Monica Marquez has held big titles at Google, EY, and Goldman Sachs, but now she's teaching companies how to ditch their outdated playbooks and embrace a new way of working with AI. In this episode, Monica and Rob unpack why the people team, not IT, needs to lead AI transformation, how to automate without losing the human touch, and what it really means to "unlearn" your way to better work. She shares how her team at Flipwork is helping organizations build adaptive, human-centered workflows and why leaders must create safe spaces for experimentation.

Also discussed: how to turn prompting into repeatable agents, the problem with "work slop," and why the best AI onboarding might come from a Clippy-inspired bot named Flippy.

• AI transformation must be people-led, not tech-led

• Unlearning is the new competitive edge in a world moving faster than ever

• "Work slop" is real, and AI isn't to blameHigh-value work starts when you stop doing what AI can do faster

• The best use of AI is treating it like an intern, not an oracle

• Prompting is table stakes. Turning prompts into agents is the real differentiator

• Empowering people to automate their own workflows requires safe space and structure

• People teams must guide AI adoption to protect ROI and increase tool adoption

• AI should amplify your "authentic intelligence," not replace it

• A modern talent strategy must account for psychological safety, rapid experimentation, and clear permission to try new things

¡Ay, Ay, Ay, AI! Newsletter Monica Marquez on LinkedIn

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A Beautiful Working World

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Tony Castellanos has seen recruiting from every angle: Google, Square, various startups, and now as Head of Compensation & Talent at Nextdoor. In this episode, Tony breaks down how his team is using AI to rethink recruiter training, eliminating the "practice on candidates" problem by simulating real conversations with virtual personas. He and Rob also dive into community-led recruiting, why values alignment trumps pedigree, and how automation should empower recruiters to be more human.

Also on the mic: the death of the "Apply Now" mentality, the future of AI interview agents, and why Nextdoor's most beloved teammate might be a benefits bot named Ben.

• AI-driven training gives recruiters reps without risking candidate experience

• Recruiter excellence starts with values alignment and relationship building

• Referrals aren't just about "who do you know", they're part of a broader community activation strategy

• Recruiters should act like talent strategists, not inbox managers

• Tools like CodeSignal enable voice-to-voice interview simulations with real-time feedback

• Giving AI agents names and personalities makes adoption more natural and team-friendly

Tony Castellanos on LinkedIn

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André Martin has been CLO at Nike, Mars, and Target, so when he talks about the cost of disengagement, we listen. In this episode, André joins Rob to talk about his new book Wrong Fit, Right Fit, why work feels broken for so many, and what leaders can do about it. From rewriting job descriptions to rethinking culture as a daily operating system instead of a poster, André lays out a blueprint for restoring energy, engagement, and trust inside modern organizations.

Also discussed: why climbing the ladder might take you further from your craft, how companies can stop catfishing candidates, and why your offsite might be a total waste of time.

• Work is always happening, which is why companies must intentionally design for recovery and restoration

• Culture is not a value statement, it's how work actually gets done, shared, and socialized

• Disengagement is expensive; $9.6 trillion in lost productivity comes from people doing the wrong work in the wrong place

• Protective narratives are a red flag; rationalizing and blaming are signs of misalignment

• The best offsites are not packed with content, they are focused on building deep relationships and trust

• Promotions should not pull people away from their craft; getting better at your job should not always mean managing more people

• A more honest hiring process that includes how ideas are shared and decisions are made can reduce bad-fit attrition

Wrong Fit, Right Fit: Why How We Work Matters More Than Ever

André Martin on LinkedIn

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Tracy Layney has led HR at iconic brands like Levi's, Old Navy, and Shutterfly, so it's no surprise she's now training the next generation of CHROs at the University of Chicago's Booth School of Business. Tracy joins Rob to unpack why HR's role is more complex (and powerful) than ever before, and how her coursework is helping senior people leaders develop the human capital strategies their companies desperately need. She breaks down the people-side of big moves—like Levi's exit from Russia—and shares the three-pillar framework she teaches for linking business goals to people strategy. Plus: why HR still doesn't speak the language of business, and how she's helping to change that

• Tracy's journey from org strategy consulting to CHRO to professor

• Why executive HR education is finally getting the attention it deserves

• A behind-the-scenes look at Booth's program for future CHROs

• The people-side of major business decisions, like Levi's exit from Russia

• Why the CHRO role is more complex, and more influential, than ever

• The three-pillar framework for building a scalable human capital strategy

• How to tailor people strategy without reinventing the wheel

• Why HR still doesn't speak the language of business, and how to change it

• The disconnect between strategic frameworks and HR's day-to-day execution

• Tracy's take on lifelong learning, fractional work, and what's next in her career

Tracey Layney on LinkedIn

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Angela Briggs-Paige, Chief People Officer at Acelero Learning, joins Rob to share why HR is not your friend—and that's a good thing. Angela breaks down how she shows up as a business leader first and a people expert always. She shares how she earned her seat at the boardroom table, what it really takes to build employee-led career paths, and why performance reviews need a serious glow-up. Plus: Angela's approach to employee growth (spoiler alert: it involves passports), starting her own fractional CPO business, and never, ever being out-peopled.

• Why HR isn't your friend

• How to speak "business" instead of "HR" to get heard in leadership rooms

• The courage it takes to challenge decisions in the boardroom

• "I will not be out-peopled": Angela's mantra for CPO credibility

• How Acelero is replacing performance reviews with employee-led "career passports"

• The mindset shift from "how do we keep people?" to "how do we make staying a meaningful choice?"

• Why enabling managers as coaches, not judges, is the key to performance development

• The case for giving employees homework before their 1:1s

• How expanding her portfolio beyond HR helped Angela grow as a business leader

• What her fractional CPO venture People Power is teaching her about right-sizing HR strategy for scale

Angela Briggs-Paige on LinkedIn

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Michelle Brooks, Chief People & Culture Officer at Security Compass, joins Rob to unpack what it really means to lead with "compassionate candor." She shares how feedback norms are shifting for Gen Z, how she built a truly strategic people function without a traditional HR background, and why HR's identity crisis is holding the industry back. Plus, Michelle gives a front-row look at how her team is driving AI adoption across the business—from launching an internal AI council to treating AI like the biggest change management initiative of the decade.

This episode is packed with spicy takes, real talk about feedback, and a blueprint for how HR and IT can actually partner to move AI from buzzword to business driver.

• Why Gen Z wants more feedback, and how to deliver it with "compassionate candor"

• The problem with radical candor and how it's been quietly rebranded

• Why feedback is often withheld from leaders, and how Michelle invites it in

• The myth that HR needs permission to have a seat at the table

• How Michelle's background in sales and recruiting helped her avoid HR "learned helplessness"

• Why HR still suffers from an identity crisis

• How Security Compass is treating AI adoption as a company-wide change management initiative

• The structure and purpose of their internal AI council, governance committee, and AI champions program

• The growing alliance between HR and IT

• How to make the business case for leading AI adoption from the people function

Michelle Brooks on LinkedIn

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Katya Laviolette, Chief People Officer at 1Password, joins Rob to unpack how the company scaled from a scrappy, consumer-first startup to a 1,400-person B2B security powerhouse. She shares why shifting from B2C to B2B hiring isn't just about adding new roles—it's about evolving core competencies. Katya also explains how her team uses "anti-recruiting" to scare off the wrong candidates, and how being brutally honest during the hiring process actually leads to better retention. Plus: why every company is a train ride, and you don't have to ride the whole way.

• Why 1Password eliminated the "Apply Now" button—and what it means for candidate experience

• How hiring changed as the company shifted from B2C to enterprise B2B

• The buy-vs-build approach to talent in cybersecurity and SaaS

• Why "anti-recruiting" is a crucial part of high-growth hiring

• How to design an interview loop that screens for ambiguity tolerance

• The difference between relevant experience and transplanting culture

• Why some hires are "lifers" and others join for a chapter—and that's OK

• Katya's metaphor for growth: scaling a company is like a train ride

• Why strong employer branding should repel as much as it attracts

• How candidate curiosity and specificity signal long-term success

Katya Laviolette on LinkedIn

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Rob reconnects with longtime friend and HubSpot's VP of Talent Acquisition & Mobility, Becky McCullough, for a conversation that spans nearly a decade of growth, both personal and organizational. Becky shares how trust, flexibility, and curiosity have kept her at HubSpot for 10+ years, and why she encourages her team to take recruiter calls (really). They also dig into HubSpot's AI-first approach to hiring, performance, and engagement, including how they're assessing AI fluency without bias, and why "show your prompt" might be the new "show your work." Plus: Becky's spicy take on why direct reports shouldn't be part of hiring their boss.

• Why Becky encourages her team to take phone screens with external recruiters—and how it builds trust

• HubSpot's shift from reactive HR to strategic workforce planning

• How AI fluency is becoming table stakes in hiring (and how to assess it equitably)

• The role of trust in employee engagement surveys—and why honesty is a signal

• Why Becky believes direct reports shouldn't help hire their boss

• How HubSpot uses Qualtrics and AI to synthesize feedback fast

• The balance between fast AI adoption and responsible implementation

• Why hiring is (still) a team sport—and TA shouldn't be "the hiring police"

Becky McCullough on LinkedIn

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Jessica Swank didn't set out to be a Chief People Officer—but when the opportunity found her, she said yes. Now CPO at Box, Jessica joins Rob to share her unconventional career journey and how she's helping lead the company into its next era as an AI-first organization. She explains why AI is more about change management than tech, what it means to build cross-functional partnerships that work, and why every Boxer (even the CEO) has to pass an AI quiz. Jessica also reveals how Box rolled out an internal AI agent that writes job descriptions in seconds, and why "return on time" is her new favorite metric. Plus: a cameo from Jeep, her 7-year-old's favorite GPT agent.

• Jessica's journey from recruiter to Chief People Officer

• Why she nearly said no to the CPO role at Box

• What it's really like to lead HR during a global shutdown

• How Box is approaching AI as a cross-functional, people-first initiative

• Why HR should lead AI strategy—not just adoption

• Box's three-pillar framework for AI: Optimize, Elevate, Amplify

• The ROI of AI? Try ROT—Return on Time

• How Box built an AI agent that drafts JDs from intake calls

• Why every employee at Box is required to pass an AI enablement course

• How to grow with a company instead of being outgrown by it

• Why "get comfortable being uncomfortable" is still the best career advice

Jessica Swank on LinkedIn

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Jim Conti, Talent Partner at Hyde Park Venture Partners, joins Rob to unpack what it really means to support startups from the VC side. He shares how his role has evolved from operator to advisor, why he often tells founders not to hire, and what makes a great first head of marketing hire. Jim also explains how talent leaders can earn influence without ownership, translate TA metrics into business outcomes, and become the first call when founders hit a crisis. Plus: the real reason boards don't care about your hiring speed.

• What a talent partner actually does at an early-stage VC

• How to support portfolio companies without getting embedded full-time

• Why hiring should be a last resort—not a first instinct

• The bowling bumper metaphor for talent advisory

• How to guide founders through hiring their first execs

• How to build trust and become the first phone call when things go sideways

• Why talent teams need to shift from "function" to "impact" when reporting to boards

• Common TA metrics boards don't care about—and what they do want instead

• Why talent leaders must stay curious about AI, automation, and tooling

• The evolution of recruiting from high-volume hiring to strategic headcount planning

Jim Conti on LinkedIn

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Delivery Hero's Chief People and Sustainability Officer, Ana Mitrasevic, joins Rob to challenge the status quo of performance management. Drawing on her experience in both HR and product, Ana makes the case for replacing rigid review cycles with tech-enabled, real-time performance enablement. She shares her vision of a two-sided internal talent marketplace, explains why traditional career ladders don't cut it anymore, and offers a smart hiring hack that both CFOs and CPOs can get behind. Plus, a friendly invite to watch high-drama basketball in Serbia.

• Why performance enablement should replace traditional performance management

• How technology can identify real-time strengths and skill gaps without a manager's input

• Why annual reviews and rigid nine-box grids no longer serve high-performing teams

• How to build an internal talent marketplace that empowers nonlinear, skill-based career moves

• How to use "next-level-down" backfills to create internal mobility and reduce costs

• What HR can learn from product management: test, iterate, de-prioritize

• Why values and behaviors may matter more than skills in internal hiring

• How to scale talent discovery beyond one-off relationships and gut feeling

Ana Mitrasevic on LinkedIn

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