662: 90.00 Alisa Cohn on her book - From Start-Up to Grown-Up

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Play to Potential Podcast. When you're the CEO, when you're the founder and you're the leader, and then you act out like a normal person when they're hungry and upset and irritated, or the little things that are bothering you, it has an outsized impact on the, on the, on the team as a whole. So you don't have the luxury of kind of giving into your triggers. And the same is true of dopamine hits, right? Something's making you feel great and you're all excited about it. You may make less good decisions. You may have team members who are trying to hold you back. Like, no, let's think about it, let's think it through. But you're not going to listen to them because you're so kind of drunk on your own, you know, like truth, like the truth inside of your head and the feel good euphoria inside of your head. So all of us have to be aware of those things about us. But when you're a leader and you're the founder, you, the things that you do that you react to have an outsized impact on the way you manage the team. That's why it's so important.

Welcome to the 90th conversation at the Play to Potential Podcast. A series of reflective conversations from leading people from various domains on three broad themes, leadership transitions and careers. Just like businesses need to proactively think about where to play and how to win in the context of their business strategy, I feel we all as individuals need to think about the two questions, where to go and how to grow at various points in our lives. And I think these questions become that much harder to navigate in a world of abundance, multiplicity of options and limited feedback. Through this podcast, I hope to share some insights and provocations that might help you navigate these questions in a more thoughtful way. If you're a regular at the podcast, you might have noticed that our frequency has come down a little bit these days. We are working on the next version of the website to hopefully improve your experience with the podcast. So we urge you to be a little patient. As we approach 100 conversations. We are taking a fresh look at what we're doing and trying to incorporate some of the things we've learned from the listeners over the years. When I'm not podcasting. I'm working with leaders and organizations with a growth mindset and helping them play to their unique potential. You can learn more about the podcast and my advisory work at www.playtopotential.com. that's P L-Y T O P-T-E-N-T-I-A L.com My guest this time is Aliza Cohn, an executive coach based in New York. She works with startup founders and helps them mature into world class CEOs as the companies scale up. She's recently authored the book From Startup to Grown Up Grow youw Leadership to Grow youw Business. I do a little bit of work with some of the founders and the startups in India and over the last few years several billion dollars of investments have flown into the Indian startup ecosystem. The way I look at it, that's the equivalent of a 15 year old who just learned to ride a bicycle suddenly being asked to ride an aeroplane while learning to fly midair. Just picture that scene for a moment. The founder experience is really not that different from this one. While the primary audience for the book and this conversation is founders and leaders in the startup ecosystem, I feel some of the principles Aliza speaks about, like giving away your Legos, policing your passions, are relevant for any leader or working professional. Without further ado, let's listen and learn from Aliza Cohn. Alyssa, thanks so much for your time on the Play to Potential podcast. Excited to be talking to you.

I'm so excited to be here. Thank you for having me.

Lovely. I'd love to dive into your book that you've published recently, Startup to Grown Up. But before that, in this podcast I'm curious about people's journeys and their choices. You have an MBA from Cornell and your early years of your professional life in PwC. I started out in KPMG as a matter of random trivia. I'd love to know how you got to what you do now and what were some of the key transitions and choices along the way.

Well, thank you for asking that. I mean there were a lot of transitions along the way and a lot of sort of like, you know, rolling around in the wilderness a little bit about what I wanted to do, but I went off to business school because I I had been working as the chief of staff to the provost at a nor at a Northeast college and we were doing strategic planning and at some point the provost said you can't manage faculty because they have tenure. And I thought it can't be that people will only do what you want them to do because otherwise you'll fire them. Can't be. So I went out to business school thinking about that. I got all turned around in business school, and I ended up focusing on finance and accounting and strategy and exited and PricewaterhouseCoopers. And I was on the fast track to partner, and I thought my life was all set. And after about two years in, I woke up one day and thought, I hope I get the flu so I don't have to go to work tomorrow. And eight. I know, right? That's intense. Like, you had some big marker. So 18 hours later, I was rushed to the emergency room, and I had the flu because I have a strong mind. And I thought, this is not it. Like, this cannot be it. So I was, like, down for the count for two weeks, and I was. My fever would go up every time I thought I'd go back to work, and I just thought, this cannot be. So then to figure out, what is it? And I did a whole bunch of seeking. And then I met a CO at a coach at a conference, and I was like, what is that? That is it. Like, violence played. So from there, it was just details. I joined the startup world. I took coach training, I coached all my friends for free. And, you know, by the time the startup world back in those days kind of imploded. So I was the CFO of one startup and the head of strategy of another startup, and that all imploded in the year, you know, 2000, 2001. And I thought, okay, I'll become a coach now. And that's how I did it. And I put one foot in front of the other from there on. And that was 20 years ago.

Wow. Wow. And cut to today. Alyssa, could you talk a little bit about the why behind the book startup to grown up, and maybe a little bit of the nature of the data behind the insights in the book.

Yeah. So I wanted to write a book because I would walk into every, you know, sort of situation, all the startups I would walk into, and I would say, how often do you meet with your leadership team? And they would say, what's a leadership team? And I realized, like, so many questions I would ask, and I saw that, like, isn't anyone teaching you this? Like, don't, like. And I realized, well, nobody teaches you this. So I thought, I wish. I wish I had a book that I could hand them. And then I realized I could write that book. And I was very inspired to write that book because I knew it'd be meaningful to people. And by the Way. I literally, an hour ago, got an email from a client of mine highlighting a section in the book and saying, that's me. And I was so gratified that people can really, you know, see themselves in my book and. And. And you and. And take it and use it. And so I would say data in the book is really from my own experiences with founders. And then I also spoke to 14 founders in the book. Sorry for the book. And I asked them questions about their journeys and whatnot. And that was also super fun and super validating, and to realize that they had the same kind of thoughts and insights as I had gained from 20 years of being a coach inside this kind of environments.

Hmm. Diving into the book, Alyssa, you know, you talk about leaders to reflect on strengths, development areas, triggers, and dopamine hits. And what I found interesting was we often talk about strengths and development areas, but the notion of triggers and dopamine hits was interesting. Can you talk a little bit about what you mean by the terms and why. Why it's important for leaders to reflect on those two as well?

Well, it's so important because basically, the triggers are the things that drive you crazy, your pet peeves, the thing that's kind of set you off. So the problem is that I'll give you an example. One of this is a long time ago. One of the founders I worked with was getting really irritated by one of his employees. And like, you know, the employee was just like a normal employee, some good, some bad, but he was getting really irritated. And I. I sort of said, why are you so particularly irritated with this person? And to his credit, he really thought about it. And he said, because whenever I walk into his office, his lights are off. And I'm like, why don't you turn your lights on? I just thought, wow, that's quite a. That's quite a strange thing. And, you know, we went into a whole deep discussion about that, why that bothered him so much. I think it was like this, why are you in a cave? And I helped him see, actually, the guy wasn't in a cave, right. But the guy didn't, like, turn the lights on. Like, what is the big deal? And that was a trigger. And it actually caused him, this founder, to avoid this employee, to not take his input in very well, you know, as. As much as he would not value. As much as he would value other people's. And it's the silliest thing in the world, and yet it had meaningful impact on the way he ran the team. If you think of your own Triggers, you have little pet peeves like that. You have little things that, that set you off. Also when you get hungry, you might be a little irritated. And then when you're the CEO, when you're the founder and you're the leader, and then you act out like a normal person when they're hungry and upset and irritated with the little things that are bothering you. It has an outsized impact on the, on the, on the team as a whole. So you don't have the luxury of kind of giving into your triggers. And the same is true of dopamine hits, right? So they make you feel great and you're all excited about it. You may make less good decisions. You may have team members who are trying to hold you back. Like, no, let's think about it, let's think it through. But you're not going to listen to them because you're so kind of drunk on your own, you know, like truth, like the truth inside of your head and the feel good euphoria inside of your head. So all of us have to be aware of those things about us. But when you're a leader and you're the founder, you, the things that you do that you react to have an outsized impact on the way you manage the team. That's why it's so important.

And on the dopamine hits, Alyssa, would you have an example to bring it to life? What sorts of things should leaders reflect on?

So one good example is this is a normal thing that happens. But there's a founder I particularly work with who when there's a new person, they always feel like, oh, this person's gonna save us and this person can do no wrong. And oh, this person is so, you know, terrific. And everybody around this founder is like, oh, here we go again. But it's an example of how the sort of shiny new is the thing that kind of turns this founder on. And the problem is that, you know, again, he's, he would be sort of over privileging the new person's input, thinking we need to do it, we need to do it that way, the way the person says. And also not giving credit to the incredible, like the hard work and the difficult work that everybody's been doing to date. So that's an example of how a dopamine hit, you know, sort of a thing that you are not aware of that makes you happy but still again, affects negatively you're the way you manage the team, basically. You know, Deepak, it's, it really has to do with this. It's being impulsive. The things that cause you to be impulsive, to react instead of. To have a reaction, instead of choosing a response. Those are the things you have to be more mindful of as any leader, but certainly as a founder, and therefore you can counteract those things as you need to.

Moving on, the other term that really caught my attention was this notion of giving away your Legos. You talk about the term used by First Round Capital in one of their articles, and you say that when companies scale up, you said that there's a point where you need to give away something that you're really passionate about in pursuit of scale. Can you talk a little bit about how founders manage this dichotomy and how they keep their mojo as they move away from things that give them joy?

Yeah. It is so difficult. You know, founders start their company to build their thing, whatever that is, and they're excited about the thing they're building, but then over time, they're like, less and less close to the building of the thing and much closer to and need to be focused on the building of the company. So founders, I'm just thinking, like, there's two or three founders in particular I'm thinking of right now who, you know, they get into the. To the. They get into the startup and they start the sort of to disrupt an industry. And someone I just got off a call with just this afternoon, he's very excited about all the success. They're. They're completely overachieving their success. They're like a series D startup, not, you know, really growing up, overachieving, and that's fantastic. But over the past few years, this founder has been focused on being an external voice for the company, fundraising when necessary, attracting new executives that they need to be successful, and really has very little to do with the product itself or the thing they're building itself. And it continues to be a source of grief for him, like, as in, that's why, you know, like, that's what he wanted to do. And so the company is succeeding and the company is going to achieve his vision. However, his hands are no longer kind of involved. And it's very difficult for people to realize that they have to give away their Legos and then to actually give away their Legos. You know, I spoke to Dennis Crowley, the founder and former CEO of Foursquare, and what he told me in my book was, which I put in my book was, you know, first you give away the things you don't like. So he gave away operations, and that was okay. He didn't really care about the legal stuff. He didn't want to really budget or learn to make payroll. That wasn't his thing. And then you have to give away the other things like sales and like having no connection anymore to kind of the engineering. And then you have to give away product. And that was his baby. And there's like really sad that he had to give away product to somebody else. But that's the Legos you have to give away over time. Now I would say on the bright side of that, for, especially for employees who come in into high growth situations, they get to give away their Lego. They don't have to give way there. They get to. Right. You earn the right. When you come into a company and you're not the founder yourself, you, your job is to be constantly hiring new people to do the things that you were going to do and then you get to move on to more strategic stuff or more, you know, high level stuff and managing more people. And it's a, it's a good, you know, it's good for the company and good for you. But you as an employee often have to sort of have faith that there'll be something there for you on the other side of that.

Hmm. But with the founders that do this, well, any, any insights around how they, like you spoke about this founder who had to give away product eventually. What have you learned about how they, how they do this effectively? Any, any thoughts there?

Yeah, a lot of thoughts. So first of all, it's accepting that that's part of the process. That's like definitely, number one. Number two is getting real alignment from the executive team of what we're trying to do here, because even if you don't have your hands in it, you want to feel the satisfaction that it's working. So being clear with your executives, your employees, what we're building, how we're building it, the specific, clear goals to get them on the same page. And the third is especially hiring people who you know are aligned with your vision and your values so that you will be able to enjoy the fruit of their, of their work and not have to constantly correct them. Because when you have confidence that they're going to do a good job, you're going to be more likely to be comfortable giving away your Legos and less likely to regret that you gave anything up because you know that they're handling it without you.

This is your host, Deepak Jayaraman. Here. Three things occurred to me here. Firstly, at a personal level, I can so relate to this point. About not wanting to give away your Legos. In my instance, people have often suggested that I should think of scaling up the podcast as a platform and maybe get other interviewers on board or scale up the advisory practice by getting more partners in, but somehow I find myself resisting it. One of my friends told me a few years back when I took the entrepreneurial plunge, that I have more of an artisanal mindset and somehow I feel this captures who I am. I derive great energy from doing small things, but going deep, having deep, purposeful one on one conversations with people. And I've tried to anchor my life around these two to lead a life which gives me flexibility to prioritize what's really important at that particular passage of play while trying to spend most of my time enjoying what I do. However, a part of me also wonders if I've developed a block here and I'm not being open to possibilities, but that's the call I've taken for now. Secondly, my observations from my conversations with founders is that a lot of them have a very strong why, and they use the why as a prioritization mechanism to focus on what might be less energizing and boring but still critical for the business for them to do in pursuit of the vision and purpose. Without that anchor, it can often be very hard for founders to give up their Legos, as Alisa says. Thirdly, I feel this is where the complementarity of the founding team or the leadership team that comes in. I was speaking with Sanjeev Agarwal and Tnhari, authors of the book From Pony to Unicorn. They talk about the three themes that a startup should think about, Growth, efficiency and foundation. They go on to say that growth often comes naturally to the founder, but the other two don't. So can they get together with somebody who can bring in that mindset?

Yes.

Actually one very simple way to think about this is that I will simplify it further to say that there is one role of growth and other role of say efficiency and foundation. Or you can say there is a role of vision and forward looking and then there is a role of minding the store day in and day out. And in our book we talk about this rhythm of Brahma and Vishnu that entrepreneurs are very good at envisioning the future and if they can surround themselves with a Vishnu who excels in day to day execution, then magic happens. And you know, if you look at all great entrepreneurs in the country, like Mukesh Ambani for example, he has Mr. Modi who plays that role of getting it done. Or if you have Sanjeev Big Chandani at Naukri, he has Hitesh Oberoi as his ally in making sure that there is world class execution. So founders can think of themselves as more the visionaries because that is a very intrinsic capability that is hard to inculcate and then surround themselves with an execution person. So a CEO co combination can do wonders to discipline growth.

As a leadership team. Do you bring in these complementarities not just in terms of functional portfolio you run, but in terms of the orientation you bring, whether it's growth efficiency or foundation? It's a question worth asking. Thank you for listening. If you're seeking value from the podcast, do take a moment to rate and review the show on Spotify, Apple or wherever you consume this content. Let's now get back to the conversation with Alyssa Cohn. A related point you make, Alyssa, is the sort of the fine line between being passionate about something and turning into a bully. Right. In one of the sections of the book you talk about founders policing the passions and you go on to say that if you don't, there's a risk that the passion could turn you into a bully. Can you talk a little bit about this phenomenon?

Yeah. You know, founders are a different breed. And so founders get into a company and it's first of all, it's their baby. And many founders call their startups their baby. And also most founders have a strong identification with their company, which makes complete sense. So this is their baby and they want it to go faster than it's going to. They want their employees to get it done quicker than they're getting it done. And part of why they built it is they're passionate and also they're self motivated, very self motivated and often have a very strong internal drive and can often be highly self critical. So if you're not self back to self awareness, if you're not self aware of all that, what happens is that you may leak all over the employees, you know, sort of let out your self criticism into criticism of them. You will, you know, be overly eager and overly anxious, I would even say to have everything go faster. And then you really push your employees past the point where they're comfortable and it's not their baby. They can be really primally excited about this company, they can be super loyal, but it's not their baby. And you have to be aware of that. Again, reflective and self aware and self and self reflective to realize that there's times to push and there's times to let it, you know, Sort of be, be more patient, but always you don't want your passion to turn into pushing people too, too much, too hard.

And another theme you talk about in the book is this notion of imposter syndrome. Alyssa?

Yes.

You know, you go on to say that entrepreneurs are dealing with this all the time. They are the cutting edge of something. They're flexing muscles that they haven't built over the years, and they're probably trying to open doors that are much bigger than them at every step. What's been your observation about how this plays out and what you've seen some of the founders do to cope with this effectively?

This plays out all the time. I literally just this week had a call with a founder and the imposter syndrome for him came out because his board would tell him, oh, you're doing good, but you should double that. You know, projection. And in his mind he's thinking, I don't know if we can double it. And also, why are you telling me that I must not be a good. Maybe all your other founders are like just naturally doubling it or tripling it, and maybe I'm the only one who's not doing it. And also, it's just really hard when it's especially early days when it's not working, but even as it gets bigger, you've never done it before. It's just really hard. And founders often don't have anyone to talk to, and so they're just sitting with their own doubt. You can't ask your board, well, wait a minute, do all your other companies just triple it without, you know, even like any trouble at all? Like, am I the only one? And it's really hard to ask those kinds of questions. So you feel all alone. That's just one of many examples. You know, another example is that, and I talk about this in the book, there's one of the founders I worked with, he, he was great at raising money, but when it comes to closing executives, he just couldn't close executives. And I, and I just kept asking him, like, what's going on? And we finally had a heart to heart discussion about it. And he said, you know, I don't mind taking the money from the VCs, that's fine. But if I think about pulling someone away from a secure job that they're doing great at, and then to join my company, what if we don't make it? And he felt like he didn't have it in him to do that. And that was his imposter syndrome. So those are all the ways that imposter syndrome comes out and plays out. They're very tangible, right? It's not just your own internal suffering. They actually cause you to, you know, not hire executives that you need to hire, not hiring them fast enough. So there's many, many ways to handle this. First of all, accepting that you have imposter syndrome, recognizing other people have it as well. And then what I like to prescribe for the founders that I work with is to do a highlight reel. So a highlight reel is where you sit down and you write down five or six successes that you've had, which is amazing, right? Like, because you're amazing. So you've done a bunch of stuff that's really impressive. And especially times you've overcome obstacles and overcome difficult things, and then you remind yourself, I'm actually really capable. It's actually like, I'm good at this. So it also reminds you that you can overcome difficult things when you need to. So when you have that, you can read that every day. It's like a ritual. You can read it every morning and remind yourself, and you could even add to it. And also, when you're about to handle something hard or the imposter syndrome comes up for you, you can pull it out right there and then to have a fighting chance of reminding of yourself of the capabilities you have to counteract the feelings of imposter syndrome.

This is your host, Deepak Jayaraman, here. I love the point that Alyssa makes about the highlights reel. We actually have a full podcast conversation on this topic with Professor Dan Cable of London Business School. He talks about the highlight reel in the context of each one of us seeking feedback from the outside and staying relevant as we go through life. But I guess similar principles apply to founders. They just encounter so many rejections and nos along the way in a day. And it can be a tough job holding your morale up, especially with your troops, who often have limited visibility to your downs. Here's Dan talking about the highlights reel.

And so anyway, over the last 10 years, I feel like I've learned a lot about how surprised people are when they get one of these highlights reels. And basically what that is, it is memories and stories from family, from friends, from colleagues, from mentors. It's people that have watched you over the years, even over the decades, and then they write a story that is their memory of a time. You've did some. You've done something exceptional. That's the name of the book. That's why that book is called Exceptional. It's. There are times when You've had an extraordinary impact. And here's my memory of you doing that. And I just can't tell you, number one, how powerful and emotional that is to read it from other people as opposed to just self reflecting. So that's one thing. I think a second thing I'd put out there is just the vast amount of new insights that you can get, because a lot of things that people remember for 15 years, 20 years, and they write down in a lot of detail you might not even think of.

Is a big deal.

You know, you might think, oh, no, that's just, that's just easy. That's what anybody would do. And if you have seven, eight, nine people writing different stories, but around that same theme, but you yourself just don't think that's a big deal. That highlight reel starts to unveil ways of you becoming exceptional, and I call them high leverage moves. It's just a way that you can do a little more in an area and create a much bigger impact, but you wouldn't, you wouldn't do it because you kind of downplay it. You, you think anybody would do it.

Like Alisa says, not only can highlight reels help pick ourselves up when we're going through a rough spot, they can also often shed insights that can be often in a blind spot that can help us become a better version of ourselves. Let's get back to the conversation with Alyssa Cohn. You know, a related theme you talk about, Alyssa, is, and I like the phrase you use, you say that stress is the child of a startup and depression is the child of stress. Once again, it's probably one of those topics where, you know, the need exists or the phenomenon exists, but it's sort of the elephant in the room that often nobody talks about. Can you talk a little bit about this? And you know what, what Fondo should watch out for and when they should seek help if they're in that zone.

Yes. So there's so much to say about this. I would just say that startups are extreme work environments, and you have to be aware of that when you're getting yourself into it as a founder. The second thing is that founders are 30% more likely than their counterparts to, to experience depression and anxiety in general. You know, I mean, other companies in general. And so that is also just very difficult to be aware of. So when you're going through the experience of the extreme work environment that a startup is, and you're going through all the ups and downs, many founders say to me, I knew there'd be Ups and downs, but I didn't realize that they would be in the, in the span of five minutes or even right on top of each other, which is so true. Then you have to kind of have the wherewithal to handle it. So first of all, you absolutely should have routines that help you. So it might be a mindfulness routine in the morning, might be like funny movies in the morning, it might be meditation, it might be fitness, whatever it is. You definitely have to have also some stress reducing mechanisms like fitness, like hobbies, like friends, to, you know, just make yourself feel good and step away from the work. And, and then you absolutely should have a team around you, maybe a coach like me, maybe a therapist, maybe just a CEO group to help you deal with the inevitable ups and downs so they don't turn into serious cases of depression and anxiety.

Hmm. In the book, you talk about the notion of praise and you actually say you don't. As a CEO, you don't often see the hidden cost of the lack of praise. I like the, the way you phrased it. Can you talk a little bit about the economics of praise, if I may ask you?

The economics of praise, that's very good. So the economics of praise are this. You've got people in your extreme work environment with you, right? You've got them. And you, you know, if you're making progress, you hope you are, but you aren't sure all the time, maybe even going backwards sometimes they don't know if they're making progress. So the way to make sure they know they're making progress is to give them positive attention and give them praise. So praise is simple, like great job facilitating that meeting or oh, you're always on time with your deliverables. Not everybody is, I really appreciate it. Or it might be you're the most strategic person we have on the team. Right. It could be any of that. And that praise helps them see the value of their work. It helps them feel seen, it helps them feel like, you know, it gives them a positive dopamine hit so they can like, you know, continue to work for you even. I'll tell you, this is a personal experience. I was working within a company and doing this very high stakes, off site, you know, sort of team building thing, team team facilitation event. And the CI was telling about what we were going to do, what was going to happen. I was telling the CEO and the CEO turned to me and said, I trust you. And to me that was the most motivating thing ever. And it made me want to do it an even better job. And because I felt super confident going into the thing. And that is a version of praise or positive attention that CEOs and founders very often forget. And then the hidden cost is that people are wondering. To me, the wondering is always the enemy. They're wondering, did he like that meeting? Did he like that presentation? Was my spreadsheet okay? He didn't say anything. I'm not really sure. You know, my book, I talk about this. That I remember vividly this experience I had with an employee named Wilson, an executive who was a great. He was a great executive. And the. You know, I was just talking about something, and out of nowhere he said about the CEO, I mean, I think she likes me. I think everything's okay. I think that she would tell me if there was a problem. And I said, wait, Wilson, she loves you. She thinks you're a creative genius. What are you talking about? And he started getting weepy because it was so meaningful to him that I was the one that gave him the praise from the CEO. And so, you know, I can only imagine the amount of wondering that he was doing, wondering how the CEO felt about him. And so I think that's the hidden. So I just want to say, like, the. The. The benefit of praise is massive. It's motivating. It helps people continue to do their work. It shows them where they should be going. It creates great culture. The. The detriment of not giving prayer. The cost of not giving praise is very high in the sense that people are not quite sure and they're not knowing and they're demotivated and they're asking their spouses at home, I hope everything's going well. They don't know. And also, when you, as a CEO, come and give them negative feedback or. Or they'd get from anybody. Negative feedback, as in, that meeting didn't go well, and you should prepare more or something. Then they're just upset, and there's no counterbalancing positive feedback. So therefore, they have this warped view of what's going on. Like, oh, I'm not very good. I did a terrible job at the meeting because you haven't praised them for, like, a year. So all of that is to say those are. That's the. That's the economics of praise, as you put it. And the actual cost of praise is zero. It's like 20 seconds. It's not even so. It's just such an incredible return on investment. And I don't know why everyone doesn't see it as, like, the Massive superpower.

And if I could build on that. Alyssa, I'm also wondering, given the last year and a bit given Covid, I'm guessing that when people are in remote environments, the wandering is even more right because of their own bubble. So it's even harder to figure out what your boss thinks of who you are. So can you talk a little bit about, is there a nuance to how this plays out in a remote work context?

Well, it just gets more amplified in a remote work context because to your point, they can't. They can't just walk into the boss's office and see how he's doing. They have their own little bubble. If something doesn't go well, they don't get any kind of informal, organic, you know, clarification, but like a smile in the cafeteria or, you know, wherever they're walking out together. Nothing like. Or no sort of coming back in. Just have a quick chat about it. They also don't have a peer sitting next to them to say, oh, that didn't go well, and to commiserate with. So they're just in their own bubble. So it's absolutely amplified during this remote environment, no question. So you have to be even more explicit about praise and explicit even about if you're irritated about something. Explicit about, this is not the biggest deal in the world. Like, I wish you'd done the meeting better. I wish you prepared more, but we didn't kill any babies here. Don't worry. I know that you'll be able to fix it. So you need to also give people a sort of a sense of encouragement, even when you do have to give them difficult feedback, which is a thing that has to happen.

Moving to getting senior leaders on board as you scale up. Alyssa, one of the themes you talk about is when you bring senior people in, the founder needs to spend disproportionate time in transferring context. Can you talk a little bit about what all you have in mind or where all the opportunities lie for a founder to transfer context to an incoming leader?

Well, transferring context is everything. I mean, when an incoming leader comes in, they don't know the norms, they don't know the culture, they don't know where everything is kept. They don't know the history. So you want them to have fresh eyes. That's actually really good. But you want to share with them how we to help. Help them get wins. How do we do things around here? How do we experience a win around here? You want to have them, the CEO and the founder, and maybe also also an Onboarding buddy, somebody else really help them figure out how to get wins quickly, how to orient themselves quickly, how who to pick, who to who to build a relationship with inside of the company immediately where all, what all the history is and what the sensitivities are so that they have, so they understand. Especially in a remote environment. That was to your point earlier. In a remote environment you're like, who are these people? Where is everything? How do I figure out how to get myself onboarded and connected into the community? How do I build the communal relationships around here? When you're the CEO and you invest the time in helping that person that is ma that will reap massive rewards for you.

And any interesting rituals you've come across off the various clients you worked with, any out of the box things that you've seen people do to transfer context?

Well, I think, I mean both transferring context and rituals are two different things, right. I think that for context, I think a ritual might be an end of day coffee or an end of day some of my clients whiskey with this person to see, you know, what have you learned, what questions do you have, that kind of thing. I think rituals overall inside of a company when a new person comes on board would be, let's do a tour, you know, we're all remote now, so let's do a tour of your house, right? Let's do a tour of your work environment or here's a collage of pictures of me of when I, you know, of my kids, of my spouse, of my hobbies or whatever and sort of do collages of each other. Those are lovely rituals. Can you that you can do as a team.

And in a related context, Alisa, you actually use an interesting term. You say that when a senior leader comes on, the founder needs to re onboard himself or herself. You know, you say that you talk about your conversation with Daniel, a Fintech founder in New York and you, you mentioned that when he brought on senior leaders from the outside, there was an opportunity for him to pause and re onboard himself. So can you talk a little bit about this notion of re onboarding?

Yeah, you know, I spoke to, I'm doing now, I'm now doing my own podcast called From Startup to Grown up also. And I interviewed Greg Gallant, who is the founder of Muckrack. He's been the founder and the CEO for 14 years and the company has grown and he made the point. It's really funny that the day one of my company I was called CEO and now 14 years later I'm still called CEO. Right. But it's a very different job. Your job as CEO, as your company scales, changes every very quickly and certainly every, you know, six to eight months and very much every 18 months. And you might need new executives around you, you might need to really orient the way you're doing it, but you're literally your job changes. So if you think about onboarding is coming onto a new role, it's very powerful for you, the CEO, to sort of like walk out and come back in as the new CEO in a way and re onboard yourself and reacquaint yourself with the way you are now, with the way the company is now. By the way, also your old employees who have been with you since day one or since the early days, they see you in some ways also as that same person. So it's very helpful also for you to help them understand how much you've changed, for you to help them understand that you're, you're a different person and the job is different, and that they have to also make those kinds of adjustments for you.

This is your host Deepak Jayaraman, here. Now this is a topic where we do have several resources of the podcast that could help you if you want to know more. I love the point Alisa makes about how founders need to adapt to the evolving context and possibly reorganize onboard themselves as the role evolves. The challenge in a lot of these situations is that when you're dealing with a continuum, it's often hard to bring in discreteness. My previous guest, Dan Pink, speaks about the notion of finding punctuation marks which help us make sense of slow changes in context. Something interesting came up in my conversation with the chess legend Vishy Anand. He speaks about the significance of movement move 40 when you play a timed chess game.

I'll give you one quick example. I would often get to move 40. And move 40 is significant because it's the end of the first time control, which means that you get a fresh amount of time on your clock and normally your time pressure is over. But a lot of people, the movement, the time between moves 32 and 40 is so tense and they are so caught up in it, they are not able to stop. They will make the 41st move anyway. And especially once upon a time, I was very prone to this error. And I was also prone to an error that when I had half an hour, my opponent had three seconds. I would try to play fast so that he wouldn't have any time to think. It doesn't take a lot of intelligence to Stop yourself and see that if you play fast, to not give him any, any time to think, you're not giving yourself any time to think either. So these were two areas where I had problem. And one of the things I did was I would simply make a mental note. I would think of some painful loss I had suffered as a result of these habits. So that when I went to the board, when I was in move 35, my opponent down to three seconds, he's shaking and the temptation is overwhelming. And I have half an hour, I'm in no pressure. I would just tell myself to get up, go to the refreshment area, have a little bit of water or some coffee, and then I'd come back. And I found that this broke the tension. I stopped. I had become too emotionally bound in the game and this broke that. And then I was able to bring some sanity to the process. And especially doing this after move 40, when neither of us is in any tension anymore. But just getting up, going away and leaving it for 10 minutes and then you come back and you find that it resets your brain almost. So that's one technique. But there are techniques like this that you learn. They're part of your bag of tools and your toolkit, and that's how it works.

What's a mechanism to walk away from the board and come back? I feel that's a question worth reflecting upon. On the subject of transitions, I had an opportunity to speak to Darlene DeRosa of Spencer Stewart, who speaks about effective transitions in the remote world.

As an example, one CEO said he literally would change his video background that sort of make it look like he was in the Switzerland office one day. And he, he got off to such a fast start because rather than taking three months to travel to every office, he could do the same thing in a month. And so he could have so many video meetings that were much more effective and one on one meetings, by the way, where he could, he has bigger reach in terms of the employee population plus a number of town halls, and said he'd never go back to the way he was doing it before. That's just one example of how, yes, it's harder and you've got to be more thoughtful, but there can be a lot of efficiency if you do it well. And so we've seen some really interesting examples of organizations who have done a nice job rethinking their onboarding strategy. So sending people care packages to help them understand the culture of the organization even before they join and sending care packages. So it's not like you're just getting a laptop. You're getting things that help you understand and learn about the company. We've seen some organizations hiring and creating new roles to really think about onboarding and culture.

The more I spend time in this space, the more I realize that the derailments rarely happen because of the gap in the new leader coming up to speed on the what of the business. More often than not, the derailments happen because a leader hasn't acclimatized on the how of the business. If you want to dig in more, you can look up the conversation with Michael Watkins, who's one of the leading thinkers in transition acceleration. You might also like the conversation with the our Gopalakrishnan, who's written the book crash, which profiles 15 high profile CEO appointments that led to derailment. You might also find the curated playlist settling into a new context. This could be a value where you have perspectives from multiple leaders and thinkers on how you can accelerate your transition. You can find all these resources@playtopotential.com and either go to the guest section if you're looking for particular guest like Michael Watkins or Gopalakrishnan, or you can go to the curated playlist section if you're looking for the playlist Settling into a New context the metaphor I use with founders is that when you're procuring new seeds, getting the high quality seed is only one part of the problem. You need to ensure that you take care of the soil, the fertilizer and the climate for the seed to grow into a plant and a tree. And that, I often notice, is left to chance. If you're deriving value from the podcast, do consider paying it forward to Antarang Foundation. You can get the details at the Paid forward section@playtopotential.com let's now get back to Aliza Cohen moving to a different theme. Alisa, you talk about this notion of you talk about this dichotomy where founders have to walk the tightrope. You say that there are situations where you often need the money from a VC firm, but you don't quite need the board member. And sometimes it's the burden of leadership to handle this dichotomy and live through it. Can you talk a little bit about, you know, the way it plays out and what you've seen some founders do in handling and walking this tightrope effectively?

Well, it's very difficult. I mean, it's no question that when you're trying to raise money, you're trying to raise money and you need it. At the same time, I think it's just super important for anytime you do a business partnership, whether you're hiring employees or when you're finding a co founder, which I was talking about my book, or when you're bringing on an investor, that's a business relationship. The more high stakes it is, and certainly with an investor it is high stakes. The more you check it out and say, and find out do we have aligned values, do we have an aligned way of looking at the world, of looking at the way the startup is going to go. And when you do that, you then it can, it can become clear, it becomes much more clear who this is you're getting into business with. And you know, I think it was Warren Buffett who said, if you wouldn't do business for a lifetime, then don't do business for a day. And I think that founders don't go to the trouble at times of really checking into how is this investor going to fit in, what their values do, that we have the same vision because they're eager to get the money, which I don't blame you, but I just think it's really worthy of pausing because you need to be able to. You're basically signing on to a 10 plus year relationship. So know who you are signing up.

With and any practices around discerning that. Is it just having conversations with the ecosystem to understand the founders and their past and some of the other founders they've invested in and so on, or is there any other nuance there?

Yeah, that's a good way to do it. But then also to have direct conversations with these investors and just sort of talk about what are the most important things to you, what are your values? Here are our values, maybe even do some scenarios what would happen if this kind of thing happened or this kind of thing happened. I think that that's like trying to discern where they're coming from. Comes through discussion, spending time together and definitely referencing, like you said.

Building on the point about boards, Alissa, you talk about triggers during board meetings and one of the points you mentioned that founders often aren't trained in or prepared for is how they handle the board. And one of the points you mentioned there is you need to clarify the triggers the board brings out in you. Can you talk a little bit about this, how the triggers play out in a board context?

Yeah, triggers happen. Well, you know, triggers happen everywhere, right? We react to things. We don't even realize it in the board context. Very often a founder will start a startup because, you know, they're not employable, like they don't want a job. They may not like authority. So even though they took the money from the board and they kind of put themselves in the situation of being, in some ways, you know, having this authority figure on top of them, they don't like it. So they rail against authority and that's a trigger. And then they might act defensive or inappropriate in a board even though it's not necessary. One founder, I work with the board. This hap. This happened in multiple, actually multiple conversations I've had with founders just like this. But basically the board said to the founder, you know, you haven't really been making your budget. You haven't making your budget targets. Be great if we would have a couple extra meetings and it'd be great if you would kind of give us an update and if you need help, let us know. And he was furious about that. Furious. And I was waiting for the thing that made him furious, but that was it. That's the whole thing. He couldn't believe that they wanted to, you know, more scrutiny and pay more attention when we unpe it, when we unpacked, that it was because from another startup in his past he had felt under the thumb of the board and he was kind of acting that out with this board. But really it was actually very collegial. They really wanted the best for him. They, you know, wanted to help him and that's where the more oversight came from. And also they deserved that as board members. So really the key was for him to make his numbers and also to build productive relationships with everybody to get their help and ultimately not get so triggered by people asking very reasonable requests.

Hmm. It's a great point. Sometimes we bring up past sort of the history with us and sometimes that's not helpful.

Right? That's so true. Yes.

Moving to a different theme, Alissa. Co founders, right. Both co founder selection and sort of working through the co founder relationship. Maybe starting with the selection. You use the term unforced error somewhere in the context of what founders and leaders could do. But what are some of the common unforced errors you see founders make in the way they go around selecting the co founders?

Well, I, it's actually the same as I talk about with the board. They, they don't check into the background of the co founder. They have a few conversations, they're excited about the same thing and that's it. They get into business together, they don't think about making sure they're both going to be have the same work ethic. Which I've seen many times where founders have different work ethics. And then they get angry at each other, understandably so, because they didn't talk about it in advance. They don't talk about how they deal with conflict. They don't, they don't even, you know, take enough time to have conflict together and then get themselves out of it. You know, in my book, I talk about two founders, one of whom wanted to build kind of a lifestyle business and one of whom wanted to build a really big business. And they never discussed that. They didn't discuss kind of the overall vision or future of what they wanted to build together. So all of those things together, you know, are just the lack of the unforced error there is. We didn't get to know each other before we got into this relationship. And what I say in the book is when you have a co founder, you have a marriage, and you have to treat it like that. And you have to kind of get to know this person and walk through their makeup to your point earlier, their baggage, the things they bring to the table, good and bad. Also, you've got to make sure you've got complimentary strengths. And if you do that, you'll have a better chance of making sure this is the right co founder. But co founder conflict is the, is the cause of actually quite a large number of startup failure. Like I think it's 65% of startup failure. Yeah.

And moving to co founder relationship, I really like one of the things you say in the book. You say that, you know, one of the questions you ask is how's the dynamic with the co founder similar to the dynamic of the family you grew up in? I thought it was an interesting question in a way. I guess it ties back to the earlier point about some of the old patterns playing out in a different canvas. But can you throw the light on this question and what the founders could reflect on here?

I think that we unconsciously put ourselves into environments that we, that we kind of replicate from childhood. And when I say unconsciously, I really mean unconsciously. But somehow you draw people to you who are going to help you play out your family drama. And then in, in doing so, hopefully you can heal, you know, in a good way. That actually helps everybody kind of heal from their, their background and their trauma. But what that means is that if you had, say, a father who was explosive and would just, you know, fly off the, off the handle any moment, you may, without realizing it, find a co founder who is just like that. It's just like your father or if you have a sense of like your brother was always the star, always a sports hero, always like the big shot in the family, you might find a co founder who's like always a star, always the big shot, kind of always looking for attention in the business and then you're going to feel resentful like you did for your brother. And so it's very, that's it comes back to self awareness. The more you're aware of what you're bringing to the table in terms of your drama and your trauma, your baggage, the more you'll be able to, first of all, try to not just replicate that drama. And also you'll be able to recognize it when it comes up in your other business relationships and then deal with it like a thing, not deal with it like you're still fighting with your father.

Moving to a different theme, Alisa, do you see any big differences in the kinds of themes that come up in your coaching work depending on the stage of life of the founders? You know, whether they're single or married or you know, when they have kids, is there a certain pattern to, to the stage of life and, and the founder journey?

Well, it's an interesting question, yes and no. First of all, if a founder I've, I've worked with many founders who, you know, get married, let's say that they're not dating anyone and then they're starting to date someone and they get engaged and then get married and they have kids. Right. All in the span of our working together. That's a long time. They're so, they're growing up and there's no question that once they are in a more, you know, stable relationship at home and then certainly once they have kids, their priorities change. And also their ability to just get a whole bunch of work done by throwing time at it is just off the table. They're no longer able to throw a bunch of, a whole bunch of time at it. So it causes them to work differently. It causes them, I think, to have more perspective. I think for a lot of founders it causes them to have a little more heart centeredness too because they suddenly have these more kind of intimate relationship, especially when they have kids, they sort of see the world differently. And so I think it's very wonderful and quite nourishing for them to go through those life stages. Obviously as they get older, they tend to mature, they're more self reflective. I think they get more confident. And I think that founders who start their companies later in life are more confident in some ways. Although they're still subject to imposter syndrome and all sorts of negativity. Yeah, I mean, that is still a thing that it never goes away, no matter what your age is. But I think it shows up a little bit differently.

And as we wrap up, Alyssa, I have a set of rapid fire questions, just top of mind responses to a few questions. The first is the one insight that came to you as a surprise when you wrote this book.

Oh, well, if it's top of mind, I'm not sure if it's an insight, but I was very validated and it was really interesting to me that all the interviews I did totally proved my point. There wasn't a single person who said something that like, oh, I didn't know that. So that was very validating to me and it was a little surprising to me.

The most common coaching theme that comes up in your work with founders, that.

They are not aware of how they show up to other people, that they don't really get the magnitude of their words and the importance of how they communicate to others. They just don't really understand their impact.

The developmental theme that founders get cognitively but find it incredibly hard to work on and bring it to life.

The development area that they get cognitively is that they have to delegate more and give people more autonomy. They know they have to, but it's really hard to do. Yes.

The one leadership hurdle that contributes to the mortality of startups when they try to scale up.

Going to. I mean, it's so funny. Going too slow or going too fast. It's both of them, right. It's both being too cautious and holding back, but it's also going way too fast and thinking that the market, the market is telling you product market fit is there when it's not. So it's about making sure that you judge the right moment and going too fast or going too slow are both they. They definitely contribute to the mortality of startups.

And something that you do with your coaches that they don't appreciate at that time enough, but they're grateful for it years later.

Answer a question with a question, which is what I do all the time.

Super annoying. And so this podcast is titled Play to Potential as we wrap up any, any headline thoughts for you from you. What does this phrase mean to you? And any thoughts for founders to play to the potential?

Well, I love that phrase. And playing to potential means envisioning really like really getting and accepting your potential. And it also means getting out of your own way in multiple ways, cognitively, psychologically, from an operations, perspective, being efficient in your work, all those things. When you can, you can shuck as many as possible of those things that get in your way. You'll be able to play to your potential.

Lovely Alisa. Thank you so much for making the time. Really exciting talking to you.

Thank you so much. I loved our conversation.

Thank you for listening. I hope you found this conversation purposeful. If this topic is of interest, you might like the conversation I had at the podcast with Sanjeev Agarwal and TN Hari. They've written the book From Pony to Unicorn which talks about very similar set of themes. You might also like the curated playlist on entrepreneurship and you can find this at the website playtopotential.com and go to the curated Playlist section. If you're deriving value from the podcast, please consider paying it forward to Antarang Foundation, a not for profit that I support through the podcast. You can find the details at the Paid forward section@playtopotential.com I look forward to having you tune into one of the subsequent conversations of the podcast. Thank you and bye now.