Fit Happens: The Executive Search Podcast

Dave Lu built a career by walking away from the ladder everyone told him to climb, and it taught him more about leadership fit than any resume ever could. In this conversation I sit down with Dave Lu, founder of Hyphen Capital, co founder of Fanpop, and the organizer behind the Enough open letter that ran as a full page ad in the Wall Street Journal. Dave is also an Emmy winning producer. We talk...

Does a leader's public failure actually tell you less than their quiet success? Here's a scenario I run into constantly in executive search: two final candidates for a CEO role, one with a spotless record, one with a very public failure in their past. The easy move is to screen out the second person. I think that instinct deserves a lot more scrutiny than it usually gets, and this episode is my at...

What actually makes a leader fit a job, when the written job spec says one thing and the company needs another? That is the question at the center of my conversation with Anand Eswaran, CEO of Veeam Software, a 15 billion dollar company that exists to put data back together after ransomware attacks, outages, and some of the worst days a company ever has. Anand is a first time CEO who will tell you...

Are you actually spotting leadership potential, or just rewarding polish and confidence? In this solo episode, I break down the most overused word in succession planning: potential. Every talent review, every nine box grid, every slate has it, and almost nobody defines it the same way. I walk through research on how companies actually measure potential (hint: it's mostly just past performance in d...

Jon Cohen spent decades calling elections before founding an AI company built to fix his own industry. I sat down with Jon Cohen, founder and CEO of TrueDot.ai, who spent his career running polling at ABC News, the Washington Post, and Pew before becoming chief research officer at SurveyMonkey. We talk about why he never let himself get promoted out of the actual work, what it felt like calling pr...

A candidate lights up the room in the debrief, and a year later the company is searching again. Here's why. I open this episode with a scene that will feel familiar to anyone who has sat in a hiring debrief. The candidate walks out, the folder full of scorecards and reference notes sits untouched on the table, and someone senior leans back and says, "I just really liked her." Heads nod. The room s...

Why does experience in one crisis so often fail a leader in the next one? I open this episode with the story of the 1949 Mann Gulch wildfire, where foreman Wagner Dodge lit an escape fire to save his crew and nobody followed him. Thirteen men died. Forty five years later, at South Canyon, fourteen more firefighters died in strikingly similar circumstances, and I use both disasters to ask a questio...

A leader who looks safe on paper might be the riskiest hire you make in the AI era. That's the paradox at the center of this conversation. I sit down with Liat Ben-Zur, a longtime technology executive who has led through four major shifts, the internet, mobile, IoT, and now generative AI, at companies including Qualcomm, Philips, and Microsoft. Liat is also the author of a new book on leadership a...

MIT built a job title from scratch because Paul Cheek didn't fit any that existed. Now he's ranking the S&P 500 on AI maturity, and the results may surprise you. We get into why AI literacy has to come before AI strategy, why the best managers may not be the ones who make you feel good, and why human fit still matters in a world full of capable agents. Paul also breaks down the four types of A...

Seventy-three seconds after launch, the warning that could have stopped the Challenger disaster had already been softened beyond recognition. In this solo episode, I break down why hierarchy filters truth out of organizations long before anyone lies, drawing on research into organizational silence, psychological safety, and the Nokia collapse. I share five specific practices, what I call the archi...

He traded Silicon Valley for the Andes and built a life around a completely different definition of leadership. In this episode, I talk with Terry Cumes, CEO of Wilkatika Resorts in Peru's Sacred Valley and author of the new book Special Guests which explores leaving a career in education technology to run his family's wellness retreat full time. We dig into cross-cultural leadership, building com...

Boards rarely hire the most capable person. They hire the one who feels the safest to defend. In this solo episode, Jason Baumgarten breaks down signaling theory and what it actually means for how leaders get chosen. He explains why credentials often function less as proof of capability and more as a shortcut decision makers use to reduce risk under uncertainty, and why that shortcut can quietly r...

He spent two decades at the frontier of tech. Then he chose a 177-year-old railroad instead. In this episode, I talk with Krishna Iyer, head of software engineering at BNSF, a Berkshire Hathaway company. Krishna spent years building enterprise software at Microsoft, scaling consumer products at Amazon's Kindle, and working at the edge of generative AI at AWS, before deciding the biggest opportunit...

A new CEO's hundred day plan sounds smart. The research says it's mostly fiction. In this solo episode, Jason Baumgarten traces the hundred day myth back to its real origin (FDR's 1933 Congress, not leadership research) and explains why boards keep asking a question that sets new leaders up to fail. Drawing on research into CEO transitions, he lays out five separate "clocks" (strategic, socializat...

Loneliness and bad fit can feel identical, but they are not the same thing at all. Lexy Franklin, founder of Sidebar and former Facebook product leader behind Messenger Kids, joins Jason to unpack why the best founders fail constantly, why groups outperform individual genius, and how AI is reshaping both hiring and leadership. Lexy shares the failure-mourning ritual he uses after a product flops,...

One stock price swing can turn the same leader from visionary genius to reckless failure overnight. In this solo episode, I break down the halo effect, the century-old psychology finding that one strong impression bleeds into every other judgment we make about a person, and outcome bias, our tendency to judge decisions by how they turned out rather than whether they were smart at the time. I walk...

Your best salesperson just got promoted to manager. Here's why that's often a mistake. In this solo episode, Jason Baumgarten unpacks the Peter Principle, the half-century-old idea that people in a hierarchy rise to their level of incompetence, and the 2019 study that proved it's not just a joke. Drawing on research covering tens of thousands of salespeople across more than 130 companies, Jason br...

If time is your most valuable asset, who's actually deciding how yours gets spent? In this solo episode, I unpack a paradox I see constantly in the leaders I work with: real authority over strategy and budget, almost none over their own calendar. I introduce the idea of designed time versus default time, walk through the three traps that quietly steal a leader's week, and give you a simple three-q...

What if the same leader, running the same playbook, could fail in one place and win big in another? That's the question at the heart of my conversation with Jim Citrin, who has spent three decades at the top of the executive search world placing and advising CEOs. Jim is also one of my mentors, so we go past the usual hiring talk into what actually decides whether a leader succeeds: fit. We trace...

What if the thing quietly undermining your team's performance isn't strategy, compensation, or culture decks, but whether people feel like they matter? Jennifer Wallace is a journalist and award-winning author of Never Enough and her newest book, Mattering . She spent years studying what allows people — children, employees, leaders — to thrive under pressure, and her answer centers on a deceptivel...

The boardroom is the last line of defense for AI governance — and most directors aren't ready. Steven Wolfe Pereira has spent 30 years at the intersection of technology, data, and leadership — from building the early internet at Akamai to now running Alpha, the AI governance intelligence firm reshaping how boards and C-suite executives prepare for the agentic era. In this conversation, Jason and S...

What if the job you have today quietly becomes the job you never agreed to take? In this solo episode, Jason Baumgarten breaks down one of the most underestimated risks facing leaders right now: not job replacement, but job transformation. Drawing on history, academic research, and real examples from his work in executive search, Jason explains how AI and automation are quietly unbundling roles fr...

The investors closest to the best founders have a front-row seat to what great fit really looks like. In this episode of Fit Happens, I sit down with Laela Sturdy, Managing Partner at CapitalG — Alphabet's growth investment fund — and one of the most thoughtful voices on leadership fit I've encountered. Laela has spent 20 years inside Google and Alphabet and 13 years partnering with hyper-growth c...

You have roughly 4,000 weeks. Are you spending them on work that actually deserves them? In this solo episode, Jason Baumgarten — senior partner and executive search specialist — explores one of the most under-examined questions in leadership: the relationship between fit and time. Drawing on Oliver Burkeman's 4,000 Weeks , decades of executive search experience, and insights from organizational p...

Dan Gertsacov, CEO of Big Green Egg, has built a career by saying no to money and yes to fit — four times over. In this episode, we dig into his non-linear path from social entrepreneur to Google exec to restaurant industry leader, and how each chapter prepared him for the challenge of revitalizing one of America's most iconic brands. Dan shares the ikigai framework he has used to navigate every m...