encouraged people to write things down because “you don’t think in PowerPoints.”
  • Milin has developed a habit of writing over time. When he gets an idea, even if it is sitting on a train, he might write it down and save it in his e-mail drafts folder to get it out of his head. Milin will then come back to it later (a day, a week, etc.) to refine it and then share with a larger audience.
  • Martin Casado also encouraged people to think like a story.
  • “The art of storytelling allows you to bring a point of view to the world.” – Milin Desai
• Nick says this idea of writing, letting it sit for a time, and coming back to refine what you wrote sounds like a great way to prepare for scenario-based interviews.
  • Milin shares some of the feedback he gives people who have completed an internship at Sentry.
  • “Make sure you have a narrative around this. If you choose not to come back to Sentry for a full-time job, when somebody asks you what you did, you have a compelling narrative around what happened and what you learned…. You’re absolutely right. You need to own the narrative and drive it. But you need to find that balance between too much, too little, too boasty, or not telling enough about yourself.” – Milin Desai
• As we develop a narrative, the brevity and depth might change as we change roles. In Milin’s case, he moved to product management but then began to move into leadership positions. How did he see his narrative change in depth and brevity over time?
  • Milin says it has been the hardest thing. Written form communication is hard.
  • We should be self-aware and self-critical but not let these things affect our confidence.
  • “I just want to make sure everybody understands when I keep saying these things, it’s not about breaking your confidence. It’s knowing who you are and then improving on it.” – Milin Desai
  • Milin tells us he is either very verbose or very succinct, and writing / narrating a full story has taken time to improve. Milin is very good with story arcs, but it’s writing the entire story which is the hard part.
  • “That’s been my strength. I can get you to understand the core, the why, very quickly. But then when I have to make it medium form or long form, I continue to struggle in that. That’s been work in progress.” – Milin Desai
  • This is the contextual communication piece of things. Milin talks about his experience doing all-hands calls as a general manager or as a CEO.
    • Giving too much information in these cases will lose the audience. Most of the time you have to find a middle ground between too much and too little information.
    • Milin says the question-and-answer section of these all-hands calls tells you where the gaps are. He would fill in the gaps either using offline mechanisms or a smaller set of meetings to address these questions. Milin also said it took him a while to get to this point.
    • “And it takes practice to take 3 pages and make it 1 page and make it relevant. It’s really art.” – Milin Desai
    • Maybe AI tools can help here, practice certainly helps, and knowing your audience helps.
    • Knowing your audience is part of contextual communication.
    • Milin says he’s done a lot of iteration and practice to develop these skills.

17:57 – Scope and Upside

• Regarding Milin’s transition away from Riverbed…
  • Milin says he really enjoyed his time at Riverbed but had hit a wall. In aggregate from a dollars and cents perspective, making the move to VMware was a step down.
    • Six months after making the move, Riverbed stock doubled and split.
  • “But I had zero regret, and this is super important. Why did I move? I moved because I had wanted to spread my wings more, and it looked like the organization that I loved could not make that happen. So, I had to do something about it. I waited, and then I moved on…. I had to take a step down to make that step up. I got lucky…good choice, great people, great mentors at VMware…. I had reached a point where I needed to spread my wings, and that opportunity was not showing up. So, I made the call.” – Milin Desai
  • Everyone has their own reasons for leaving a company. Milin would first encourage us to be patient and not make abrupt decisions. We should seek to leave a company better than when we joined it.
  • When Milin made the decision to leave Riverbed, people immediately thought it was because something was wrong. Nothing was wrong with the company. Milin needed to spread his wings.
  • “Career trajectory does not always have to be a step up. It can be sideways or…down. You look at the opportunity…. I looked at scope, upside, and then I believed that if the scope and upside would work out, things would work out for me. And they did.” – Milin Desai
  • Milin had the opportunity to go and focus on networking at VMware at a time when this was an emerging area of focus within the company. It was a chance to build upon his existing expertise.
  • Milin talks a little bit about his first manager at VMware (Ushan) and how that person’s support accelerated his progression within the company. When the time came, this manager supported Milin taking on a different role within the company.
    • “It’s crazy. I’m telling you…people make people.” – Milin Desai, on having great managers
  • Milin would encourage listeners to optimize for scope and upside, even if you need to take a small detour.
  • In Milin’s case, he did not know many people at VMware when he made the move from Riverbed. It was a risk he took based on the scope of the role he would be in, and it worked out.

21:20 – Necessary Skills at Different Leadership Levels

• John asks Milin about the difference in skills for each of the roles he has held from individual contributor to first-line manager and upward. John says getting to the next management level does not mean all the skills you had to that point are going to help you (i.e. new skills may be required).
  • “The first thing I am going to tell you is that management is hard. You should know you want it because it’s more than you…. I want everybody kind of walking into that role to realize that it’s a lot of work, and it will never get easy.” – Milin Desai
  • A manager has team members working for them, but there is an additional burden that requires translation of the greater organization’s expectations to your team.
  • Milin says the skills you need as a manager are not something you can take a class to gain but rather something you learn over time. We can also learn from the great managers we’ve had.
  • Milin knew what great managers looked like. They let him be himself, allowed him to take initiative, had high expectations, and they gave him context.
  • Milin found it easy to manage people who were like him, but his biggest lesson was adjusting to the different ways in which people on the team operate and bring value. It was important to create a forum to enable all types of people to succeed.
  • John says we learn how we as individuals are managed well (because it is modeled for us) but not necessarily how to best manage people who need to be managed differently (i.e. needing different types of guidance / structure / guardrails, etc.). Milin continues to struggle with this.
  • Milin likes to be pointed in a direction by a manager, and he can do the rest. Milin would come to a manager with problems when needed, but he will figure out how to get what he wants from a manager.
    • Milin reminds us of the time he was asked to go find a new role and how much it changed him.
    • Learning how to manage people different than you is a skill that takes time to acquire.
  • “There’s a point in time when it’s not about you or what you bring to a team. It’s about who you can hire….” – Milin Desai, on an aspect of rising to more senior leadership levels
  • When Milin was moving up to senior vice president, it became more about whether he could bring in exceptional senior talent. This kind of caught him by surprise, but Milin knew he could go and figure out how to do it well even though it might not have come naturally to him. This was a new aspect of leadership after he had gained experience running a business unit and making it profitable.
    • “If you bring in the right people, you automatically become potentially a great manager because they unburden you. They understand you really well.” – Milin Desai
    • Milin says we should be willing to bring in people who are smarter than us, and we should be ok with that. He’s never had an issue with it, but some people do.
  • Hiring the right people is a form of leaving an organization in a better state than you found it.
  • Moving on from people is also something you learn as you move up. Milin calls this active management.
    • “There’s a point in time where a person could be doing everything they are supposed to be doing. They have been with the organization, but the organization has shifted…. And this person is not able to adapt to it. It’s the company transitioning at that point. It’s not the person. And the ability for you to quickly recognize that for this phase of the journey…somebody you had loved before is not going to work out is probably one of the hardest things you will do as a people leader.” – Milin Desai
• When John was at Google, they talked about rearchitecting a product when the user base increases by a factor of ten. Similarly, the people organization has to be rearchitected.
  • “There is a journey of an organization. It is a living, breathing thing, and it goes through its own phases. And through that phase, there are some people who grow through every phase and continue to be part of the organization…. There is a time when somebody who was a perfect fit no longer is a fit…. To identify that and to make that person successful in a different role in the company or something else…those were the things I had to…learn at these different levels. It’s hard.” – Milin Desai
    • Some employees may only be part of 1 or a couple of phases of an organization’s growth / change.
  • Milin gives the example of people later in their careers who are very self-aware. They might understand that the most enjoyment for them is found when they work in startups that have between $10 million and $100 million in annual recurring revenue, for example.
  • Milin shares the example of bringing in someone to work with him who helped build a specific team and then others who helped scale the team and greater organization.
  • Other senior leaders taught Milin that bringing in the right kind of senior talent would free up some of his bandwidth to be spent in other areas.
  • Milin says he has luckily not needed to let people go because a business was not profitable.
  • “Through that journey, the thing that has inherently worked, continues to work, is writing down my intention for the org, for the team, for the company…what we will bring to the table and keeping that written and clean 24 by 7. It doesn’t become stale…. That has been the consistent point of help besides having great people to work for.” – Milin Desai
  • According to Milin, someone can write an 18-month strategy, but they should go and clean it up every 3 months.

29:55 – Enabling Active Participation

• Nick says by maintaining clarity on all of these things, it cascades to help leaders like Milin understand what the roles and job requirements within the organization should be, even if they are not formally changed.
  • Milin says having it written down helps with everything.
  • “It’s super hard to cascade a point of view or a vision. You have to repeat it multiple times, in multiple forums, and everything else. But if that itself is stale…it becomes really hard. So, I still to this day tell everyone, ‘give me a one-pager of where you’re taking the team for the next 3-6 months. If you don’t have that, how will you be effective?’” – Milin Desai
  • The one-pager Milin mentioned is different than a feature or function to be built. It’s more about outlining the set of problems a team will solve in the short term (i.e. next 6 months) and then coming up with the measurements of how to do it within that specific time frame. He suggests highlighting the longer-term problems the team wants to solve as well.
    • These things are written down and get revisited regularly by the team (maybe every 3 months) to determine if they are still relevant. Milin calls this “active participation.”
    • “Are these still relevant? I want you all to think about it. Active participation, right? Now they get a point of view on the 3 things next six months we agree and the 4 things long term maybe we need to change or something like that. So that allows for active participation. I would say that’s another great thing I learned as my roles started getting bigger and the scope started getting bigger.” – Milin Desai

Mentioned in the Outro

• Contextual communication has many layers to it.
  • We can share context verbally with others but also gain it from them in the way we ask questions.
  • We can also provide context to others through writing. Milin has done this for a long time. He will write a draft and iterate on it regularly to keep it fresh and clear.
  • Duncan Epping uses writing to learn
    • Episode 303 – Write to Learn and Learn to Present with Duncan Epping (1/2)
  • Jason Belk emphasized developing his narrative through writing before talking about it
    • Episode 284 – Draft Your Narrative: Writing and Building a Technical Portfolio with Jason Belk (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_
  • Leave a Comment on Your Favorite Episode on YouTube
• If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.
• If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

How curious do you think you are at work? Take a second to rate yourself. After today’s conversation with guest Milin Desai, you’re going to want to dial that curiosity up a notch.

Milin is currently the CEO of Sentry, and one of the keys to his success from the very beginning was allowing the scope of his curiosity to expand over time…beyond specific projects and even beyond his job role. Perhaps without realizing it, Milin was doing the work to build and maintain professional relevance.

Listen closely in episode 349 as we follow Milin from his early days as a computer science student through roles as a QA tester and software developer all the way into technical marketing. You’ll hear advice for expanding your own curiosity inside your current company, ways you can provide value to a mentor, and an empathetic approach to customer conversations that can help you build relevance and develop a strong reputation.

Original Recording Date: 09-29-2025

Topics – Meet Milin Desai, A Unique Trait, Internships and Job Interviews, Curiosity and the Importance of Control, Mentorship as a Stream of Active Conversations, Beyond the Scope, Becoming Relevant in Something Different

2:40 – Meet Milin Desai

• Milin Desai is currently the CEO of Sentry.
  • Sentry helps teams find where code is broken in production and helps them fix it fast, and with AI, fixing it faster is greatly accelerated.

3:15 – A Unique Trait

• Around 7th or 8th grade Milin recognized how much he enjoyed math and science in school. Milin had an affinity for STEM (Science, Technology, Engineering, and Mathematics).
• Milin cites his dad, a mechanical and electrical engineer, as a big influence. Going into 10th grade, Milin thought he would pursue mechanical engineering.
• Milin’s cousin Rajiv (who had worked for NASA) would come visit and began showing Milin some of the work he was doing. This is the point at which “everything changed” for Milin, and he decided to pursue computer engineering / computer science.
  • Milin also tells us he built hundreds of websites in India during the time of dial up modems.
• Milin pursued an undergraduate degree at a school in Mumbai, but his family knew he wanted to come to the United States.
  • Milin came to the United States in 1999 and attended USC (University of Southern California) to purse a master’s degree.
  • The potential for opportunity and the vastness of the United States captivated Milin.
• Did Milin ever ask Rajiv what he should study, or did he naturally gravitate toward those areas?
  • Rajiv would have conversations with Milina and show him the work he was doing.
  • Milin started working for Rajiv while pursuing his undergraduate degree. He was building websites for companies in India.
  • The building of the websites was interesting to Milin, but he was also doing the selling part. Milin had to make a pitch to companies explaining what a website could do for them, share the price, and collect the check if they said yes.
  • “Not only did he influence me in kind of figuring out…this is where the opportunity is and inspire me…but he also went on to tell me that I have a unique trait where I can talk business tech selling, and I know the technology part. And I can bridge the two worlds. He was one of the early people to recommend that in the long run I may want to think about the business side or…the entrepreneurship side of things when it comes to tech, not just the programming or the systems side of things. And he in fact felt my combo made me more relevant…in that lane versus just staying a programmer.” – Milin Desai
  • Rajiv gave Milin these cues early on in addition to inspiring him to do the work.
  • As people who work in sales engineering today, John and Nick agree that the combination of technology and business value is very valuable.

7:49 – Internships and Job Interviews

• Milin began working for Veritas after he finished his master’s program as an entry-level software engineer.
  • Pursuing an advanced degree can give you the chance to pursue internships, and Milin had a family friend working at Veritas who introduced him to the hiring manager for a quality assurance (or QA) internship.
  • After successfully getting the internship at Veritas, Milin was doing QA for software-defined storage volume management.
  • Milin’s work during the internship led to a full-time offer from Veritas upon his graduation.
  • “The first break is always hard, by the way, to get. I see it even to this day with folks coming out of school. Not everyone…lands in the perfect opportunity right away, and the dots need to be connected. I’ve been fortunate enough to have people open doors and open opportunities…. But I remember being rejected a lot.” – Milin Desai
  • Milin tells us he struggled in job interviews as a new graduate. Many of his friends from school had multiple job offers from these conversations, and compared to them, Milin had much less success getting offers outside of the one from Veritas.
  • From a timing perspective, this was around the time of the market crash following the events of September 11, 2001.
    • “Even timing-wise, the difference between graduating with your master’s degree a year and a half versus 2 years. That six months made all the difference. A little luck, a little timing, and a lot of support.” – Milin Desai
• Did the degree program Milin pursued prepare students for job interviews at all?
  • Milin tells us that a school doesn’t really prepare you for the conversation you have in an interview. While you do learn deep systems concepts in school, for example, the interview questions are often situational.
    • “You definitely use those concepts, but you’re never in that setup until you go through that process. And I think interviewing is a little bit of an art form. Some folks are really good at it, and some folks even study it. There is some element of that. But I think the school prepares you with fundamentals. It doesn’t necessarily prepare you for that interview per se, and you have to kind of connect the dots…. You can prepare for it. Some people are just naturally good at it, and some people like me just suck at it.” – Milin Desai
    • Milin feels interviewing is sort of an art form. You can work to prepare yourself
• Did Milin think of interviews as somewhat similar to pitching a company on a website?
  • The selling part is easy according to Milin. In this motion you are telling a story, bringing a problem statement, and delivering value. It’s less about solving some kind of algorithm but rather trying to figure out if what you have to offer will address someone’s pain point.
  • Milin emphasizes the storytelling element of the sales process and the collaborative problem solving you’re doing with someone. It’s more of a conversation.
  • Selling is not about getting into an extreme level of detail like a technical interview can be. Someone could easily make a mistake in a technical interview when describing a specific step in the process and get off track. People can feel a great deal of pressure when in a job interview.
  • Milin feels job interviews are much more difficult than a business conversation. The latter is about human connection and building rapport with the other person.
    • Milin tells us his interview style is more about building human connections than testing the limits of a person’s technical depth.
• John mentions the difficulty in choosing a technical interview style that is well suited for effectively evaluating multiple job candidates. Does having a portfolio of code that is applicable to the role help with this?
  • John also brings up LeetCode style interviews if you’d like to read more about them.
  • Milin says quickly assessing a fit can be a challenge. It can be a combination of skills and experiences with other things layered on top.
    • Milin says the first interview might be more focused on solving some basic elements. But it’s helpful if a candidate can talk about and contextualize other work they have done (like working on an open-source project, for example).
    • "But to get in, there has to be a common baseline, a language, a form…. " – Milin Desai, on early round interviews
    • If interviews are challenging for you as they have been for Milin, you have to work through them over time.
    • “In the later stages what I would tell you is what is most attractive is people who have been from what I call 0 to 1 project where they start something are through the end. The end is not shipping actually. Shipping is just an intermediate point. End is adoption and the scaling and all of those elements. And to be through that journey 1, 2, 3 times is interesting to almost every organization out there…because through that you learn a sense of people, ownership, outcomes.” – Milin Desai
    • Early on the baseline is some kind of entry test. When looking for people with more experience, interviewers will ask about projects people have written about on their resume or elsewhere and how they solved problems within those projects. At this point, the portfolio becomes more interesting and can help you get an opportunity.
  • We emphasize the importance of a portfolio of projects and not just a portfolio of code.

16:16 – Curiosity and the Importance of Control

• How did the role Milin had at Veritas shape the rest of his career?
  • Milin says this was his first job and was an amazing experience that has filled him with fond memories of that time.
  • Milin emphasizes the importance of help from others during the course of his career.
  • The Veritas experience gave Milin the chance to work with great people, but he also found mentors within his area at the time (software volume management).
    • Milin mentions a mentor named Mark who remains a dear friend to this day.
    • “He kind of took me under his wing and explained stuff and was just there. And he didn’t need to do that…. Please, when somebody…experienced takes the time to go that extra mile you make sure you better jump on and do what’s needed. That was a friendship and mentorship I would say on a regular basis that really helped shaped my system thinking…. It was just the way we would talk about systems and concepts, and it really kind of expanded my mind…. The discussions are not always about this piece of code as much as how does this work with this part of the system…?” – Milin Desai
    • Mark was in a leadership role at the company and understood other projects that were in the works. Milin really enjoyed learning about those things even though they were outside his area.
    • Milin emphasizes the importance of curiosity that extends beyond what we own and even what others own. This ever-expanding curiosity was one of the most helpful things in addition to mentors early in Milin’s career.
    • We should also be willing to raise our hands to volunteer to solve a problem or work on something extra. This quality, in conjunction with being curious and having effective mentors, was essential to Milin’s success.
• After completing his first year at Veritas and getting a great review, Milin’s manager told him he needed to find a different role. This was not about job performance.
  • “I’ll tell you the positive out of it. It basically made me realize that I need to control my destiny. I need to keep working at it, not assume anything. It was the best thing that happened to me…. At that point in time, I found a different role. I found another set of great mentors. And things just took off because my mindset shifted from not just being curious and raising my hand. It changed into…I’ve got to take care of myself. No one else will. It was a healthy sense of paranoia of constantly wanting to prove myself. Again, not lack of confidence, impostor syndrome…none of that stuff. It was just about ‘am I doing everything absolutely possible that I become unshakeable?’ That was the most helpful thing that person did for me, but it changed everything.” – Milin Desai
• Did the manager who mentioned Milin would need to find a different role tell him he needed to search inside the company or externally?
  • Milin had to go do the homework to assess his options for new roles. It was up to him to make it happen.
  • “Being curious means you work beyond your project scope, you talk to other people, you get to know other teams. They get to know you. So, when something like this happens it is not like you just showed up at their door. It’s all connected in a way when you are part of something bigger than your project, your team. You take interest. You have conversations. You have lunch with people beyond your team. You do things kind of outside just general scope.” – Milin Desai, on curiosity as a network builder
  • When a job loss type of situation happens and people know you, it is a jumpstart on internal opportunities. A mentor, for example, might vouch for you as well when trying for a new role.
  • “At the end of the day there are humans involved in the process, and that’s where the first connection happens.” – Milin Desai

22:43 – Mentorship as a Stream of Active Conversations

• As Milin looks back, how would he describe ways we can be an effective mentee to a mentor?
  • It’s not about showing up unprepared and expecting magical wisdom to come from a mentor.
  • It’s also not about taking a wide set of problems.
  • “It’s an active conversation. It’s a relationship. And the relationship is not transactional…. It’s a constant stream of active conversations….” – Milin Desai
  • We should go into a meeting with our mentor prepared just like a board meeting. Take with you a set of 1-3 things the mentor could help you with.
  • Milin suggests we figure out how the mentor operates, and figure out how to leverage this. It’s about reverse engineering what a mentor brings to see if they can bring value to you.
  • “And it’s not like they are going to help you suddenly go from point A to point B. I think that’s another big misnomer around this. It’s just somebody as a guide point, as a reference point of…additional data.” – Milin Desai
  • When Milin looks back at the people who have helped him, most mentors were within the same company, but there were external mentors as well.
  • People tend to think a mentor only helps them (a unidirectional relationship). Throughout Milin’s career, he tried to find ways to help his mentors (i.e. taking something off the mentor’s plate).
  • “It became a mutually beneficial thing where they were being successful as well in spending time with someone like me…. It’s various phases, but I always tell people there is no professional mentor. There are professional coaches. That’s different.” – Milin Desai
  • Milin says active mentorship on scenarios or career things requires someone be in the business with you (in the same company), and it also benefits the mentor.
  • People confuse mentors and coaches, but any given person may need both an external coach and internal support systems (like symbiotic relationships with mentors).
• Was it the series of active conversations with mentors that pushed Milin in the direction of product management?
  • Milin encourages us to think back to his time focusing on storytelling and selling before graduating and put it together with his curiosity during his first year at Veritas.
    • Milin mentions spending time with leaders who worked across different functions of the company and how interesting it was to learn about interconnected projects across the company.
  • Now we fast forward to the time after Milin needed to find a new role.
  • “By the way, I was an average coder, but I made up for it with a lot of testing – making sure that it worked, it worked in different scenarios, the UX, the experience…. That’s where I learned…everything is about the user, not about me writing code.” – Milin Desai
  • Milin would send e-mails to product leaders inside the company asking if they had explored specific problem domains. He would make these messages thoughtful and include research. He would also ask questions offline after all-hands calls.
    • Milin mentions names like Jeremy Burton and Mike Spicer as leaders who took the time to respond to his messages.
    • The continued dialogue with product leaders helped Milin realize he wanted to try something different.
    • “I wanted to kind of go to the product definition side because I was really enjoying it, but it was a series of all of these coming together to that culmination. That encouragement, that active encouragement from the folks I just mentioned definitely also helped….” – Milin Desai

29:52 – Beyond the Scope

• Did Milin have any conversations with his manager at the time about pursuing product management before he made the move?
  • Milin feels he may have been operating like a product manager in some form by asking the right questions and being a little disruptive. He thinks people started to see this.
  • Milin’s next role was a technical marketing engineer at Riverbed. He did have the option to become a product manager under Symantec but chose to go to Riverbed.
  • “I made the shift first to a technical marketing engineer, and within a year they said…move over to product management…. I think people realized my aptitude, the way I was spending time, the contributions I was bringing…. I think I had to just make up my mind and start making that choice, which is what I did in 2006.” – Milin Desai
• John emphasizes that we do not always know how the puzzle pieces of experience will fit together later. Without exposure to different things, there is no way to put these together when it’s needed.
  • Milin says many people want to join startups because it will allow them to do many different things in an organization with fewer people. While this is true, not everyone takes advantage of everything a startup can offer in this regard.
  • While it is likely harder in a large organization to do this (do many different things to gain different experience), it is not impossible according to Milin. In fact, he’s changed roles within large organizations to do different things over the course of his career.
  • “There is so much you can learn by just inherently listening for the signals, being curious about it, having lunch with different folks.” – Milin Desai
  • Milin tells us that having lunch with different people or participating in extracurricular activities with your team can be a great time for networking. It’s something that takes you outside the scope of your role, and when you do it, you do not know where it might take you.
    • Milin used to play soccer during lunch, for example, which gave him the chance to network with people in the bay area.
  • Milin says we do not need to be extroverts and should do what is most comfortable for us.
  • "If you’re a curious person and you want to learn a little bit about marketing, you can just ask. And most organizations have good people. They will respond, which is what I was telling you about when I was talking to…all these people who were like 7 levels above me in the larger organization…. They chose to take the time to respond, which created encouragement…. " – Milin Desai
  • John says these are practical tips in going from 0 to 1 in one’s own career management.

33:40 – Becoming Relevant in Something Different

• What led Milin to apply for the technical marketing engineer role?
  • It started by being ready to do something different.
  • “I don’t even remember how I applied for it, but all I can tell you is when I spoke to the team and the people I was like, ‘wow. This is going to be so much fun.’” – Milin Desai
  • The role as a technical marketing engineer was really about telling people how to use a Riverbed product focused on WAN optimization. We might call it developer experience or developer advocacy today.
  • In the job interview, there were no questions about coding because this was a technical marketing job. But they gave Milin a homework assignment as part of the interview to share how he would test something.
    • According to the hiring manager at the time, (Phil), Milin went above and beyond for this assignment. In addition to explaining how he would do the testing, Milin built a PowerPoint representing the story he would use to educate people on this scenario complete with preconditions, advantages, etc.
    • It was the extra push on this exercise that got Milin the job.
  • At the time, Milin didn’t understand what it meant to work for a pre-IPO company (which Riverbed was at the time).
    • “But I didn’t even think about all this stuff. I just literally loved the people and the scope of the role, and I felt like this would be exciting. And I took it…. There will be a point in time in your career where you can choose the people you work for and choose the people you work with, and there is nothing more important than those two things in my opinion when thinking of what you want to do next. Where do you want to spend your time? And most people don’t optimize for that. They optimize for everything else…. Day to day, you’re going to spend more time with these people. As soon as I got to know this group I am like, ‘man, I want to be with this group.’ …It was the people. Just like everywhere else…it starts with people.” – Milin Desai
• John mentions part of technical marketing roles as well as developer relations roles is being what he likes to call “nerd famous.” You have to be a little bit of a draw for attendees. Does this align with Milin’s experience in technical marketing?
  • Milin says yes and no. He feels the people who succeed in these roles are there because they have depth.
  • “That, I think, should not be lost. There have been a lot of people who have come and gone if you notice in that…what people call devrel or whatever…. The ones who have survived and thrived and continue to be respected are the ones with depth.” – Milin Desai
  • Whether it’s writing a product design document or an engineering design document, Milin tells us it is a story very much like a movie script with a beginning, middle, and end. Great storytellers who can simplify things will do well in a technical marketing or similar role.
  • Another thing to consider is whether you are bringing value. If someone comes to talk to you about cooking and you love eating but not cooking, the conversation is kind of pointless.
  • “When you are not famous, the way you become relevant is you bring relevance to the other person in terms of what they care about and then to be able to help solve their problem.” – Milin Desai
  • Milin says when it comes to people in customer facing roles (product managers and many others), it is easy to get into “the diarrhea of our mindset.”
    • People get into the mindset that they are building a feature and need to tell the customer everything about it. And sometimes customers will just let you tell them.
    • “If you pause a little bit, understand what the other side wants, do the storytelling from that standpoint…highly, highly transformational.” – Milin Desai
  • Milin also tells us that keeping our word helps build our professional brand. Are we doing what we say we will do?
    • Getting someone an answer because you said you would, even if the answer is no, build rapport and relationship.
  • The personality aspect is needed to get the best opportunities according to Milin.
    • Milin gives the example of posting some information on bulletin boards about using Riverbed and NetApp together. People got to know him through the content he had shared and the value it brought them. Listen to the specifics of what happened when people would meet him in person.
    • “I feel like if you do it right, you do it for your audience, you know your audience…day in the life of…be in their shoes. I think that’s super important in that TME role, in the product manager role versus the internal, inside view of…we are building something. Nobody cares about your algorithm if it doesn’t work. So, tell me how I am going to use it. If it breaks, tell me when it’s broken…all of that fun stuff. Live in the life, live in the shoes of your customer. Understand what they want, empathize with that, and from there, magic will happen.” – Milin Desai

Mentioned in the Outro

• There is a slow build of through Milin’s experience of developing that relevance. Examples would be:
  • Discussions with early mentors to understand systems and how projects within the company were connected
    • It takes curiosity to understand these things, and we need to have that same kind of curiosity when we help our co-workers or external customers with technical problems.
  • The questions Milin would ask and suggestions he would make to senior product leaders
    • Taking the time to put together thoughtful questions and suggestions made Milin relevant to those leaders, and they took the time to respond to his messages. That kind of thing does not happen unless you are bringing something relevant.
  • Creating the content at Riverbed
    • Milin was relevant to others because of the content he created. We can build relevance through content we create as part of our portfolio of work / public proof of work.
  • Much of Milin’s relevance came after he listened well or listened actively to be thoughtful in his responses.
    • This is what we should be doing in any role that has customers (externally facing or internal customers). If you’re in IT, your customers are the people whose problems you are trying to solve or those for whom you are trying to provide a technical solution.
  • Optimizing who we work for and who we work with is another way to remain relevant.
    • If we like who we work for and with we will want to provide value to them and therefore remain relevant as a member of that team.
• We talked about mentorship in Milin’s career and the bidirectional value flow between mentor and mentee, emphasizing that the mentee should try to bring value to a mentor.
  • For more discussions about mentoring, check out episodes under the mentoring tag on our website.
  • We would also point you to 2 specific episodes that represent a masterclass in mentoring:
    • 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)

Contact the Hosts

• The hosts of Nerd Journey are John White and Nick Korte.
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• If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.
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As managers inherit larger teams inside flatter organizations, we might immediately point out the challenges. But what about opportunities? Despite the trend, those who seek to lead (in a management capacity or otherwise) have the chance to intentionally build a better culture.

We pulled in former guests Shailvi Wakhlu, Neil Thompson, and Abby Clobridge in a roundtable format to get actionable strategies.

In episode 348, we present actionable strategies for managers and individual contributors to thrive in this new environment. Listen closely to understand the importance of improving one’s communication skills, the unique opportunity and impact of the player coach / team lead, the critical elements of a manager’s role, and advice for job seekers in a tough market.

Original Recording Date: 09-27-2025

Topics – Framing Part 2 of Our Discussion, Opportunity for the Player Coach, Modeling the Benefits of Improved Communication Skills, Management Support of Strong Communicators, Individual Contributors and Communication, Succeeding as a Manager of a Large Team, The Culture of Large Teams, Advice for Job Seekers in a Tough Market, In Closing

1:01 – Framing Part 2 of Our Discussion

• Last week in Episode 347 – Organizational Flattening: Understanding the Trend, Career Challenges, and Opportunities (1/2), we introduced a slightly different format that we’re continuing this week based on an industry trend.
  • The trend of organizational flattening in our industry has been top of mind for us. We’re seeing the continued layoffs in tech often times result in fewer management layers and an increase in the number of people reporting to a single manager.
  • This topic is too big and has too many angles for a single conversation. We wanted to bring together multiple expert perspectives on this issue in a single episode. We’ve reached out to a handful of former guests and sent them specific questions on this topic. Those guests were kind enough to record their answers and send them back to us.
  • Consider this a Nerd Journey roundtable or collection of hot takes from trusted voices. Our goal is to amplify their advice and provide a diverse set of strategies for navigating this landscape.
  • In the first episode (last week), we explored the trend of flatter organizations and the consequences for your career path and team culture. This week in part 2 we will focus on actionable insights for thriving in this environment.
• Here’s the full set of episode links we will share throughout the conversation if you would like to hear more from one of the former guests who participated:
  • Shailvi Wakhlu
    • Episode 210 – A Collection of Ambiguous Experiments with Shailvi Wakhlu (1/2)
    • Episode 211 – Structure the Levels of Contribution with Shailvi Wakhlu (2/2)
    • Self-Advocacy: Your Guide to Getting What You Deserve at Work by Shailvi Wakhlu
    • A special 15% off link for Nerd Journey listeners to Shailvi’s self-advocacy course can be found here.
  • Neil Thompson
    • Episode 193 – Communication for Specialists with Neil Thompson (1/2)
    • Episode 194 – Question Askers and Problem Solvers with Neil Thompson (2/2)
    • Teach the Geek YouTube Channel
  • Abby Clobridge
    • Episode 292 – Library Science: Information Architecture and the Synthesis of Details with Abby Clobridge (1/2)
    • Episode 293 – Enterprise Knowledge Management: A Consultative Approach to Solving the Right Problems with Abby Clobridge (2/2)

1:42 – Opportunity for the Player Coach

• We’ll start by discussing the opportunity of being a player coach (another way we often reference the team lead or tech lead role).
• Shailvi Wakhlu is a leadership speaker and data consultant with experience building and leading large organizations, including structuring of job levels for career paths. We spoke to her in episodes 210 and 211 She’s also the author of Self-Advocacy: Your Guide to Getting What You Deserve at Work.

Our question for Shailvi:

• As organizations flatten and there are less manager roles, does this create an opportunity for people to become a technical lead or team lead to help the manager scale? We would love to hear any perspective you have on how the team lead / tech lead (i.e. player coach type role) changes as a result of the org changes.
  • Even without the trend of flattening or decreasing the number of managers, there has consistently been an opportunity for people to demonstrate the mindset of group leadership. Someone could be a project lead, a team lead, or a technical lead.
  • The technical lead focuses more on technical standards to which a team needs to adhere.
  • “I think anything that you do that helps your manager manage the team, scale the team, grow the output, or just have better focus…has always been a good way to get your foot in the door for those type of roles in the future.” – Shailvi Wakhlu
  • Shailvi remembers working at companies where several people wanted to someday get into a management role. Even in times of heavy hiring, there is no way to accommodate everyone who wants to eventually do this.
    • People stepping into those lead roles would have a leg up on other candidates for future management roles.
    • “If I see somebody is doing a fantastic job of managing a project, I know that there is a subset of manager responsibilities that they’re able to handle. If I see them doing team events…if I see them stepping up on technical leadership, defining standards…all of these things kind of point to that same larger skillset. And I always encourage that even if there is no formal capacity in which you can do this, even if you create your own opportunity and showcase that…this is a space where I see our team could improve…even without the manager title I think you have plenty of options to contribute at that stage…and definitely in this type of a market where there are less manager roles.” – Shailvi Wakhlu
  • Shailvi believes the job market will bounce back, and when it does, there will not be enough people who have been managers and have done things like performance management, skill assessment, and hiring. People who can showcase they have some of this experience and the right mindset have a good start toward landing a management role.
    • Before Shailvi was a manager, she was the hiring lead on her team of 2 people. Shailvi defined the standards (measurements, rubrics, etc.) for the interview process. She tells us doing this made it far easier to transition into a full-time manager role.

5:25 – Modeling the Benefits of Improved Communication Skills

• We wanted a perspective on communication in this current climate and reached out to a former guest with expertise in this area.
• Neil Thompson is the founder of Teach the Geek, an organization that helps technical professionals in STEM (science, technology, engineering, and mathematics) improve their public speaking and presentation skills. He’s also the host of the Teach the Geek Podcast. We originally spoke to Neil in episodes 193 and 194.

Here’s what we asked Neil:

• How do you think team leads or technical leads (sort of that player coach role) play into the development of strong communicators? Where do they help people where managers cannot?
  • Players (or individual contributors on a team) don’t see themselves as managers and would not be modeling themselves after managers. A player coach is way closer to each member of the team’s current role than a manager.
  • Player coaches who are adept at communicating well can model these skills for other members of technical staff and educate them on the benefits (and potential opportunities) of improving their communication skills.
  • Neil points out it could very well be a player coach was moved into that role because of their communication skills. Technical staff members are far more likely to want to invest in improving their communication skills once they see and understand the benefits of doing so (thanks to the modeling of player coaches).

7:09 – Management Support of Strong Communicators

Another question we had for Neil:

• "What challenges will managers face trying to develop good communicators when their team is huge, and what can they do to be more effective when this happens?
  • With a large team, one challenge will be getting buy-in from all team members on the idea of improving their speaking skills.
  • Assuming this is the case within your organization…Neil encourages leaders to let their direct reports know that improving speaking skills increases visibility within the organization, and opportunities tend to come to those with greater visibility.
  • Technical people will not want to be passed over for opportunities based on something they can control, especially if they recognize the reasons others have been given new opportunities was due to improved communication skills. And they would certainly be motivated to improve communication with decision makers who can give them opportunity.
  • As part of his work at Teach the Geek, Neil encourages companies to develop speaker training programs for developing technical staff members.
    • One challenge to this approach is getting technical staff to agree on the priorities of this kind of training program. Neil suggests sending out a survey to technical staff members to make sure this is well understood. Technical staff may want to understand how to better engage an audience, get ideas for balancing technical depth and clarity, ways to minimize the use of jargon, etc.
    • If you do take a survey of technical staff, incorporate at least the top 3 priorities as indicated by survey results into a speaker training program.

9:07 – Individual Contributors and Communication

We also wanted to know from Neil:

• How can the individual contributor develop those strong communication skills to build rapport and communicate the value of their work to a busy leader?
  • If technical staff members have gone through a speaker training program like was mentioned earlier, they will want to look for opportunities to practice continued development of those skills.
  • Neil highlights the importance of organizations offering speaking practice opportunities for members of technical staff.
    • One easy way to do this is through a lunch and learn. This forum is a great way to allow people to give presentations covering their work progress / accomplishments that both managers and even non-technical staff members can listen to and learn from.
    • Neil points out the usefulness of this information for nontechnical staff members such as HR personnel responsible for screening job candidates. Sitting in on these presentations can, for example, improve the quality of those screening conversations and overall candidate selection rather than relying solely on job descriptions which may be outdated.

10:31 – Succeeding as a Manager of a Large Team

Another question for Shailvi:

• What are your top suggestions for succeeding as a manager of a large team in this environment?
  • Shailvi says in today’s environment, the definition of a larger team of direct reports has changed.
  • “A few years back that large team definition was…more than 8. Nowadays I think it’s very common to see people who have 8, 10, 12, 15 direct reports…and nobody’s blinking an eye.” – Shailvi Wakhlu
  • At her previous job, Shailvi had 6 direct results that trickled down to an organization of 30 people total reporting up to her.
  • Success when you have a large number of direct reports takes a lot of intentionality.
  • “What is your role as a manager? One is to provide clarity for your team to make sure they are aligned with business goals…to make sure they know what is going to be rewarded, what is not rewarded, things like that. The other big piece is making sure you are available to help grow the careers of everybody who has taken a chance on you and is putting the fate of their careers…in your hands. So how do you make sure you do those two pieces successfully?” – Shailvi Wakhlu
  • Shailvi emphasizes the importance of streamlining communication and information sharing in both directions (from you to your employees and in the other direction). Make sure people know what they can expect from you.
    • Do people know what you will communicate and when you will communicate it? For example, will you openly communicate the necessary context so that people can effectively recalibrate?
    • Do people have the psychological safety to share their challenges and concerns with you?
    • Are team members comfortable sharing their professional goals with you (i.e. opportunities and growth areas), and are you providing critical feedback to support pursuit of these goals?
  • Shailvi also highlights the way a manager delegates as key to success.
    • Having a large team means there is opportunity for people who want to move into some type of leadership role to gain experience.
    • “It’s very important to make sure that you are public in your appreciation for people who help you in the smooth running of the team…. If it’s a non-promotable task…if it’s a housekeeping task that nobody’s ever going to get promoted because of…do not outsource that. I think you do a disservice to people’s careers if you’re asking them to do…general housekeeping and you’re basically asking them to do it above their existing job. And, you’re never going to consider that work important enough to actually think that they’re performing at a higher level. So, delegate work that is actually useful. Delegate work that is actually helping them improve their skills and their visibility in showcasing that they have leadership capabilities….” – Shailvi Wakhlu, on managers delegating responsibility which allows the right type of experience

14:48 – The Culture of Large Teams

One last question for Shailvi:

• How can leaders create a culture that is impactful within their organization when the structure of the organization is designed to allow less time spent with each person underneath a leader?
  • Shailvi feels this is extremely relevant in a world where managers have too many people reporting to them. There is often not enough time to get information flowing between the manager and direct reports for the benefit of the company.
  • Some of the work Shailvi does as a consultant is with organizations who want to build strong teams optimized for performance, productivity, and profitability.
  • “I feel that…leaders tend to anchor on the limited time they have with all the people who report up to them that they just sort of spend that in getting status updates…. It’s very one-sided.” – Shailvi Wakhlu
    • Status updates can be shared in an e-mail or updated on a JIRA board.
  • “The part that I encourage leaders to think about is how do you create a situation where everybody on your team understands the link between their work and business success…where there is no ambiguity about it, where they clearly understand…this is the part of my job that is going to help the company succeed? And that is how you build that excitement with people….” – Shailvi Wakhlu
    • A sense of personal ownership usually breeds accountability. To them it won’t just be finishing a project but rather helping the company succeed with a specific goal.
  • “Creating that culture of transparency, open communication…I think that is something that takes intentionality on the part of the managers. It takes repetition where you keep showcasing how you’re rewarding work, how you are setting expectations. You can’t have unevenness….” – Shailvi Wakhlu
    • Leaders should use the limited time they have with employees to understand their motivations. Work to help your people with their careers, help them understand the opportunity in front of them, and consistently provide clarity.
  • “How you show up as a leader is something that is more important than anything else that you say. Are you accountable for your own actions? Are you taking ownership of larger pieces that are under your area of ownership? When leaders can…structure what they want to spend time on, it goes a really long way.” – Shailvi Wakhlu

17:57 – Advice for Job Seekers in a Tough Market

• To close our discussion, we wanted some actionable advice for navigating a tough job market. We’ll hear once again from Abby Clobridge. Abby is the founder and principal consultant at FireOak Strategies and has deep expertise in the realm of knowledge management. Abby was a guest in episodes 292 and 293.

Our question for Abby:

• In a tough job market, what do you think job seekers should be doing to stand out that maybe they aren’t right now?
  • Treat your job search like you would a portfolio project. Show what you are doing and what you are learning by building something tangible. It could be automating something, creating a dashboard, or writing a blog describing how you would solve a problem.
  • Abby says we can also host micro conversations made up of 3-4 peers, mentors, or formal colleagues in a roundtable format. These can be virtual or in-person. This can strengthen your network and benefit everyone involved.
  • We can also practice visible curiosity by posting about a book we read or a tool we used. Abby calls this “learning out loud” and something that can act as a signal to future employers that we are engaged, adaptable, and someone who wants to connect people.

19:12 – In Closing

• We want to say a huge thank you to all of the guests who contributed to this episode! If you want to hear more from them, you can find the full conversations…

  • Abby Clobridge was a guest in episodes 292 and 293.
  • We spoke to Shailvi Wakhlu in episodes 210 and 211 She’s also the author of Self-Advocacy: Your Guide to Getting What You Deserve at Work.
    • Here’s a special 15% off link for Nerd Journey listeners to Shailvi’s self-advocacy course.
  • We spoke to Neil Thompson in episodes 193 and 194.

• What did you think of this format, and what other questions need to be answered on this topic? Send us an e-mail at [email protected] to chime in.

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_
  • Leave a Comment on Your Favorite Episode on YouTube
• If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.
• If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

What happens when layoffs lead to organizational flattening, fewer managers, and larger teams? It’s a trend we’re seeing in the tech industry at large right now impacting team dynamics and career paths. To understand what’s really happening and the overall impact, we pulled in former guests Abby Clobridge, Shailvi Wakhlu, and Leanne Elliott in a roundtable format.

In episode 347, we explore the trend and the unique challenges it presents to consulting firms, managers, and individual contributors working with and inside flatter organizations. Listen closely for the impact to job levels, what this means for top-tier individual contributors, how companies are thinking about knowledge management, employee loneliness and wellbeing, and where some unexpected opportunities lie for those willing to step up.

Original Recording Date: 09-27-2025

Topics – Framing Our Discussion and a Slightly Different Format, Defining the Trend, Impact on Career Structure and Ambiguity, The Challenge of Reaching Top Tier Positions, Internal Risk and Potential Loss of Knowledge, Strains on Execution, Impact to Team Dynamics, From Problem to Opportunity

1:01 – Framing Our Discussion and a Slightly Different Format

• For today and in next week’s episode, rather than introducing a guest to share their career story and lessons learned, we’re trying something a little different.
• Recently we sent a follow up question to a former guest whose response sparked an idea for this format.
  • The trend of organizational flattening in our industry has been top of mind for us. We’re seeing the continued layoffs in tech often times result in fewer management layers and an increase in the number of people reporting to a single manager.
  • This topic is too big and has too many angles for a single conversation. We wanted to bring together multiple expert perspectives on this issue in a single episode. We’ve reached out to a handful of former guests and sent them specific questions on this topic. Those guests were kind enough to record their answers and send them back to us.
  • Consider this a Nerd Journey roundtable or collection of hot takes from trusted voices. Our goal is to amplify their advice and provide a diverse set of strategies for navigating this landscape.
  • In the first episode (this week), we explore the trend of flatter organizations and the consequences for your career path and team culture. Next week in part 2 we will focus on actionable insights for thriving in this environment.
• Here’s the full set of episode links we will share throughout the conversation if you would like to hear more from one of the former guests who participated:
  • Abby Clobridge
    • Episode 292 – Library Science: Information Architecture and the Synthesis of Details with Abby Clobridge (1/2)
    • Episode 293 – Enterprise Knowledge Management: A Consultative Approach to Solving the Right Problems with Abby Clobridge (2/2)
  • Shailvi Wakhlu
    • Episode 210 – A Collection of Ambiguous Experiments with Shailvi Wakhlu (1/2)
    • Episode 211 – Structure the Levels of Contribution with Shailvi Wakhlu (2/2)
    • Self-Advocacy: Your Guide to Getting What You Deserve at Work by Shailvi Wakhlu
    • A special 15% off link for Nerd Journey listeners to Shailvi’s self-advocacy course can be found here.
  • Leanne Elliott
    • Episode 237 – The Psychological Transition of Layoffs with Leanne Elliott (1/2)
    • Episode 238 – Managers as Culture Keepers with Leanne Elliott (2/2)
    • Episode 340 – Task Cohesion: Managing a Larger Team in a Flatter Organization amidst a Climate of Uncertainty with Al and Leanne Elliott (1/2)
    • Episode 341 – Champion Your People: Role Clarity for the IC in the Chaotic World of Work with Al and Leanne Elliott (2/2)
    • Subscribe to the Truth, Lies and Work Podcast

2:48 – Defining the Trend

• Abby Clobridge is the founder and principal consultant at FireOak Strategies and has deep expertise in the realm of knowledge management. Abby was a guest in episodes 292 and 293. We wanted to get an outside perspective from someone who works with many different organizations on various projects.

Our question for Abby:

• Within your customer base and set of prospects, do you see companies currently doing organizational flattening of management layers with an increased number of direct reports for managers? And if you have seen it, what do you think is the reason for this? We’ve heard of 20 or more people under a single people manager.
  • Several of Abby’s clients are going through huge changes, sometimes resulting in entire teams and departments (like IT) being eliminated. In some cases, IT work is being shifted to MSPs (managed service providers), which has pros and cons.
  • According to Abby, the economic climate and the rise of AI adoption has made this year tumultuous for everyone.
  • Abby is seeing companies put more and more people under a single people manager.
  • She tells us that managers with extremely large teams have no way to build real relationships. The large team often results in employees not being able to rely on their manager for much from day to day.
  • “That kind of dynamic is a recipe for cultural toxicity really quickly too.” – Abby Clobridge

4:25 – Impact on Career Structure and Ambiguity

• Shailvi Wakhlu is a leadership speaker and data consultant with experience building and leading large organizations, including structuring of job levels for career paths. We spoke to her in episodes 210 and 211 She’s also the author of Self-Advocacy: Your Guide to Getting What You Deserve at Work.

Our question for Shailvi:

• In our previous conversation we talked a lot about job levels. Do you think flatter organizations make it more difficult to clearly define those job levels, or are big companies that are cutting head count to flatten even thinking about this? What do you wish these companies would consider?
  • “The stated reason that companies move towards flatter organizations, I think, is because they want to get rid of hierarchy. They want to say…we don’t want the lack of a higher title to restrict you from having a greater impact on the company. And I think that’s a fair goal…. However, I think in reality how it actually ends up playing out is, one, when you have a very flat organization…people don’t know what will be rewarded. And two, there is a lot of ambiguity about what everyone’s job is…. If everyone is responsible for something, typically no one is responsible for something.” – Shailvi Wakhlu
  • It makes sense that a company would want people at all levels to feel empowered to contribute.
  • Accountability comes through making distinctions in roles. Shailvi gives the example of senior engineers being expected to be more on top of certain things, and the same expectation would then not apply to junior engineers.
  • People are thinking about the kind of contributions that would be rewarded within an organization as well as how to grow their career. Typically, titles are used to acknowledge the level of contributions an employee has made. Moving from one well-defined job level to another gives a person a sense of progress and something to aim for.
    • “So, if there is not that definition of what is expected at each level, some people…may not have the tools to figure out what they should aim for…. Instead, I think the reason people started defining job levels was so that you could anchor on outcomes and impact.” – Shailvi Wakhlu
  • Years ago, companies would anchor on years of experience and hand out titles based on that metric, but the flaw in this approach was that it did not reward impact.
    • A specific job level shares the expectation of an employee’s impact on technical progress for the company, business results, communication skills, etc.
    • “If you want people to anchor on that, if you want people to strive for that higher skill set, you have to actually define them. If you keep them super ambiguous, if you keep it super hidden, then…I think that’s also a reason why companies end up with things that look like favoritism.” – Shailvi Wakhlu, on job levels
    • Without clearly defined job levels, a person doesn’t know what they need to do to showcase the kind of impact a company would like them to have.

8:41 – The Challenge of Reaching Top Tier Positions

Another question for Shailvi:

• We’ve spoken a lot on the show about the individual contributor’s career path or what we call the technical career path and getting up to the role of principal engineer inside an organization. Would the flatter organization mean it becomes infinitely harder to rise to the level of principal engineer, that highest tier of individual contributors?
  • Flatter organizations are not necessarily handing out titles that can help you when applying for a different job.
  • “Even if within your own company people know you contribute at a very high level, that external signaling may not be very obvious to another employer. When you have…principal engineer, staff engineer, those type of titles…it is easier for a new company to understand just in context that you were in the highest tier of individual contributors.” – Shailvi Wakhlu
  • Shailvi might split this into 2 pieces – rising up inside your existing organization and transitioning to a new job or different organization which may have a harder time measuring your impact.
    • Shailvi does not think a flatter organization stops you from reaching top-tier individual contributor. It may, in fact, open up new opportunities to work on highly impactful projects. Access to these projects is usually based on past performance on projects, how you advocate for your work, etc.
    • “If you keep showcasing that you are capable of handling more and more complexity, eventually you will get the highest value projects that have that very high C-suite level visibility…. Just the fact that it’s a flatter org should not stop you from having impact at the highest levels of what affects the business, what has the most visibility, and what is most critical to the company’s stated goals.” – Shailvi Wakhlu
    • The problem will come when you are trying to join an organization where job levels are very clearly defined. A company may want a principal engineer, and even if you have the impact of one but don’t have the title on your resume, applicant tracking systems may disqualify you automatically. If you are relying on people reading your resume, add as many indicators as possible that the projects you worked on were at the highest level of impact. Shailvi suggests possibly stating that the principal engineer title did not exist because of the flat organization (if that was the case).
    • Professional networking is very important to help showcase the level of your impact if you’re looking to land a principal title somewhere but don’t have that at your current company. Shailvi mentions talking with others in our industry, talking with recruiters, and talking with hiring managers.
    • “There are many ways that you can show up as an industry leader that are outside of your company. You can talk at industry conferences. You can have a lot of content that you put out there which makes it very clear to people….” – Shailvi Wakhlu

12:43 – Internal Risk and Potential Loss of Knowledge

Another question for Abby:

• "Is organizational flattening causing significant skill gaps at companies and creating opportunities for companies like yours or actually making it more difficult? In other words, are companies wanting to cut employee head count also cutting down the number of consulting firms they will partner with, or are they leaning into working with consulting firms more than they were previously?
  • “Layoffs and organizational flattening and, weirdly enough, AI…that’s all creating a heightened awareness of the importance of organizational knowledge management.” – Abby Clobridge
  • Abby says executive teams are starting to understand the importance of having organizational knowledge captured in a way that is documented well and easy to access, reuse, and build upon.
    • It is important to allow people to shift roles without losing more organizational knowledge than necessary.
    • “While we’ve made huge strides with AI adoption in the workplace, there still isn’t a magic vacuum that can pull knowledge out of someone’s head. When critical staff members leave, institutional memory leaves with them. Good knowledge management can’t stop that entirely, but it can soften the blow and help organizations keep moving forward.” – Abby Clobridge
  • Flattening is a chance to re-think how knowledge flows across your organization. Fewer management layers could mean fewer bottlenecks. If done correctly, flattening can lead to greater transparency within teams and the mindset that knowledge is a shared asset. There is a balance between keeping the right level of security and making knowledge accessible, and it can look different for different organizations.
  • For companies partnering with consulting firms, Abby says it’s a “mixed bag.”
    • Some companies are cutting consulting budgets, while others are shifting to more fractional and outsourced roles. It depends on the company.
    • “To be honest, it feels a lot like the summer of 2020 where organizations were suddenly trying to pivot or figure out what they were going to do and how to handle COVID.” – Abby Clobridge

14:54 – Strains on Execution

• We wanted to know how this climate impacts company execution.

Another question for Abby:

• Does the current climate make it more difficult to help your customers “solve the right problems” when the team is leaner / smaller and is under a heavier workload? How have you adjusted your strategy to help customers solve the right problem as a result of these situations? For example, does a flatter organization make it more difficult for customers to commit to spending time in the diagnosis / discovery phase because executive leaders want faster results from smaller teams?
  • Abby says she has seen it go both ways.
    • Some teams want to get through discovery and diagnosis quickly because they are stretched too thin, but experience has revealed moving past discovery too quickly or without talking to all the right people is a mistake.
    • Most of the time Abby and her team have been able to build an approach with clients to balance speed with getting things right.
    • Several new projects are focused on preparing organizations for knowledge management in the age of AI.
    • “These are really long term investments that the organization wants to get right, so even though everyone is anxious to get started, execs realize that it’s worth a few extra weeks or a few extra interviews to make sure we’re able to get a good sense of what’s going on and what the organization is really trying to accomplish so we can give the best possible advice.” – Abby Clobridge
    • Some companies end up making big platform or system decisions far too quickly and often times without the right voices in the room. This only leads to costly mistakes.
    • “Technology decisions aren’t made in a vacuum anymore. Very few platforms live as silos. There are almost always downstream effects. So, if you move too quickly without requirements, impact analysis, and honest conversation about tradeoffs…you end up with ripple effects that can be very costly and disruptive. It doesn’t mean decisions have to drag on for months. The key is balance – moving at a healthy pace but giving people enough time to digest, weigh impacts, and make better informed decisions.” – Abby Clobridge

16:57 – Impact to Team Dynamics

• We wanted a perspective on team dynamics, so we brought in Leanne Elliott. Leanne is a business psychologist and with her husband Al, hosts the Truth, Lies, and Work podcast. We spoke to Leanne in episodes 237 and 238, and she also appeared along with Al in episode 340 and 341. The questions we’re asking her are follow ups from the conversation we had with them on organizational flattening.

Our question for Leanne:

• We have seen companies with 1 or more pods under each manager where there is some kind of pod lead / team lead within each pod who helps the manager do things like track work, give team members feedback, etc. Have you seen this structure work well in flatter organizations?
  • Leanne has seen the pod structure work quite well, but more often than not, she has seen it go badly.
  • This has a tendency to create an “us and them” culture, especially when people do similar work but are part of different teams. If there is not advertisement or reinforcement of the core mission bringing everyone together, this can breed workplace incivility (cliques, gossip, division, etc.) and create microcultures.
  • With a complex structure like this, it requires more care, close monitoring, intentional management, and a willingness to make adjustments when needed.
    • “My worry is that if it’s not handled well, it’s not done with the best of intentions…then it can mean that people feel more disconnected, there’s more infighting, and ultimately more isolated.” -Leanne Elliott
  • The latest State of the Workplace Report from Gallup found that 1 in 5 employees have stated they feel lonely at work. This is an organizational issue and not just a personal issue.
    • “People often think that loneliness is about maybe being shy or introverted, but it really isn’t. There’s no link between personality and how lonely somebody feels. What does matter, according to the research, is the environment. It’s a complicated thing as well to look at your organization as a supervisor, as a colleague, as a senior manager and try and identify the people that are lonely and try to fix that. People don’t act lonely at work.” – Leanne Elliott
    • People are skilled at masking how they really feel and may seem chatty, gregarious, or outgoing.
    • “…because that loneliness is so stigmatized that people will pretend it’s fine rather than the fear of repercussions because that psychological safety doesn’t exist if they did speak up and say something about it.” – Leanne Elliott
    • Having leads in each pod who are closer to the group may foster an environment of psychological safety. But, this is not necessarily going to be the same behavior senior leaders who have the power to do something to change the environment will exhibit. A lead / supervisor may recognize there is a problem with how someone is feeling but be unable to do anything to really change the overall environment.
    • If people do open up inside the pod structure, there is a chance they will remain disconnected over time, which chips away at wellbeing.
    • “As with anything in the workplace, these types of things to…have the most positive impact require attention, require support, and require the agility to change these experimental structures when they’re not working.” – Leanne Elliott

21:13 – From Problem to Opportunity

• Maybe we could look at this trend as an opportunity?

Another question for Leanne:

• In a world where manager to individual contributor ratios are changing, does this create an opportunity for individual contributors to take more of a player / coach or team leader kind of role?

  • Leanne does think this will create an opportunity for individual contributors to take on a coach, team leader, or supervisor kind of role. People will step up into these roles when needed, and it’s usually the more conscientious members of the team who do.
    • Some may seek this role out of ego, but the small nature of the team will make this highly visible. It’s not usually out of ego that someone takes the role, but it can happen.
    • If this role is an official role, it can be a great way to develop people.
    • “It’s that chance to try out people management in a more hands-on, practical way…so less theory, on the job training. You’re close to the work as well so you understand what it really takes to deliver that rather than being a removed senior manager…. And for the group as well, people do look for someone to follow.” – Leanne Elliott
    • For groups of this size (larger than 12 or 13), it is hard to connect with everyone individually. We would often look for a shared goal, mission, or values. People look for someone to show them what that is and how to make sense of it all. The leader in larger groups gives us clarity, sets a tone, and demonstrates what is expected. This helps employees feel safe, more confident, and like they belong (all of which are great for wellbeing and lead to team cohesion).
    • “The issue with these types of supervisor roles is typically they aren’t formal. So, someone will step up, or maybe they’ll get nudged into it by a senior manager. But there’s no support, there’s no extra pay, and there’s no real recognition. Now, that’s fine initially. That’s what we call ‘hope work,’ work where someone can see the benefit of stepping into an informal role without any kind of extra pay or recognition on the understanding and the view that this will be for a finite period of time. And then the pay and the support and the recognition will come. If it doesn’t (and it typically doesn’t in informal supervisor roles), then that can build resentment over time, and it can lead to this person disengaging and burning out…which is a danger because typically it’s the high performers that will step into these types of roles. But when it is done properly…right structure, right support…then yeah, it can be a great steppingstone for anyone who is looking to move into a management role who doesn’t have any experience or training at that point.” – Leanne Elliott

• We want to say a huge thank you to all of the guests who contributed to this episode! If you want to hear more from them, you can find the full conversations…

  • Abby Clobridge was a guest in episodes 292 and 293.
  • We spoke to Shailvi Wakhlu in episodes 210 and 211 She’s also the author of Self-Advocacy: Your Guide to Getting What You Deserve at Work.
    • Here’s a special 15% off link for Nerd Journey listeners to Shailvi’s self-advocacy course.
  • We spoke to Leanne Elliott in episodes 237 and 238, and she also appeared along with Al in episode 340 and 341.

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_
  • Leave a Comment on Your Favorite Episode on YouTube
• If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.
• If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

Episode 346 is dedicated to the memory of Todd Cochrane. Todd was the founder of Blubrry Podcasting, a Navy veteran and electronics technician, a geek and lover of technology at heart, a content creator, a podcasting pioneer, and a consistent friend to the greater podcast community. This week we’re airing our full interview with Todd as a single episode (previously released in episodes 250 and 251).

As we begin this week, Nick and John frame what you’re about to hear with a story from Podcast Movement 2025 where Nick got to meet Todd in person. Listen closely for the shifts Todd made to his company as market conditions changed, and think about the applicability of this strategy for your career.

Original Recording Date of the Interview with Todd: 10-06-2023

Topics – Meet Todd Cochrane, Naval Service and Technical Knowledge, Program Management, An Injury and a Different Role, Getting into Podcasting and Monetization, A Tech Wave and a Shift, Diversification of Focus and Expertise, Corporate and Individual Roadmaps, Leadership and Employee Engagement, Developing a Useful AI Strategy

5:49 – Meet Todd Cochrane

• Todd Cochrane is the founder and CEO of Blubrry Podcasting. Blubrry is a full service podcast hosting platform.
  • At the time of this recording they are working with around 100,000 shows / podcasts at a variety of levels (some shows using Blubrry for hosting, some for analytics, some using the PowerPress plugin for WordPress).
  • The team at Blubrry is about 17 people, and they have been in business since 2005.
  • Nerd Journey proudly uses Blubrry statistics and the PowerPress plugin!

6:51 – Naval Service and Technical Knowledge

• In vocational tech school Todd took 2 years of electronics and then joined the Navy in 1983. His official title at that time was aviation electronics technician.
• Todd also served as a back end operator in specialized P3 aircraft used more as platforms for intelligence collection. Todd tells us he was involved in this kind of work for 25 years.
  • During his tenure in the Navy, Todd got exposed to something called special projects.
  • People would bring a box for a specific function in the plane (a “box de jour”), and Todd would do the mechanical and electrical designs for these to get them in the planes quickly.
• Todd’s true Navy background was in synthetic aperture radar and involved work with Sandia National Labs.
• To pair with his deep technical knowledge of electronics, Todd started to tinker with other things like bulletin boards and downloading shareware while stationed in Guam.
  • This was back in the days of dial up modems.
  • “I really was kind of a geek in all aspects of job and life….When the bulletin board era died, I basically became a blogger.” – Todd Cochrane, reflecting on his time in the Navy.
  • Todd calls himself a failed blogger, feeling he was not great at it. This was around 2002.
  • In 2004 Todd got into podcasting but continued to work another job. After retiring from the Navy in 2007, Todd spent 12 years as a tech rep (basically the same job he had been doing but as a civilian).
  • Todd continued to work with and for Naval personnel until 2019 while running his own company on the side.
  • “Needless to say those were some exciting years because there was not a lot of free time.” – Todd Cochrane, on working a full time job and running his own company on the side
  • Todd has only been out of aviation for about 4 years now but has been running his business (Blubrry) the entire time along the way since it began as a side project.
• Todd retired from the Navy as a senior chief (an E8). He did have the opportunity to go warrant officer but was happy being a chief, “punching out” just before hitting the 26 year mark for Navy service.
  • This was largely because they offered him a civilian job, and he took the opportunity to make the change.
  • Todd tells us he was exposed to a great deal of high end technology during his work (much of it will remain classified for many years).
  • Looking back, Todd says it’s pretty amazing to see the advances in technology from 1983 when he joined to when he retired and up to the time of this recording because of the technology changing so fast.

11:08 – Program Management

• Was designing the boxes for airplanes like being a product designer or a product maanger?
  • Todd’s degree from Emory Riddle is in professional aeronautics with a minor in program management, and he was able to put the program management skills to good work.
  • For systems that the Navy personnel designed, built, and owned they had input into the capabilities desired as well as features they wanted.
    • “It was a full scheme. Some of the systems were born from an idea – built, designed, UX, UI, the whole nine yards…that I was able to have a hand touch in.” – Todd Cochrane, on working with a team to design and build systems for Naval aviation
  • In the last 15 years of his work, Todd says someone would show up with a box that he and others would have to wire up / connect. These ranged from computers that needed installing to electronics that need to hook into multiple systems in an aircraft.
    • From day to day, Todd didn’t really know what might come his way. This made the job quite unique.
    • They might get a call from a well known company who wanted them to test something, for example.
    • “So our job was really to kind of test and evaluate, and more importantly, in a real world situation, not necessarily on some range….It was fun.” – Todd Cochrane
  • In the case of 787 or 777 commercial aircraft, they are built exactly the same (with exception of some of the electronics in the cockpit). Often times the supply chain is setup so you could walk over to the airplane next to you and “rob it” for the parts you needed.
    • In Todd’s situation, everything was unique, and each airplane was different in some sense. It was important to have configuration control across multiple aircraft.
    • Sometimes they would need to upgrade multiple airplanes at a time.

14:06 – An Injury and a Different Role

• In 2004 Todd was hurt badly in a swimming accident in Bahrain, which grounded him from flying.
• Todd was in Waco, Texas doing contract enforcement – making sure taxpayer money was spent wisely and monitoring aircraft builds.
  • Todd says he saw a lot of the government / civilian interaction during this time, and it was a very interesting job to do for a few years.
• Todd had insight into the process of building aircraft from beginning to delivery of and testing of aircraft.
  • The team was multi-faceted and in multiple locations (i.e. teams with some specialties in the northern US, others elsewhere, etc.).
  • Specific systems might require their own reviews and discussions and planning.
  • Budget and what could be done within the time frame were also factors. It was a team effort.
  • Todd tells us there were also subject matter experts (or SMEs) for various systems.
  • Todd has publicly shared that his background was in electronic warfare, synthetic aperture radar, etc. while on active duty for the Navy. He would have been considered a SME for these kinds of systems during his service.
    • Todd would work with and support the team putting in systems for which he was SME as well as the sailor who was deployed and had run into issues (i.e. provide troubleshooting / fly out somewhere to resolve the issue, etc.).
    • The role was part design and implementation as well as ongoing platform support.
• Nick feels like this SME role is extremely analogous to life as an IT generalist.
  • Todd says it would have been very bad for someone to infiltrate the software they used software. As such a number of security measures were put into place to help prevent this.
  • The IT group gave people like Todd the hardest time because they might lock something down so tight it causes something else to break. And Todd calls this “par for the course.”
  • Todd says having this experience set him up well for success later when he pursued working for his company full-time.
  • “For me the transition from military to civilian was pretty smooth because I had worked with civilians a lot….So I didn’t have this mindset of someone that maybe just came out of the military that had never had a lot of civilian interaction.” – Todd Cochrane, on transitioning out of the Navy and how it might be different than others leaving military service
• Todd had been running his company as his part-time job for a number of years until he transitioned to working there full time.
  • While still working in the Navy, Todd had to be very careful about keeping his business and Navy work completely separate.
  • The separation was an important part of security clearance reviews, and Todd even had to ask permission to have his own business.
  • Todd would leave his phone in the car during his normal workday and take business calls either during lunch or after work to help keep the separation.
  • “But when I transitioned, it really made me realize I should have probably done it about 10 years earlier.” – Todd Cochrane, reflecting on his transition to running his business full time
• For the last 4 years, Todd’s job as CEO of Blubrry has been coordinating with the software development teams, production, and marketing.
  • Todd says they use Scrum at Blubrry and that he is essentially the Scrum Master in many ways despite being the owner. His project management skills have come in handy.

19:29 – Getting into Podcasting and Monetization

• When Todd speaks to being in Waco, TX he was in a full body clam shell after smashing his L1 vertebrae in a swimming pool accident.
  • Todd tells us he was lucky to be alive and be able to walk after the huge spinal cord displacement from the accident.
  • Todd worked in an unairconditioned shop after being able to walk again (still in Waco) and was exhausted at the end of most days.
  • He would spend evenings on his laptop surfing the internet and stumbled upon Adam Curry’s Daily Source Code, one of the early podcasts.
  • At this time (October 2004) Todd was a tech blogger who didn’t have many people reading his site, but he liked to talk.
  • Todd picked up a cheap portable microphone at Wal-Mart and started recording a podcast. He already understood things like XML that one needed to know to get a podcast online back then and was able to execute on his own.
  • “Really the eureka moment came when I woke up one morning and my webhost said, ‘hey, you’re out of bandwidth. We’ve shut you down.’” – Todd Cochrane, on an interesting situation after starting a podcast in the early days
  • There was no Blubrry at this time, and the only way to fix the problem was to spend more money on shared hosting accounts. Todd’s podcast website had to be moved around every few days at that time to keep it going.
    • October 9th, 2023 marked the anniversary of Todd’s 19th year of doing podcasting!
• Todd was spending a lot of money to keep the show online. When he returned to Hawaii and let his wife know what he was doing, she didn’t really know what podcasting was (almost no one did at that time). But, Todd’s wife told him he needed to be making money from this endeavor after a year or two or would have to stop.
• In November of the same year, Todd received an e-mail from a publishing company asking him to write the first book on podcasting.
  • At first he was not sure if they were serious. But it turns out they were and offered him a sizable advance to do the book even though he did not consider himself good with grammar or a writer.
  • Agreeing to write the book fixed Todd’s money issue.
  • Todd eventually started his own tech network and then in 2005 GoDaddy called Todd wanting to sponsor his podcast.
    • GoDaddy is still a sponsor of Todd’s show Geek News Central.
  • At this time Todd was one of the very few who had advertising on his podcast. He wasn’t quite sure how to charge in the beginning. After a month of sponsorship GoDaddy got around 370 customers and wanted to sponsor Todd’s show for a full year.
    • “Here’s one of those things where you have to understand your worth, and I really had no idea what my worth was.” – Todd Cochrane, on having to come up with an amount to charge GoDaddy to sponsor his show
    • Todd says he ultimately gave a price that was far too low (an underbid as he calls it), but in the moment he suggested a bonus if GoDaddy converted a certain number of customers as a result of the show. Ultimately Todd’s contact at GoDaddy agreed to this.
    • The lady Todd was working with to construct a deal asked if he knew anyone else looking to advertise with GoDaddy. Todd said yes and that he needed a couple of weeks to get back to her.
  • The tech network Todd had built had 12-13 shows he could potentially represent and take a percentage of the proceeds.
  • “And on my next podcast I said, ‘I need a lawyer, I need a MBA, I need a graphics guy, and I need programmer. And we’re having a call in 10 days. If you’re one of those, be on it……’ And in the end we formed RawVoice, which is the parent company for Blubrry, over the telephone. And we all had regular jobs, so everyone was working this at night.” – Todd Cochrane, on the beginnings of his business
    • Todd made the ask on his show and got all the personas he needed on a call.
    • The company was profitable from month 1, and each member of the group contributed some of their own money in the beginning to fund the startup.
    • Todd was told he was too old at 40 to receive a round of funding from venture capitalists in silicon valley. And it would have required the entire team to move there (not feasible with everyone having a family).
    • “But the one thing we were always smart with is we knew that we had to have money in the bank. We knew we had to be profitable. We knew we had to make payroll because…I didn’t have $25 million of VC to use. We had to build this slowly, and that’s what we did over the years. We built it slowly and never extended ourselves too far.” – Todd Cochrane

26:16 – A Tech Wave and a Shift

• John mentions Todd identified what we would call a technology wave, was passionate about what he was doing, and he made a bet.
  • Todd maybe could have gone to work for someone looking to monetize in this space but made a bet. The structures Todd had put in place enabled starting a business without too much work compared to someone with a cold start.
  • Todd says in a lot of ways the team figured things out as they went with the first product being an “abject failure.” But the team learned from this experience and made changes to their model.
  • "We build a lot of stuff, and if something is not working, I don’t dwell on it. I don’t ride that ship into the ground. We move on. Maybe we keep the product, and maybe we don’t. " – Todd Cochrane
  • Todd mentions many people with a product or idea believe in it so much they burn all their money and don’t make a change or shift early enough.
  • In the early days Todd’s company was like a media agency and represented podcasters for ad deals. Most shows they represented were fairly small, and their second product in 2006 allowed them to track podcast listening statistics.
  • As larger more popular shows came online, Todd could see the advertising budgets shrink and shift to be put into these larger shows.
    • As a result of seeing this trend, Todd’s company did a strategic shift to become a service provider.
    • “So as the advertising revenue was declining the service business kind of crossed in the middle, and we dodged a bullet. We would not have made it had we not shifted to a service business….Keep your eye on the ball, what’s going on in the space. At that time I had 5 competitors. Now I have 30.” – Todd Cochrane, on a strategic company shift
  • Todd tell us his product is commoditized today and competes today on features based on feedback from customers and the market.
    • In the technology sector, companies have to look around and understand what is happening (cannot be blind to this).
    • “You do have to teach the old dog new tricks. You have to.” – Todd Cochrane, on the need for companies to adapt to changing market conditions
    • The above is also true for knowledge workers, especially with the growth and emphasis on AI (artificial intelligence). If people do not stay current and get educated on these technologies, they may find themselves out of a job in a few years.
  • When Todd originally built his show (that first podcast), he was trying to build authority. Todd wanted a press pass to CES (Consumer Electronics Show), which he eventually did get.
    • This was before his wife’s mention of monetization.
    • “I did it out of pure desire just to go and hag out and check that show out….Then things kind of morphed as time went on.” – Todd Cochrane, on the reason he started his podcast in the first place

30:42 – Diversification of Focus and Expertise

• John says we’ve heard about startups and the term “pivoting.” It may not be a pivot of the company but a diversification of where success and money will come from (which is also true for an individual).
  • John shares that at one point his ability to crimp a CAT5 cable was a skill that brought money in. But if he had held tight to this and focused on it holistically forever, John would not have a job right now.
  • Diversifying a skill base or what provides value to an employer or a business (i.e. your own business) is something we can do to keep ourselves from having market forces destroy us.
  • As we age we get more expensive to employers, making it even more important to keep our skills current and requiring that we bring expertise to our next role.
  • Early on in Todd’s Navy career a friend / mentor named Randy gave him some great advice.
    • “You just need to attach yourself to the smartest person in the room and suck them dry, basically learn everything they know or everything they will tell you.” – Advice from Todd Cochrane’s friend Randy
  • Todd says using this strategy has really paid off for him long term, and he does this today with his CTO at Blubrry (someone who knows the tech well and someone that Todd trusts to provide direction).
  • “I think it’s more than surrounding yourself. I think if you are in a field that you’re trying to stay current on, you need to become the person other people want to attach to. But when you’re early in your career it’s easy to be annoyed by that older wise individual. But they have so much experience.” – Todd Cochrane
  • Todd tells the story of asking someone with more experience at Sandia National Labs for help on a schematic. The person told Todd exactly what to do to fix the problem (which worked). But Todd didn’t leave it there. He went back to the person and asked how they knew their suggestion would fix the problem.
    • “A 15-minute conversation I had with him literally fixed hundreds of problems that I had going forward years in advance. When you have that opportunity to get help from…a genius and they can bring the topic down to your level, man you just need to…milk that dry.” – Todd Cochrane, on picking the brain of a brilliant colleague with more experience
    • Todd thinks that advice from Randy (who is still a friend to this day) was one of those pivotal moments / pieces of career advice.
• Nick feels like the above experience is an iteration of being mindful of our gaps in knowledge just like when Todd got on his show and asked people with different expertise for help. It’s learning from others but also humility.
  • Todd says he was a high school graduate going into the Navy and didn’t get a degree until he had been in the Navy for 20 years. In a way he was getting credit for much of what he had learned via the school of hard knocks.
  • Todd has seen people fail because they hung out with others who may have been fun people but who just were not going to advance in a company. It’s important to surround ourselves with good people.
• John points out that just like skills diversification when one is riding a technology wave, it’s also about having a diverse set of people around us whose experience we can call upon to fill gaps in our own expertise.
  • We cannot be experts in everything. Having access to others with different expertise can enable the kinds of pivots we spoke about earlier (for the individual or for a business).
  • As company owner and founder, Todd would rather collaboratively come up with a plan with his team than just give them a directive.
    • Todd calls himself a geek and says there are times where he wants something geeky (i.e. a feature) that 90% of his customers may not ever need. It’s important to be careful and prioritize for the 90%.
    • There are certainly times when Todd’s team are building a feature that is intended to promote adoption (i.e. building it for only a small subset of customers) like some of the podcasting 2.0 work they have done. But these occasions are pretty rare, and the team knows why they are building it.
  • Todd says the team are very cognizant of the products and services roadmap when making decisions, and he looks at the year’s roadmap every day. Every 2 weeks there is an oversight meeting to discuss the roadmap with other company leaders.
    • Priorities may need to change based on the marketplace conditions.
    • “You have to be careful. Because if you’re working Scrum…if you interrupt the cycle you could really do huge damage.” – Todd Cochrane, on being flexible in your product roadmaps

38:47 – Corporate and Individual Roadmaps

• Nick posits that most of us do not have a roadmap for ourselves and our careers, nor do we look at it daily.
  • Todd says the roadmap is the company roadmap but might as well be his personal roadmap.
  • John emphasizes the company’s execution on a roadmap is analogous to a individual contributor’s view of themselves / their career as a product.
    • Excellence in what a company is doing today is of course important.
    • Companies often have innovation budgets to enable building products people might not know they need until they use it / can have it (i.e. the iPhone or perhaps certain podcast hosting features).
    • Maybe as individuals, in addition to excelling at what we do today (a baseline of excellence in execution), we should have our own innovation budget allotted for building new skills and learning about the next / current technology wave. This avoids us from being locked into excellence in only what we do today just like Todd’s company was able to shift away from being only a media intermediary in the early days.
  • Todd says his team is fully remote but does come together a couple of times per year for planning purposes (1 time in person, 1 time 6 months later remotely as a follow up to that).
    • These meetings are a chance to look at what is going well, what isn’t, and a chance to solicit new ideas.
    • During these discussions, teams criticize one another and give feedback. It is a very frank set of discussions that results in action items. Todd says they try to preserve people’s feelings during the discussions, but it is about honest evaluation of how things are going.
    • The above will be quite difficult for companies with more than 20 employees. Todd says the approach works well for his company.
    • Todd also tells us a bad apple (1 person) can make a very negative impact on the company. This person might not be staying current or is constantly fighting with others.
    • “Sometimes it’s better to cut those folks loose. Even though you think you shouldn’t, sometimes getting rid of that just maybe 1 person can completely change how a company’s atmosphere is and the flow and the speed….So I learned this late – that sometimes it’s just better to say ‘thank you for your work it’s time to part ways.’ It’s just like pivoting. Sometimes the employee mix needs to change.” – Todd Cochrane, on making difficult decisions around people
    • Todd says there was someone who left the company about a year ago, and the business had a complete transformation (in a good way) as a result.

43:10 – Leadership and Employee Engagement

• Many people moving into leadership are not prepared for the hard personnel decisions. What are other challenges Todd has noticed as CEO, being in charge of the roadmap and the people?
  • Todd says he has been quite lucky with very little turnover, having only a couple of people leave the company over time and a couple of others get asked to leave. Overall the team has been strong (a possible sign they are doing something right).
  • “We all get bored if we’re doing the same thing, but we’re in a business where we can build new stuff all the time and have new challenges. So I think from my perspective…if you’re not innovating, then your employees are going to get bored, and they’re going to go some place that is innovating to give them a challenge.” – Todd Cochrane
  • Ideally Todd wants employees to feel their work is exciting, that it is making a difference, and for them to be excited to start work on it again each day.
  • In IT sometimes work is drudgery (or “the thunking” as Todd calls it) and is not something we enjoy doing but need to do (i.e. keeping servers up to date).
  • Nick mentions Todd recognized the need for people to be interested and engaged in their work, and Todd has iterated upon that methodology in terms of the way people engage with the company and its products.
    • If you’re listening to this episode and intend to become a leader but have not thought through the importance of people understanding the purpose in their work, think on it. It was extremely important for Todd to share the vision with employees.
    • “How is my role here having a larger purpose for this organization? And hopefully that gives me some personal satisfaction and sense of accomplishment.” – Nick Korte, on the importance of leaders helping employees to understand the purpose of their work
  • Todd says he came from a field where he was able to work on multiple projects on a monthly / semi-annual basis. This kept him excited about the job.
    • There were legacy systems to support, of course, but there were brand new systems.
    • “I understood that that job satisfaction of having something new to work on is fresh, challenging, you have to really think…I mean hard, hard problems to solve.” – Todd Cochrane
    • Todd gives the analogy of working with airplanes. Both power and space are constrained resources, and there is a give and take between them.
    • Translating this to running a company, there is server space as well as mind space. They would not want to do something that will be an extreme burden from a technical support perspective, for example.
  • AI (artificial intelligence) has Todd a little frightened, but the strategy for the company is to not be locked into a single language model (Claude, ChatGPT, Meta, etc.).
    • “We’re using the dumbest AI we’ll ever use today. It’s exciting at the same time, but it’s hard to pick a strategy that is not going to be obsolete in 2 weeks.” – Todd Cochrane
  • Todd says right now (at the time of this recording), the economy is tight with podcasting being fairly flat. But he and his team have been through cycles of economic downturn and know what to expect, having been profitable every year of their existence.
    • “As long as you keep the green line above the red line I think that’s the key in almost any business industry. Otherwise you don’t survive.” – Todd Cochrane

48:36 – Developing a Useful AI Strategy

• John understands the desire to stay flexible and diverse in terms of different language models and asks Todd about his AI strategy and where he feels like it will help podcasters.

  • Todd always likes to ask himself whether something the company is doing will help the customer base by saving time or making a customer product better.
  • Todd says helpful areas for AI use will likely be content creation and post production. Many companies are doing things related to social media, and Todd doesn’t think he wants to compete in that space.
  • The number one question Todd gets asked consistently by content creators is “how do I grow my show?” Any use of AI tools would need to help in this area.
  • The team at Blubrry has taken several months to think through a strategy.
    • For those who follow Todd’s shows Geek News Central and New Media Show, he is public about the things in the AI space with which he has experimented.
    • The “thunking” is in creating documents (outlines, drafts, proposals, etc.) and will likely be done by the AI. The creative individual will still be needed, but some of the show prep (based on creative thinking) could be handled by AI, for example.
    • “On the other side of it, you have to be the subject matter expert of your topic, your content, so that when the production piece is done by the AI you can validate….You are going to be the person that is going to review the output.” – Todd Cochrane
    • We need to remember that the output from AI tools will not be perfect and won’t be for some time. Todd says the work of his team will be to educate creators on this fact.
    • Todd references a book on NATOPS with all the information needed (sort of like a bible for the airplane). There is a disclaimer on the book that it is not a substitute for common sense.
    • For example, if an AI provides poor topic suggestions, we need to not use them. Podcasters need to know that these are merely tools to help with content creation and production.
    • Blubrry will be working on tools to help podcasters grow their show, but it will be tricky. People need to understand the models / AI tools will lie.
    • Todd says for a show like ours where we are having a ranging discussion, AI has a hard time summarizing it. But for shows that are one point after another, AI does well there. Nerd Journey may not get as much value out of a transcript analysis as a news show covering a set number of topics.
    • Todd shares the results of some tests lately that were lower quality than what an intern at his company should produce.
  • Nick feels like this is just the tools and the SME (subject matter expert) changing a little.
    • Todd says we (as the SME) need to be able to check to see if output is too flowery, if the AI added something that wasn’t discussed in a show summary, etc. He feels the tools will get better over time (pretty quickly) but just are not there yet.
  • John mentions these tools help with the problem of starting with a blank page as well as with summarization. It’s easier to work from a draft than from nothing.
    • Todd says podcasters have often been lazy with show notes.
    • “You record for your audience. You write for Google.” – Todd Cochrane on podcast creation and show notes (advice for the podcaster)
    • As language models become more widespread searches will change, and we want our content to be easily findable. The metadata we feed into Google is becoming more important.

• To listen to other tributes to Todd, check out Remembering Todd Cochrane – Podcast Hall of Famer and Blubrry CEO and, GNC Host and Geek News Central # 1843

• For links to the individual episodes with Todd that were combined for this special episode, check out:

  • Episode 250 – From Naval Electronics to Podcaster and Business Owner with Todd Cochrane (1/2)
  • Episode 251 – A CEO’s Approach to Product and Career Roadmaps with Todd Cochrane (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_
  • Leave a Comment on Your Favorite Episode on YouTube
• If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.
• If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

Pursuing a role in leadership is one thing, but what happens when you try to return to life as an individual contributor? Our guest, Paul Nadeau, equates this experience to having “resume damage.”

Join us for episode 345 as we dive into the differences between pursuing a technical career path as an individual contributor and a career path in people management from a guest who has experienced both. Paul reveals a strategy for gaining expertise by sharing examples of his willingness to find and clean up a mess.

Through turbulent times in the tech industry, how can we give to our network with no agenda? Listen to Paul describe his approach to meeting new people, supporting them through layoffs, or just providing advice…all through merely having a conversation.

Original Recording Date: 08-28-2025

Topics – Technical Career Paths vs. Management Career Paths, Returning to Individual Contributor, Specialty Decisions, Nurturing Your Network and a Focus on Helping Others

3:15 – Technical Career Paths vs. Management Career Paths

• John mentions we have spoken on the show about the technical / individual contributor path to progression as well as the management career path.
  • There is usually a path to stay an individual contributor in medium to large size organizations (i.e. the ability to progress to senior engineer, staff engineer, principal engineer, distinguished engineer, etc.).
  • “If you want to progress in your career and you don’t have that path, management is not the natural thing to look at…unless you actually want to stop what you are doing and become a manager…. Becoming a manager does not make you…tech lead. It makes you manager. It’s a hard piece of advice to give somebody if they’re in an organization that does not have a next title, a next promotion for that person where they stay an individual contributor…. You shouldn’t try to become a manager. You should try to move organizations. That’s hard advice to give. I’ve had to do that a couple times.” – John White
  • Paul recalls a conversation with his manager not long after the manager had been promoted into the position.
    • “There’s no comparison between the management going up a chain of command and the engineer going up a chain of command. It’s a completely different skillset altogether….” – Paul Nadeau
  • Paul tells us that as leaders progress to higher levels in an organization they take on more responsibility but also begin to manage a profit and loss center (or PNL). Rather than individual expense reports you’re looking at what the team is spending and what they are spending it on.
  • The next level up is leading an entire division and considering how to distribute funds within your budget for salary raises, bonuses, or other types of compensation.
    • Paul tells us that many leaders love to hand out promotions, but no one likes to fire people.
  • When evaluating a technical career, Paul likes to think about the following:
    • Am I having fun?
    • Am I a benefit to the company?
    • Where will I be a bigger benefit to the company…in my current role or in a management role?
    • If applicable, are customers happy with me in my role (tech support, professional services, etc.)?
  • “I think one of the big reasons why people leave companies is…whenever they say there’s no room for promotion; it doesn’t have anything to do with promotion into management. A lot of times they think that’s what it is. But it has to do with promotion of their brand, their career path. What are they doing, and how are they getting there? That’s what it has to do with.” – Paul Nadeau
  • Management is a lot like herding cats, and according to Paul, not everyone is going to have fun doing that job.
  • Paul has fun whiteboarding and providing technical solutions for his customers. This makes him happy.
    • We have to define what success is for ourselves and not rely on how other people define success. Some people in technology define success as the level of management they have achieved.
    • “Quite honestly, whenever somebody comes and says, ‘are you interested in management?’ Not really…because I can make a bigger impact here where I am now and I can go to club and make a lot of money getting there as a systems engineer…. In management…when you equate it all out, is it really as much fun? I don’t know. When you walk in and you go to dinner, nobody wants to sit with you because you’re the boss. Nobody comes to your table. Why not just be the fun individual contributor that’s the natural leader guy where everybody comes over to the table and you just kind of have fun doing what you do?” – Paul Nadeau
• Nick says Paul’s comments seem to hint at the importance of working for the right leader if you take on a role as a first-time people manager.
  • Paul tells us it’s more than that. Managers have a ton of resources at their disposal, but their number 1 job is to protect the company above all else.
  • “A lot of people say…I’m here to protect the people. No, you’re here to protect the company number 1. That’s why the company promoted you. The second thing is to protect your people. If you’re protecting the company you’re naturally protecting the people. Because now you don’t have a toxic work environment. You don’t have any kind of discord. You don’t have any kind of rule breakers. All that’s taken care of because you’re protecting the company first.” – Paul Nadeau
  • One of a manager’s greatest resources is HR (Human Resources).
    • “They are there as an advocate to help you as a manager to work through problems and issues. That should be your best friend in the whole world.” – Paul Nadeau, on HR
  • Many leaders miss the opportunity to leverage HR as an advocate and helpful resource. One of the first things Paul did after becoming a leader was go make friends with his HR. He also highlights how communication with HR about more than just immediate problems can help (i.e., employees who are performing well that you want to retain).
  • If you’re giving pointers to someone who wants to go into management or continue down that path, Paul tells us it’s not just about taking a class. You need an increased level of involvement with other people.
    • Instead, do things to get involved in different user groups.
    • Take on different roles that you can have fun doing.
    • An increased overall level of involvement fosters strong relationships with different people. This is how to begin and continue building a professional network.
    • As layoffs happen in the industry and people reign to move to different companies, the relationships can be retained.
    • “These are still people. Humans first, right? That’s what it all boils down to…it’s still people dealing with people at the end of the day.” – Paul Nadeau

11:37 – Returning to Individual Contributor

• At some point after working in leadership, Paul chose to return to being an individual contributor. What went into that decision?
  • “Actually, it’s harder to go backwards than it is to go forward. It’s harder to go from a management role into an individual contributor role.” – Paul Nadeau
  • From the time Paul was promoted to director of worldwide services to his return to individual contributor was a span of about 8 years.
  • Paul remembers a specific trip to Asia to spend time with a director under him and to attend to different organizational changes. It was 2 AM, and he received an unexpected phone call from a friend. Someone wanted Paul fired and wanted to take his job.
    • Paul reminds us that at this time things were running smoothly. The services organization was making money ($48 million in the black). Employee morale was in great standing, and attrition was low.
    • When he took over the services organization at this company after a massive restructuring years earlier, it was $18 million in the red, and the company was considering removing it completely.
    • “The politics side of it…I’ve never done well with. I’ve never really done well with that. It is inherent. It is something that happens…. Human beings…we just naturally get political about things…. We have opinions…sometimes a little jaded opinions on somethings…or a little strong opinions…. And when the politics started to come out, I was like, ‘you know what? I’m not even cut out for this.’ And the worse it got, the less tolerance I had for it….” – Paul Nadeau
    • Paul told his boss he wanted to move back to individual contributor again. Paul was ok with just being an individual contributor inside an organization he had built. He missed being in front of customers.
    • “It is fun. It is rewarding to help people with their career and help them develop leadership skills that they didn’t know that they had, to see things in people that they don’t even know that they had and kind of help them evolve. However, there’s also the other side of it, which is, I can’t take this being up 17 hours a day, getting 3 or 4 hours of sleep a night, and being on airplanes all the time. It’s just taking a toll…. Everything considered, I want to go back to an individual contributor role.” – Paul Nadeau
    • After talking through it together, Paul’s boss at the time was supportive of the move back to individual contributor.
  • Paul also spoke to a really good friend who had progressed from individual contributor to being a peer of his in management about making the change back to being an individual contributor. At first that friend thought it wasn’t a good idea. It would remove some elements of compensation that were present at the leadership level.
    • But, when the friend could see Paul was determined, he mentioned to Paul that there was an opening for a systems engineer. Paul made the move and took the role.
    • After moving into the individual contributor role, Paul said one thing he did not expect was to have to still sit at a dinner table by himself.
    • “It was so isolating. It was absolutely unbelievable. So, whenever they say it’s lonely at the top, it is. But it’s also lonely when you get back into the ranks…moving back in from management back into an individual contributor role. If I were to move into a different company where I didn’t know anybody or maybe just knew one or two people, it might have been a little easier. But moving up the ranks and back down the ranks was quite telling…. It was kind of surprising.” – Paul Nadeau
• Remember, Paul had gone from member of a team to leading an entire division. What we’re talking about now is going the opposite direction.
  • Paul says he worked at his first two employers after being in the Navy for many years (over 17 years at the first company and about 8 at the second). It was all about loyalty.
  • But, does a company reciprocate the loyalty, or would it be better to move to a different company?
  • Even when trying to move to a new company after experience in that director role, Paul tells us the “resume damage” followed him.
    • Hiring managers were initially hesitant to hire Paul as an individual contributor. They thought Paul might tell them how to run their team or be targeting another director role.
    • After Paul had landed an individual contributor role, his manager or other leaders who knew about his management experience might ask him if he had ever experienced a specific situation. Listen to some of the specific situations Paul experienced when he was a leader. Would you know how to handle them?
    • “These are all things that they don’t teach you…. There’s no book that says…go to page 15 and this is what happens when this happens…. There’s a lot of these things that you just have to kind of learn under fire. Again, that HR advisor is the person you have to go to…. Moving into those roles a lot of times is really difficult. It will follow you. Then it becomes kind of a distant memory….” – Paul Nadeau, on situations one experiences as a manager
    • Paul says the transition would be equally difficult to go back from individual contributor to manager if enough time had passed since the last management experience. It’s not that someone would forget how to perform the role, but there is a perception shaped by amount of time not in the role one must combat.
    • The decision points for Paul when it comes to manager / individual contributor come down to passion and what he wants to do in life.
• Many people we’ve spoken to who when back to individual contributor roles missed being close to the technology.
  • Paul tells us people in leadership (like leading a worldwide services organization) don’t have time for building a home lab. You start to feel like you’re getting behind.
  • Paul mentions it can be difficult to have your resume stand out when applying for a role as a manager or director because every organization has them.
  • If you’re an individual contributor in sales engineering, for example, the industry is a lot smaller than you think. Many people know each other. Paul shares the example of getting laid off last year and receiving multiple calls from his network very quickly after it happened. In this industry, our reputation precedes us. And this is also the case for leaders.
  • “If somebody were to call me and say, ‘hey, we want you in this management role….’ Sure, no problem. What’s the organization? Tell me about it. ‘It’s a well-oiled machine….’ Forget it. I don’t want it…. Anybody can just take a well-oiled machine…and maintain it.” – Paul Nadeau
  • Paul would rather lead an organization that is in disarray and needs fixing than a well-oiled machine. You are much more likely to get more leeway for fixing big problems from your boss than when things are working well. Rather than being given a strategy on which to execute from upper management, Paul would rather build the team and develop the plan to do it.
  • We should also remember interviews are for the job candidate to ask questions to interview the company (not just the other way around. This is especially important when applying for a management role.
  • “During an interview process, that’s as good as it’s going to get. Everybody has their best face on at that point. So, if it’s not working at that point, forget it. Just walk….” – Paul Nadeau
  • Ask upper-level leaders in interviews what they expect out of a leader. Paul says sometimes people cannot answer this question because they aren’t sure or haven’t really thought it through. This is the person who would be your boss. If they can’t tell you how you will be measured, that is a red flag!
  • “Are they really looking for a partner? Are they looking for somebody that’s going to help them…get through some of these issues and problems and build an organization that’s going to be world class and is going to be top performing? Or do they just want a placeholder? Do they just want somebody there because I have a req and that’s it?” – Paul Nadeau
  • Watch out for meaningless cliches from leaders that don’t really tell you as an individual contributor what you need to be doing.

23:44 – Specialty Decisions

• Paul remained in the networking and telecommunications space after returning to individual contributor. Why did Paul choose to take on different specialties over time within these areas? People listening may be afraid to specialize.
  • All of the specializations Paul ended up focusing on came from someone telling him that he couldn’t do it or figure it out.
  • Take ATM (Asynchronous Transfer Mode), for example. It’s a technology used to connect the world together. People thought Paul could never figure it out. But he did anyway.
  • Gigabit ethernet came out right after the ATM wave. There was also telephony (Voice over IP / VOIP and other traditional telecommunications), and one of the companies where Paul worked helped customers in this area.
    • Paul found himself needing to learn about 66 Blocks.
  • “Every part of it, believe it or not, there was an overlap in it. But it boiled down to somebody said you can’t do that. And being the last of 6 kids, I got so tired of hearing that when I was growing up…. And that was a lot of the career, quite honestly, the hard headedness I guess of it and the challenge of it.” – Paul Nadeau
  • Paul learned about Checkpoint firewalls, and when Fortinet entered the scene, he started to learn that technology as well.
  • Looking back on the experience, Paul says the opportunities just dovetailed into one another.
  • “You’re sitting in a room, and they said, ‘hey, we need somebody to do this.’ And everybody looks around…. Yeah, I’ll do it. It’s new. I don’t know anything about it. It’s interesting. Let’s go. What could possibly go wrong? That’s my favorite saying in the world. What could possibly go wrong? …So let’s just go jump in. That’s been my entire career quite honestly…. Sometimes it doesn’t work out so well. Sometimes it works out great. It just kind of depends. Risk taking…as long as it’s a calculated risk, it’s fine. As long as you think it through, you’ll be totally fine with it.” – Paul Nadeau
• Was learning something he didn’t know anything about the same as walking into an organization that is a complete mess and cleaning it up?
  • Yes! Paul says it’s the same thing.
  • Paul gives the example of leaving a telecommunications company to go and focus on NSX. He knew nothing about NSX at the time, but it had all the elements of his background (networking, security, etc.). Paul didn’t know virtualization, so he decided to build a lab to help himself learn what was missing at the level he needed to learn it (not at an expert level but at a level of competence for his role).
  • It was very similar when Paul moved to his role at Palo Alto Networks. They have an enormous portfolio of products, and Paul had to put in the time to learn the products at the deep level he needed to (i.e. getting his hands on it).
  • “If you’re looking to get into management or you’re looking to get promoted in management and you’re not looking for a mess or somebody that’s almost in tears when they interview you…then you’re not applying for the right job. You’ve gotta get out of your comfort zone. You really do. And I’m not saying go do crazy stuff, but you have to keep yourself uncomfortable in order to keep learning, to keep progressing.” – Paul Nadeau

29:15 – Nurturing Your Network and a Focus on Helping Others

• Paul does a really good job of nurturing his extended professional network. How does he do it exactly?
  • Paul is a people person, referring to himself as not really introverted but not really extroverted. He likes to have face-to-face conversations with others over a meal, for coffee, etc.
    • COVID was difficult for Paul.
  • Paul isn’t afraid to reach out to people he has not yet met. He will introduce himself to people at industry events, share what he does, and just have a conversation.
    • “There’s a lot of things you can glean…if you ask somebody about themselves and just sit back and listen, man, you’ll learn so much out of it.” – Paul Nadeau
    • Paul tells us we can learn so much about new ways of thinking, progression paths in tech, etc. through conversations with others (much like we’ve showcased on the podcast).
  • It’s ok to reach out to people we haven’t talked to in several years and ask to catch up. Paul sees this as an opportunity to pick up where you previously left off. We tend to fall out of touch with others because of various life events. It just happens.
  • Paul is a true believer in helping others. He gives the example of the tech downturn / season of layoffs we’re seeing right now. It’s an opportunity to have a different kind of conversation with people impacted.
    • “If there’s a layoff, I call. And a lot of times that person…day 2 is like, ‘man, I haven’t talked to anybody in the last day. It’s like all of a sudden, I had the plague. Nobody wants to call me.’ It’s not contagious. The person got hit in a layoff. What can I do to legitimately help you? And I will go to my network…but first I need to find out from you – what do you want to do? Do you want to change career paths? Do you want to stay on a career path? …This is an opportunity for you to kind of branch out a little bit and look at it. And you can have really kind of good conversations with people that you wouldn’t have if they were still employed…. It’s a different conversation.” – Paul Nadeau
    • Once you understand what someone wants to do after being impacted by a layoff, you can then introduce them to someone in your network. Many times, that person will introduce them to someone else because they know about an opening, which creates further momentum. We should not be afraid of making an introduction for someone.
    • Paul tells us he does not like asking for help.
    • “But, at the end of the day, people like to help. That’s what they want to do…. You’re giving them a gift by saying, ‘hey, can you help me?’” – Paul Nadeau
    • If you ask someone to make an introduction for you, it empowers them to take action.
    • If people are not willing to make an introduction for you, it may be a sign of a bigger problem you have.
  • Nick says we’re highlighting the importance of telling people the kind of help we need and what we want to do next.
    • Paul tells a story from early in his career when a teammate of his was laid off. He did all kinds of things to try and help the person find their next opportunity, but what the person wanted was to take some time off before looking for a next role. Paul didn’t understand that when he first dove in to help and advises us to be helpful without being assertive.
    • Paul remembers getting calls after being laid off from people asking what he wanted to do. Some of them were from managers who had no openings at the time but wanted to have a conversation.
    • “It’s rewarding on both levels…. I know now what I can do to help them, and I know what part of my network I can introduce them to based on what they want to do next….” – Paul Nadeau
    • A next step for some people after a layoff may be starting their own business, for example. Paul knows people who became franchise owners after getting laid off from a tech job.
• Paul mentioned making strong connections with co-workers as well as special interest groups. Which of these special interest groups has Paul frequented over the course of his career, and what would he encourage people earlier in their career to do?
  • There are many different groups that meet based on commonalities like technology, veterans or something else. You might hear about these groups on Facebook or LinkedIn, for example.
  • “If I look at a LinkedIn feed and somebody says, ‘hey we’re having a technology meeting…’ and you have somebody from 5 different companies…I know the companies because they’re in tech. I don’t know any of these people. I’m going. I’m definitely going. Because one, it puts me outside my comfort zone. Second of all, you have some of the most riveting conversations with people you don’t even know, but they’re in the same industry. And now all of a sudden you know them.” – Paul Nadeau
  • Paul says these types of conversations could result in…
    • Someone reaching out to you months later asking for help after a layoff – this enables the conversation about what they want to do and creates an opportunity to help
    • Someone letting you know they will be in your area – this creates an opportunity to get together
  • Listen to Paul tell the story of a dinner conversation that allowed him to help someone on a personal level based on previous experience.
  • “So, it’s not just about tech. It’s just about jobs. A lot of people look at it in the wrong respect, or they look at it like, ‘I need to do it because I need to get something out of it.’ And a lot of times you’re doing it because there’s a lot you can give. There’s a lot of insight you can…give out to help other people.” – Paul Nadeau
  • While having a professional network with strong connections can definitely help you should you lose your job, Paul tells us that’s not the way we should approach building our network. John calls it trying to put good vibes out into the universe.
  • Paul finds people who work in technology fascinating. It takes a special mindset to get into this industry, and there is a very cool commonality in being part of the industry.
    • Some people we meet we may only speak to once. Others we might speak with multiple times.
    • Paul tells the story of someone reaching out to him on LinkedIn, and it turned out the two of them were at a technology conference several years before then.
    • “It is a small world, small industry. It’s all about just getting out there and just who can you help. And then if you ever need help, hopefully it’s there for you.” – Paul Nadeau
• We’re going to feel better when we’re able to help someone else, but you may never know all of the people you end up helping.
  • Paul recently learned about the impact of a conversation with someone that really helped that person after they lost their job. But Paul didn’t go into that conversation with an agenda. He was just having a good conversation.
  • “Good people know good people. That’s what it boils down to. So, your network, if you’re a good solid person, good engineer…chances are your network is good solid people. It kind of lays the groundwork for helping everybody out. I agree 100%. It’s all about who you can help.” – Paul Nadeau
  • This is a parallel to what we heard Don Jones mention in Episode 137 – Something to Offer, Something to Share with Don Jones (1/2) about managers not knowing if today was a good day.
    • This is very similar to when we help someone with a job search or career advice. We don’t know what the impact is / will be. The intention is to leave a positive trail behind us.
  • Paul says we need to be able to have confidence in what we do, who we help, how we conduct ourselves.
  • “Everything has been a learning experience. Everything has been interesting. Have there been bumps in the road? Yes, absolutely…a ton of bumps. But it’s like anything else. If you’re on a cross-country flight in an airplane, you’re going to hit bumps. There’s going to be turbulence. You just fly through it. And then whenever you get there, you feel a little bit better about it, right? Because you made it through the turbulence…. What kind of impact am I going to make on humanity…at the end of the day? That’s the big goal right there…. How are people going to remember you? Are they going to remember you as the helpful person who just went out of their way to help people out? …It doesn’t have anything to do with money. It doesn’t have anything to do with prestige or being in a public eye. That just has to do with…being a good, solid human being. If you live your life like that…you really don’t have much to worry about.” – Paul Nadeau
• Connect with Paul on LinkedIn if you would like to follow up on this episode. Any subject goes.

Mentioned in the Outro

• As technical people we sometimes jump into solutioning too quickly. When it comes to speaking to those who have been laid off, we need to ask more questions and perform some discovery. What do they want to do next?
  • This could be an opportunity to brainstorm with that person and point out a role they could be qualified for but didn’t realize it.
  • What if someone doesn’t know what they want to do next? Outside of encouraging the person to give it some thought, you could suggest they read What to Do Next by Jeff Henderson, which was recommended by former guest Daniel Lemire.
• Paul said the job of a people leader is to protect the company first and foremost. By doing that they will protect their people.
  • This adds another element to the advice Richard Russell shared in Episode 319 – Upward Focus: Manage, Coach, and Create Value in the Space that Fits You with Richard Russell (2/2). Richard said the job of a manager or leader is not to serve their team but to provide value to the business, the organization, and their leadership. Serving the team is the HOW of doing the job and not the what.
• Do you know someone else who has suffered from resume damage? Send us an e-mail to recommend new guests. We would love to feature their story on the show.

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_
  • Leave a Comment on Your Favorite Episode on YouTube
• If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.
• If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

Imagine transitioning from individual contributor at a company to managing an organization of 155 people. That’s quite the promotion. How would you approach that kind of change?

Before you get too anxious about what’s coming, Paul Nadeau, our guest this week in episode 344, has two pieces of advice: stay calm, and don’t panic.

Paul’s career began as a Radioman in the Navy where he focused on telecommunications, but he later pursued law enforcement. You’ll hear firsthand about the experiences that cemented this mantra of remaining calm in Paul’s mind and follow him through leadership training in the Navy. Listen in to hear how a specific mix of classroom instruction and practical experience forged a leadership philosophy that is widely applicable both in the military and in the corporate world.

Whether you are an individual contributor or a people leader today, you’ll learn how to identify the traits of natural leaders and understand some of the real challenges of stepping into a management role.

Original Recording Date: 08-28-2025

Topics – Meet Paul Nadeau, Birth of a Specialty, The Importance of Staying Calm, Leadership Training and Gaining Experience, Assessing Leadership Talent

2:28 – Meet Paul Nadeau

• Paul Nadeau is a Solutions Consultant at Palo Alto Networks.
• Paul’s early career began with joining the Navy, but his decision to join starts even earlier.
  • Paul grew up in the Texas Hill Country (areas around Fredericksburg and Kerrville) and attended a private school for most of his young life.
  • Though the academics were great at private school, Paul talked his father into letting him attend public school for his junior year of high school.
  • At the public high school, Paul started to get into trouble. At one point his father had a very frank conversation with him.
  • “You need to do something with your life.” – advice from Paul Nadeau’s father
  • Paul’s father was a Marine who served in World War II and was awarded a Purple Heart for his service. He suggested Paul consider joining the military. Paul’s father wanted him to have some type of trade to fall back on after military service.
  • While the Air Force did seem appealing, Paul ended up joining the Navy in 1988. After boot camp, Paul was sent to all kinds of schools before serving on the USS America in Norfolk, Virginia in 1989.
  • Paul was serving when Desert Storm broke out in 1990.
  • After serving in the Navy, Paul decided to go into law enforcement (something he had always wanted to do). Though his work in the Navy focused on telecommunications / satellite communications, Paul didn’t want to keep doing it after serving in the Navy. He chose to attend the police academy instead.
  • Though Paul enjoyed being a police officer, the pay did not support starting a family.
  • Paul re-enlisted in the Navy in 1995 to once again focus on telecommunications, trading some of the re-enlistment bonus money to use for school.
    • Paul says he did Cisco training, Novell training, Unix administration, and even Windows administration training. He and co-workers were pioneering running these systems across satellite links (from ship to shore).
  • When Paul went into the Navy, they were looking for people who had clean backgrounds. He was able to obtain a security clearance after joining.

7:07 – Birth of a Specialty

• How did Paul end up in telecommunications after joining the Navy?
  • At age 17 when he first enlisted in the Navy, Paul wanted to do something in the medical field. He was told no.
  • Paul’s second choice for occupation was to be a cop. At the time, you had to have at least 4 years of service to do this.
  • The there was an opening for a job (or ratings as they are called) called Radioman focused on telecommunications. Though the nuclear program was an option at the time, Paul wanted nothing to do with it.
  • “Whenever we say option, it was pretty much like, ‘this is what you’re going to do. We’re going to send you over here, and you’re going to learn this….’ That’s what got me into telecommunications as a whole and into networking. Yeah, it was a good step.” – Paul Nadeau
  • The job placements were generally based on ASVAB scores, and it was Paul’s high scores that presented the opportunities for different fields.
    • Maybe we should have a military recruiter on the show at some point to better understand how this process works?
  • What drew Paul to law enforcement after getting exposure to telecommunications in the Navy?
    • When Paul was a kid (even as young as kindergarten), his dad (a disabled veteran) would walk him to school each day. Every day he would ask Paul what he wanted to do when he grew up. Paul always said he wanted to be a cop.
      • Paul isn’t 100% sure why he wanted to be a cop from such a young age, but there was a state trooper who lived in the same neighborhood. Paul loved his car and thought he was one of the nicest guys in the world.
    • Six-year-old Paul wanted a career in law enforcement.
• John asks about access to schools in the military. The training seems relevant to a field even for the person who has not yet worked in that field.
  • Paul says his training for Cisco and Novell, for example, was delivered by a civilian instructor who visited the Naval base. It was civilian training paid for and sponsored by the Navy.
  • After Desert Storm while still stationed in Norfolk, Paul wanted to attend Old Dominion University.
    • He remembers having to attend in uniform, but the cost of attending was covered by the Navy. Paul wanted to take advantage of the opportunity to get more education.
  • There was also a Radioman “A” school Paul attended and some “Sea” schools. He learned satellite communication and cryptology, for example. The training courses for Cisco and Novell were mixed into the same curriculum as these Naval schools.
  • The schools you were eligible to attend were based on your job. Paul tells us the Radioman rating from years ago has changed to IT (according to Naval classification / rating).
    • He remembers studying morse code and HF (high frequency) communications (ship-to-ship, ship-to-shore, communication over satellite, etc.).
    • Radio was considered a secure space, and the personnel focused in these areas got exposed to all of the new technologies. Paul liked being able to tinker with it.
    • In addition to attending school, working on a ship 7 days per week is on-the-job training. Paul worked 7 days per week for 7 months during Desert Storm.

14:34 – The Importance of Staying Calm

• How did military training translate to intense / hostile situations in law enforcement?
  • Paul was assigned to an AMCC (American Mobile Communications Center) unit for Desert Storm, and as a result he went through a lot of training (hand-to-hand combat, logistics training, and other things one might use when forward deployed).
  • “The number one thing that you actually learn, believe it or not, is the key to success – stay calm. Don’t panic…. Panic is the number one thing that will get you in trouble every time…. It’s kind of been the guiding light in life…that one little bit of information.” – Paul Nadeau
    • Paul is a private pilot and understands the importance of staying calm while he is in the cockpit of a plane. This translates to so many areas of life (interactions with kids, situations at work, etc.).
  • Did Paul do anything specific to help himself stay calm? What would he tell people who are not good at this?
    • Listen to Paul’s story of being a field training officer during his time in law enforcement.
    • The instinct to stay calm sort of came naturally to him.
    • When situations begin to escalate, take a second to think about them rationally. It won’t do us any good to let our mind run away with a situation and have it take control of us.
    • Many people consistently fight anxiety. Paul has been fortunate enough not to struggle with it.
  • Was what Paul describes (staying calm even in difficult situations) a result of basic training and becoming a little bit desensitized?
    • Paul tells the story of basic training and getting exposed to tear gas.
    • “You can panic and pass out because you will. You will stop breathing and just hit the ground. Or you can stay calm and regulate your breathing and kind of center yourself. And when you do, you can…overcome the problem or issue. That was my initial wow. This is a really good thing for life in general…. Whenever you make it out, yeah, you’re coughing. You’re hacking. Your eyes are burning…. But you were still able to actually perform. You were actually able to breathe. You were actually able to say a sentence…. They want you to have that levity to do that….” – Paul Nadeau, on staying calm in basic training
    • Paul describes a similar type of training for firefighters. You’re in a giant room of 2-3-foot deep water, and someone dumps gasoline on the water to start a fire with it. Then it’s the firefighter’s job to put out the fire.
      • Despite instructors demonstrating how to put out the fire, people will panic when put in the situation.
    • Some of this may go back to the training Paul received on how to perform under pressure and stress.
  • Maybe we can practice responding calmly to high stress situations?
    • Paul shares the story of being a newly trained police officer. After 2 weeks of training, he was sent out on patrol by the sheriff. The first thing he had to respond to was the scene of a vehicle accident (a head on collision).
    • Paul remembers how quiet the accident scene was. He could hear the cracking of metal and steam from car engines.
    • “All of a sudden you hit that moment of levity. Don’t panic. You can’t panic with this. You got called here to do a job. You’re going to be the only person here that can actually do that job…. You have to kind of be that leader so to speak, that calm amongst the storm, and just do your job. And it’s difficult….” – Paul Nadeau, on being the first to the scene of an accident
    • Even if you are calm during difficult situations like the one above, Paul tells us you have to take time to decompress afterward and work through the situation mentally.
    • “I felt like maybe there was maybe something wrong because I wasn’t breaking down…I hadn’t lost my cool with it…. I was functioning perfectly fine. Did it affect me? Absolutely. There’s no doubt about it…. If you say that it didn’t affect you, you’re not human…. There’s still that human emotion side of it. But it wasn’t to an incapacitating level.” – Paul Nadeau
  • John has heard a panic or anxiety response is a lot like a glass of water. If the glass is close to full, it doesn’t take much to overflow. But if you intentionally keep the water level low, it takes a lot more to cause spills.
    • Paul has seen different people handle stressful situations differently over time. It’s not right or wrong but the way they handle it.
  • Does Paul not have an adrenaline response?
    • A pilot needs a healthy dose of fear when flying a plane.
    • Paul says it’s more of a primal fear response that we’re talking about. Panic in the early days of civilization, for example, might mean you get eaten.

24:26 – Leadership Training and Gaining Experience

• Where does leadership play into the story?
  • In the military, ranks of E-1 through E-3 are usually entry level. Being promoted to the rank of E-4 is normally when leadership responsibility comes into play.
  • In the area of radio, there were 2 subdivisions. E-4 was more of a leadership role in the message center because it staffed so many more people than the tech control side. Usually there is an E-5 and an E-6 to look over operations as well.
    • Tech control – setting up circuits
    • Message center – where all messages came in (could result of hundreds of messages per minute)
  • Paul says you get leadership training, but it is mixed with a lot of real-world, practical experience. In Paul’s first 4 years, he made it to E-6.
    • In the military, things are pretty black and white without a lot of ambiguity.
    • There are situations both in the military and in the civilian world in which leaders are expected to perform conflict resolution.
  • Listen to the lesson a senior leader in the military taught Paul after his leadership training about the difference between productivity and activity.
    • “We have to be productive, not just active. So, it doesn’t matter if you go have 15 conversations with customers. Did you have a meaningful interaction with them? That’s more important. The same thing when you’re in leadership…if you’re not having meaningful interactions or conversations with the people that work for you or the people that you work for, then you’re missing out. You’re really missing out…. There’s a lot of things you can talk about, but it has to be meaningful. It has to be directional. That’s what I learned…and it wasn’t actually in the training itself. It was actually from a chief warrant officer.” – Paul Nadeau
  • The activity vs. productivity idea applies to any technology job. There’s always another ticket to work on.
    • “Each one of those jobs…yeah, you can do a lot of activity. And you can be…the person that is just burned out at the end of the day…. If you sit back and look at it…, am I truly productive? Have I actually done something that has been great for the customer, good for the company, good for me…?” – Paul Nadeau
    • If we try to get more productive instead of more active, it could reduce our workload. Everyone around you will value this shift. Paul tells us it has a lot to do with meaningful interactions with others.
• Did the leadership training and the lesson Paul learned from the chief warrant officer make him want to pursue more of a leadership role in the future?
  • “The training itself was fantastic. What I learned was how much I didn’t know. And I learned what level I didn’t know it at.” – Paul Nadeau
  • Paul says anyone can take a group of people and manage them (i.e. make sure the tasks get completed). That’s management. True leaders can take groups of disparate people together and lead the team.
    • When Paul was in the military, he would ask other leaders how he could help the people under him evolve in such a score-based environment.
  • “To me, what was exciting about it was the ability to actually be able to connect and actually be able to help people with their career…. Nothing really dealt with your personal ability, your brand. You didn’t really have a brand, and then you do whenever you get out. And all of a sudden you don’t really know what this brand is because in the military you’re a collective. In the civilian world it’s more of an individual that works in a collective environment…. Taking that and fostering it was a really interesting evolution.” – Paul Nadeau
  • Paul’s first people management opportunity in the corporate world was at a telecommunications company where he worked as an individual contributor.
    • Paul’s neighbor worked for a power company and wanted someone to come run their operations. He had known Paul for a few years and knew he had military experience.
    • The neighbor made Paul an offer, and he decided to resign from his employer. But the story took an unexpected twist when Paul received a call from the CEO of the telecommunications company who would not accept his resignation without a face-to-face conversation.
    • The CEO told Paul they were about to flatten the company’s management structure the following week and made him an offer to be director of worldwide services. Paul had a good reputation, and the military leadership training made him a great fit for the role in the CEO’s eyes.
    • “I thought about it all the way home…. I’ve been here. I know these people. I know where the problems are and where the issues are…. One of the things that I didn’t anticipate – I was a colleague. I went from colleague to suddenly I was in charge…. And there’s a big difference whenever you do that.” – Paul Nadeau, on taking a new role within his current company
    • Paul says taking on the leadership role had a number of trials and tribulations he never expected. But it was a lot of fun and very rewarding.
• Paul was an ATM Engineer and then had to lead teams of ATM engineers. ATM stands for Asynchronous Transfer Mode in the telecommunications world.
  • “I went from managing myself to managing 155 people in 3 different geos around the world.” – Paul Nadeau
  • Paul had to manage a $35 million profit and loss center that was in disarray, his first task was to systematically understand the problems and prioritize them appropriately.
  • It was a large, complex organization. Paul needed front-line managers underneath him, and it was important to take time to train and mentor those managers (some of which were first-time managers).
    • “Not only am I now managing North America along with the rest of the world…now I have to train somebody on how to be a leader. Now you kind of have extra hours built into your day…. You can’t just do your job and then go home….” – Paul Nadeau, on supporting first-time managers
  • An engineer who once worked for Paul went on to become the COO of a company in Canada. This person thanked Paul for everything he had learned about leadership while working on that team.
    • Paul cites military leadership principles as providing the foundation of what he needed to succeed.
    • “Everybody thinks the military is like Full Metal Jacket…. That’s not it at all.” – Paul Nadeau
    • In his role now at Palo Alto Networks, Paul is part of the Vets Net program. The skills of military veterans are widely applicable outside the military.
• Was there a specific NCO leadership training track or course that was especially useful to Paul, or was learning on the job from experienced leaders more useful?
  • Paul says it was really a mix of both.
  • There are advancement cycles in the military during which people go up for promotion. This involves taking tests and getting recommendation letters as well as usually going before a board of review. People either get promoted or are classified as PNA (Pass, Not Advanced), but there are only so many openings.
  • When you get promoted up to E-5 or E-6, this is middle management in the military. Once you are promoted to either E-6 or E-7, Paul says there is a structured, required class.
    • One part of the class is instructor-led training.
    • The second class is for reinforcement and absorbing knowledge from other leaders.
    • Paul tells us this is a really good combination of classroom training and hands-on experiential training.
    • Also, advancing from E-1 to E-6 in the same area taught Paul a lot about promotion from within, and he was able to apply this to roles outside the military.

38:48 – Assessing Leadership Talent

• Paul spoke about hiring new leaders and knowing he would incur an overhead of mentoring a new leader, which sounds like an idea built into the training he received and experienced in the military.
  • “One of the things that’s really amazing to me, and I see this all the time…. People think that because you’re a great engineer, you’re going to be a great engineering leader. They think because you’re a great salesperson you’re going to be a great sales leader…. It’s a completely different skill set altogether. Just because you can sell like there’s no tomorrow doesn’t mean that you’re going to be a great leader….” – Paul Nadeau
  • Paul talks about another type of person that is an individual contributor who may be struggling but has a number of really good skills we might consider leadership skills – being structured, being helpful, wanting to help people.
    • But even if someone has these skills, would they want to be a people leader? They might not. Paul mentions cases where he tried to persuade people to pursue leadership, and they refused because they were happy in their role.
  • There’s another group of people who want to be in management and continue to try for and chase it (like a dog chasing a car). But once they finally get the management role, they don’t really know what to do with it.
    • Once this leader begins to struggle, morale on their team goes down.
    • Sometimes higher-level leaders aren’t training their front line managers or other leaders underneath them. There are multiple negative downstream impacts of this.
    • Paul thinks being a leader should be embedded within us. Even if it isn’t, people can learn how to do it.
    • It can be difficult to find someone who has the skill set of being both technical and being a leader, but when you see it, you know that person needs to be in leadership.
• If Paul recognized leadership traits in someone, what would he say to the person to encourage them to pursue leadership?
  • Paul would start by asking whether the person had ever thought about leadership.
  • If the person did not think they had the skill set, Paul would politely correct them and tell them why they have the skills to do it. It could be transparency, conflict resolution, not avoiding problems, etc.
  • “The second part of it is…do you know what you’re getting into?” – Paul Nadeau, encouraging someone to become a leader
    • People might not realize managing upward is something required when you’re a people leader. You have to pick your battles, decide what to filter, and provide feedback to your boss (which might mean voicing concerns about an idea being silly).
    • Many times, people not in leadership don’t know they are qualified for it.
  • “You have that person in every organization that when they leave, it’s worse than if their leader left. If that first-level manager left, a lot of times that’s less of an impact than the natural born leaders that you have that are individual contributors on the team. Because that’s who actually rallies the team. That’s who actually gets people to do things.” – Paul Nadeau, on leadership qualities in individual contributors
  • Overall, it’s a fun conversation to have with someone according to Paul, but does the person really know what they are getting into by pursuing people management?

Mentioned in the Outro

• Paul’s move into law enforcement after being trained in telecommunications in the Navy might on the surface look like an odd choice, but he’s modeling going to try something new for the rest of us.
  • Paul wanted to be in law enforcement from a young age. It was his ambition.
  • Past guests like Daniel Paluszek and Brad Christian wanted to try working for startups and decided to make job changes, for example.
  • The decision to go and try something nets us experience we can take to our next role, whatever it may be. We’re confident Paul’s time in law enforcement helped him in his next roles back in the Navy and in civilian life.
• Many technology companies are looking for veterans who have transferrable skills from military service to apply in our industry.
• For more stories of veterans whose technology careers began in the military, check out our veteran tag and list of episodes.
• The comment about the impact of individual contributors leaving a team made Nick think a lot about our conversations on the role of tech lead or team lead. For discussions with guests where we focused on these roles and reasons for taking them, check out these tags on our site:
  • Team Lead
  • Tech Lead
• Paul’s move to director of worldwide services and the need to focus and prioritize for a large organization reminded us of the conversation about manager priorities from Episode 328 – A Manager’s Preoccupation: 1-1 Meetings and Focused Prioritization with Joseph Griffiths (2/2)

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• The hosts of Nerd Journey are John White and Nick Korte.
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