Caroline Webb: Leadership Intelligence
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Apple Podcastsby The Second City
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Sep 08, 2026
Kelly welcomes the always amazing Caroline Webb back to the podcast. Caroline is a former Partner at McKinsey, where she continues to serve as a Senior Advisor, and is now CEO of her own firm, Sevenshift. We spoke to Caroline some years back about her book How to Have a Good Day: Harness the Power of Behavioral Science to Transform Your Working Life. She has another terrific book called Leadership Intelligence: Science-Backed Strategies for Mastering 21 Everyday Management Challenges.
You have a kind of caveat early in the book about AI.
“I tried to write the book so that it was really evergreen. And, you know, if you try to frame the book in the context of AI, it’s going to be pretty tough right now. But actually, the roots of the book came from me thinking about eight years ago: we can see where what we used to call it automation is going. The robots are coming. So, what does that mean for us humans? We need to raise our game. I mean, there are things that we’re distinctively good at and we sort of half ass it. We just sort of drift into it. We sort of think, yeah, you know, I can be I can be creative. Yeah, I can be resilient. I can be good at building relationships, building trust, right? If we just drift into it, we do an okay job, but we don’t do a brilliant job. If AI is getting more capable, we humans need to learn how to use the soft machinery in our heads to the best effect possible.”
Language is so important in these conversations, can you talk about the difference between experiential and deliberate wisdom?
“I make a distinction between experiential and deliberate wisdom. When we imagine someone wise, we imagine someone who is perhaps a little further on in their life and they’ve seen a lot. That experience has value, but when everything is changing it has limited value because you’ve never experienced what’s going on right now. Deliberate wisdom is what I call the set of critical thinking habits that can help you assess a situation clearly. You see things as clearly as possible, as objectively as possible, so that you can then make good choices. When we think about someone we think of as wise in our lives, maybe a friend or a mentor, they almost always have that ability to take a step back and see the bigger picture.”
You pair the concept of widening our perspectives with the concept of lightening. What do you mean by that?
“If we’re going to widen our perspective, we definitely also need to find ways to lighten it where we can, to lighten the load. That means, you know, closing down any number of things that are in your field of vision or removing them, removing distractions, being smart and quick about putting your devices on, not getting disturbed when you need to really think, when you need to bring your whole self to a conversation or to a task.”