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

Additional resources:

Leadership Intelligence: https://www.penguinrandomhouse.com/books/801146/leadership-intelligence-by-caroline-webb/
Caroline Webb's website (newsletter + free resources): https://carolinewebb.co
Caroline Webb on LinkedIn: https://www.linkedin.com/in/carolinewebbauthor/

Thank you to our guest, Caroline Webb.

Thank you to our executive producer Zach Ness, our producer Nazanin Homayoun Jam and our editor James Pearce. If you enjoyed this episode, please follow, download, and subscribe. I’m your host, Kaihan Krippendorff—thank you for listening.

Follow us at outthinker.com/podcast

Julie Averill is a technology and transformation executive with nearly three decades of experience scaling global businesses. As Global CIO and EVP at Lululemon, she led an eight-year transformation that helped grow the company from $2 billion to over $10 billion in revenue and built its award-winning India Technology Hub. She previously served as CIO at REI and held senior technology leadership roles at Nordstrom, where she helped pioneer early omnichannel retail. Today she runs Gold Thread LLC, advising boards, CEOs and CIOs on leadership, culture and decision-making in moments of change. She is the author of Chief Impact Officer: Real Transformation Comes from Human — Not Just Artificial — Intelligence.

Imagine starting a new job as global CIO and discovering, on your very first call, that every page of the company website returns nothing but an error — with no monitoring, no alerting, and no one who can even tell you who's responsible for fixing it. That was Julie's welcome to Lululemon, and she argues it turned out to be the making of her career. In an age where every company claims to be "doing AI," Julie makes the case that the winners won't be the ones with the flashiest technology — they'll be the ones with the strongest culture behind it.

In this episode, we dive into why every transformation she's led actually started with a crisis, why she calls culture competitive infrastructure rather than a soft skill, and how to tell real AI progress apart from euphoric hype.

In this episode we cover:

- Why every transformation began with a crisis — and how to turn a "burning platform" into a mandate for change
- Why culture is competitive infrastructure, not a soft skill
- What a major-league catcher taught her about reading people and seeing the whole system
- How to separate real AI progress from "euphoric confusion" and headline-driven hype
- Why the best leaders never have to choose between technology and people


Additional resources:

Chief Impact Officer: https://www.simonandschuster.com/books/Chief-Impact-Officer/Julie-Averill/9798993755380
Julie Averill on LinkedIn: https://www.linkedin.com/in/julieaverill/
Gold Thread LLC: https://goldthreadllc.com/

Thank you to our guest, Julie Averill.

Thank you to our executive producer Zach Ness, our producer Nazanin Homayoun Jam and our editor James Pearce. If you enjoyed this episode, please follow, download, and subscribe. I’m your host, Kaihan Krippendorff—thank you for listening.

Follow us at outthinker.com/podcast

New on the Outthinkers Podcast, supported by LHH, host Kaihan Krippendorff speaks with Vijay Govindarajan — VG — about why the next breakthrough American innovation may be discovered in a village in India before it ever reaches Silicon Valley. Fifteen years after introducing the world to reverse innovation, VG returns with a new book co-written with MIT mechanical engineer Amos Winter, Global by Design, and a sharper argument: the strategy is only half the story. Someone still has to engineer the $400 ECG machine that replaces the $20,000 one.

VG walks through what he calls problem merit — the discipline of finding a problem worth solving before anyone is allowed to propose a solution — and why most innovation teams fail at exactly this step. He explains why you should never define a problem in terms of its solution, why "raid the parts bin" beats reinventing from scratch, and why the affordability crisis now dominating American politics may already have its answer sitting in a market that had no choice but to solve it cheaply first.

The conversation covers:

• Why innovation never actually fails — and what does: design requirements nobody took the time to define
• What six months of watching people shave in the dark gave Gillette — a two-cent blade, after the $7 Mach3 reached only 1% of Indiae
• How Uber, the iPhone and the $400 ECG were built largely from technology that already existed, and why you innovate only for the part nobody has solved yet
• Where the answer to America's affordability crisis may already be sitting — and why it isn't about importing the product, but bringing back the core value and making it here

Additional Resources:
Global by Design: How to Create Innovations That Scale, Travel, and Transform (Amos Winter & Vijay Govindarajan)
VG at Tuck: https://tuck.dartmouth.edu/faculty/faculty-directory/vijay-govindarajan
LinkedIn: https://www.linkedin.com/in/vg-govindarajan/

Thank you again to our sponsor, LHH.

Thank you to our executive producer Zach Ness, our producer Nazanin Homayoun Jam and our editor James Pearce. If you enjoyed this episode, please follow, download, and subscribe. I’m your host, Kaihan Krippendorff—thank you for listening.

Follow us at outthinker.com/podcast