Mastering the Cycles of Leadership with Carolyn Dewar

Drawing on decades of experience advising the world’s top CEOs, Carolyn shared practical insights applicable at every stage of a career - from the mindsets that distinguish top performers to the importance of making bold moves with speed and conviction.

Together, she and Willy explored how leaders can avoid complacency, reframe their thinking to unlock latent potential, use AI as a thought partner, and set a strategic vision for the future amid ongoing uncertainty.

‍1. Who is Carolyn Dewar? 

Carolyn Dewar is a senior partner at McKinsey & Company and co-founder of the firm’s global CEO practice. She advises CEOs, founders, boards, and senior executives across financial services, technology, and consumer sectors on hypergrowth, transformation, crises, and M&A.

Carolyn is a two-time New York Times bestselling author, co-author of CEO Excellence, and author of CEO for All Seasons, which also became a USA Today and Publishers Weekly bestseller. She has written more than 30 articles for Harvard Business Review and McKinsey Quarterly and publishes a monthly LinkedIn newsletter for strategic CEOs.

2. What are the top reasons to listen to this webcast? 

• A grounded take on leading through uncertainty: From AI disruption to economic volatility, Carolyn offers perspective on staying focused when noise is everywhere. 
• Leadership lessons that apply beyond the C-suite: While the research focuses on Fortune 500 CEOs, the insights translate directly to anyone leading teams at scale. 
• Why bold moves early matter more than perfection: The conversation explains why CEOs who delay decisive action often lose credibility with both markets and employees. 

3. What are the six CEO mindsets that distinguish top performers? 

Carolyn outlines six core responsibilities: setting bold direction, aligning the organization, mobilizing teams, engaging the board, connecting with stakeholders, and prioritizing CEO-only work. Top CEOs treat these as non-negotiable parts of the job. 

‍4. Why does Carolyn focus on “mindsets” instead of traits or habits? 

Because styles vary widely among successful CEOs. What’s consistent is how they think about their role, even when their personalities, industries, and companies differ. 

‍5. Why are the first two years as CEO so critical? 

Roughly one-third of CEOs don’t make it past year three. Early momentum signals credibility to investors, boards, and employees shaping how the organization responds to future change. 

‍6. How do S-curves help leaders avoid complacency? 

Each S-curve represents a strategic growth phase. High-performing CEOs start designing the next curve while the current one is still working. 

‍7. Is a mindset innate or can it be learned? 

Carolyn argues it can be learned. Mindsets evolve through experience, reflection, and reframing how leaders see their role and impact. 

8. What is a “to-be list,” and why does it matter for leaders? 

Carolyn shares a practice from a top-performing CEO. Alongside the “to-do list,” leaders should define a “to-be list”, how they need to show up in key moments. The idea is that a CEO’s mood, energy, and presence create a ripple effect, so intentionality isn’t soft but operational. 

9. How can leaders separate signal from noise at the start of a new year? 

Carolyn recommends identifying the year’s “big rocks”, the few priorities that truly matter, and proactively blocking time for thinking and planning. For senior leaders especially, stepping back isn’t a luxury; it’s part of the job because they’re often the only ones who can connect the dots across the whole enterprise. 

10. What sustains leaders beyond the honeymoon phase? 


Carolyn argues that long-term leaders are powered by purpose, not position. Their focus on impact, inside and outside the organization, gives them staying power when the job gets hard. 

11. What is “followership,” and how can boards or teams spot it? 

Carolyn points to practical markers: do people choose to follow you, even outside your reporting line? When leaders change roles, do strong performers try to come with them? Followership shows up when influence extends beyond title, and when people want to be led by you, not just managed by you. 

‍12. How do great leaders build buy-in without turning strategy into a democracy? ‍

Carolyn uses the “lottery ticket” idea to explain ownership: people commit more deeply to what they help create. Strong leaders don’t ask thousands of people to vote on strategy. But they do invite teams to shape how the strategy wins, what execution requires, and what each group owns. So, the organization moves with energy instead of compliance. 

Watch or listen to the replay.