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PODCAST

Fit Happens: Why CEOs and Leaders Succeed or Fail

Jason Baumgarten

Why do talented leaders fail in one role and thrive in the next? Jason Baumgarten has led hundreds of Board, CEO and c-suite transitions at Spencer Stuart. He covers CEO succession, how boards hire a CEO, and shares leadership research alongside candid opinions about leadership and governance. His guests include CEOs, Board Directors, Researchers, Authors and unique executives who share their own observations about leadership but also their own lessons and life stories. Jason covers everything from

business management

All Episodes

52:03

How Market Research Tricks Leaders into Making The...

Fit Happens: Why CEOs and Leaders Succeed or Fail ·

2026/10/01

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 presidential elections on deadline, and why he thinks executive fit depends on leaders getting

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22:55

Stop Hiring The Person Who Wins The Room

Fit Happens: Why CEOs and Leaders Succeed or Fail ·

2026/09/24

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 shifts from evaluation to formality. Nobody compares evidence. The verdict arrives before anyone

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25:23

What Wildfires Can Teach Executives About Leadership

Fit Happens: Why CEOs and Leaders Succeed or Fail ·

2026/09/17

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 question that matters far beyond wildland fire: why is it so hard to drop the tool that once made you

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50:55

What AI Is Doing To Leadership with Liat Ben-Zur

Fit Happens: Why CEOs and Leaders Succeed or Fail ·

2026/09/10

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 and bias, and we get into why the very experience that used to make someone a safe executive hire

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82:58

No One Works Here: What AI Actually Changes About Work

Fit Happens: Why CEOs and Leaders Succeed or Fail ·

2026/09/03

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 AI adopters he found in corporate America and why some of the loudest companies about AI are

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24:15

Why Nobody Tells the CEO the Truth

Fit Happens: Why CEOs and Leaders Succeed or Fail ·

2026/08/27

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 architecture of candor, for building a system that actually surfaces bad news before it's too

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52:45

He Left Silicon Valley to Run a Retreat in the Andes

Fit Happens: Why CEOs and Leaders Succeed or Fail ·

2026/08/20

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 community far from home, and why executive coaching and hospitality have more in common than

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21:43

Why Six Months Can Turn You Into a Better CEO Candidate

Fit Happens: Why CEOs and Leaders Succeed or Fail ·

2026/08/13

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 reward the wrong things. Drawing on real examples from board and CEO searches, Jason unpacks how

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46:07

Why Krishna Iyer Left Big Tech for a 170-Year-Old...

Fit Happens: Why CEOs and Leaders Succeed or Fail ·

2026/08/06

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 opportunity wasn't in another tech company. It was in applying AI to a foundational industry the world

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18:31

The 100 Day Plan Is a Lie. Here's What Actually Works.

Fit Happens: Why CEOs and Leaders Succeed or Fail ·

2026/07/30

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, socialization, team, cultural, and performance) that all move at different speeds, and why compressing

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66:48

Group Intelligence Beats Individual Genius with Lexy...

Fit Happens: Why CEOs and Leaders Succeed or Fail ·

2026/07/23

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, the "9010 rule" for navigating uncharted leadership territory, and why chasing scale before you

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20:44

Don't Cast a Halo: Why Great Leaders Get Blamed for...

Fit Happens: Why CEOs and Leaders Succeed or Fail ·

2026/07/16

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 through Edward Thorndike's original research, Phil Rosenzweig's work on corporate storytelling,

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17:02

Why Your Best Salesperson Makes Your Worst Manager

Fit Happens: Why CEOs and Leaders Succeed or Fail ·

2026/07/09

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 breaks down why raw performance predicts promotion but not management success, what signal

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16:05

Why Busy Leaders Still Don't Control Their Own Calendar

Fit Happens: Why CEOs and Leaders Succeed or Fail ·

2026/07/02

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-question audit for finding out how much control you actually have.Key Takeaways:Positional power

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48:32

Why the Obvious CEO Hire Is So Often the Wrong One

Fit Happens: Why CEOs and Leaders Succeed or Fail ·

2026/06/25

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 the Bill Perez story across Nike and Wrigley, why the surprising hire is so often the right one,

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41:36

Beyond Employee Engagement: How Mattering Transforms...

Fit Happens: Why CEOs and Leaders Succeed or Fail ·

2026/06/18

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 deceptively simple idea: that humans have a fundamental need not just to feel valued, but to add value. In

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55:09

The Boardroom Is Broken: How AI Changes Executive...

Fit Happens: Why CEOs and Leaders Succeed or Fail ·

2026/06/11

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 Steven explore what real fit looks like across a career, why command-and-control management is

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26:08

Your Schedule Is Your Job — How AI Affects Job Fit

Fit Happens: Why CEOs and Leaders Succeed or Fail ·

2026/06/04

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 from the inside out — and why your calendar tells more truth than your job description. He

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51:03

The Spikiness Principle: What Executive Search Gets...

Fit Happens: Why CEOs and Leaders Succeed or Fail ·

2026/05/28

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 companies like CrowdStrike, Duolingo, UiPath, and Lovable. She brings a rare investor's lens to

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20:45

Is Your Job Worth It? The Hidden Cost of Being in the...

Fit Happens: Why CEOs and Leaders Succeed or Fail ·

2026/05/21

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 psychology, Jason reframes fit not as a career preference, but as a life decision. If the middle

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