From In-House Analyst to Independent Thought Leader | Charlene Li | 723

What is thought leadership and how does it work? Why does it matter? I stumbled into this field in the early 2000s, and I've been exploring these questions for the last 20 years. This podcast episode is a companion to our new book, The Thought Leadership Handbook. And in this series of episodes, we want to do something a little bit different. We speak with many of the exemplars who appear in the book, and we have conversations about thought leadership. In today's episode, I speak with Charlene Li, who published her new book, Winning with AI, in spring of 2026. In this conversation, we talk about practicing thought leadership as an in-house expert for her at Forrester, where she wrote her first book, Groundswell, with Josh Bernoff. We discuss concepts such as co-authorship, and we explore why she continues to practice thought leadership and the impact she hopes to make. I'm Bill Sherman. You're listening to Leveraging Thought Leadership. Let's begin. Welcome to the show, Charlene.

Thank you so much for having me.

So I wanna ask you a question around— you write a book that's titled Winning with AI, and you're in a space where there are a lot of books coming out with AI, but you've been looking at technology questions very differently your entire journey. What is it that makes Winning with AI stand out?

Well, this book is different 'cause it has a lot of frameworks in it, but it's also a book about how do you execute on it. And, and the difficulty is that this is a book being written when everything is changing all the time. And so we wanted to write a book. Our purpose was to write a book about how do you create value? How do you get started? And my co-author Katja Welch has been a chief AI officer for 15 years. And so it, it was great combination of my, my thinking and, and writing around disruptive technologies and leadership and her practical approaches to things. And so that combination is, it's, it's a very, very different book than my other ones that were looking at new trends also on these disruptive technologies, but there wasn't so much pressure to say, okay, so what do you do with it? This time it's very different. Things are happening so quickly, we felt we needed to give an explanation to people to say, you know, this is a doing book. This isn't just an explaining book.

So the book came out in March, if I remember right, which means your hands-on experience was done somewhere in the fall, October, November.

November 10th, 2025. I know the date very well.

How do you deal with the topic that where the case studies and examples that were true in fall, well, summer and fall of 2025 as you're finalizing the book, we're now summer of '26. How are you keeping it fresh?

Well, we knew the book would get outdated and, and not so much because the frameworks would be outdated, but there would be new case studies and, and people are always asking like, I need more case studies. I need more examples. And so our plan was always to update the book, uh, again, with whatever has changed on the technology front and, and also with brand new fresh case studies. See, our, our goal is that when 20% of the book needed to change, that's when we would publish a new edition. So we're getting close to that already, but the frameworks and the thinking behind them still remain. I, I recently, uh, had talked to a professor who said, I'm still teaching some of the frameworks from your first book, Groundswell. The ladder of engagement was something he goes, it, it's still really relevant. And you, you know, that book was published 18 years ago, but the framework, and I think again, 20 years ago, the idea that you could have a two-way conversation with somebody was revolutionary. Now it's still really important to understand how that happens, and that framework still has lasted the test of time.

So let's stay on Groundswell for a moment. You and Josh Vernoff, who both of us know very well and who has been passionate about books probably more than most anyone else I know in the business book space, right? How did you and Josh come together to write Groundswell? You were at Forrester at the time. Did they lean in? Were they encouraging it? How did the book come to be?

Oh, we had worked together for 8 years already. And so I knew Josh. I knew that he always wanted to write a book. And I literally had a book in my belly. I've been writing all these reports about social media. I was blogging and I had been blogging for 3 years by the time I started the book. And I just went, you know, it's, there's a book that needs to be written here. This is bigger. This is a much bigger phenomenon and a social change and a leadership change that was happening. And so we need a book to explain this to people. And so Josh, I said to Josh, you wanna write? He goes, yeah. This is great. He'd been looking for a topic. He wanted to write a book and he was looking for the topic. And then we went to Forrester together and Forrester fortunately said, yes, yes, write the book. And they had done other books and so they could see that this could be a really interesting thing for us to work on.

So the two of you co-authoring, and at this point you're both in Boston?

He's in Boston. I'm in San Francisco. We started the book working completely. Okay. Yeah.

Okay.

Yeah. Yeah. So we, we wrote the entire book completely remote from each other. We didn't see each other once through the whole book. Right.

I thought that where you'd worked together for 8 years, but you also had this sense of distance. Right. And I, you've had a number of co-authors through your career. What makes the co-authoring work?

A tremendous amount of trust. I mean, I worked with Josh for 8 years. I worked with Brian Solis for, I think, 2, 3 years before we wrote our book. And my latest co-author, Katya Welsh— and I say this with the biggest, joyous smile on my face— have known each other for 25 years. We had babies at the same time. We've gone through life together. I mean, we're deep, dear friends. And it was such a privilege to work on the book with her. And the trust that's there, that she can tell me what she's thinking and I can take it, and she knows that. And that I can listen with an open heart and that she can accept my experiences too, it's, it's just, there's nothing better. So when you can have that exchange, and I'm not saying it's easy 'cause we disagreed on quite a few things and our writing styles, even though we're trained in the forest, our writing style is different. And it, and so the, it's like, how do you modulate all these things together into a cohesive work. And I mean, there were times when we're like, okay, we need to take a break here. It's just like, go away and then come back. Take a deep breath. Take a break. Especially when you're on deadline, you know, it's hard. It's really hard.

So if we go through the number of books that you have, as well as different co-authors, different writing styles, like you said, Josh was at Forrester as well, trained in the Forrester writing style. But you've had to adapt not only with different co-authors, but you've written inside of Forrester and been an advocate for ideas while still wearing the Forrester hat. You've written books while leading Altimeter and being the founder and CEO there, and now you've written books in other entities' relationships, and now You're continuing to advocate, right? So what makes it work when you're working within the context of an organization? What made it work at Forrester? What made it work at Altimeter?

Right. Again, I think at Forrester, it was that they could see that the market was there, but they also trusted us. As two senior principal analysts that we knew what we were doing. And they, they wanted to support our passion project here, this little book that we wanted to write about social media. Right, right. And they, they said, well, if you can get a publisher to do this, then great. We'll sign on. And our book went to auction and Harvard Business Publishing signed on. And it was a big deal for this book to come out, a really big deal. And it did extremely well. Uh, at Altimeter.

Well, Groundswell created a groundswell, right?

It, it did. It really did. I mean, it's, it's I think well into the 150,000, 180,000 printed copies now.

So were there any moments where marketing or legal said, oh, we're looking at the manuscript. Are you sure you wanna say that? Or when you're out talking, say this instead of that. Was there tension?

No, no. And it's because they knew that we knew what to talk about. And, and I had been writing about social media. At Forrester. I think the only time it came to be an issue is George Colony said to me once, you know, our company's based on roles, and we market roles, and we write to roles. There isn't a role for social media. And I kind of tongue-in-cheek said, not yet, George, but there will be. So this is new. And, you know, his objection was that we didn't fit into any particular department yet at the time.

But clearly— Who was the buyer for this idea, right?

Exactly. Because we have to have a buyer. And, and I appreciated that his perspective as a CEO of a company that had to make revenues didn't have this. And, and so when I, I left Forrester shortly after that because I didn't fit into these boxes anymore. I didn't wanna be in the constraints of writing to a particular buyer in a department, 'cause I believe that disruption goes across an entire organization. And so I wanted that freedom. So at Altimeter, again, I was a CEO, so I could write any book that I wanted. But it was again, in support of the business. And in particular, I recruited analysts who it was very clear that you are promoting your brand and you're promoting the company brand and the two are going to live in harmony.

And it was an expectation of the people coming in that they were going to do both. They couldn't just be a good analyst and sort of hide behind the paywall, right? You were very conscious about How did Altimeter put its ideas out into the world?

It was a choice. Yeah. We, we intentionally gave our research away for free and people thought we were crazy, but it's very difficult for the traditional players to come after free 'cause they couldn't do it. Mm-hmm. Uh, and so we built an audience almost overnight. We had 100,000 people reading our reports versus maybe 5,000 or 7,000 who would read a Forrester report. I mean, it was just magnitudes of difference. And as a result, we built our entire business on inbound. People calling, picking up the phone and saying, you just wrote about a major problem we had, you need to get in here. And, and so we changed and disrupted the way thought leadership worked. And, you know, they, the, the way that we looked at books is like, if you got a book in you, write it. You know, we just ask that it, it be in harmony with the work that you're trying to do as a firm because our people and our work had to live together, uh, and, and, and be under one brand.

What happens when your idea is bigger than your current reach? That's the question behind The Thought Leadership Handbook. Peter Winick, Naren Ariyal, and myself wrote it to help experts, authors, speakers, and executives understand their thought leadership path and build the systems that help ideas scale. Learn more at thoughtleadershiphandbook.com and preorder the book at Amazon, Barnes Noble, Bookshop, or Amplify. Well, and many of the big consultancies for many years had a reputation of, we have the smartest people, hire us and we'll show you what's behind the curtain. What encouraged you to take that sort of step and go, nah, that's not the way I'm building?

Yeah. Well, I said I could fight in this red ocean where there's just tons of blood and hire sales force and go after this and get as much vendor money as I could. And I, I don't wanna sell my soul that way. And, um, and I just, I'm gonna go to the blue ocean over here where it's a completely different business model, plan, uh, sell only to people who actually needed the help. And they would call us because they could see, and we took a design thinking approach where we spent a third of our research cycle just on defining what the right question was. And so superficial question up here everyone else is answering, we're gonna go a couple layers deeper, right?

Right.

What's the underlying question? And that was the thing that distinguished our research was that we were hitting these topics and we could go again, where the traditional analyst firms couldn't, because they were segmented by existing roles. We were talking about new disruptions that had no roles and were in— it was just disrupting across the entire enterprise. So we were playing a completely different game.

So if we look at the underpinnings, and I did a fair amount of looking at this in preparation for our book, the Thought Leadership Handbook, because thought leadership exists in a weird space. Where you can do a TED Talk, which is now then on YouTube and is virtually free as long as you have an internet connection. A book at $30 representing years of your best thinking, again, nominal cost. But if you look at a keynote rate or a day rate for consulting, those are much different numbers. And so the question I asked was, Okay, how— what's the relationship in the economics? Closest answer I found was Elinor Ostrom looked at the commons and the tragedy of the commons, and specifically she wrote about knowledge as a commons where you can put ideas into the commons and then people can take them out. And so it becomes a both and. You can enrich the world with knowledge, and you can also make a good living. And, you know, with her having earned the Nobel in Economics, seems a good model to me.

Yeah. Again, I, I think about thought leadership as this act of creating change in the world. And if you want your leadership, your thought leadership to actually grab people and really inspire them to create that change, then it really has to resonate with them. And I, I feel like the ideas need to be out there and free. And if it comes back to you, if, and then if it comes back to you, if you're helping people make that change, inevitably somebody will like, I need help making that change. I need inspiration to make that change. Come and give us more of this goodness that's in this book. And I will speak to you.

How does this work in my situation? Not because my situation is different than everybody else's, but I want you as a guide. I want you there, or explain this to my people, or help us craft the strategy that we can execute. You want the deeper, richer conversations. The book is the overture to those conversations. The article is the interview. They're all opportunities. And I know you've done thought leadership in a number of different modalities from everywhere from the dinners to the talks to the books. Here's my question, Charlene. What keeps you going? And why do you practice thought leadership? And what sparks you?

Yeah, in the end, I do this because of this incredible feeling of aha. That people get. I love the aha feeling that somebody goes from a point of confusion and, um, inaction to a place of understanding. And then because they understand, they can take a decision and make— take action. And it— that is the most beautiful moment for me, that if I could help somebody get to that point of action, because my belief is that we need disruptors in this world to make the change happen that we want to see. We, we're not gonna get there by incrementally changing things. And so my point in doing this leadership is the thought leadership is to inspire people to create change. And if I can explain all this changing complex world of ours and simplify in a way, uh, so that they can take action, then that is very satisfying. My favorite thing to do after a speech is to ask people, you know, they come up to you and say like, oh, that was great. That was great. We loved it and everything. Like, thank you so much. But, and what was your takeaway? And it's, it's a, it's such a gift for me to hear like, oh, I got this out of it. And it just lights me up. And it also helps them figure out, well, what am I taking away from this? What am I gonna do with that? So that feeds me, that keeps me going. And again, there's also the selfish thing. I love ideas and books and thought leadership is a great way for me to work through something. So I'll take a research, I'll even do like a livestream or write an article and pick a topic that I don't know the answer to, just so I can think about it, spend some dedicated time, do research, do some interviews, and so that I can like, oh, so that's how that works.

The great thing on Thought Leadership and that diving into ideas is you can find the smartest people on a topic and say, let's talk. And so whether it's on AI or I think you're working on another topic ahead.

Working on— yes, I'm working on wisdom. Like, talk about like gnarly topics. What is wisdom and how do we get wiser?

Oh, but that interview list for the book, if you want to discover, you can be talking to neuroscientists, you can talk to philosophers, various cultures, various religious traditions, the world is your oyster.

And, and this is the thing, it's, it's amazing when you call up somebody, I'm working on a book, I'd like to talk to you about your area of expertise. And amazingly, people say yes. Yeah. They say yes. And, and so that's, and I always, people will ask me like, how do I write something original? You know, I, I don't have anything original to say. It's all been said. And I'm like, agreed. We are standing on the shoulders of giants here. And we're taking our experiences, our questions, our perspectives, and forming something new out of it. Uh, it's all derivative works, but it becomes something completely different the more you shape it. And this is what I love about that, that whole writing process, that thinking process is you're shaping it. You're putting your own imprint on top of these ideas that have been said a thousand times before, millions of times before. And it comes out— it's unique and different.

It's continuing the conversation, advancing the conversation, or in some cases bringing the conversation to people who haven't had the time to explore or think about it. And if the option or the other alternative is silence and no one's speaking about the topic, we are all poorer for it. Charlene Li, I want to thank you for joining us today. It's been a delightful conversation.

Thank you so much for having me.

If you'd like to hear more of Charlene Li's story, you can listen to episode 113 of Leveraging Thought Leadership or pick up a copy of The Thought Leadership Handbook available at Amazon, B&N, bookshop.org, and Amplify Publishing. Thanks for listening.