Thinkers50 Curated LinkedIn Live with Alisa Cohn | The Ultimate Startup Coach

Hello, welcome to another Thinkers50 curated session. I'm Des Dilove.

And I'm Stuart Krainer and we are the founders of Thinkers50, the world's most reliable resource for identifying, ranking and sharing the leading management ideas of our age.

Our belief in the power of ideas has been the foundation of our work since we launched the first ever global ranking of management thinkers in 2001, and we've published a new Thinkers50 ranking every two years since, and it remains the premier ranking of its kind.

So we are excited that 2021, a year in which fresh thinking and human ingenuity are more important than ever, is also a Thinkers 50 year. Nominations are now open for both the Ranking of Management Thinkers and the Distinguished Achievement Awards, which the Financial Times very accurately calls the Oscars of Management Thinking.

The award shortlists will be announced at the end of July and the year's finale on the 15th and 16th of November will bring all the excitement of a new ranking and the naming of our Thinkers50 2021 award winners.

Our theme this year is Ideas with Purpose and our guest today fits this description to a T. She is Alyssa Cohn. Alyssa has been coaching startup founders to grow into world class CEOs for nearly 20 years. A one time startup CFO, strategy consultant, and current angel investor, she has worked with startup companies such as Etsy, DraftKings, the Wirecutter, Matt Weldon and Tory Burch and many mores. Many, many more.

She's also coached CEOs and C suite executives at some of the world's best known companies including Dell, Sony, IBM, Google and Microsoft. Alyssa is a guest lecturer at Harvard and Cornell University's Henley Business School and the Naval War College. She's the executive coach for Runway, the incubator at Cornell nyc subtitled Grow youw.

Leadership to Grow your Business.

And if that wasn't enough, Alyssa is also a Broadway investor in productions which have won two Tony Awards and has warned us in advance that she's prone to burst into so at the slightest provocation, she's also an amateur rap artist.

Please send in your questions for Alyssa at any time and also let us know where you are joining us from today.

So let's get started. What's the secret to being an effective executive coach?

Oh, well. So first of all, thank you for having me. It's really a pleasure to be with you today. And I think the secret to being an effective executive coach is two things. One. One is that you really have to sort of love to understand with curiosity how people think and why they do what they do, you have to have like a innate curiosity about human behavior. And the second thing is that you have to be willing and able to meet people where they are in adjust your style. Because at the end of the day, my success as an executive coach really corresponds to, is really measured by my success of my clients. So I've got to walk beside them and help them self actualize and achieve greatness in their leadership context.

So during the pandemic, you've been busy, Alyssa. New book coming out, published by Kogan Page in October. Tell us more about the new book.

Oh, well, my new book is a passion that I have been thinking about for a number of years and it's called From Startup to Grown Up. And it's the idea, the basis for thinking about how do you grow from being a founder to a CEO, from somebody who's busy building a product to someone who's busy building a business. And it's not really a straight line. And what I have seen in my 20 years of coaching, and in particular coaching founders, is that founders make the same mistakes over and over again. So for me, it's a passion to be able to reveal the tools and techniques that they can use so they don't make those mistakes and they can accelerate their ability to be successful and optimize their ability to be successful.

Have you ever had, I mean, you must have had clients that were resistant to coaching. You must have had clients who didn't stick. I mean, is that, how does that happen sometimes? And what do you do about it?

Oh, yeah. Well, first of all, it's two different things, right? One is about resistance and the second is about sticking. So resistance is about skeptics, right? I've had coaches before. I don't believe in coaches. I don't really know or you can't really help me, you don't know your business. The truth is, I welcome skeptics. I. When I first meet somebody, my first goal is to add value within 20 minutes and, you know, back to what's a successful executive coach? My ability to listen and really understand what they're saying, synthesize and sort of mirror back what they're saying and then help them get out of the problem so they can look at the problem and then together we can solve the problem. That is very convincing to people that executive coaching can be helpful to them. The other thing is that sometimes people will say, you need a coach like it's a punishment. So what I do is I help them see it's not a punishment, it's A perk. And so that helps get over the resistance. I think stickiness is like a different question. So the question is how open are people to actually be willing and able to change? And that to me is like a whole masterclass about what makes people tick and what makes them willing and able to change.

And you really can make a difference in 20. In 20 minutes.

You think, yeah, you want to do it right now.

Make a difference in Stuart's life right now.

It might take longer, who knows? But I can see that quick wins in. In any kind of change program are important. And I can see that in coaching. It's probably. I can see it is probably achievable. What if it doesn't work in 20 minutes?

Right? Well, the thing is that what people really value in the muck and mire of a busy professional life. And I think about a startup founder that I met with initially, right? He, he came the same kind of thing. His board said, you need coaching. He's like, I need coaching. But finally he's like, fine, I'll talk to the coach. So we sit down together and he's skeptical. But I just say, what's the problem that you are thinking about and thinking about and can't make any progress on it. He immediately came up with his head of product. So what's the problem with the head of product? Well, all these different things and we talked it through and we came up with in a really great solution for what is he going to do now? Like, what specifically is the conversation he needs to have with his head of product with a script and a role play and everything in 20 minutes? So why were we able to do that? Well, the truth is that as a startup founder, he's got a lot of things to do. The thing that he doesn't really want to do is deal with Eddie, right? Because it's complicated. He doesn't know what to do. It makes him uncomfortable. So he's able to focus on all those different things and not focus on this important problem in front of him, which is Eddie. So when I show up, I kind of help him clear the space. And all we're going to do for 20 minutes is talk about Eddie because it's actually a really important problem for him to solve. And it doesn't take that much time of devoted thinking and being commonsensical, but also recognizing where his emotions are playing out. That helps us make progress on this, like what seemed to be an intractable problem.

Okay, I see we've got. We're being joined by. We've got people, we've got people joining us from Bucharest, from Baghdad, from Bangalore, from Brazil, the bees Poland Poland, Amsterdam, UK. So it's a very international audience. Please put your questions in the comments and we will certainly try to get through as many questions as we can. You mentioned, well, I mentioned in the introduction that you not only coach startups but you also coach, you know, really established companies. What's the difference? I mean in terms of coaching a founder of a startup versus, you know, an established CEO or somebody who's, who's been an executive at a large organization.

Yeah. So founder and the CEO of a startup. Think about this. The leadership like the entry level position inside of a startup is leader, is boss. So that person hasn't typically grown up in business. They haven't managed a team before, they haven't managed a business before. So they're learning on the job all the different traits. So on the one hand that makes them very open to like new ideas and trying to do it this way and so that's really wonderful. But there's really a lot of learning they really have to do on the job. When I work inside of an established company, the CEO I work with, public company, last year now it goes without saying he was a CEO after 25 years of growing up inside of this organization. So he's got a lot of those skills. But sometimes the problem is he doesn't have a strong beginner's mind. He's not open to experimenting. So I have to help him think about how do you experiment with a different style, how do you think about what maybe hasn't worked here in the past, but now you're the CEO might work here. So what I think about is I bring an entrepreneurial mindset to large companies and large company CEOs and executives and I bring process and system orientation to entrepreneurs and to founders.

So it's a kind of cross pollination sort of process going on there. Taking from one and giving to the other. We've got a good question, got a good question from Pranav asking so startup to grown up. What are the main roadblocks in the thought process of founders? You said they make the same mistakes again and again. What are those roadblocks?

Well, there are predictable roadblocks that happen with founders. So number one is they hire their friends and they don't have a conversation with their friends about how it's going to change their friendship. And then what happens over time is that they hire other employees. But like they know there's a protected class of People called the friends of the founder, that's one predictable pitfall. Another is they're not intentional about building culture. So they sort of like, oh, culture will happen once we're after already a big company. But the prime, that's by the time they have 30 or 40 people inside of the company, there's already a culture and it's mostly accidental. So they haven't really thought about how do I create a high performing culture. People feel cared for. And then the third thing I would say is they don't think about the way their communication needs to scale. So when I'm talking to like you, eight people in my early days, the startup, it's like it's easy, we're all in the same room. But as the company grows from 8 to 30 to 100 to 1000, you need to adapt your communication style. And founders tend to be really behind on recognizing they have to do that and learning the skills to do that.

I suppose the reverse is true as well in that, I mean, Chris Zook has done work on the founder's mentality and how you can take the founder's mentality and apply it to a big organization. I did some interviews at Infosys, the Indian company, a few years ago and what struck me there was that they had taken the founders mentality, the entrepreneurial energy and sense of owning the company, being the company, and they managed to transform, translate that to a big company. So you don't, you don't want to lose the what makes the founders great in the first place, I guess.

Stuart, I think that's exactly right. And that's very like insightful, especially as it relates to culture. So how do you create a culture where people do feel the owner's mentality, sense of urgency and sense of innovation even as you grow and as you scale and it has to do with who you hire in the beginning and then who you keep hiring. Do they have those traits? And then are the people who are kind of your cultural co founders, are they imbibing and embedding the atmosphere around them with the same sense of innovation? There's also, I think, a change, right? How do you kind of manage innovation using systems and processes and tools, but without squeezing all the life out of what could be exciting or innovative?

Okay, we've got some more questions coming in. You mentioned the scaling communication issue because you know, when you're in a small, tight knit group, you can project your personality and your Persona quite easily. Diana's asking, can you highlight most significant Persona that anyone can relate to? Is there a. I mean, how important is it to project Persona and personality? And how do you do that as a. Gets bigger and bigger.

Yeah. I think there's this tension between, or I should say this interesting, like word and this tension on this word called authenticity. So we want our leaders to be authentic. But the truth is, if you as a leader are worried about stuff or you're feeling grumpy and you're addressing the all hands and you're sharing your worry with everybody and your grumpiness with everybody, that's your authentic style. And it's actually not helpful. Not do that. Or if you're sort of like a clown, like funny. And then you. There's actually a great story with. With a founder that I know. He addressed the all hands and he actually said, oh, we're just making half this stuff up. That's okay when you're 30, it's kind of, we are really making all this stuff up. But they already reached like 500 people and there's no longer really appetite to be making all this up. People are making decisions and building a career inside of their company. They need you to take that serious. So you as the authentic leader, need to think about how can I bring my humanity to this? Maybe I'm funny, maybe I'm serious, maybe I'm intense. That's great. But then you need to really make sure that you're sort of scripted and polished when it comes to addressing people, whether it's in the all hands or in small groups or one on ones, so that you're aware of how you're coming across. And is that playing appropriately for the context of your current company, not your company. Last year, your company. Now.

Des and I did some work with Gareth Jones and Rob Goffey, authors of a book called why Should Anyone Be Led by You? And their kind of slogan was be yourself more with skill. So you had to be a kind of adapt your authenticity for context.

Yes, that's a great expression.

Yeah. And I think at times that CEOs can't be authentic, as you say, because they don't. They don't want to communicate worry and concern. It may be completely inappropriate for them to do that.

Right. One thing I would say is when I think about, you know, when people ask me about authenticity, I say, listen, bring your humanity. Because it is true that some appropriate humanity, appropriate vulnerability does help people connect to you. And that connection is going to help them be led by you. Right to your point about the book. And those are some of the secrets to be able to Be sort of authentic in quotation marks and not just let it all hang out authentic.

I mean, again, coming back to Robin Gareth's work, they would talk about a repertoire we all have. None of us are just one thing. We have different aspects and dimensions. And they would say, and perhaps you would agree that we have a repertoire. It's about choosing from our repertoire so that you don't become totally inauthentic, but you're selective in terms of which aspect of yourself that you show.

I think definitely, definitely. And all CEOs also have to have hats, right? I think of it as hats. Like this is your I'm presenting to the board hat. This is your I'm now leading the all hands hat. This is your having a one on one with a sensitive topic with someone who's kind of upset hat. If you can change your hat, then you can change your style. It kind of triggers you to remember, I need to pull the right from the right repertoire, as you said, to what's required here in this moment.

As a man who doesn't suit hats, I'm going to move on. That's a good question from Pranav Kumar. In your coaching experience, who you found more open to the ideas? CEOs. I mean, the kind of stereotype of the modern CEO is they're not particularly open, actually. And you would expect entrepreneurial founders to be open. But I suspect that both don't really conform to stereotype.

Yeah, both do not conform to stereotypes. And I would say both startup CEOs and large company executives can be super open in some circumstances, but if you push them on something that they are shut down on for some reason, they are super closed. And so I think as a coach, the trick for me is to kind of always find the gateway about what's going to help someone keep their mind a little more open. But I've worked with all kinds of people and I think it really has to do with do you as an executive have a growth mindset and a learning orientation or do you think you've kind of figured it all out? Most of my clients have a growth mindset, otherwise they would not be being coached.

Yeah, no, absolutely. I mean, it's interesting that the point you made, one of your three sort of points about founders of startups, the culture piece. Because spent a couple of days with Reed Hastings from Netflix and it's very evident that what he, what he tried to do with Netflix is learn the lessons of his first company, which I think it's pure software.

Pure software. Yeah, yeah.

And Exactly. That he didn't. They didn't consciously create a culture. And in fact, it turned into it. It became a stifling culture because as they introduced the rules, they lost the. They lost the spontaneity and the dynamism. So I think what he's tried to do with Netflix, and obviously we all read a lot about that culture, is consciously try to build the culture in. From the. From the beginning. So I guess that's the sign of someone who's. Who's on an interesting journey.

Yeah. And a learning journey. And I think the learning journey didn't start when he started Netflix. It's like their culture has been built through experimentation and trial and error all the way. An example of what you said, like, in pure software, they had a lot of rules. And so he recognized that the rules didn't always bring that much value, and that rules sometimes stifle creativity. So then at Netflix, people are getting their expenses approved, and he began to realize, like, gosh, it's taking a lot of time to get your expenses approved around here. No more approval. We trust you. Right. But then they have. What I am impressed with Netflix is they have checks around that. Right. So that no one's taking advantage. And also, I think their hiring process is super rigorous in order to support the kind of culture that he has been trying to build there.

Yeah, yeah. He talks about high talent density. If you have good people and you make sure you hire very, very good people, you can allow them to not have so many rules. But if you. If you dilute that and you get the wrong people in place, you'll have the usual. The usual troubles, I think, that a lot of organizations have. And the reason that we have rules.

Yeah, I think that's right.

There's a good point from Rick Spann, who joins our. This. This. This session most weeks and tends to make musical analogies, which are sometimes. Sometimes helpful, which I think it is in this case. And he said much can be learned from the way leaders in music like Duke Ellington, etcetera, Engage in different types of projects. And it teaches about learning, leadership, agility, and entrepreneurial mindset. And here, the development of an authentic tone is key from your experience in music. Metaphorical connections here.

Well, thank you, Rick, for putting me on the spot here. I think that there's a lot of. There's a lot of lessons to be learned from music. And I'll just say two right now. I think of the CEO as the conductor. So actually, your job as the CEO is to make sure all these units all these groups, all these instruments are quite playing well together with music that we want to hear so that we can all feel successful. That's one. The second is to your point about jazz. I mean, it's well known that people have to kind of learn their craft and learn to play the instrument well and learn to read music. And then once they kind of have the muscle memory about how you actually execute this instrument, then you can improvise. And I think there's a tension between, you know, doing in the classically trained way, doing it the right way, and then recognizing that it's time to shift your style and make something up. I think startup founders are like pristinely and exquisitely tuned to make things up. They also need to work on kind of getting the basics underneath their belts.

Isn't that one of the problems with CEOs, that the CEO role is conductor, but actually their background tends to be in one particular instrument?

Yes, that is totally true. And actually normal founders will think that they have to know all the answers and that their job is to know all the answers. And by the way, in the beginning, after they've been thinking about this for a year or two or three, and then they hire some people. The truth is they are the smartest one in the room. They do know all the answers, but over time that's not sustainable. They need to conduct this orchestra and hire people who are better than them and then hire the right people and then train themselves to recognize they don't need to be the last one word or the decider on everything that goes on. That's a very difficult leap to make for a startup founder.

Okay, and then there's a step beyond that when presumably, I mean, because typically leaders, CEOs aren't. Haven't been historically good at managing their own exits because presumably there comes a point when perhaps they're not the right person to conduct the orchestra anymore. Have you had situations where you have to kind of help someone move a bit closer to the exit?

Yes, actually, I talk about that in my book, in the first chapter. It's about self awareness. Do you even want to be the CEO? The truth is that as a founder, most founders are really focused on or that what their their natural strength is peering over your shoulder into the future that you cannot see. That is a superpower. And then they can inspire people to follow them, inspire venture capitalists to invest in them. That is a wonderful skill. But then over time, people in their company want performance reviews and career ladderings and there needs to be like a machine that's kind of cranking out the product at scale. They may not be suited to do that. They may not have the temperament, they may not have the desire to do that. There's one founder that I've worked with a few times, he's a three time founder and he realizes that after a certain point in the company, it's like he's no longer the guy to want to build this company. Right? So he's kind of, kind of figured that out after painful experiences of running into a brick wall of what happens once it becomes more at scale.

Interesting question from Ola. Did you end up having to rethink the way you coach execs or startup founders during the pandemic? If so, how did the pandemic change your kind of practice of coaching and the way you think about it?

Yeah, thanks Ola. I think it's like books will be written around how we all changed during the pandemic. But I will say a couple of things. One is that originally all the founders that I worked with did a couple of things. We immediately had like a bunch of emergency meetings with the executive team and had daily meetings on a regular basis to make sure that communication was pristine. So the way I changed my coaching was that I really helped them think about their role as being the communicator in chief so people knew what was going on because people were craving certainty. So actually I wrote an article for Forbes which was how do you plan for a future that you can't plan for? So it's about how do you communicate certainty in a time of uncertainty. So my coaching definitely shifted with that. Also, it goes without saying there was a whole focus on self care, which I don't think is going to change. The CEOs I work with, to their credit, credit got very focused on the well being of their people. However, they did not focus as much on their own well being. And so a number of them just had some dark moments. And there was one in particular. The CEO of one startup I worked with in particular, he didn't have like a single day off for about eight weeks, right? So eight or nine weeks he was just working, working, working around the clock. And when we caught up at some point I could just tell like you are no longer any good for anyone because he was really like just working himself to the point of burnout. So I think for me I got much more attuned to self care. Definitely the executives I work with are much more attuned to self care or to the well being of their employees. And I don't think that's going to go away anytime soon, especially in our new remote and hybrid work environment that we're looking into the future.

Okay, another question here. From your experience, what are the top five leadership skills? I'm going to add a bit to that. And are they changing? Have they changed because of the pandemic or are they constant? Are they universals?

Yeah, well, the top, to me, the top leadership skill is your ability to shift to the circumstances. So your situational agility, knowing what's required here and being able to activate that, that is by far number one. And that has not changed. Our circumstances have changed quite a bit. So I think if anything, that's kind of compounded. The second is probably aligned with that is communication. And I think communication has changed because the founders and the executives that I work with have had to learn how to use video and phone in a way that if they were working in person, they did not have to. For example, they used to put off having difficult conversations like, oh, it's video. I'll do when I see him in person. That is no longer an option when you've gone remote and your employees are scattered throughout the company. The third one I'll talk about is actually back to coaching. So what's necessary definitely right now is for leaders and managers to double down on coaching their employees. Because there's a lot of what's happening now where playbooks have not been written. So it's the idea of coaching to evoke excellence in their employees, helping them feel supported, helping them make good decisions. When you, the leader, are not necessarily around, I think that's going to become very much a skill for the future. That's only three.

Do you think the entrepreneurial and corporate worlds better understand each other than they have done in the past? Because it always strikes me that when I talk to, we're a small company, I talk to people who work for big companies. And just seems the gulf of perspective and the context is so different that they don't really understand us and we're mystified by them.

Yeah, I think it is that way. I think that, you know, you pointed out earlier the idea of stereotypes. There's a stereotype of how the large company executive is. And then definitely there's mythology around startups. Mythology or, you know, even that show Silicon Valley just perpetuated this myth of what it is to be a startup founder. It is not really like that. And I think when large company executives or professionals come inside of a startup, they are startled about how like little sort of administrative support they have and how much they have to really wrangle people themselves. But I think they think it's refreshing about how much ownership they have inside of large companies. There's a feeling of getting like, you know, eight different approvals all the way down the chain of command. Startup people most likely can't tolerate that environment. Founders definitely can't tolerate that environment. That's why they became founders. Okay.

You talked earlier about the need for people to have a growth mindset in order to be coachable. And, you know, a lot of these things goes to that. If someone's got a fixed mindset, I mean, are we one or the other? Do we move between. How do you help someone move from fixed mindset to growth mindset?

I love the sophisticated nature of the question of how do you create a growth mindset from a fixed mindset? How do you grow yourself out of a fixed mindset? I think, you know, it's a nature of, like, people and their place in development. I don't think a coach can really change somebody. I think people are willing and able to change based on, in some ways, their makeup, but also based on experiences that they have had in their lives. We have all experienced something for the past 16 months or so that has really made us stop and pause and reflect. And I think right now is a time where people are all reevaluating their lives. And that is the definition kind of a growth mindset, where like, new ideas, new frameworks, new skills, new ideas, new belief systems are. It's fertile ground to grow all of those right now. So if you think you have a fixed mindset, right now is the time to open up your mind and think of yourself as someone who's got a growth mindset, because it's a great time to make changes in your life.

One of the amazing things when we were reading out, talking about your biography, Alyssa, at the start is you involved in so many things. And it's a bit daunting for people like us who live quiet, mundane lives. But how do you manage all that portfolio of activities? Because I think we're all juggling, juggling things, but you're juggling an incredible range of activities. How do you manage to do that?

You know, I always wanted an interesting life, and so I really made it my business to get involved with a lot of things that were going to give me an interesting life. And the way I handle all of it is to recognize that there are times where I've got to be solely focused on this thing. And not those things or this thing and not those things. And so I find the ways to, like, balance.