Leveraging Thought Leadership Live featuring Charlene Li

And welcome, welcome, welcome. This is Peter Winick. I'm the founder and CEO at Thought Leadership Leverage. And you're joining us on this edition of the podcast, which is a special LinkedIn Live edition with my friend Charlene Li. I'll give you the quick intro on Charlene as if you might not know who she is. I'm assuming you do, but she's a New York Times bestselling author of 6 books, including The Disruption Mindset and Groundswell, and a business transformation strategist who has spent more than 2 decades guiding organizations through disruptive change. She founded Altimeter Group and has advised executives and boards from startups to the Fortune 500. Graduate of Harvard College and Harvard Business School. And here she is with us today. So welcome, Charlene. Thank you.

Yeah, glad to be here. Thank you for having me.

So first, thanks for coming. And secondly, thanks for writing this book because I— and we were just talking about this before— I feel like every other book I get my hands on, and I get a bunch sent to me all the time, AI is either in the title, subtitle, or inferred. And I would say 80% of them are somewhere between useless and opportunistic. And what I loved about yours is you— and maybe this wasn't the challenge you chose to accept, but you wrote a book about AI that I believe is evergreen, which is sort of counterintuitive today. So tell me about why you chose the topic that you did and how you you chose to frame it the way that you did?

Well, I tend to write books to explain things to people. Like, these are— this is a very complex issue. It could be digital transformation or social media and the mysteries of leadership, for example. And then try to make it simple so you can understand. Not make it easy, but make it simple. And I wanted to do that with AI. And then I started working with my co-author, Katya Welsh, who has been a longtime Chief AI Officer, so she knows this. And what we quickly realized is that we didn't need to explain it. We needed to tell people what to do. And in particular, where do you start to create value with AI? And so it's a 12-week plan of over 90 days. This is how you create value. Step 1, step 2, step 3. And we just felt it was really needed in a space where there's just so much out there. Like, how do you tell what's real, what's not?

And there's just so much noise. So I want to just give— a couple of the things that you open with, and I love the way you open the book with things that the book tells you that others don't, right? So it's some things that seem basic but aren't basic today when you start to talk to senior execs and say, what's your AI strategy? What's your implementation? Like, what's going on? So one, you don't need an AI strategy. You're asking the wrong question, and use cases are not a strategy, or like some of the foundational pieces here. But then you go into this, here's a 12-day plan, a 12-week plan, what to do, how to do it. And it's very— it's not simple, like overly simplified, but it feels like if you follow the recipe, you'll bake the right cake.

Right. And the way that we thought about it, there are many right ways to do AI, but there are definitely wrong ways to do AI. And so we wanted to steer people away from the wrong things and things like thinking about AI as a technology, thinking you need an AI strategy that is separate from your core strategy. and not putting value at the core of everything that you do. Because we fundamentally see AI not as a technology issue or problem to be solved. It really is a leadership and strategy problem. And when you look at it that way, that's what makes this book evergreen, right? It's leadership and strategy that doesn't go out of date.

And it's different than, let's say, the— and it's almost a period piece now— the digital transformation stuff that was out, what, 5, 10 years ago. where you did need a digital transformation strategy if you were an analog business or a product, like whatever, that was a transformation and different than your core business. But in essence, one of the core things that you're saying here is you already have a business strategy, like you know what that is, and where does IA— AI, IA, when I'm looking backwards here— how does AI support that, enhance that, etc.? And then there's this whole other piece of Well, who owns it, right? Because there's a whole wave now of bringing in a chief AI officer, or who actually owns this? And you answer that in an interesting way. Talk about that for a moment, if you would.

Well, typically, we think of it, again, as a technology. So we traditionally just naturally give it to the CIO, the CTO, or whoever is in technology. And unfortunately, they do not have the strategic remit. They're not typically change agents. They probably haven't built anything in decades. And so this— and first and foremost, you need somebody who's a change agent.

Yeah.

And in particular, about who owns AI, everyone owns AI. Everyone has a piece of AI. HR is responsible for thinking about the future workforce. Finance is responsible for thinking about how are we going to fund this and what's going to be the impact on our balance sheet. We have go-to-market thinking we're going to go to market in a completely different way because our customers are changing and demanding it. So everybody has a piece of AI, but one person has to wake up every single morning thinking about how are we driving value across the entire organization with AI. And that's the person who has to orchestrate everybody else.

And I think that's the scariest piece because it's not like, oh, there's a new SEC regulation, that's compliance or finance. Like, it doesn't fit into a place, but it is everywhere. There's an ethical piece, there's a regulatory piece, there's a compliance piece, there's a customer-facing piece, like all those things. That's really hard, right? And you could argue that sometimes strategy does that as well, but it's more trickle-down from a strategic perspective than permeating from all over the place. So a couple of sort of random thoughts I had getting ready for today was, was this your first book— I could have done the research on this— with a co-author?

No, my very first book was a co-authored book. I've co-authored officially 3 books with co-authors. So my first book was Josh Bernoff. I did another one with Brian Solis, and this is my third one. And I've also used ghostwriters. I've written one book completely on my own. So that was my previous book, The Disruption Mindset. But I like the collaboration. It's harder, but I really enjoy it. This book is so much better because Katya is part of it.

Right. I forgot that Josh was the named author on So talk about, because writing with someone as opposed to having a ghostwriter that they're supporting you, you have a different style, you have a different perspective, different personalities, different time zones. Like, how do you find your rhythm? How do you find, how do you get to be good dance partners?

Well, Katya and I have the advantage of that we worked at Forrester together. We joined Forrester within a few months of each other. And so we've known each other for, oh my goodness, 20 years. you know, 27 years. It's a really long time. And we're first and foremost really good friends. Uh, we had babies at the same time. We literally had grown up together in our life and careers. And so there's a foundation of a friendship. And that was true with Josh and with Brian too, as well. To this day, I'm, I'm really good friends with all of them. And, and so that is first and foremost, there's a tremendous level of trust. And so we could tell each other when we didn't like something, that this was off, that this was right, or not.

Right.

pushing hard enough or you're pushing too hard. And that trust is immutable. And so that's the core foundation. And then both Josh and Katya, we both benefited— we all benefited from having been trained in the Forrester way of thinking and writing. And so there's a definite style that is direct. It's simple. It uses plain language. We had a list of forbidden words, for example, that we were just banned from using and stylistic things.

The banned buzzwords?

Oh, align, alignment, journeys, capabilities. What's a capability? Be specific what that is. Alignment is usually a code word for something else. So it's, again, is it agreement? Is it consensus? I mean, just let's be specific about what we mean. And so having that deliberation is very important.

Let me flip that a little. Because what I see often, I see 2 different ways that people write together. One is exactly what you said. There's trust, there's history, we have similar styles, and we respect each other, et cetera, et cetera. And the other is they come together for the project and they don't know— I mean, they know of each other and they know who each other is, but you don't really know, does someone keep deadlines? Does someone not keep deadlines? Like, so—

Yeah.

Maybe is before you take on a big kahuna like a book, Maybe start on an article or something small to see if you're compatible, because you just might not be, right? And that's, that's stressful.

Right. I mean, I mean, Josh and I had worked together on the same team. Katya and I were not on the same team, so we had to figure those things out right from the very beginning. How do we prefer to work? The fact that we're on completely different coasts and not the same time zones. I'm independent. She works for a company. I mean, it's just her availability, right? Right. And capacity for doing this and who does what. What roles do we have to play? So there was that norming that has to happen at the very beginning of the process, and it took us a little while to figure that out. We do have different writing styles. We do think about things differently. We have areas of passion and areas of like, we just don't want to go near that if we don't have to kind of stuff. So I—

Yeah.

And then this is the stuff that takes time to figure out. And the book took— it took us about 2 and a half years from from beginning to end to actually finish writing the book. And that's a long time. And it's partly because the space was changing, our focus changed.

Well, I was going to say, stay there for a minute because, you know, 2 and a half years is not unusual. But if somebody's sitting there today thinking, brainstorming a book idea relative that will be valid in 2 and a half years, that's not a challenge most people are up for. Because even think what the tools were when you started this, the Claude and the chat, you know, and all that versus where they are today. It's like lightning. It's, I mean, it's like 100 years in terms of any other technology, right? Yet it's still very valid. It's still incredibly valid. I wanna ask another question in terms of the way you went about this book. Was this the first book that you did non-traditional hybrid publishing?

No, it's my second. My second. My previous book, Disruption Mindset, I also did with a hybrid publisher.

Okay, and tell me a bit about sort of the, the pros and cons and the why and, and all that, that you— because there's so many choices you have today as an author in terms of how you—

Yeah, I, I've gone traditional publishing with 5 of my books and then 2— I've written 7 books, um, altogether. And the first 2 major books that I had went to auction with traditional publishing. I mean, it's, it's a very different process. I had an agent, um, book proposals, everything. And I, again, as an unknown first-time author, that was absolutely the right way to go back in 2007 when we began that process. So this is a very different time now. There are options that you can have. I've chosen not to go the complete self-publishing for lots of different reasons. I might do that in the future, but I have to say my last publisher, my current publisher Amplify, has been absolutely fantastic to work with. So could not be happier. not only hit the deadlines, deliver things ahead of deadline. And so as somebody who works independently, I really need to watch my time carefully, and they were just fantastic partners in that. That said, again, publishing is one of those weird things where, again, we decided to do print on demand for this book because it doesn't make any sense to have a book that is probably going to be out of—

Yeah.

Yeah, we did print on demand because the quality of hardcover books now is just tremendous. It's excellent. You can't tell the difference between—

Yeah.

A traditionally published print-on-demand book and a print-on-demand. And this is a book about AI, and we knew we were going to have to update it at some point. So having hundreds and thousands of books in a warehouse someplace sitting that are out of date made absolutely no sense. But it does make things like bulk printing and bulk orders really difficult. So that's why we have a paper book. Paperback cover too, as well. So we can print those very quickly, have a short supply available for bulk orders in the warehouse. But it's, again, it's thinking about things differently. The timeframe is differently. There's no presale period with a print-on-demand book. We discovered with Matsuri I Just Make, so we couldn't drive preorders. So it's a very different process, not only doing hybrid, but doing print-on-demand.

And how, how are you going to manage? Because I could imagine you could spend the next 10 years doing a little update. What's the difference, or how are you defining, or how are you and Katya defining an update, a new, or a new version, or a derivative version of it or something?

Well, the thing is, for the first edition, we're planning on updating it sometime this summer or fall. It's a rough idea is that when 20% of the content changes, that's when you should put out a new edition. And it's not so much the frameworks that change. There's a little tweaking. There's a little— again, both Katya and I are out there practicing and applying these ideas. So I have a new way of thinking about driving fluency with tools, training, and time. Gotta love 3 things, right? 3 Ts of AI fluency.

Right.

That we'll put into the book because it's a helpful mnemonic to remember. But the thing that really matters is updating the case studies, the examples.

Yeah.

For example, we don't have cloud coworking in there. And we know we need to update just how our organization is thinking about this, deploying it, and just having a little sec— it's a little section in there, but having an example of that. And so just keeping it fresh and updated in that way is a fantastic way to do things. And so that's a commitment. to just keep it fresh. But what we've worked really hard on is that the framework, the 12 weeks, the fundamentals do not change. They make a tweak to it, but those things don't change.

And I think that is great advice for any thought leader out there. If you're constantly morphing, changing, tweaking, lock and load your frameworks, right, to the 90th percentile, whatever. And when you get those locked, everything else can move and morph and be a little bit more fluid against the constraints, because you need those constraints of a model, a method, a framework, definition, languages, etc. I want to touch on a little other things that you're not writing, right? Like you're working with clients, you're speaking. Talk to me about sort of your— because you're an independent versus— how your ecosystem is changing. in terms of how you're serving clients and what you're doing now versus, you know, a year ago before the book was out?

Well, I'm still primarily— my revenues are driven by speaking. But I am, because the book is now out, I'm also expanding into workshops and, you know, one-day kind of versions for multi-clients or for a single company, 12-week sprints, because conveniently the book is in 12 weeks. And so you meet every week to go through one of the weeks and increase accountability. but also this community of cohorts who are going through the same thing. So it's one thing to work with me. It's another thing to work with peers who are going through the exact same questions and issues that you are. Invaluable. I run a cohort of AI leaders. Is that a mastermind? It's a short-term mastermind. Yeah, that's a short-term, just 12 weeks. And I run a— I co-lead a mastermind called Samudra for AI leaders. That, again, is just fantastic because nobody wants to go on the record and talk about what they're doing, but they will in a confidential space. And then I am spinning up a mastermind, but primarily for C-suite leaders.

Yeah.

Because, again, this is a leadership and strategy issue. And the biggest challenge right now is if you're in a C-suite and you have to buy this— drive this transformational change, where on earth are you going to go and talk to people about what's going on? And, uh, and again, I, I love being there for people. But yeah, go ahead.

Yeah, stay there for a minute. When you're taking a cohort through this experience, right, one of the things that I find interesting when clients and such are doing that is it's a little bit— and I don't want to say this— less work and less pressure on you. If you're running a 2-day thing, that's all you. Like, there's a lot of work and pressure. But I would say when you're taking a cohort through it, I don't know what the math is, but it's probably 50/50 you and the other 50 is them sharing with each other the trials and tribulations and the experiences that they're having in real time doing whatever we did this week, week 5, right? Is that, is that a fair statement?

It's, it's partly that, but also I do believe in the collective wisdom that's created. I, I only know so much, right? I know a lot, but I only know so much. And When you're talking to peers who are going through the same thing, they sit in similar chairs and wear the same shoes you do, wearing the same tread in the rug because of the worries that you have. It's a very different seat that you occupy. And there is— again, I've been in a peer group with YPO now for 15 years. And there is just no replacement of that—

Yes.

—to be with fellow CEOs who are going through the same thing across all aspects of our lives. And so being able to have that as a resource is an incredible opportunity. And it's very rare to find. And to have it facilitated with a foundation of some frameworks. And also one of the things that is— that I'm trying to put in place is I'm going to use AI up the wazoo for all of these. In that when somebody comes in, they're not just going to come in with a simple workbook on a PDF or a Word document.

Right.

They will have an LLM and a wiki that they can use. And keep with them throughout the entire experience that learns along with their experiences.

Stay there for a moment because I want to get your thoughts on this as a thought leader. This is your business, right? Over the last, let's call it 2 years, I have seen probably a dozen different variations of the model of, hey, here's a new startup or whatever, whatever. We're going to take your body of work, Charlene, and we're gonna feed it into the LLM, and then you can go license this and sell this to your clients as an on-demand coach, whatever, whatever. Thoughts, reactions?

I've definitely looked at that, and I have all my stuff in a knowledge base. And I just recently put Andrej Karpathy's LLM Wiki in place for my own knowledge base, like thousands of pieces of knowledge, all organized and beautifully annotated and contextualized to each other. ingesting constantly. It'll ingest this podcast, for example, into its knowledge base. The difference is I'm using that, right? Somebody else using it may have a completely different purpose and context. And that is missing if you're just opening up a chatbot to use that knowledge. For what end? For what purpose? And it's lacking that. Versus in a peer group or mastermind cohort, there's an intake that we do. That's being used to train your personal wiki.

Mm-hmm.

that's sitting there alongside my knowledge base. And it's going to grow over time as your experience grows. And so it's knowledge base plus the context of how it's going to be applied. That is what is missing.

So it sounds like it's the content, it's the context wrapped in community really is the secret sauce.

Exactly. And, you know, the thing about, This is that it's taking all of the knowledge that you have as an individual, and it's helping— it's making sure that the AI, that knowledge graph you're using, has that as a full context to apply it to my knowledge graph. And we're constantly building this together. It is not— it is something that's living.

And even though it's your stuff, AI probably does a better job of retrieving something you might have written 12 years ago that you forgot about that's relative to something that you're working on today, right? Because human memory is what it is.

I can't remember. And so I use it every time. I have these little agents and tools that are doing everything from— again, I've had different agents to deal my— read my emails and respond to them, prepare for podcasts, write my presentations, and also create articles for me. And it's remembering, like, and it's also looking across my conversations each week and saying, here are some interesting tension points to explore. It's also doing research outside and saying, how would I think about this interesting article? There's a lot of conversation about this. What would be your take on that? So it just gives me some options and just doing a lot of that heavy lifting. And so my judgment still applies. And I'm sitting there having deep conversations with my own, with my knowledge base, with myself, and saying, No, take it in this direction, take it in that direction, or this sparks another idea. And I'll say this, people say AI can't be creative, it can't emulate your voice. It does a good enough job.

Right.

And one day I had to write a script for a webinar that I was doing, and they required me to have it pre-approved, and it was regulated industry. So I had the script, I was practicing it, and I'm like, oh, it doesn't sound like me. So I gave it to AI and said, go look for interviews of me speaking and make this sound like me. Voilà, it did a better job of me than I could, because I can write in my writing voice, I can't write in my speaking voice. And it did a much better job of me by my speaking voice.

And that's a huge difference in that your writing voice and your speaking voice are 2 totally separate things. And when someone's speaking their written word, like, this is why people come out there and say, oh, read a chapter of your book. No, God, no, please don't do that. I'd rather say, tell me a story from chapter 5 that brings to light this concept you were bringing just on the fly. That's going to be a richer experience than reading it verbatim. I could read the book, right? I can have audio read the book to me. I want to take advantage of what you have to offer, right? What's different for you this time with this work than some of the previous things that you've launched in terms of expectations? Because the world keeps changing, but what's different for you now?

Well, the major thing about this book is that it's a much more detailed book, which is why it took so long. It was a different writing exercise. It was much more detailed. The case studies had to be exact. Our prescriptions and literally what comes first, second, and third. I can't tell you how many times we moved chapter 4 to chapter 8 and 7 to 3 and moved things around and jiggered again. And it just was a huge amount of knowledge.

Yeah.

To organize. And what I'm looking forward to even now, we didn't have the knowledge graph when we were writing the book, and we finished writing the book in November 2025.

Right.

Now that we have this knowledge graph, oh my gosh, writing is going to be so much easier because I literally have one of the things in the knowledge graph is remember this to update the book with, you know, it just kind of puts it there and then I don't have to think about it anymore. It just knows what's not in the book and what are the things I'm talking about. And these are things that you can consider for updating the book.

And I think a lot of times when you read, I typically don't enjoy books that are so prescriptive because it assumes, you know, I don't like being told what to do, right? Like, that's maybe that's part of it. But, you know, this is prescriptive, which leads, you know, you got to have the courage to put it out there and go, no, there's a reason 5 comes after 4 and before 6 and 7. And let me defend my logic. You could choose to do it backwards or do it a different way, but let me tell you what the potential pitfalls are that you're not aware of because you're only doing this once and we've seen this many times. Any other differences that you're seeing now? Maybe even on the— I'll throw this one out at you. So even on the speaking side, the standard keynote speech not all that long ago was an hour, maybe 45, 50 minutes. Are you getting a lot of Keynotes where they're compressing it and saying, can you do your thing in 25 or 35? You feeling that?

It's— I would say a little bit, just on the edges, a little bit. And it's usually when the entire conference is 15 and 20-minute segments because they know people's attention span is too short. So everyone is speaking for 15 or 20 minutes. And again, there's a benefit to that and also a disadvantage to that. I have to tell you, when somebody says, we want you to be speaking for an hour, I'm like, please, no. No, this is way too long. And so for me, building in that interactivity or breaks for people to engage with themselves or with each other, absolutely essential in keeping people's attention because it is out of necessity at this point. You're guaranteed people are not listening, they're multitasking when they're on their screens. And if I could, I would have subtitles on my slides so people could be reading my comments and not just listening to it because some people just are so used to watching video, watching something on stage with subtitles. And we haven't gotten to that, and I wish we would. And so people just learn and absorb conversation in different ways.

Yeah, I mean, the next step would— everybody has their, their, their goggles and can put you at, you know, playback speed of 1.5 because they want to hear you speak faster. You know, that's the mass customization. So yeah.

Well, the thing I've been playing with is avatars, like, because I think the opportunity to take my message And give it to, again, using AI to script it, because I pretty much give the same speech every time, and AI is putting the same speech together. You have tons of videos of me doing this. Now you can customize it for an audience. Let's say it's car dealers in Bulgaria, and I can deliver it in Bulgarian. Why not?

Right.

So that's, I think it's an interesting future. I don't think anybody's ready for that, but I think that's something I'm playing with.

Cool. So if there's someone out there, and I'm sure there is, that is where you were 2 and a half years ago when you were starting this project and this book, what, what, what advice would you give them?

It's the same advice I would give to anybody who's thinking about a world that's going to be impacted by AI. Don't think about what you're going to do. Think about the problem you're trying to solve. Because if the problem that you're solving is, is a big one, it's a hard one, it's an eternal one. but the way you solve it could change over time. And so that way, it allows you that flexibility to say, maybe the way I approach this problem and define that problem is the real value that I create.

Yeah.

When I started Altimeter Group, we did a huge investment in design thinking for everybody, because we built the entire firm around design thinking, which is you're spending most of your time identifying what the problem is before you figure out the solution. And what oftentimes what thought leaders do is we think we have the solutions. We just run and go solve the solution. But that solution may be temporary. It doesn't address the underlying problem. So what I say is really figure out the problem you're going to live with and grapple with for the next few years.

Fantastic. Well, I appreciate Appreciate your time, appreciate your knowledge, and really enjoyed the book. And grab one today or wait a month till the newer revised version.

It might be more than a month. Yeah, again, thank you so much, Peter, for your leadership and bringing to light how thought leadership works, because it is, it's like a weird, mysterious thing that sits out there. Like, how do you actually do it? So thank you for the opportunity to share.

Thank you. Good stuff. Thanks.