Every ambitious leader imagines being CEO someday. But as Jason Baumgarten told me on The Scaling CEO, the question isn’t whether you can do the job. It’s whether you should.
Jason is the Global Head of the CEO and Board Practice at Spencer Stuart, one of the world’s top executive search firms. He advises Fortune 500 boards and founders alike on one of the most consequential questions in business: who should lead next. Having guided thousands of C-level transitions, he knows the difference between those who scale companies and those who collapse under the title.
The Dot Most Leaders Miss
Jason calls himself a “dot connector.” He looks at context, capability, and timing—and finds where they align.
“The thing most people get lost in is their desire to be a CEO… Sometimes you need to slow down the energy and enthusiasm of being wanted, being liked, and being asked to do the job, and ask: “Is this what you want?” and “Is this what the company needs?”
For CEOs, that reflection matters. If either answer is no, you’ll eventually find yourself in a job you don’t want or a company you can’t help.
The Pendulum Problem
Jason sees the same pattern in nearly every new CEO: they swing too far.
“Leaders either cling too much to the strategy and operating model of their predecessor… or they swing all the way to the other side and tear everything down.”
Organizations can only handle so much change at once. The smartest CEOs pace transformation. They build a metronome, deciding when to move fast, when to stabilize, and how much change their culture can absorb without breaking.
Vision Without Pragmatism Fails
When boards evaluate whether a CEO can scale, they look for two things you won’t find on a balance sheet.
“One is ambition, a big enough vision to excite people. The second is the pragmatic ability to connect financial results to what they’re doing.”
Charisma without operational understanding creates chaos. Discipline without ambition creates mediocrity. The CEOs who scale master both.
Self-Awareness Is a Growth Strategy
Jason sees self-awareness as a competitive advantage. But awareness alone isn’t enough; you must prioritize what to change.
“Really be clear about what is holding you back right now that you have to improve… Change requires intensity and duration.”
Coaches can help leaders see blind spots, but only CEOs themselves can commit to sustained change. Self-awareness is insight; prioritization turns it into progress.
What CEOs Can Learn From Nonprofits
Jason chaired a nonprofit board for 14 years, including through COVID. The experience reframed how he views motivation.
“In nonprofits, you can’t just pay people more. You have to pull different levers to attract and retain great talent.”
He also learned how to engage board members who aren’t paid, but still want to contribute meaningfully. His takeaway for CEOs: people want to feel heard and valued, whether they’re employees or directors. Motivation isn’t just money. It’s meaning.
The Tech Mindset Every CEO Needs
Before Spencer Stuart, Jason led McKinsey’s technology practice. That background shapes how he evaluates leaders now.
“Every great talent decision is linked to strategy. The right leader depends on what the company is trying to achieve at that moment.”
He argues that every CEO, not just those in tech, must understand technology deeply enough to see both opportunity and disruption. The pace of change is faster than any leadership cycle in history.
AI as the Ultimate Leadership Test
AI, Jason says, will separate learners from laggards.
“For a lot of CEOs, if AI is impacting their business broadly, they need to lead as learners. They have to do the hard work to figure out what could change, what they need to learn, and how to push that change through the organization.”
It’s not enough to delegate AI to IT. Every function, from legal to HR, will be reshaped. CEOs who treat AI as an operational detail risk missing its strategic potential.
Final Takeaway
Jason Baumgarten’s advice cuts to the core of leadership: being CEO is not a reward, it’s a responsibility. Before chasing the title, ask the harder question: Why you? Why now? Why this company?
I’m Glenn Gow. I coach CEOs who want to scale with clarity and confidence. On my podcast, I uncover the strategies top leaders use to grow bigger, faster, and choose the right roles at the right time.
Scaling requires vision, timing, and humility in equal measure. The right role at the wrong time is still the wrong move.
Listen to the full episode of The Scaling CEO with Jason Baumgarten for an inside look at how the world’s top companies choose and challenge their leaders.
