Part 1 of 2: Alisa Cohn: From Start-Up Coach To Grown-Up Super Hero

This is Alyssa Cohn. I'm an executive coach and I'm the author of From Startup to Grownup and I am going to be on the Dove Barron show and I'm so excited about this because Dov is a deep thinker and an incredible, curious, questioning mind and we had such a fantastic conversation and you're going to want to listen in.

Welcome. Unless you are a full blown narcissist, there's a pretty good chance you've had some doubts about yourself from time to time head maybe even to the degree that you felt like an imposter. You should know that imposter syndrome appears in as many as 72% of all people in leadership positions and it's actually even higher in women executives. But could there be an advantage to struggling with imposter syndrome? So we're about to discover over the next two episodes with the world's number one coach for startups, Alyssa Cohen. Welcome to the Dolph Baron Show. Join the movement of deeply curious learners by hitting the subscribe button now. The Do Varin show is not just another podcast. It's your passport to unparalleled insights. Each episode is filled with wisdom of global leaders, scientists, entertainers, philosophers, theologians and journalists. From astronauts who have traveled the vastness of space to presidential candidates trying to make sense of a world on the brink, we dive into the most intriguing minds. For the next two episodes, our guest is insights are going to captivate and inspire you. Simply hit the subscribe button and become part of the global community. Alyssa Cohn is a force of nature. Not only has she been named the number one startup coach in the world, she also wrote a book on startups titled From Startup to Grown Up. Alyssa was named as the top startup coach in the world at the Thinkers50, which is Marshall Goldsmith Global Coach Awards and ranked globally as the number one startup coach by Global Gurus. For the past three years she is a sought after speaker. She's been named as one of the top 100 leadership speakers by Inc. She has keynoted events for IBM, PwC, Dell and Citi. She is an experienced and executive coach for Runway Incubator at Cornell's New York City campus. She is a regular contributor to Harvard Business Review, Forbes and Inc. She's been featured as an expert on the BBC World News and the New York Times as well as the Wall Street Journal. She's an angel investor and a Broadway investor. Ladies and gentlemen, put your hands together. Turn up the volume. Help me to welcome the powerhouse of startups and a woman who can probably Deadlift you, Alyssa, call.

Well, I don't know what to say, Dov. That was a pretty nice introduction. Thank you. So happy to be here. Thanks for referencing my deadlifting.

Your deadlifting. We'll get into that. I promise you. As somebody who's spent a lot of years in that world, I will definitely go down that road with you. So where I want to start today is I said in the intro, imposter syndrome. I think in many ways it's stronger than ever. Because when I certainly started in the workforce, we were asked, what do you want to do? That was a 40 year career question. 20 to 40 year career question. People now saying careers for an average of about four years. It's very easy to feel like an imposter while you're climbing up through the ladder. And so what I want to ask you, because you're not a millennial and you're younger than me, so what is the one thing that you did for a long time that made you feel like an imposter? And how did you break it?

Oh, my goodness. Well, let me count the ways. I became a coach when I was still in my late 20s. So certainly I felt like an imposter, quote unquote, when I was an executive coach in my late twenties. Now the only thing I can say is that I did have executive roles. I'd been the CFO of a startup and the head of the strategy of another startup. Because with startups, you can take on those roles quickly at a young age. Even there, I felt like an imposter. Certainly, I would say when I started my own podcast, From Startup to Grown up, based on my book, From Startup to Ground up, all of those things around, putting myself out there as a public figure or like a guru of sorts, those brought up actually kicked up the dust, let's say, of imposter syndrome for me as well.

So from a psychological point of view, because that's where I always go, who are you holding on to that you were. That didn't match this role that you're in? Because often it's not whether we're capable or not capable. It is a counter identity. Do you have a sense of who that was for you or what it was you were holding onto?

Yeah, that's a great question. We're going to get along just fine. Because I'm also very psychologically minded. Just like that. And listen, honestly, I was grew up in a small town. I was. I had this image of myself as like a little girl from a small town. And it took a lot to unearth that kind of self image, to now see myself as like on the playing field, helping people, a powerhouse in my own right. It just took a while to disengage with that voice in my head, which was, I'm a little girl from a small town. And I think part of the way to do that for all of us, I always think about change is inside out and outside in. So inside out is to your point, you have to tap into what am I telling myself, what is holding me back, what's going on inside of me that's telling me I can't do it and deal with that, heal that, resolve that, talk about that, really handle that. And then equally outside in, feel the fear and do it anyway. Try, get yourself out there, try again, debrief with yourself, see how it went, do it more. And those are the things that convince you that it's safe to have confidence because you can perform in those things that are sort of scaring you.

You said you had to confront that part. How did you directly confront that with yourself? Because that incessant itty bitty committee inside of your own coconut saying you're just a small town girl and you don't know what you're doing and blah, blah, blah, it can get pretty loud and pretty repetitive while you're sitting in front of some executive that you're trying to coach.

Yeah, 100%. So, first of all, I don't think I did it all by myself. I had a wonderful therapist who really helped me with that. And I think everyone should find help from therapists, from coaches, from other guides that can help you handle your own inner life. You can't see the label when you're in the jar. Yeah. And so all of us see that outside perspective. But the second thing is that I am very well attuned to my own personal reflection. I happen to be excellent at being willing and able to confront my inner demons, to confront my inner voices, to get quiet and really tune into what is that voice really going on inside of me? Who is that voice? Where does it come from? And just doing the deep work and reflection and feeling upset about it and crying about it and getting upset about it, journaling about it, but being prepared to accept that that was my inner voice or what you say, the itty bitty committee. And then helping when you can rise up and surface those voices and be clear about them, especially when you can put them in writing, because then it becomes very concrete, you're able to then put them to the side and then do the thing you want to go do. And I think that is the key. And it doesn't just happen. It's not one and done. It's a repeated basis of really coming to terms with your demons, your inklings, your critical voices, and then figuring out how to put them to the side so you can do the important things. And as I said, though, when you keep doing that over and over, it gets you in the habit. You build a new muscle of being able to do that, and it proves to yourself that you are the kind of person who can take on those challenges.

So you and I both work in the space of working with these very high level, powerful individuals who have needed a certain amount of ego to get to those positions. And that same ego that allowed them to elevate is the same ego that stops them from getting help. Oftentimes there's leaders listening right now who maybe can recognize that they're running the imposter syndrome stuff in their coconut. But at the same time, there's a difficulty with how do I get over my ego and ask for help? I know how they come to me. You know how they come to you. But what would you say directly to that person who knows it's there, but is terrified, quite literally terrified of confronting that voice out in the world with someone like you or me?

Yeah, I think that being terrified is different from having ego. Right. So being right. So if you're terrified to confront that voice, I think that's a good moment to confront. What are you terrified about? You're just a human being, welcome to the human race. And I think the question you might want to ask you and do journaling about, maybe talk to a trusted therapist or colleague or friend, if you can, is, what am I so afraid of if I let that out? So that's kind of the thing. One, if you're terrified, you've got to come to kind of terms with that terror is. But the second part is ego. And for that I would say it is very simple. When you become world class, when you become an Olympian in a sport, you get more coaches, not fewer coaches. When you become an Olympian, when you become world class in a sport, you have all these people around you helping you with training, with recovery, with fitness, with meal prep. And so I think the same is true. If you want to be a world class executive, you need to have world class support and partners around you that to help you achieve your potential to be that world class.

I couldn't agree more. I often will say to clients, when Tiger woods was at the Top of his game. How many coaches did he have? And people go, one or two. And I'm like, he had five. He had five regular coaches. And people like, really? And I'm like, yeah. And who was the best golfer in the world at that time? Was it his coaches or him? It was him because he had the five coaches. And then I asked this question, how many coaches did he have for relationship? And they go, I don't know. And I go, zero. And he's divorced. He screwed around and he's Mrs. And he's divorced. So there's a great example of why you need great coaches to be world class and why if you don't have them, you're going in the wrong direction. Because most of those people who are at that high level say, I don't need it. And I think that that's a lot of what I've heard in your messaging is like, you've got to recognize that the only way to stay on top is to embrace that. For me, what I find interesting about your work is you work in the startup space. We talk a lot about niches and everybody's going to find their niche. And you've got this very weird niche as far as I'm concerned. I don't mean that disrespectfully, but you're the number one, the world's number one startup coach. Talk to us about that space particularly.

I had lunch with a colleague a few years ago and he weirdly didn't really know that I was indeed the top coach in startups in the world. So he was confiding in me. I've just started working with startups. I said, it's certainly a kind of place. And he said, alyssa, if you're going to get involved, you need to know it's the wild west. I was like, yes, Steve, I actually know that already. I kind of been working in startups for about 20 years. But it is, it's the wild west in the sense that things change all the time. You got all these personalities. Founders are a certain breed, they're amazing. And also they are unreasonable. They have to be unreasonable, otherwise they would not start a company. So that is it. You have people who are used to no structure, very loose kind of boundaries. Founders tend to hire their friends. And so an early stage company is quite chaotic and exciting and everyone's doing everything as the company, either rapidly or slowly, rapidly or slowly, one or the other grows into this, let's say middle stage, sort of the teenager of a company. The truth is that you Bring people in who bring more structure. And they're like wondering what's going on around here. This place is chaotic. Meanwhile, the early employees are still around wondering, who are all these big corporate guys? Who are these guys from IBM coming in with their suits and imposing structure? You can no longer meet in the same room. People have expecting to have a say in everything that's going on. They no longer have a say. And so all of that sort of in a petri dish, along with tough macroeconomics and the high stakes involved and losing customers, a really big deal, it becomes very intense. I would call it an extreme work environment.

So I always say, people beginning of a startup is everybody's juggling hats. You're wearing 20 hats and you're just juggling who's going to throw which hat on. And oftentimes what kills a startup is they bring in those structured people too early who now structure things and everybody's creativity gets crushed. Do you have to deal with that sort of on the shoulder between those two worlds?

Oh, yeah, all the time. Because I work with startups at all stages and sometimes they hit a stage and they kind of even go backwards. If you sort of think about in a progression. Your point is exactly right. When you as a startup bring in executives who are too quick to add process and too quick to scale, in addition to squashing creativity and also being maybe just a little bit too authoritarian, you may have missed the fact that, for example, we think that we have product market fit, which means we think that this is the right product for the market, and now we are scaling that product. Except that, oops, once we scale, we've realized we didn't really have product market fit. We need to go back to the drawing board in terms of being more creative, understanding our customers better. But you've got a whole bunch of process people who are not really attuned to stopping the process and adapting very quickly to what they're seeing is market signals. So that's kind of some of the complexity of it. The other thing is that you grow rapidly. You've got all these different kinds of people who need different kinds of leadership inside of the company. And very often startups do not invest in building managers and leaders. So you've got a whole bunch of people who are not being led. They're going off in a whole bunch of different directions and it slows things down because it's like you got the best rowers in the world, but they're. If they're not rowing in the same direction, the boat is going round and round in circles.

I know you did a TED Talk around conflict avoidance and how to deal with that, et cetera.

Yeah.

What you're speaking about really is quite literally a petri dish for exactly that. Because on one side is these fast moving, high creative hat jugglers and on the other side these people who are trying to get the structure in place to move things along incrementally and to look at how do we structure the funnel, et cetera. Can you talk to us about bringing those two groups of people together and how you have navigated that very turbulent water?

For me, it's all about real talk, which is one of my religions. Right. What I like to do is convene a group of executives and say what's going on around here. And very often I will get input from the employees about what's working about the company and what's not working about the company and what suggestions they have to make this company better. And then we all look at it together. It's a close system. We all, the executive team look and see what are people saying and what do they need differently. And so you can be the kind of person dove that thinks like we need structure around here, but if what the company is crying out for is adaptability or even actually more management leadership has nothing to do with structure, then even you who thinks that's your point of view cannot deny that something different is needed. The same is true. I worked in this company one time and one of the employees just said to me, oh, that's big company stuff, I can't stand it. Meanwhile, it was a hundred person company. I mean, I don't know what he would have done if he'd gone out to work at IBM. However, my point was this is what the people are telling you. We did a whole survey, we found out what's working and not working. What people are telling you is that they are dying for more structure and more consistency. I understand that you don't like that, that you're not attuned that way. However, think about other people around you and recognize that you're not the only one here. And so kind of melding those together in a fact based, data based way is the way to start that conversation. Also, at the end of the day, everyone can self select. That's why a lot of early employees of startups end up leaving. They don't enjoy the structured approach. They don't enjoy what it requires of you to grow into an employee who would operate in a different way in a different company.

And that's also true at the person who is responsible for the startup because oftentimes they're masterful at creating this amazing thing out of nothing, but it strangles them to do the structure piece. And this is why on the other side of it, there are a lot of people who are very brilliantly structured and they can put all things together and they can never get an idea off the ground because they need that other side. And it seems like what you do is negotiate these two worlds. Is that a fair input or is it different?

I like that word, negotiate these two elements. And also a founder is a founder because he or she is willing to take the bet on themselves to build this thing, even though it seems improbable. And we all know the data that most startups fail. So they have to be a certain kind of person. As the company matures, the founder has to decide and really look at the mirror and decide, am I interested and willing and able to learn the management skills, the budgeting skills, the structure skills, the leadership skills, the people skills to grow into the CEO of a large public company? So we know many examples of founders who have done that. Mark Zuckerberg, Jeff Bezos, obviously Steve Jobs. Right. I was thinking Daniel Elk, the CEO of Spotify. These founders have decided that they're wanting to invest in that time and energy, but that's not for everybody. If you're a founder, you're not necessarily a great leader. I spoke to a founder just a year ago who told me this is my fourth startup and I finally realized that I am a zero to 50,000 guy. Like that's kind of what I want to do. I just want to do the initial stages until we get to revenue and then I'm out. I don't want to do it anymore. And I think that self knowledge is so important for everybody when they embark on this journey for sure.

That really brings me to what I think is the most interesting point is I think that you can have all the knowledge in the world about your subject and about your product and about even the industry. But I, in my experience, and I've been doing this for 30 odd years, have never met a leader who can really make it without self knowledge. There's these categories you've just put forward which is that I am the guy who does the startup, I am the big thinker about the vision and all this kind of stuff. Then there's a leader, different structure again, and then there's the leader who has deep self knowledge, which is a different category again. And I think if you want to stay in one of the places that is, you're a founder, you got the great ideas, great. If you want to be a leader who is kind of what I would call an elevated manager, fine. But if you really want to go to a place that is going to be profound, then there's a need for self knowledge. Do you bang up against that? Do you find that there are people? Because I know in jobs there are people who think they are something and then they actually discover there's something else. You find out that in this level too when you are coaching.

Well, certainly I think that there's this mystery and maybe a mindset that when you start a company, you have to be able to take it all the way through and then past ipo and that's going to be success. And so it takes them a while to get away from that myth of that's the way it's supposed to be and that's what success looks like. That's first of all, second of all, you can think that all you want, but in year five of the grind, or year seven of the grind, or year 11 of the grind, it is challenging to constantly playing different from type, to not want to do this. There's so many ups and downs of founders and startups, their mood swings. It's very challenging. And so at some point it might just be, I don't want to run this big company. That's just not what I wanted to do. And that is totally fine. I worked with a founder once who got to the end of his realization that this is not making me happy and hasn't made me happy for years. And so the work we did together was to help him really come to terms with that, to set a finish line for himself. So what's a finish line? A finish line is these conditions have to be met and then I will be able to gracefully step aside and be chief evangelist or chief product guy or whatever it is, because I'll be able to install a CEO, will be able to take it from here. And that was the work that we did. But it is painful to come to that realization. And by the time they've come to that realization, they've usually been pretty upset without even realizing it for years.

What you said that I think is profoundly important to and we set these goals and we say, okay, I'm going to achieve this or I'm going to get to a million dollars, I'm going to get to $10 billion or whatever it is. And I think that oftentimes we don't build in the recognition of when it's time to walk away. I talk about this even in thinking about it in a private, personal level where I say to people, here's my philosophy around marriage. And they go, what? And I said, you should only divorce somebody you love. And they go, what do you mean? And I go, if you wait till you hate each other, that's such a tragedy, because you did love each other at some point. You should only walk away when you love each other and you realize we're not going to the same place. And as a CEO or as a founder, it's the same thing. Walk away when you love. But you've got to know this is no longer going in the direction that's aligned with my heart, my soul, my vision of me in this position. It doesn't mean I want to kill the company, because I think a lot of times those founders kill their own company because it's not doing what they think it should be doing, as opposed to saying, I've outgrown it or it's outgrown me and I love you enough to let you go onto this new CEO and I'm going to have a radically loving divorce from the situation and let you find another partner.

Yeah. Well, that's very romantic, Dove, the way you frame all that, I think that's the truth. And I think that you are presupposing a lot of self awareness. And I think the truth is that people mostly find their limits by pushing past them.

I fully agree. And that's why I said I think that self awareness is key. And so to sort of look back to where we started at the beginning, you came into being an executive coach very young, and as you said, with not a lot of background and experience and all the rest of those things. So talk to us about your self awareness. I know you said you did therapy and you had coaches and all the rest of it, but that self awareness process, while you're in the water, if you will, talk to us a little bit about that and what made you realize, I gotta get some. I really gotta get some help.

So many things to say. First of all, I have always been a seeker. Even as a kid, I was always a seeker. I was always interested in the world around me. And I was always also someone that people came to for advice and counsel for whatever reason. I remember when I was like in sixth grade, I was sitting there in homeroom, we were doing some play, and for whatever reason, all the kids came over to me and said, alyssa, Can I be this part? Can I be that part? Can I be this part? And I'm thinking, why are they asking me? So I had a little sort of something inside of me and I think that also came to the fore when I met a coach. So I'd done a few things. I was in the nonprofit world, I was a manager at a very young age. As I said, I was in the startup world. And I was also at Price Warnerhouse Coopers. I was a strategy consultant and I'm also a cpa. For my sins. I'm a recovering cpa. Yeah, not a lot of self awareness maybe for that. But I got into this so called accelerator development program or whatnot. I went to this conference and I was volunteering at the conference and they said, okay, now this coach is going to speak at the conference and they were going to speak to the volunteers and I thought, all right, can I leave? Do I have to stay for this? And then she gets up to the show, gets up to the podium, she starts speaking and I thought, ah, what is that? I want to do that. And it was like violins played. I just knew that is me. And then I followed her around the conference and I saw her in this large room in front of 500 people. She said, who wants to stand up right now and get live coached? I thought what's going to happen? And someone stood up and she got live coach for 20 minutes. And I thought, oh, I could never do that. But at the very same time I thought I could do that. And for whatever reason I saw myself in that. So I had my path, I had my path right there. And then the rest is kind of details. I got my own coach, then I got another coach. I had been in therapy, I did landmark education, which I really thought was fantastic for me, to help me uncover the difference between facts on the ground versus the stories in my head. Also to really help me understand interpersonal dynamics and, and then I put one foot in front of the other. So I think it was the sort of understanding that I want to do this. Having normal and natural resistance come up and being able to, having the wherewithal to navigate around that. When I was at one of the startups, the CEO at one point later on, years later said to me about the head of sales of the startup, his name was Danny and he was from the UK and he had never gone to college. And Jim said to me, Danny is different from us. He never went to college. He had no expectations for his life. Whatever he's got to do is like Gravy. He can't believe his luck. You and me, we went to great schools. We have a weight and a pressure on us to achieve and succeed. So of course we are going to feel the weight of that. We're going to feel uncomfortable, nervous about the pressure of what we're going to do with our lives because it feels like the stakes are high. And I thought that was really wise. And then you have to unlearn that pressure, right? You have to sort of spend your life unlearning the pressure that society puts on you so you can learn instead what your own inner voice says.

We talked a lot about self awareness even in this first half, but do you think people even have that self awareness that they're living under pressure that was given to them societally and never even question that that's not their own voice, that itty bitty committee inside of the coconut. They actually think that that's them talking to them as opposed to the social conditioning or the familial conditioning.

This is really the human struggle, right? I mean, some people probably do and some people don't. Joseph Campbell, the philosopher, he said if you can see your path all the way through to the end, you are following someone else's path. What I think is so important about that is he only commented on the human condition because it's the human condition of seeing your path all the way through to the end. As we say in the career world, having your ladder, climbing the career ladder only to find it was lined up against the wrong wall. And so I think all of us have less or more of that social conditioning and social pressures. But all of us have the mandate to discover and then ultimately invent our own path.

I think that's beautifully said. And I will push a little further and say, because I'm a huge Joseph Campbell fan too. And that is, the treasure you seek can only be found in the cave you fear to enter. It's stepping into that darkness. But when you step into that darkness, your eyes will adjust not so that you can see the end, but so that you can see the next three feet. And as you step into that three feet, three feet more. But there has to be a calling. And I want to talk a little bit more about that with you in the second part about the calling. Because I think that a lot of people call out for a coach because they're stuck and they don't realize that they're stuck. They think they're stuck because they don't have a skill set, but they're stuck because they're not listening to the calling. Is it okay if we go there in the second half of the show?

Yeah, let's do it.

Before we go, please. I'd love for you to tell everybody whether you find out more about you, about your book, about all the services you have, all the wonderful reasons.

Oh, well, thank you so much. Well, come to my website, alyssacon.com, a l I s a c o h n.com scripts where you can download my five scripts to help you with delicate conversations and one to make your life better. You can also go to Amazon or anywhere else to find my book From Startup to Grownup. And my podcast is available on Apple Podcasts, Spotify or anywhere else. It's also called From Startup to Grownup where I interview amazing founders on their own personal journeys. From Startup to Grownup.

Beautiful. Thank you so much. And again, we'll make sure that we post all of those links in the show notes, including social media links where you can find Alyssa and you can check out more of her. And I encourage you to do that. We're going to be back in just one click for more of our delicious conversation with Alyssa Cohn. Just one click. Remember, stay curious, my friends. Stay curious.

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