Caroline Webb is an executive coach, economist, and former McKinsey partner. She is the author of the global bestseller How to Have a Good Day, published in more than 60 countries, and has been named one of the world's top 50 executive coaches by Thinkers50. Her new book, Leadership Intelligence, distills three decades of advising CEOs and senior leaders into a science-backed playbook for mastering 21 everyday leadership challenges — and draws praise from Amy Edmondson, Jonathan Haidt, Daniel Pink, and Marshall Goldsmith. What sets Caroline apart is that everything she teaches is rooted in neuroscience, psychology, and behavioral economics, not management folklore.
Most leadership advice is folklore — someone's one good instinct generalised into a rule. Caroline takes the opposite approach: every tool she teaches is grounded in how the brain actually works. Rather than march through all 21 chapters of her new book, we ran this conversation as a live coaching session on the situations strategy and transformation leaders face most often — from diagnosing the real problem to getting a strategy to travel through an organisation.
In this episode, we dive into why you should walk into any complex situation assuming you're partly wrong, how to surface the doubts your team won't say out loud, and how to make change actually stick.
In this episode we cover:
— Why you should walk into any complex situation assuming you're at least partly wrong — How "360-degree vision" helps you see what your brain is filtering out — Why the problem everyone expects you to fix often isn't the real problem — and how causal mapping reveals it — How hypothetical questions surface the half-formed doubts people won't say out loud — The CASE model for change, and the four "frequencies" that make a strategy actually travel
Episode timeline:
00:00 — Welcome and today's highlight 01:30 — Introducing Caroline Webb and the episode 04:00 — "If you really know me…" 07:00 — Caroline's definition of strategy: clarity about what you don't do 09:00 — Diagnosing the right problem, and the "top of mind" trap 11:00 — Why you should assume you're at least partly wrong 16:00 — Michael Roberts, the opera singer turned "Chief Question Officer" 18:30 — The CMO who found the brand wasn't the problem: causal mapping 24:00 — When people nod in the meeting, then message the CEO to disagree 26:00 — Hypothetical questions: surfacing half-formed thoughts 30:00 — The GUIDE coaching model and the power of "tell me more" 35:30 — What culture really is, and the CASE model for change 41:00 — Influencing without authority: the fix-flex approach 45:00 — The four frequencies that make strategy travel 49:00 — Where to find Caroline
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