AI, Executive Coaching, and the Future of Thought Leadership | Alisa Cohn | 681

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 Alyssa Cohen, and without getting into her long bio, but I'll, 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 30 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, uh, welcome, Melissa. How you been?

Yeah, I'm great. Thanks so much, Peter. It's really exciting to be here. And, um, I appreciate that kind introduction. And I also have a podcast, which is also called, which is called From Startup to Grownup, which is the name of my book. So I just wanted to. Throw that out there because you're not the only podcaster of this conversation.

Exactly.

Yeah.

So let's start with the, like, the short version or the shorter version of how did this happen, right? Like, like my fascination, one of my fascinations with thought leadership is it's usually not logical, rational, or linear, right?

Yeah.

So how'd you get here?

Yeah, that is, it has not, it was not rational, logical, or linear. That's for sure. So listen, I started my career. In the nonprofit world, and I was the, um, chief of staff to the provost at Northeastern University. And I, as, 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, right? Or you'll fire them, right? So I kind of went off to business school with thinking about that, but I got a little waylaid 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 PricewaterhouseCoopers in their so-called Fast Track to Partner program, 2 year, 5 years to partner, and my life was all set. But then I just realized this is not it. You know, no más, like I can't take this after 2 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, bah, that's what I wanna 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 that had a 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 25 years ago.

Wow.

Yeah.

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 the coach is a therapist, an advisor, or consultant, this mystery consigliere. How do you define what a good coach is? And, and, and you've got an interesting perspective because you're doing it at sort of the, the top of the house.

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, I work with some 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 stages. 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.

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, what's your sort of dream list for a client and maybe nightmare profile of a client?

Well, I've kind of come to understand that I'm, 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.

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. 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 'em to get coaching, so they're trying to check the box. And so, yeah, 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 wanna, 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.

So I wanna, 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.

I mean, it's such an interesting question. I mean, AI is changing everything, right? And AI is kind of maybe driving people to hopefully move faster, but hopefully not move, not, 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.

Yeah. So stay there for a minute cuz I think that people don't realize that the, the practitioners of thought leadership, it's somewhat lonely, right? It felt like, yeah, I was in the office every day with 1,000 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, this sort of interesting stuff that happens, whether it's, you know, 2 or 3 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, the, you know, standing out there talking to a neighbor who happens to be another thought leader, right? You might be that in other professions. 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 wanna say narrow, but they've got, they're 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, tell me about some of your experiences in some of these thought leadership communities.

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 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 9-to-5 jobs, or if they're not 9-to-5, it's, you know, I'm not saying like 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 climbing the corporate ladder. 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 been important to me as part of the 100 Coaches, you know, the, the collective, the collection of top coaches in the world and, you know, of course being friends with Dori 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.

Well, I also think there's a, uh, a willingness to share because I don't think most, like 99% 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, we're willing to share with one another and, you know, give some feedback and, and all those sort of things, which I think, yeah, is kind of cool.

Uh, it is very cool. And I will say like, just, just literally today I got two people in my community, thought leaders who are writing books who are 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, when people, when I need people's help, I can get their help too.

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 5-star review at ratethispodcast.com. /ltl and share it with your friends. We're available on Apple Podcasts and on all major listening apps, as well as at thoughtleadershipleverage.com/podcast. The other thing I would say is there, 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 though they might be out there talking about their stuff, they're, you know, they're researchers. 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, right? 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 5 days, right?

Totally.

Yes. But, but there's a hunger that, that, uh, folks have to say, you know, I wanna learn about things so outside of my world, like, you know, aeronautics or robot, like whatever. That curiosity piece, do you see that as, as well?

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, 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 is in the '70s. I just, uh, saw John Hagel speaking of, um, Renaissance Weekend. John Hagel's, I think, he's in his late '70s or maybe older. He's like writing his like 6th book or something. Good for him.

Which is pretty cool. So yeah, I mentioned the B word, right? So, 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 next, you know, it's like write the least amount of you need to because it take, you know, it's the only thing worse is renovating a home in terms of takes more time and more money. But tell me about your thinking.

Well, I mean, I've written only one book, you know, like all my colleagues have written 4 or 5, 6 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, 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.

Yeah.

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

Exactly. And then, and then as difficult as that is, it's actually getting the book out into the marketplace.

Much worse, much harder. Yeah.

Right. As hard, as hard as that is. And there's, you know, everybody's looking for the, you know, what are the 3 tips to sell more books or whatever? And, and the reality is there aren't any. What, what works for you doesn't work for me. And totally like common threads of wanting a community to support you. But other than that, like it's, it's, you know, it's, 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. You're a fall release, a spring release, whatever. You know, you wrote your book, I don't know how many, how many years ago now?

3 years ago.

3. But that doesn't mean it's dated, right?

Right. You said to me, not at all. I was just gonna say it's like a 5-year march. You have to think about every, any book that you write as not kind of just launch week. It's a 5-year march to get there.

Yes, exactly. Exactly. And I think if you get that, 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, what are the things that you're seeing? You know, we talk about AI and I think AI's 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, their AI, their bot, right? Like, hey, you could, you know, here's, here's the me Right. Mm-hmm. Which assumes that all everybody in an, in your 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.

Yeah. And it keeps changing. I mean, what I've found remarkable is that I've done now over 100 podcasts myself.

Yeah.

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, uh, 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 8. Oh, you're right. That's, that was a great topic of episode 8, right? I'm on episode like 100+ now. So it reminds you and keeps current and fresh for you the, what you, you, what you've already done. And so it helps your content, it helps you sort your content.

Yeah. 'Cause we're, you know, we're at like 700 episodes now and, you know, I barely remember what I had for breakfast, let alone an episode I, I did 5 years ago. But with this—

Exactly.

Melise. Themes pop up that you might not have remembered. This person, this person, this person, 4 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, but I think you're right that I think one of the secrets to AI is if it's cut and paste, people know it's cut and paste. Dan Ivey, of course, amazing people. But if it becomes a sparring partner, someone that could challenge you, or someone could 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 can't. And that's why.

I mean, yeah, I don't know who's really doing cut and paste. I mean, I, I, I don't even know what to say about that because it's so obvious. Like, don't do cut and paste. I don't know. Did you, 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, I find it really, and, 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.

Yeah. And it's interesting. So, you know, your, 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, how do you think about that?

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? What's a more scaled offering? What I like to do is one-on-one, and what I like to do is offsites. 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, and also thought leadership is satisfying for its own sake.

Yeah. But we'll stay there for a minute, you know, in terms of the, 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, 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 hour. Like, if this is a premium solution, it feels more premium. Yeah. But you've already sort of flexed your your intellectual muscles and say, but you kind of know how I think and what I'm capable of.

Totally. Yeah. Also, people have read my book and listened 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 pers— they already know me kind of, and they have a respect.

I feel like it, it's 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 quoting you to you. And it feels like you're having a conversation with an old friend cuz they kind of know what to expect. From you.

Definitely.

You know, which is kind of fun, right? Versus having to create that. Well, this has been great. I appreciate your time and sharing your story with us.

It's always great to talk to you, Peter. I always enjoy it.

Thank you. Good to talk to you. Be good. Thanks. 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@thoughtleadershipleverage.com. And please subscribe to Leveraging Thought Leadership on iTunes or your favorite podcast app to get your weekly episode automatically.