Caroline Webb has built her career around understanding how people think and perform at their best. An economist, leadership coach, and former McKinsey partner, she is the bestselling author of How to Have a Good Day, which translated insights from behavioral science into practical tools for making work—and life—better.
Her new book, Leadership Intelligence, turns that lens on what it takes to lead well now, whether you’re running a team or simply trying to make better decisions, give useful feedback, and work effectively with other people. As AI becomes more advanced, Webb argues that human intelligence matters more, not less. Drawing on behavioral and cognitive science and decades of advising leaders, she offers practical strategies for 21 common workplace challenges.
21 Questions with Caroline Webb
1. I couldn’t have written my last book without…
The many thousands of scientists who did the primary research underpinning each piece of advice I give readers. I had room to cite 300 or so papers directly, but I read easily over a thousand in the process of writing the book. I am in awe of the painstaking work that researchers do, as they go deeper and deeper into understanding the human mind and body.
2. What’s the thing most people get wrong about being a writer?
One is that there is such a thing as a “book tour.” My friends have given up asking me when I am going “on tour” — they know by now that you never stop talking about a book, if you’re lucky. You keep going, everywhere, all the time, for as long as anyone will have you.
3. What’s your most common form of procrastination?
Online thrift shopping.
4. Do you read your reviews?
It’s hard not to, because it’s so wonderful to read how your work has helped your readers. In my genre of prescriptive non-fiction, you really want to know that your work has made people’s lives better in some way. But I do it less and less on sites with a known troll problem, because you only have to see one weirdly horrible review to feel bad in ten different ways.
If you’re lucky enough to have a colleague who can read reviews for you, that’s potentially a good middle ground—they can share with you what’s most uplifting and share what’s useful in the rest. That’s what I’m going to do this time around.
5. What’s the first thing you do after you finish a draft?
I never really feel like a draft is “finished.” It’s always a work in progress, plus my day job continues to flow around it. But I try to treat myself to an easy couple of days after sending a draft to my editor, and maybe one (1) martini.
6. Kiss, marry, kill: podcasts, newsletters, and speaking gigs.
A little bit of kiss, marry, kill to all three. On balance, I’m really happy that they’re all in my life.
I usually love podcasts because I relish a great conversation, and some hosts are so good that I end up having new thoughts as we’re talking. Some hosts unintentionally make you work really hard through sheer disorganization.
Newsletters make me feel very connected to my network. I always open with a personal story, so I also get to make something useful out of every difficult situation I’ve ever experienced in my life, which is like highly cost-efficient therapy. That said, they take a lot of work, and you don’t get a lot of feedback.
And speaking allows me to dive into a wide range of industries, at least for a short while, and I always find that really fascinating. But you never know how good the hotel room is going to be... so I travel with bulldog clips to close the curtains, and yes, I do jam my own tiny pillow into my carry-on when I can.
7. What’s a writing habit you’re embarrassingly superstitious about?
Emailing a draft to myself at the end of each day, even though it’s already backed up in a couple of other ways. It’s actually as much a close-out ritual—I can switch off after I’ve done it.
8. What’s something you wish you’d started doing five years ago?
Saying yes to connection requests on LinkedIn. I didn’t realize authors were supposed to do that!
9. Where do you find new ideas, and how do you keep track of them?
My coaching sessions always sharpen my sense of what people really need from me as a writer on leadership and professional effectiveness, and I take close notes on a digital tablet (or on my phone if I’m on the run). I kept coaching clients all the way through my work on Leadership Intelligence, and although that wasn’t always easy to juggle, it was the right thing to do. My coaching made the writing better—and the writing made the coaching better, too, because it helped me get ever crisper on how to communicate the right approach to common management situations.
10. What’s on your nightstand right now?
The Bee Sting by Paul Murray, a sunrise wake-up lamp, and a bottle of water. We won’t talk about the mess around those.
11. How did you find your agent?
By asking all my fanciest non-fiction author friends who their favorite agent was. Jim Levine’s name came up again and again.
12. What’s a writing rule you’ve happily broken?
I always end up in a tussle with copy-editors about using digits for timings, rather than spelling them out in words (“block time for 25 minutes” versus “block time for twenty-five minutes”). When busy business readers are scanning for advice, I want them to be able to quickly see what they’re supposed to do.
13. What tech tools (AI included) do you actually use—and which ones do you actively ignore?
I use the Freedom platform to block my access to websites and apps when I need to focus. I am not on retainer, although maybe I should let them know that I am a fan!
I’m happy to use ChatGPT or Claude to shorten a piece of text or check my syntax. I never let AI tools write for me because, for me, writing is thinking. Writing prose, taking handwritten notes, diagramming concepts—these are key cognitive techniques that allow me to synthesize vast quantities of scientific research. When someone sends me something that’s been written by AI, it’s usually overwrought and overlong, and although the document looks polished on the surface, the arguments are all too often quite muddled once you really poke them.
14. What’s the best non-writing skill that’s helped your writing career?
Producers tell me that my singing experience has given me decent breath control when recording my audiobooks. I think it’s as much that as I know about the existence of Throat Coat tea, which many singers use before concerts.
15. How many drafts before you show your editor?
As many as I can write before I hit the deadline I agreed to with the editor. I find deadlines a good forcing mechanism.
16. Can you describe your ideal workday?
I’m a late-night person. So I like a gentle start to the day, with coffee made by my lovely husband, then a walk outdoors (or an inexpert run on the treadmill) while listening to a podcast. Even better if I get to do that walk with a friend or colleague. Formal meetings happen from 11 am onward, and I see clients ideally in the afternoon. My peak writing time is 4 - 8 pm and I typically work until about 8.30 pm. When I need extra time, it’s much smarter for me to work until 11 pm than to get up early. Since this is a version of the Proust questionnaire, I will mention that Proust was even more nocturnal than I am, though left to myself, my body clock easily drifts toward his kind of routine.
17. How does that compare to your actual workday?
Pretty close! I advise people to be proactive about scheduling their time intentionally, so I do have to walk my own talk on this. Sometimes I start meetings earlier, obviously, for example, with the UK and the rest of Europe. But since my twenties, I have found that it’s fine to be clear about my preferences, so long as I’m flexible and keep delivering good work.
18. If you could write one book in a totally different genre than you usually do, which would it be?
A memoir about being a late-night person, maybe. I apparently have a lot to say about it.
19. What’s something about the writing life that still surprises you?
You think you’re done. But you’re not done. You’re never done.
20. Fill in the blank: In five years, successful authors will be…
Highly intentional about showing that their thinking is fundamentally their own.
21. What is your new book about?
It’s a leadership playbook that helps readers make the most of the human intelligence on their team, across 21 common management situations. I wrote it for leaders of all types, whether they’re formally managing people in a company or just trying to marshal a book group.
It’s got a strong backbone of behavioral and cognitive science, but I designed it to be very practical and easy to use when you have only six minutes to gather yourself before a meeting or a deadline. I hope it helps a lot of people who are trying to get good things done with their teams.
You can learn more about Caroline’s book here: Leadership Intelligence: Science-Backed Strategies for Mastering 21 Everyday Management Challenges.
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Panio
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