The Journey of Leadership || Alisa Cohn

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Sri Lanka. She's the author of From Startup to Grown Up, which won the twenty twenty two Independent Press Award, and she's also the creator and host of a podcast of the same name. In this episode, I talked to Alyssa Cohne about the journey of leadership. Before we can guide others, Alyssa believes we need to lead ourselves first. There are days when we just don't feel up to the task, but Alissa gives us practical advice on how to show

up on those difficult days. Drawing on her own legendary coaching experience with executives, she shares with us that even the most successful entrepreneurs experienced poster syndrome and negative self talk, but these can be overcome with the right management tools. It was so much fun chatting with Alyssa. She has such a positive energy, and she has so much experience and wisdom helping people become really great leaders. So I think you'll have a lot to learn in this episode.

So now I bring you Alissa Cohne. Hi.

with the process in anything you're trying to do. And kettlebells and strength training has taught me to fall in love with the process because I don't like strength training, and also I don't like fitness is uncomfortable, but it gives you a lot of benefits. There's a discipline to it. And when I started my own podcast called From Startup to Grown Up after writing my book From Startup to

Grown Up, both of those were really freaking hard. And the notion of like putting one foot in front on the other and just trying and getting over your resistance and falling in love with the process that I learned from fitness and from strength training, I really drew on those resources to do these hard things.

But the process is, you know, helping someone by asking the right questions and also kind of sharing my own expertise over time, helping someone be able to shortcut the process that it would have taken them to do it by themselves. So hopefully we together accelerate a process of growth and development and achievement and accomplishment that helps them move forward faster.

They do have certificates or programs in coaching. But I think if you're being honest, like for me, first of all, I got my MBA from Cornell. I'm a CPA. I have a lot of business experience and business background, so I was also the CFO of a startup and the head strategy and other startup. So like having had leadership roles, having a business background, speaking the language of business, that really helps. You're talking about executive coaching, right, the idea

of understanding business. The second part of that, the coaching part of that. I think it's really important to have done your own personal work. So I've done all my workshops, I did landmark education, I did different kinds of like my own training programs to get a handle on myself. And then when you combine that with specific coach training as well as you know, I was mentored by the greatest coach of all time, Marshall Goldsmith and other amazing peers.

Then you practice on clients. I apologize to you, my early clients, for practicing on you. That's how you become a great coach. It's a combination of formal education but also your ability to learn from others out there there and learn from your clients.

great questions, different tools and techniques. A master coach we use all those together to help her clients get great results.

being a startup founder, getting your kids to school. You've got to start with you and figure out the ways that you can feel good and you can get yourself together and you can have intention about what you want, what you're going to do today, and that is going to help you be great in all the other activities that you have to do every day.

self awareness is the key. The second is to then do the things you need to do to be that person. So it might be setting up structure for yourself, it might be creating, you know, space for yourself, to have spontaneous, spontaneity and choice in the morning or throughout the day. And then it's about you know, doing the doing the things that make a human being kind of work. So it's like making sure that you probably get some fitness in or some movement in the morning. Maybe it's meditation

in the morning. Having those kinds of strong routines really help you. The second part of self awareness is figuring out in the workplace what you're about, so what sets you off. So you have employees who will come to you and they ask you questions, and some people, for some reason, it's like you're really vibing with that person and you're happy to answer the question, and for some reason,

this other person's always asking these annoying questions. Well, how come like to really figure out your own operating system so you can teach other people how to get your best as a leader, and then you can coach and train other people about how they can get their best and how you can work together better. And then the third part has to do with managing your psychology because we all get through so many ups and downs in

a day and an intense work environment. As you get more advanced in your career, you have a more and more intense work environment. Startup founders of an extreme work environment, and there are lots of ups and downs, and you need to find the different ways to manage your own psychology during the throughout the day.

day went. And if the first one didn't go well and the second one didn't go well, then I can almost I can predict your third one is not going to go well. So you've got to find the tools to pause. What I encourage people to do is to take the five minutes between meetings. Pause physically. When I say physically, in your mind's eye, take all the issues from that meeting and kind of like put them somewhere,

like in your drawer, in your desk. You might touch the door handle of the next meeting, and you can leave them on the door handle and remind yourself, I've got to reset for this meeting, and then back to managing yourself, like first thing in the morning. Kind of remind yourself the leader, I want to be the professional, I want to be the product manager. I want to be the parent, I want to be whatever that is. And reset in those five minutes and bring that to

the next meeting. That's one way of encouraging yourself to do the day, even though how you feel right now is not like doing the day, and your your mood follows your actions.

going on inside of you right now. It's not like it's not just like part of you. Can make a separation between you and how you're experiencing you. And then I think self compassion is really important because we all screw up, we all have difficult moments, we all are negative. Whatever it is, the only way you'll be able to counteract that is to be able to separate that and to be or to I should say, not separate that, but like give yourself compassion. Accept that. That's what I

wanted to say. Accept that about yourself and let it be that way with love and acceptance, and it's then that you can then transform and add in separate self talk and self talk can be positive, as in, instead of I really screwed that up, it could be listen, I'm doing my best, or I really screwed that up. One of the things I like is, you know what ballplayers fail most of the time, and find the tools and the specific self talk that's going to help you

reorient and get represenced to this moment. So when you apply self awareness, self compassion, and self talk, that helps you lose that difficult identify and then lose a difficult state and then transform it into a better state right here in the moment.

with this one. But I want you to tell me a little bit in the work you've done dealing with founders and how they deal with imposters like founders of companies, you know, or other kinds of leaders, and how you help them overcome it.

never done before. You know, I talked to one of my uh more mature startup founders and he told and they're at Series E now and even now he says, everything I'm doing, I'm doing it for a first time. I'm still a rookie CEO. So because of that, you get confronted with this imposter syndrome, and impost for startup founders very much looks like I don't know what I'm doing. I can't do it. Jeff Bezos would know how to

do this. I know Jeff Bezos, you know, like that kind of you know, come comparison to like, you know, the sort of storied CEOs of our time. And so I think the way to counteract counteract imposter syndrome is first of all, to accept imposter sendrom is a thing. Everybody is going to experience it, and I'm going to experience it. And then some of the tools that I

give my clients to counteract to. But my favorite tool is called the highlight reel, and the highlight reel is your best of moments, moments where you accomplished big things and in particular when you overcame challenges. And if you step back and actually allocate some time and write down your best of moments times, especially overcame challenges, you will be able to remind yourself of evidence that you're actually

very competent. And it's not going to cure your imposter numb once and for all, but it's like actually something you can go back to time and time again to remind yourself of your greatness and to kind of hold on to when you're feeling kind of shaky.

And he's like, oh, I don't want to do that, And I said, let's just do it together right now. So we did. We did it together, and we like reminded him of him talking himself actually into getting his first role in VC, which had been ten years prior. We talked about even his experience in getting helping the firm land a deal they were not going to land, but specifically because of his efforts, they landed that deal.

So things like that, and so he wrote more and more, and the next time I saw him and had a meeting with him, he was transformed. He's like, oh my god, I did this highlight reel and I can't believe it. It really works. It just helps me dredge up the things in my mind that I don't tend to remember, and it puts them front and center. And then when I start off reading that in a day, it gives me kind of like feel good mojo, and then I

go tackle something hard. And then once I've tackle something hard, it kind of boys me for the day, and so it kind of lets me keep going even though I still can have these feelings of self doubt. That's what he told me, And that's one small example of how it works.

And she said, I am an impostor. I've never done this before, right, So I think that that is very helpful. And then I think the depth of your question is are you an impostor and you know it and you're learning? Are you significantly under like under resourced in terms of having way too much self doubt and too much you know, like doubt in your abilities or to your point, are

you a narcissist? And do you not have any sense of you know, your own you know, lack of competence Here, I think the best way to do this is to realize you're an impostor and you have to learn, and then to aggressively do what you have to do to learn and grow. That's the best way for all of us.

and we're all the expert on his action and his impact. So, of course, from our point of view, from his impact, of course we say that, But it would only be really finding out what's going on inside of him, to use an extreme example, to find out what's really making

him tick or away driving him. And as I have coached people for the past two decades, I have been surprised at how many arrogant, entitled, you know, quote unquote narcissistic people or you know that's a technical term, right, but how many very arrogant people who come across as a certain way. Inside feel a lot of self doubt, and they're using this behavior to cover over their self

doubt ineffectively, of course. But I think it's only when you really get in the sense of what's inside someone that you know what's going on with them.

don't feel like getting out of bed? Them? What if you don't feel like, you know, having a good day, So everything around leadership is learned behavior, and I think people don't quite get that.

motivated and finish the project right. You know, it's counterintuitive to give people or unnatural to give people feedback, to give adults feedback in front of front. In fact, one of my clients once said to me, you know, when he wasn't giving his team feedback, I was like, what is going on and when and when? On and on and on, and he finally said to me, I just don't feel comfortable telling other adults what to do.

them what's going wrong. Not really could be that your most important job as a leader is to praise them and show them what's going right in order to give them confidence and build them up so they will take the action you want them to take and be proactive and be diligent and you know, kind of go above and beyond. So I think that praise is your superpower and a secret weapon that people don't use enough praise.

And she said, because when I get negative feedback, they explained to me what's going on and why, and then I know what to do. When they give me positive feedback, it just feels like, oh, good job, and it feels really superficial. Well there you go. So that's not good. Positive feedback has to be as specific as negative or

constructive feedback. You have to really point out what they did that had an impact, what the impact was, right, So you achieved on you went to this, you were in this meeting, and it's not just good job in the meeting, it's you did the meeting. You first of all designed the meeting to get to our outcome, and in the middle of the meeting, someone was trying to pull us off track, but you politely and graciously but insistently got us back on track. And that was a

really great job in that meeting. Keep doing that. Now that's good feedback. Now I understand, that's very good feedback.

today and tomorrow, but for the future. The same is true with co founders. You're going to be spending an incredible amount of time in this person making very difficult, important life decisions and career decisions and the life of your baby, your business together. So you better have kind of talked through some of the key issues. So what I have is a tool called the co founder prenup.

don't talk about that in advance. And you know, I worked with two co founders who one of them once said to me, I just liked it when we were fifty people, and the other one was focused on getting to five hundred people, as in building a really big business, and they taken an undure of capital money to do it, and they had never discussed their two thoughts about how

they wanted to run the business. And so then right, life got in the way, and five years later they were really at odds with each other because they had different visions for the business together. So you have to talk about that in advance.

And on the other hand, this we just got a biggest client ever and sold our best order ever and everything in between. And so it's like recognizing that it's not just the ups and downs in a given day or even a given week. It's it's the ups and downs in a given hour. And so that's back to managing your psychology. You need to manage your psychology through those steep ups and downs and find tools to help you stand in even keel and not go crazy in

this extreme work environment. That's one thing that surprises people on the journey of entrepreneurship.

you're a real company. And it's surprising to entrepreneurs how quickly they have to make a shift from we're just making it all up to structure and communication. One of the founders I work with he did an all hands to his one hundred and fifty employees and definitely was super flip and like, oh, we're just making it all up, and uh, you know, well, I'm sure we'll figure it out,

and if we don't, you know, we'll be okay. And his head of HR came to him and said, you know, you guys did that when it was like twenty five people, but we're now over one hundred people and there are people making mortgage decisions based on what we do with this company. There are people who are relying on you. You can't be flipped and say, oh, we're just making it up as we go along anymore. And I think that's that quick transition is very surprising for entrepreneurs.

them and their company and the bottom line. Yeah.

We're solving a problem. It's a dynamic experience. Unfortunately, most people don't have that experience of meetings because they don't do enough work preparing for the meeting, and they don't do enough work thinking about how they're going to keep the meeting on track, and then they certainly don't do enough work at the end of the meeting asking my three questions to end the meeting, here you go, would you like to hear my three questions? Of course, of course,

what do we decide here? Who else needs to know? And who will do what by when? If you just add those questions to your meetings, you'll make progress. What people don't like about meetings is that they're boring, they're a waste of time, and then we just go back and re meet on the same topics. But if you follow my process about having an agenda, keeping it on track, and asking those three questions to end the meeting, you two will love meetings.

from all of those discussions. And then though it was done with that part of the book, I was done, and I thought, oh gosh, if only I had a way to continue the conversations I've been having with founders. I know, I'll do a podcast ton of like no one's ever thought of that before, right, And so I started my podcast from Startup to Growing Up to be

able to continue having these conversations with founders. And so far I've talked to thirty different founders and other people in the ecosystem about their experiences, and I've learned so much about the way they handle I just talked to Hubert Palin of product Board that episode's coming out in a few weeks, and I asked him, I really pushed him for specifics about how do you know when it's

time to, as we say, upgrade on executive. How do you know when this executive that you have in your team who's worked very well so far, you've had them for eighteen months, or that you've had them for three years, is no longer going to be up to the task of what it takes to scale in the future. And I really pushed him on that and he said it was it was powerful. He's talked about how you know you have data that the job is not being done. You can see the job is not being done. You

have a sense that they're overwhelmed. They talk about being overwhelmed, but they aren't able to do anything about it. And also their own self awareness is missing, that there are gaps here. And if you can kind of have all those things together, you definitely have a strong sense that an executive is not going to scale to the next level. And I thought, I've never heard it said that beautifully.

That's that's perfect. So that's the one example of all the many, many, many things I've learned from the founders I've talked to on my podcast, from Sharotte to grown Up.

people around you. If you're a stay at home parent and you've got people, little people dealing with you deal with little people, you will learn something from my book about how to deal with those little people called children. If you are in school, that you'll be able to learn how to manage yourself and also think about your

professors as your board and manage your board. Yes, and so there's a lot of tools in the book that are very much applicable to people who are not startup founders are not leaders.

Although I would also just say from me to you, the most important thing you should be doing if you want to pivot in your career is building a network which is deep and broad to help you get exposed to different people, different professions, different sets of skills, and help you kind of learn what's out there and help you find people who want to pull you into opportunities rather than you constantly having to apply to new things, because people who know you are going to give you

a chance, and people who know you are going to refer you to opportunities which are not the ones which you're out there. And so blanket statement, build your network. It's good for everything.

all hands in their company. So finding ways to communicate in that way and take action to then affect kind of that big battleship is a very different mindset and a very different skill set, And the CEOs of those companies are rarely, if ever hands on. If I shift that to startup founders, depending on what stage they're in, they're I wouldn't even say, depending on what stage you're in, they're always very hands on. One way or the other.

There's something that is taking their attention that's very hands on. They can't just assume things are running. They also cannot take downturns in the business like, oh it's okay, I'm sure we'll be okay, Like IBM. You know, no, as a startup, you might run out of money. You can't be sure you're going to be okay, and so it can be a five alarm fire what you need to do if things go wrong. So I think just those

different mindsets are important. And so when I'm coaching someone and the pace is different from that point of view, and the things we talk about is different from that point of view. With the CEO, we tend to be talking about the same thing for a longer. You have a fortune five hundred company, we talk about something for a longer time. With a founder CEO, it can sometimes be like game changer, over and over and over again,

depending on what's happening in the business at the same time. Yes, people are people, like you just said, people are people. And I will be working with my startup founders who are who have very little leadership experience, maybe no leadership experience, and they are trying to get their team, they're trying to learn to delegate better and they don't know how to do it and it's hard, and I teach them how to delegate and I help them kind of build

their own stuff delegation. Now fast forward to working with a fortune five hundred, a fortune fifty CEO. When I'm thinking of particular, he never learned to delegate. It was really hard from a delegate, and so surprisingly maybe but maybe not so surprisingly, we had to spend a lot of time helping him both learned the right techniques to delegate and also the right level of supervision, and he had to reshape his perspective, which is not about him

and his leadership style. It's about his specific executives who needed certain things from him and their leadership stee or their style, their working style. And so I see that over and over and over again that you think that somebody with no leadership experience whatsoever would somehow be much worse at delegating, But actually it has to do so much with the person and what they've learned as habits

as leaders. Same as true of feedback, the same as true as holding people accountable, And so we ultimately talk about the same kinds of things as well as just the inner experience of what it is to be the leader of a massive company or what it is to be the leader of a startup, and we just deal with those things together.

There are moments of imposter syndrome. They're concerns, their fears, and that is, by the way, that's what makes coaching so beautiful, is that having this real relationship with somebody and helping them overcome whatever is going on, the negative difficulty and resistance is going on with them and helping them make a difference. Because my mandate emission is to make a difference, and I can do the leadership level if I enable them to make a difference.

I don't want to turn on me all of a sudden. Also, we are interested in Broadway, which I am too, and so this is something that we both share. I don't best in Broadway like you do because I don't have the money, but by invest by my tickets buying tickets to Broadway shows. What are some musicals that you've invested in. I'm just curious.

executive coach and no struggles. It's been a little bit of a winding road for you, right.

I thought, this is not it. I hope I get the flu so I don't have to go to work tomorrow, right And eighteen hours later I was rushed to the emergency room with the flu. Be careful what you ask for exactly, and then I was like down for the count for two weeks and I just thought, oh God, washed up at twenty seven. What am I going to do? I didn't know what to do because I just thought like, this is not going to work for me, and I'm not sure what to do, and I'm also sick with

the flu. So I had to kind of put one foot in front of the other and figure out and seek around. And the only thing in my head was the music in my head, which was to make a difference that the work of my hands matters. And that's when I met a coach, and that's when like violence played, like, well, you know, that's what I want to do, and I followed her around the conference and I was like, that's what I want to do. And then you know, I

was too young to be an executive coach. I took coach training and I coached all my friends for free, and I ended up being the CFO of a startup and the head to judge of another startup. And when that all imploded in the two thousands, I just said, well, I'm going to become a coach now. And on Friday I said I'm going to come a coach, And on Monday I became a coach. And it's been one foot in front of the other since then.

at www. Dot A l I s A c o h N. I'll spell it out for people so they can just you know, type it in easily dot com A l I S A c o h n dot com, slash five scripts, the number five and then s c r ipts super helpful, especially around the holiday family table when the topic of politics comes up. I'm sure that's really important, that's true. Thank you. Thank you so much for being on this show and for all the great work you're doing.