In conversation with Carolyn Dewar, co-author of A CEO for All Seasons — a sweeping study of 83 top-performing CEOs and what sets enduring leaders apart.
By Sunita Sehmi, Thrive Global Contributor
“The very best CEOs were also the most humble learners.”
Q: Your book features interviews with 83 top-performing CEOs. What was the most surprising or unexpected insight that emerged?
Carolyn Dewar: We deliberately spoke with CEOs who had sustained excellence — at least six years of consistent outperformance. You might expect that kind of track record to breed supreme confidence and a top-down leadership style. The opposite was true. The very best CEOs were also the most humble learners.
They admitted they didn’t have all the answers and made time — daily, weekly, monthly — to keep testing ideas and expanding their perspective.
And the biggest surprise? They never hit the “sophomore slump.” Where many leaders plateau or lose steam mid-tenure, these CEOs kept raising the bar. They saw leadership not as one long marathon, but as a series of sprints — each demanding fresh focus and energy.
“Without honest feedback, leaders risk operating from an echo chamber.”
Q: You write about blind spots that can hinder even the most experienced leaders. Could you share one example — and how to address it?
Carolyn Dewar: When we compared CEOs’ self-ratings with feedback from their boards and top teams, we found a striking blind spot: every CEO rated themselves higher than their direct reports did. That’s a flashing red light. Without honest feedback, leaders risk operating from an echo chamber.
The best CEOs counter this by building what I call a “kitchen cabinet of truth-tellers” — a handful of trusted people who will tell them what others won’t. In the loneliest job in business, that kind of candid mirror is priceless.
Leading Through the Seasons
Q: The title, A CEO for All Seasons, suggests leadership is cyclical. What’s the biggest mistake leaders make when they fail to recognize which “season” they’re in?
Carolyn Dewar: We found that 68% of CEOs said the job wasn’t what they expected — partly because the role keeps shifting. How you show up as a candidate in “spring” is different from the decisive “summer,” the reinvention of “fall,” or the graceful handoff of “winter.”
The mistake? Treating every season the same. What drives success in one phase can hold you back in the next.
Q: Could you briefly define the four “seasons” of leadership?
Carolyn Dewar:
- Spring — Stepping Up: Deciding if you’re ready and broadening your skills to be a credible candidate.
- Summer — Starting Strong: The riskiest season, when 30% of CEOs don’t make it past year three. Listening deeply, learning fast, and making bold early moves matter most.
- Fall — Staying Ahead: After early success, complacency is the danger. The best CEOs reinvent, spotting the next curve before the current one peaks.
- Winter — Sending It Forward: Leadership’s final act. Great CEOs prepare successors early, hand over with grace, and focus on renewal.
“Curiosity is the antidote.”
Q: Many leaders face a mid-career slump. What’s one way to avoid it?
Carolyn Dewar: Stay a student. The CEOs who outperform never stop learning. Satya Nadella devotes one day a month solely to learning. Bill Gates used to take a “think week” every year with nothing but books. Michael Dell challenged his team to imagine a rival who knew their customers better — and then asked, “How do we become that rival?”
The slump begins when leaders stop questioning themselves. Curiosity is the antidote.
“Succession isn’t the end of leadership. It’s the beginning of legacy.”
Q: Succession can be a sensitive topic. What’s one powerful lesson you learned about making succession your legacy?
Carolyn Dewar: Succession isn’t an afterthought — it’s your final, defining act of leadership. The best CEOs normalise succession talks years in advance and invest deeply in grooming future leaders. And when the time comes, they step away with generosity.
Brad Smith at Intuit put it beautifully: “I stopped focusing on what I was leaving behind — the jersey, the scoreboard — and started running toward what was next.”
Quiet Ambition and Servant Leadership
Q: You describe “quiet ambition” and “servant leadership” as underrated power moves, especially for women. How can women lead this way without being seen as less assertive?
Carolyn Dewar: Quiet ambition isn’t small ambition. Women like Mary Barra and Adena Friedman pair servant leadership with audacity. They set bold visions with humility and clarity of purpose. When ambition is rooted in service to something bigger than yourself, it commands deep respect.
Servant leadership isn’t meekness — it’s power with purpose.
“Empathy and decisiveness. Ambition and humility. That duality is a superpower.”
Q: How do women navigate the four seasons differently from men?
Carolyn Dewar: Many women face the “double bind”: be strong but not too strong, warm but not too soft. It’s a constant balancing act — but many turned it into an advantage, mastering the art of both/and: empathy and decisiveness, ambition and humility. That duality became their superpower, especially in “summer,” when trust-building and bold moves must happen simultaneously.
Authentic Leadership
Q: What’s one common piece of advice for women leaders that you believe is unhelpful?
Carolyn Dewar: “Act more like a man.” It’s outdated — and wrong. The most successful leaders didn’t break through by imitation. They did it by amplifying their own authentic voice and values.
“The best leaders don’t have all the answers — they create the space for truth to emerge.”
Q: On a personal note — what leadership lesson from your own journey at McKinsey most shaped this book?
Carolyn Dewar: Early in my career, I thought leadership meant having the answers. Over time, I learned it’s about creating the conditions for the right answers to emerge — often from others.
The best leaders I’ve seen weren’t the loudest in the room; they were the ones who drew out truth, synthesized it, and acted fast. That realization changed how I lead teams, work with clients — and even how I parent.
“Conviction with curiosity — that’s how leaders stay relevant.”
Q: In today’s volatile business climate, what single quality matters most in a CEO?
Carolyn Dewar: Curiosity. The world is moving too fast for certainty. The CEOs who last pair conviction with curiosity — and have the humility to keep listening, testing, and adapting. That’s not weakness; it’s wisdom.
The First 90 Days
Q: For an aspiring leader stepping into a new role, what should they focus on in their first 90 days?
Carolyn Dewar: The first 90 days are a paradox: you need to listen deeply and move decisively. Everyone is watching — your first board meeting, your first town hall, your first big call. Those moments set your tone.
Resist the urge to prove yourself through answers. Instead, signal clarity and curiosity. Those early impressions define your runway more than any single decision.
About Carolyn Dewar
Carolyn Dewar is a Senior Partner at McKinsey & Company and co-author of CEO Excellence and A CEO for All Seasons. She advises CEOs and boards on leadership transitions, performance, and purpose. Her work centres on helping leaders sustain long-term impact through humility, curiosity, and authenticity
