AI, Executive Coaching, and the Future of Thought Leadership | Alisa Cohn

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Coaching at the Top, Leveraging AI, and Playing the Five-Year Book Game

This episode explores how executive coaching and thought leadership operate as strategic levers to help leaders navigate complexity and scale. It also shows how AI can act as a force multiplier for serious thinkers without replacing human insight.

What if your most valuable business asset isn’t your product, but the way you think?

In this episode of Leveraging Thought Leadership, Peter Winick sits down with Alisa Cohn—one of the world’s top startup coaches, Thinkers50 and Marshall Goldsmith award winner, author of From Startup to Grown Up, and host of a podcast by the same name. Together, they unpack what it really takes to turn expertise into a scalable thought leadership platform that attracts premium clients.

Alisa breaks down what great coaching actually is at the top of the house. Not therapy. Not box-checking. It’s the disciplined work of helping senior leaders see where they are, where they’re going, and how they’ll get there. She explains why she now focuses almost exclusively on experienced founders and C-suite executives—and why the best clients see coaching as a sign of strength, not weakness.

Peter and Alisa explore the often-lonely reality of thought leadership work. You’re on planes. In hotels. Delivering keynotes. Building IP. Yet rarely surrounded by true peers. Alisa shares how communities like 100 Coaches, mastermind groups, and curated gatherings of top thinkers create “connective tissue” between experts—and why those collisions of adjacent ideas (resilience meets agility meets questioning) are rocket fuel for new IP and offerings.

Then they turn to AI. Not as a shortcut, but as a force multiplier for serious thinkers. Alisa explains how she feeds transcripts of 100+ podcast episodes and her HBR/Forbes pieces into AI tools to surface patterns, themes, and questions she’d forgotten—and then does the real work of shaping those into sharp, human insights. They talk about AI as a research partner, synthesis engine, and creative sparring partner—not a cut-and-paste content mill.

Alisa also reframes the business model of thought leadership. Her core work is high-touch: one-on-one coaching, offsites, and select speaking. Everything else—books, articles, podcasts, media—exists to build a premium brand, generate demand, and give her the right to charge at the top of the market. She and Peter dig into why a book should be treated as a five-year march, not a launch-week event, and how evergreen ideas keep attracting ideal clients years after
publication.

If you’re a founder, executive, or expert looking to scale your impact without becoming a commodity, this conversation is a masterclass in how to think about your IP, your business model, and your relationship with AI.

Three Key Takeaways

• Coaching at the top is a strategic asset, not a remedial fix. Great coaching helps senior leaders clarify where they are, where they’re going, and how they’ll get there. The best clients see coaching as a sign of strength and leverage it to navigate different stages of growth—from early-stage chaos to pre-IPO scale.
• Thought leadership plus brand equals pricing power. Alisa treats her thought leadership—book, podcast, HBR/Forbes articles—as the engine that builds a premium brand. That brand brings her better-fit clients and gives her permission to charge premium rates for high-touch coaching, offsites, and speaking.
• AI is a force multiplier for serious thinkers, not a replacement. AI accelerates research and content creation, but the real value of thought leadership still comes from deep expertise, synthesis, and conviction. The challenge (and opportunity) is to use AI to move faster without letting the thinking get sloppy.

If you’re intrigued by how this episode unpacks coaching at the top, building a premium thought leadership brand, and using your IP more strategically, you’ll love the episode with Cara Macklin. Both conversations look at how to design your business model as intentionally as your ideas—shifting from “doing the work” to building scalable offers, curating the right clients, and creating more freedom and impact. Listen to them together as a mini-masterclass in turning expertise, coaching, and content into a focused, high-value business.

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Transcript

Peter Winick And welcome, welcome, welcome. This is Peter Winick. I’m the founder and CEO at Thought Leadership Leverage. And you’re joining us on the podcast, which is Leveraging Thought Leadership. Today my guest is Alisa Cohn. And without getting into her long bio, but I’ll give you a touch of that, we’ll get right into it. But she is one of the number one startup coaches in the world based on the Thinkers 50 Marshall Goldsmith Leading Coaches Award. She’s a top thirty global guru. She’s based in New York. She is a coach, she’s an author, and she does all sorts of other fun things like investing in Broadway as a hobby. So welcome, Alisa. How you been?

Peter Winick Please stop.

Alisa Cohn Yeah.

Peter Winick So let’s start with the like the short version or the shorter version of how did this happen, right? Like my fascination, one of my fascinations with thought leadership is it’s usually not logical, rational, or linear. Yeah. So how’d you get here?

Alisa Cohn Yeah, that is has not it was not r rational, logical, or linear, that’s for sure. So listen, I started my career in the nonprofit world and I was the chief of staff to the provost at Northeastern University. And I as part of that, I was super young, but I got exposed to so many things. And one thing I did was I led strategic planning for the university. And at that time, the provost said, You can’t manage faculty because they have tenure. And I thought, it can’t be. Like people only do what you want them to do, otherwise they’ll quit, or you’ll fire them, right? So I kind of went off to business school with thinking about that, but I got a little way later along the way. I started I went to the monitor group, I did strategic management consulting, and then I went to Cornell for Business School, and I got all turned around and I focused in finance and accounting and strategy. And I ended up going to Price Waterhouse Cooper’s in their so-called fast track to partner program. Two year five years to partner, and my life was all set. But then I just realized this is not it. You know, no mass like I can’t take this after two and a half years. And so I thought, what am I gonna do now? And I went seeking, seeking, seeking, and I just knew that I wanted to make a difference. The music in my head was to make a difference. Right. I met a coach at a conference and I was like, that’s what I want to do. And I didn’t know what a coach was. So I just kind of followed her around took coach training. I then, you know, I was pretty young to be a coach. So I was in the startup world. I was the CFO of one startup, the head of strategy another startup, and that all imploded. I said, Okay, I’m trained about to be a coach, I’m gonna be a coach now. And that was twenty five years ago.

Peter Winick Wow.

Alisa Cohn Yeah.

Peter Winick So, you know, the coaching is sort of vague, right? If you say to somebody, what does an accountant do? They do accounting. People kind of know that. So in some instances, people think a coach is a therapist, an advisor, or consultant, this mystery consigliary. How do you define what a good coach is? And you’ve got an interesting perspective because you’re doing it at sort of the top of the house.

Alisa Cohn Yeah. I you know, broadly speaking, a coach helps you get to where you’re going. And so what I think about coaching in my practice, I think about helping you assess where are you, where are you going, and how will you get there. And so that takes a lot of different forms depending on the context I’m in. It’s different for startup founders and C suite executives in large established companies. It’s different for workers on public figures. It’s different for teams and individuals. So the frame is the same, but that shows up in different ways, even with startups in like terms of what their stage is. So like an early stage founder is going to have to really like master the skills of building and inspiring a team and kind of figuring it out. And that’s very different from a Series D founder who’s going to have to master the skills about what does it take to be, you know, a much more systematized company getting ready to IPO.

Peter Winick Got it. Got it. And where what are the best type of clients for you? Because I think the other thing that good coaches know is I’m a really good fit for X, but I’m not a good fit for Y based on either personality or life experience or whatever. What is yeah what’s your sort of dream list for a client and maybe nightmare profile?

Alisa Cohn Well, I’ve kind of come to understand that I’m in as my career has gotten longer and I have more experience and worked with more people, then I just really need to work with senior people. Because honestly, like junior people just don’t have kind of even like, let’s say, the wisdom or expertise to kind of know what they don’t know. And so that is one thing I would say. The second thing I would say is that what’s helpful for me is to work with people who understand that making a change, having a coach, reflecting is not a sign of weakness. It is very much a sign of strength and a sign of empowerment. You know, Olympic Olympians, as they get better, they get more coaches, not fewer. And so those are the kinds of markers that make a good client for me.

Peter Winick But wouldn’t that be self selection, right? If you really have to sell somebody on the power of coaching, that’s probably a good sign that this might not be a great client or they might not be ready at that moment.

Alisa Cohn Yes. I mean, some people think they want coaching and then once we talk, I kind of get the impression that they’re like they don’t know what that really means and they sort of someone told them to get coaching. So they’re trying to check the box. And so just really diving into when I work with when I first meet somebody and we’re kind of assessing whether or not there’s a fit, I try to do a little piece of coaching with them right there and then. And the reason I do that is ’cause I want them to get an experience of coaching, like what’s coaching like. And then I also want them to I wanna myself assess whether or not they’re gonna be able to, you know, deal with my direct feedback or, you know, my perspective or that they really want to solve a problem and not just talk about a problem, which is a common thing for people.

Peter Winick So I wanna pivot to a different thread. You’ve been in this thought leadership world for a while, right? And you’ve been in it at the center of it and around it in terms of things like the MG. What is it, you know, tell me what you saw when you first started in this space and what has evolved and what is currently changing that’s impacting thought leaders.

Alisa Cohn I mean, it’s a I such an interesting question. I mean, AI is changing everything. Yeah. Right. And AI is kind of maybe driving people to hopefully move faster, but hopefully not move, not think more sloppily. Right. You sort of think about like thought leadership, you’re trying to have a synthesized point of view. You’re trying to have conviction on a set of topics that you have deep experience and an expertise in. And so the, you know, the AI, I think has made everybody almost like it makes everything faster and your ability to put stuff out there is in some ways faster. And the question is, is it better? That’s one thing. I also think in terms of thought leadership, you know, there’s a lot of sense of people learning from each other. And that’s a good thing, right? There’s like increasing, I think, community around thought leadership and increasingly increasing ability to pull practices from each other and work together and be more collaborative. And I think that’s a great healthy trend.

Peter Winick Yeah. So stay there for a minute, because I think that people don’t realize that the practitioners of thought leadership, it’s somewhat lonely, right? It’s not like, yeah, I was office every day with a thousand people, whatever. You’re doing your thing, you’re serving your client, you’re spending too much time at airport lounges, totally hotels, that sort of thing, et cetera. So there’s always been this sort of interesting stuff that happens, whether it’s, you know, two or three thought leaders get together for cocktails, or 20 or 30 or 100 get together under some umbrella of something, that cool stuff happens. And I think that, you know, you’re not gonna be on the, you know, standing out there talking to a neighbor who happens to be another thought leader, right? You might be that another profession. So I think some of that is there’s a need for that. And then the other piece is, you know, most thought leaders are, I don’t want to say narrow, but they’ve got their laser focused and they’re best in class at what they do. And then you start to see these collisions of ideas where the resilient expert meets the agility expert meets the questioning expert. It’s like, wow, they can all actually take a little piece of each other. So tell me about some of your experiences in some of these thought leadership communities.

Alisa Cohn Well, it’s such a great point. I mean, I one thing I’m also gonna say, just to amplify your point, like, you know, it’s like y you’re sort of lonely doing your thing, as you said, spending too much time in airports and on airplanes. And also, you talk to people who’ve got these sort of nine to five jobs, whereas they’re not nine to five, it’s you know, not saying like they’re they’re small jobs, but they’re very structured. You go into an office or workplace, you sort of, you know, are doing the easy, normal, everybody knows the mechanics of c of climbing the corporate ladder.

Peter Winick Yeah.

Alisa Cohn And so sometimes it can be hard to relate to that job, right? That kind of, you know, sort of experience where everyone is so structured and one day is like another. I think that like what’s a bit important to me as part of the 100 coaches, you know, that the collective, the collection of top coaches in the world. And, you know, of course, being friends with Dory and like just being in part as part of like creator masterminds and other thought leadership masterminds, is that you really get a sense of people who know your life a lot better, like they just get it a lot more. And obviously there’s like a lot of great, I don’t know, connective tissue that can go together when you begin to see what they’re how they’re practicing their craft. And there’s a lot of adjacent ideas that come together too. So it’s also it’s more community, but it’s also just more fruitful.

Peter Winick What I also think there’s a willingness to share because I don’t think most like ninety nine percent of thought leaders that I know and I know lots and lots and lots, they’re pretty generous, right? And they’re pretty willing to say, Hey, here’s what’s working for me. Because it’s not like, you know, if you owned a pizza shop and I owned a pizza shop in our local town, I’m gonna tell you my secret, like whatever that might be, right? Like we’re willing to share with one another and hey, give some feedback and all those sort of things, which I think yeah, is kind of cool.

Alisa Cohn It is very cool. And I will say, like just re just literally today, I got two people in my community, thought leaders, who are writing books who were like, Can you please weigh in on this title or this, you know, chapter or whatnot? And that’s just like normal. And by the way, I and also someone else was like, Will you please put in your newsletter this thing about my book? And I do those things, of course. I’m happy to do that. And then, you know, when I need people’s help, I can get their help too.

Peter Winick Yeah, it is pretty helpful. If you’re enjoying this episode of Leveraging Thought Leadership, please make sure to subscribe. If you’d like to help spread the word about our podcast, please leave a five-star review at ratethispodcast.com forward slash L T L and share it with your friends. We’re available on Apple Podcasts and on all major listening apps, as well as at Thought Leadership Leverage dot com forward slash podcast.

Peter Winick The other thing I would say is there aren’t a lot of commonalities that you can say across, you know, actuaries tend to be sort of, you know, introverts, whatever, whatever. But thought leaders are all over the place, right? You have thought leaders that are, even though they might be making most of their money as a keynoter, they’re actually introverts. Even the you know, might be out there talking about their stuff, their they’re you know, their researches. I think that one of the common threads though is this lifelong learning. Like I think you and I originally met at Renaissance weekend years ago. Yeah, Brian. Yeah. And like what a nerdfest. Like I know. And it’s the coolest thing ever. It’s like living in a TED talk for five days, right?

Alisa Cohn Totally.

Peter Winick Yes. But there’s a hunger that that folks have to say, you know, I want to learn about things so outside of my world, like, you know, aeronautics or robot like whatever. That curiosity piece. Do you see that as well?

Alisa Cohn Totally. Yeah. I mean, that’s I think that’s almost the definition of a thought leader, someone who is curious. Also, I find that people tend to be they don’t retire, quote unquote, right? They continue doing what they’re doing and they’re very vibrant and robust in their thinking for decades. You know, Marshall Goldsmith’s is in the seventies. I just saw John Hagel speaking of Renaissance weekend. John Hagel’s, I think he’s in his late seventies or maybe older. He’s like writing his like sixth book or something. Good for him.

Peter Winick Which is pretty cool. So you mentioned the B word, right? So tell me about what your thought process is when you choose to write a book and go for it, right? Because something one wants to do. You know, people ask me how many you know, when should I write my n you know, it’s like write the leak amount of you need to because it takes you know, it’s the only thing worse is renovating a home in terms of takes more time and more money. But totally but you’re thinking.

Alisa Cohn Well, I mean, I’ve written only one book. You know, like all my colleagues have written four, five, six books, right? So I it was very challenging to find the time to put your thoughts together. It’s also very rewarding because you’re really asked to come up with your framework and your thinking, and it requires you to really refine your thinking. And I think it is a very rewarding journey, but it’s also it’s frustrating. Also, your first draft is always like terrible. And then you’re like, oh, it’s so terrible.

Peter Winick Yeah.

Alisa Cohn You have to be able to have faith that you’re gonna go through it and you’re gonna kind of figure out the breaking the back of it, like kind of really figure out the unlock that’s gonna help you actually write a book that’s worth writing.

Peter Winick Exactly. And then and then as difficult as that is, it’s actually getting the book out into the marketplace that much worse. Much harder.

Alisa Cohn Yeah.

Peter Winick Yeah. Right. As far as hard as that is. And there’s you know, everybody’s looking for the, you know, what are the three tips to sell more books or whatever? And the reality is there aren’t any. What works for you doesn’t work for me and totally common threads of wanting a community to support you. But other than that, like it’s, you know, it’s and you know, the other thing I would say it’s a long game, right? A lot of it’s the industry is focused on short term, your fall release, a spring release, whatever. You know, you wrote your book I don’t know how many years ago now.

Alisa Cohn Years ago.

Peter Winick Three. But that doesn’t mean it’s dated, right?

Alisa Cohn Right. Not at all. I was just gonna say it’s like a five year march. You have to think about every any book that you write as not kind of just launch week. It’s a five year march to get there, yes.

Peter Winick Exactly. Exactly. And I think if you get the right book in the hands of the right people, whether it’s today or a week after it launched, it’s just as relevant, just as valid, particularly if things are written in an evergreen style. Yeah. What are the one of the things that you’re seeing, you know, we talk about AI, and I think AI is interesting right now to say the least. But I think a lot of people are like, we’re not sure what to do with it as thought leaders. So on the one hand, I see everybody building their AI their bot, right? Like, hey, you could, you know, here’s the me thing, which assumes that all everybody in an in a client organization wants is to talk to you, which maybe in some cases is true. Is it a research tool? Is it is it a content creator? Like we’re seeing some it’s just kind of fun to see everybody experiment and ’cause nobody has really cracked the code, whatever that means.

Alisa Cohn Yeah, and it keeps changing. I mean, what I’ve found remarkable is that I’ve done now over a hundred podcasts myself. And I’ve also written numerous Forbes articles, HBR articles, and I’ve created a ton of content. So I can take categories of that content. So for example, all my podcast transcripts, and I can put them into Google Notebook, for example, and ask Google Notebook, for example, what are the 10 insights that you know these kind of founders say about leadership? And then it’s remarkable what it gives back to me. Now it doesn’t give me back, you know, ready to write insights. Like the writing comes from me, but it’s like, oh yeah, I forgot about episode eight. Oh, you’re right. That’s was a great topic of episode eight, right? I’m on episode like a hundred plus now. So it reminds you and keeps current and fresh for what you’ve already done. And so it helps you content, helps you sort your content.

Peter Winick Yeah, ’cause we’re you know, we’re at like seven hundred episodes now, and you know, I barely remember what I had for breakfast, let alone an episode I did five years ago. But with themes pop up that you might not have remembered this person, this person, this person, four years apart, had a similar perspective on something. Yeah. Like what if I reached out to them and asked them a couple of different questions? But I think you’re right that I I think one of the secrets to AI is if it’s cut and paste, people know it’s cut and paste. Dana estimate people. But if it becomes a sparring partner, someone that could challenge you or someone can maybe play with tone or do that research, like know what it’s good for and what it’s not. And I think lazy marketers and lazy thought leaders, if you will, are just sort of doing the cut and paste thing because it’s can’t it it can’t, and that’s

Alisa Cohn I mean, yeah, I don’t know who’s really doing cut and paste. I mean, like I don’t even know what to say about that because it’s so obvious, like, you don’t do cut and paste. I don’t know. Did you read it? If you read it, you might not have cut and pasted it, right? So yeah, but I think it’s a very powerful, helpful tool to synthesize things, to research things. Yeah. I find it really and then I think over time it will become a much better tool and companion for writing as well. I don’t think it’s there yet, but I think it’ll get there.

Peter Winick Yeah. And it’s interesting. So, you know, your business is a fairly personal, intimate, you know, it’s one on one services, right? That that you’re delivering. So all this scale, all this leverage, all that can really do for you is sort of elevate your brand, make more people aware of who you are. Totally. Probably give you more to select from in terms of the client and the right piece. How do you think about that?

Alisa Cohn I well, that’s that is the way I scale. So I mean, I do one on one, as you know. And so then I’ve experimented with courses. I, you know, continue to think about what can I do? It’s a more scaled offering. What I like to do is one on one, and what I like to do is off sites. And then I do some speaking and other things. And then everything around that is so-called brand building to feed that business that I have. And, you know, the brand building is important because it does help me charge premium rates and it gets me amazing, you know, clients who are interested in talking to me. So those are that’s what and also thought leadership is satisfying for its own sake.

Peter Winick Yeah. But we’ll stay there for a minute, you know, in terms of the rates and such, you know, if you see a coach speak at your local chamber of commerce and podunk, there’s almost a price associated with that. If you read somebody’s thought, you know, thought leadership in a place like HBR or Forbes, yeah, not necessarily connecting a price to that, but when that client reaches out to you, there’s an expectation of, oh, this probably isn’t someone that charges by the air. Like this is a premium.

Alisa Cohn It feels more premium.

PW Yeah, but you’ve already sort of flexed your intellectual muscles and said, But you kinda know how I think and what I’m capable of.

Alisa Cohn Totally. Yeah. Also people have read my book and listen to my podcast and they’ve reached out to me, you know, and so it’s like it’s also they already do have a pr they already know me, kind of they have

Peter Winick I feel like it interesting. I find that when clients come as a result of having consumed a bunch of thought leadership that we’ve put out, whether that’s video or podcast or audio, they’re almost coding you to you. And it feels like you’re having a conversation with an old friend ’cause they kind of know what to expect from you.

Alisa Cohn Definitely.

Peter Winick Which is kinda fun, right? Versus having

Alisa Cohn Definitely.

Peter Winick Create that. Well, this has been great. I appreciate your time and sharing your story with us.

Alisa Cohn It’s always great to talk to you, Peter. I always enjoy it.

Peter Winick Thank you. Good to talk to you. Be good. Thanks.

Peter Winick To learn more about Thought Leadership Leverage, please visit our website at thoughtleadershipleverage.com. To reach me directly, feel free to email me at peter at thoughtleadershipleverage.com, and please subscribe to Leveraging Thought Leadership on iTunes or your favorite podcast app to get your weekly episode automatically.