Live Bold & Boss Up: From Imposter Syndrome to Leading with Confidence – with Alisa Cohn

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Hi, guys. Welcome back to another episode of Live Bold and Boss Up. We chat today with Alyssa Cohn. Guys. She is number one startup coach in the world. She was named that from Thinkers50 Marshall Goldsmith Leading Coaches Award in London. Say that five times fast. And she was also named one of the top 30 global gurus for startups. She does amazing work with startup CEOs, co founders, all also leaders from Fortune 500 companies. And, and she's worked with organizations like Venmo, Foursquare, Etsy, Tory Burch, Calvin Klein, Dell, IBM. I mean, the list goes on. It's really, really impressive. She, she's really a wealth of knowledge and we just like, tap into it and. And talk about some goodies that you can take home.

No, there's some good things in this conversation. You don't want to miss it. We talk about how to get comfortable with topics and getting out of your comfort zone. So you don't want to miss it. Check it out.

You just got back from Italy recording your ted talk.

My TEDx talk.

Oh, my gosh, how exciting.

Tell us about it.

It was super exciting. So first of all, I was in Italy for a week, so that was amazing. And I was in Florence in the fall, so again, incredibly beautiful. And we spent, you know, I got to know some of the other TEDx speaker, and we spend a lot of time, obviously practicing and kind of getting used to it. And I prepared quite a bit. I am not afraid to say. I'm not ashamed to admit that I prepared a lot. And when I got on stage at 9:45 at night, Italian time, I was like, I'm ready to go. I'm ready to do it. So I'm very happy with how it went. I got some great pictures and the video will be released, you know, some month from now. And I'm excited, both because I think it went well, but also because I'm very passionate about my topic.

Right. What was your topic? What did you talk about?

My topic was how to increase your disagreement quotient, your ability to tolerate. Your capacity to tolerate disagreement. Because I feel like our polarized society is in part because we just can't deal with people who disagree with our point of view.

That's a good one.

Oh, my gosh. I'm gonna have to tune into that.

Right?

Yeah.

Wow. So is it more on like, how to. Not how to, like, debate, but how to just tolerate the disagreement?

How to get better comfortable?

Yeah, comfortable with it, not how to.

Debate and not how to influence someone else and convince them of your point of view, but simply how to deal with and be with in the face of someone else's not agreeing with your point of view. And I presented three strategies to do that because I think, you know, find that we want to debate the topics and find that we want to influence each other. We should. That actually is my point, is that if you can hear other people and deal with them and be with them and not make them feel bad and be in conversation with people, we're all going to get more information and we are all going to be able to hammer out, you know, the truth of what we should do of paths forward. But we'll never do that if we're just basically canceling each other.

Elizabeth, that is so great. I love that. I think everyone needs to hear that.

Right?

Yeah. Yeah.

So hopefully. Well, I guess whenever your TED Talks is finally released, let us know. And we can push it out too, to all of our listeners because I know they're gonna be dying to hear it and watch it.

That's a great topic. Yeah, I can't wait to hear it.

I appreciate it. Thank you.

So, Alyssa, tell us about what you do. Tell us. I know you do coaching. You have, you have a lot of areas that you coach on. And I want to hear more about that.

Absolutely. Well, I am an executive coach. I've been one for over 20 years. And I think when I think about coaching, I think it's really about helping people figure out where are they, where are they going and how can they get there. And that's true for, for individuals is the CEOs that I coach. So I coach CEOs and of startups, founders, co founders, executive teams, and I also coach CEOs and other sweet suite executives in large public companies. So it's kind of the population I work with as well as their teams. And I just wrot a book, it's coming up on a year. So my book came out last October and it's called From Startup to Grown Up. And that's about how really the topic is around how do you go from founder to CEO? But actually it's really part of the journey that all leaders have to go through as they grow in their personal growth journey as leaders.

That's great. What is, what is one piece of advice that you give to like a new leader, someone who's never been a leader before. What would be like the first thing that you tell them?

Who's never been a leader before? Yeah, I would say the first thing I would tell them is that you have to make the psychological transformation, the psychological shift from getting satisfaction from your own results to getting satisfaction from the results of others. So it's really a mindset shift that new managers and new leaders have to get through. And by the way, it is very difficult. And even senior seasoned leaders, if they don't make that shift along the way, they end up, you know, constantly meddling and stepping in because they themselves feel a need to do the work themselves.

That is great advice. I know. I'm like, mind blown already.

Yeah, yeah.

That you're.

You're right. Right. Because otherwise, if you can't make that mind shift, I could see people like, holding on. Holding on to the work, which is what people do. Yeah, right.

I feel like I'm. I'm bad at that.

Yeah. I felt like you were just talking to me. Right.

I know. Okay, great. Yeah.

I think Ash and I were just having this conversation last week and I tend to, like, hold on a lot of. Hold on to a lot of responsibility because in my head, it's just easier for me to do it rather than delegate and let other people do it.

Yeah.

So, yeah, we were just having this conversation.

That's crazy. That was like, right to us.

Well, there you go. Right. You know, when the. It's always like, there's no coincidences. Right. Like, you hear and what we're talking about right now. But I am curious and I don't want to coach you necessarily, but like, just to say what's in your mind's eye because you say it's easy to do myself, and I can relate to that too. But you know that what you should do is free yourself up. And so I'm really curious, like, what's in the way of stopping and reflecting and realizing that you do need to delegate and build your skills and delegation and build the skills of the team around you.

Right. That's a good question. And I feel like I don't have.

The answer for that one.

In regards to what? To the topic we were kind of talking about is Ash and I planned a golf tournament on Friday. And we were like the ones kind of leading charge with it. And it was just easier for me to do the signs and do all this stuff and just. And we had a committee, so they were more than willing to help. But I was like, no, I'll do that. I'll do this, this, and this. Because I already know who it goes to, and it's just easier for me to do it. And Ash is like, why are you doing all this? Stuff and I'm like. Because I. I don't know, I just, you know, I want to give myself this added stress. So I don't know. I don't know why. I guess it's just, I feel like it takes practice doing that and you gotta.

Yes.

Yeah.

Yes. What I was just about to say is it sounds like it's a habit.

It is a habit.

It's a habit of just holding on and not giving it away and just like, I'll just do it myself. And that's like part of your habit. So it's an interesting question for you to think about is how would I go about breaking that habit?

Yeah, no, I love that. I love that. Tell us more. So your book is from. From Startup to Grown Up. Did I say that right? Yeah, because we talk to a lot of entrepreneurs on here that have startups, Tampa Bay, where, where we are is a big startup environment here, which we are, you know, very proud of. And it's getting growing that way. So I love that topic. And I want to put the link to your book on our. On our show notes.

Thank you.

But what, what made you write that book?

Like, you know, I've been a coach for a long time and I've worked with startups quite a bit for the past, let's say, 15 years. And every time I'd walk into a new startup, I would say something like, how often do you meet with your leadership team? And they would say to me, what's a leadership team? And I realized that I wish I had a book to hand them to sort of show some of these things that are just kind of the basics about how they have to manage themselves and manage the team so that they could prevent unforced errors. And so I thought, well, there is no book. I'm going to write that book.

No, that's great. Because I feel like, what's the percentage of startups actually, you know, succeeding or long term?

Right, right.

I feel like is very small.

Very small. Yeah. 99 of startups fail.

Right.

And then the ones who don't fail, you know, they may be okay, but they don't always, you know, sort of fulfill their potential. And part of it, a lot of it actually really is about execution. So what does it mean about execution? It really means the basics of how do you hire the right people for the right job at the right time? How do you delegate the right things to the right people? Ch on it. How do you think about how do you manage your psychology? You know, I talked to a founder, I Have my own podcast, also called From Startup to Grownup. And I talked to Raul Vora, who is the founder of Superhuman, and one thing that he said was, you know, I sold my first company because I was tired, and maybe if I had taken a month long vacation, I would have not sold it. And so the reason that's important is because you have to realize as a founder that sometimes your own stamina is the, is the key factor. Certainly who you hire, who you surround yourself with is the key. Are key factors, and then how you've managed to kind of pull all the levers of the people and the business. So there's a lot to it. That's what my, my book is, is divided into three sections. Managing you yourself, managing them, the team, and managing the business. And if you can get better at all those skills, you're going to have a much better chance of succeeding.

Oh, that's.

That's on my list now, the book. Yeah.

Oh, absolutely.

Did you, did you happen to do the audible version of it too? Yes, yes.

You can listen to an audible.

And is it your voice?

Yes, I read it.

Oh, nice.

I love that.

I think that that makes it even better because then it's like you, you can hear your passion and your, your feelings.

Right? Yeah. And how it was meant to be heard.

Right, Right, exactly.

Yeah.

Yeah.

When we were talk. Went to Italy, you have. We were talking about all this great advice that you could give, and, you know, we were like, where do we want to go? What do we want to talk about? And one of the things that stuck out to me was talking about how you can do anything that's hard.

Yeah.

So first of all, define hard. Like, what would be hard? Is it just like something that you don't really want to do, you'd rather watch a show, or is it like significantly difficult?

You mean for me personally?

Anybody?

Well, I, I think, yeah, it's all relative to anybody. So I have friends, including Erica Dwan, who introduced us.

Yes.

Who are natural. I think that Eric is a natural speaker also. She's been speaking for a long time. I'm. I've been speaking for a long time, but in fits and starts and not really with critical mass. So, like, public speaking is new for me. So honestly, for her, public speaking is not hard. Other things in her life are hard. For me, building my repertoire in public speaking is actually a push out of my comfort zone, as an example. And that's true. You know, if I think about the founders I work with, one of them has trouble going out and you know, talking to VCs and raising money like that is really hard for her, really hard for the language. And she's all in her head about it. Another one, no problem with that, but cannot bring himself to hire good executives in a structured way. Right. But she, the other founder, she's great at that. So we all have our own unique makeup of our comfort zone, of what works. Right. And then kind of the consensus circle around our comfort, what we can do, it's stretching out of that concentric circle. It's getting to that next level that for all of us, I think it's, like, really helpful to identify, huh, what's super hard for me. And then what we all do is we spend all our time doing the things which are easy, like, easy, easy, easy, or, you know, easier, and again, in that concentric circles of your comfort zone. So then we don't apply ourselves to the hard things. Then they get even harder.

Right, that makes sense.

So my advice to everybody is to set aside time every quarter, every year, every week, if you're me, whatever it is, to do hard things, to build your muscle about getting out of your comfort zone, and also to not get kind of stuck in a whole subset of things which, like, I'm not good at, I'm not able to do. You've got to keep pushing yourself forward.

I am taking notes over here because I feel like that's so great. And we all need to remember that it's so easy to do the easy things, but to do those hard things, it's like, right, I don't want to do it.

I know. And then you don't develop yourself in that way.

Yes, totally. You don't grow.

So in other words, you would recommend trying to work on the hard stuff to. To round yourself out, so to speak.

Yes. And you don't have to be, you know, as a whole, people don't say, I don't want to work on my weaknesses. How do you know if it's a weakness? How do. If you haven't tried, if you haven't stretched yourself, have you even taken the thing outside of your comfort zone and put it into your comfort zone? How do you know you don't like it? How do you know it's a weakness? And so that's, like, one thing to really, like, hold yourself accountable to, like, what actually you're great at, because you can probably do a lot more if you just would try. And then also, I really think the ability to go do hard things is itself a skill. And no matter what you should practice the skill of going out and doing hard things.

Right? No, that makes so much sense because I used to think that I wasn't good at sales, but I don't. I didn't understand what sales was. Was really the issue.

Right. Yeah.

Until you. That's such a great example. That's such a perfect example. Yeah. And then of course, you shied away from it, right?

Of course I did. I absolutely did not do sales. I was like, that is not me.

Right, right. Even an identity, that's not me.

Yeah.

Like. And now you realize it's a different thing, right? Yeah.

That's so great. Do you mainly coach individuals or like, do you. Does a company hire you to train their staff or employees?

Typically the company hires me and they hire me to coach their executives like this, you know, the CEO or the, as I said, you know, CEO, founder and co founders and sometimes the executive team. And then I will sometimes do training on more. More often I'll do like workshops, like team building workshops or team communication workshops with the senior team or maybe one level below. And then probably those. I mean, those are the kinds of things I do sometimes one off, like other things like speaking or I guess different kinds of facilitation.

Okay. And then another question. I keep thinking of all these questions I want to ask. So whenever you're doing coaching, do you have them take a personality assessment and does that have a lot to do with it?

Sometimes. So I like to see like what's going on first and then once I see what's going on. Yeah, sometimes we like to do a personality assessment. You know what really helps with the personality system or communication assessment or behavioral assessment is that people really look in the mirror and like, oh, yeah, I am like that. And it's very helpful for a lot of reasons. First of all, it gives them language for something that's always just been a personality quirk or personality style. It helps them see that other people aren't like that. So what that means is there's another way to be. So it opens up the aperture of there being another way to be. And then the third thing is that it's then helpful to kind of have community. Like, oh, I always thought I was weird. No, other people are like that too. So those, like I'll use the Myers Briggs for that or the Hogan assessment, which I really like that kind of stuff.

That makes sense, right?

Yeah.

I was wondering how, you know, with the, the coaching, how much people really looked at that, how valid it was and how much you put into that.

Yeah. Sometimes it can be very helpful. But I think some people have their own formula. Like, I always like to joke around. I say that people have the Plum model. Like, I do the Plum model. It's like, I actually want to know what you need, not so much like, what my model is. Right. My model can be. I have a lot of different tools I can use. I don't think that, like, any one mod fits everyone.

Right. That makes sense.

Yeah.

And then last question. What has been your favorite, like, memory or transformation in coaching? I feel like you've probably seen so many great transformations or growth with people that you've coached. Is there any, like, one example that sticks out in. In your mind that you're, like, super proud of or.

Yeah, I. So I'm very interested, especially, you know, increasingly so, in imposter syndrome. So you know about imposter syndrome, right? The feeling that you're going to be found out like a fraud, that you're like, you've accomplished everything in your life because of luck, and your luck is about to run out. So the truth is that 95% of successful people, 95% at some point, feel imposter syndrome, and that includes the CEOs I work with. So there's one CEO that I work with, and he was sharing with me his imposter syndrome and about how he always felt, like, against the wall and everyone was going to find him out. And we went through a tool that I use, which I call the highlight reel, which is about him writing down his past successes and the things that he was able in particular to overcome a challenge. So successes, things he was proud of, and especially challenges he overcame. I asked him to write those down, like, physically write those. We talked through them, and instantly it cured his imposter syndrome. Wow. Yeah, I'm really proud of that. I'm proud of him. I'm delighted for him because it's so draining to have this imposter syndrome. And frankly, as a coach, I'm very proud of that.

Well, right. And then that probably boosted his confidence immediately.

Totally. Yes, it did.

Well, doesn't imposter syndrome and confidence kind of go hand in hand?

Say that again.

Does imposter syndrome and confidence go hand in hand?

Like, if you have the confidence, confident. If you have the imposter syndrome type of thing?

Yeah, I guess so.

The thing is that you put yourself. I think. I think it's very accurate what you're saying. Like, high achievers push themselves to the point about comfort zone. Push themselves hard and out of their comfort zone. A lot. So you have to have a certain level of confidence and even, let's call it ego to do that. And then you're constantly on the skinny branches, like, nervous. Is it not going to go well? Because everything I've done so far in my. Everything I've accomplished so far in my life is because of luck. And here I am on the skinny branches, and my luck is about to run out, about to fall. And so I think there is an interesting tension between confidence, achievement, and imposter syndrome.

The skinny branches.

I like that. I definitely see this CEO trying everything out on this tree, like, balancing, hoping it doesn't break. I love the.

The visual. So what's next for you, Alyssa? Any exciting things coming up?

A lot of things coming up. I'm excited about this TEDx talk. Seeing the light of day, for sure. I'm about to head to Lisbon to speak at Web summit, actually, about difficult conversations, about how to engage in delicate, difficult conversations. Actually, in my book. The appendix of my book is Scripts for Delicate Conversations. So I'll be talking a little bit about that at web summit in Lisbon.

I love Lisbon. So gorgeous.

Have you been?

I have. Like, a long time ago.

Yeah.

You're gonna have a great time. Have you been?

I've been before, yeah. I'm excited.

So you have the opportunity to travel all over and speak to people all over the world. That's amazing.

It is amazing. It is. Alex. Sometimes I pinch myself.

Right.

I just came back from. I was telling you, I just came back from Baja, where I was asked to speak at a. At a Mastermind. And I'm like, not a bad gig.

Right? Right. So do you ever have that. Do you ever have, like, imposter syndrome? Like, how did I get. Get here to do all of this and to train all these amazing CEOs.

And, you know, I do have imposter syndrome. You know, 95% of high performers have. I am privileged to have imposter syndrome. So badge of honor, not so much. Oh. I get to, you know, go all over the world and speak. I have to say, like, I very intentionally designed my life and my career. So for me, I'm like, more. I'm not more than. I'm just really grateful. Like, oh, look at that. That I knew I could do it. Great. My imposter comes out. I think when I'm. It's hard to explain, but, like, when I'm trying new things in terms of, let's say, building my network, I can sometimes. That's where I can sometimes fall into imposter.

Syndrome, like when you're introducing yourself to someone new kind of thing, Maybe. Yeah, yeah.

Especially, you know, increasingly I'm thrown into, let's say, more high status environments. And that's, I think, where I'm like, you know, me, me. I think that's the element that I sometimes get. Imposters.

Right. Like, they're like, oh, well, what do you do? And it's like, oh, just staffing. Like, you know, you just whatever.

Right.

You know, and. And I have no. I'm. That's kind of what I'm relating it to. Like, you're just like, what do I say about myself? Without like, you know, tooting your own horn. But you're happy about it, but then you don't, you know.

Yeah, yeah. Well, I deal with a lot of founders, a lot of very successful founders. And so that's where it's like, wow, you've done a lot, you know, and you're only 29.

Oh my gosh.

Yeah.

Right, right.

That could be like that. Yeah.

Right. So how did you get to this point where, like, is this what you always wanted to do your whole life? Like, is what you do coaching and coach CEOs and executives, or did you kind of work your way up to that point?

Well, I went to business school with this thing in my head that I was like, I want to figure out why people do things in service of the organization or sadly don't. And I got all turned around in business school and so I exited into PricewaterhouseCoopers. And PricewaterhouseCoopers, which is a fantastic. I was on the so called fast track to partner program and five years to partner, and I'm like, my life is all set. And it's like that Joseph Campbell quote, I think of it all the time. If you can see your path all the way through to the end, you are following someone else's path. Your path only becomes clear as each foot hits the ground.

Wow.

I know.

I love that.

Yeah. And so I saw my path all the way through to the end and I woke up and realized I'm following someone else's path. And I have this kind of dramatic moment of truth. And then I was like, well, what else am I going to do? And I had to go and seek, seek, seek. What am I going to do? It's like, oh, no. Washed up at 27. What am I going to do? And then I went to a conference and I met a coach. I met Cheryl Richardson, who was at the time a big deal coach. And she'd been On Oprah, but I'd never heard of her. And I was like, what is this? Who's speaking? And then she spoke to the. I was volunteer. She spoke to the volunteers. I was like, like, violins played. I was like, what is that? I want to do that. And then I followed around the conference, and in one of the. In one of the sessions, and she said, okay, who wants to get up now and get live coached? And I thought, what's going to happen now? I know.

In front of everybody.

In front of everybody, yeah. And so someone stood up, and she did live coaching in front of everybody for 20 minutes. And I thought, I could never do that, but at the same exact time, I thought I could do that.

Wow.

And since then, I've done a ton of live coaching, actually.

So did you get up at that moment?

I didn't get up. Someone else did. I watch the whole thing play out. And I was like, wow.

Oh, my God.

I know. I was expecting you to say that you volunteered, and you were the one that she coached. It must have been just watching her life coach. Now it's just as impactful. I feel like it was more impactful because I just.

I thought, what is this? What is this? I mean, I. I'd never heard of coaching. I couldn't imagine which coaching was. And she spoke to the volunteers, and I was like, wow. I don't even know what she said. It was just her. Her just, you know, energy or whatever. And then when I saw her do live coaching in this session, it was a sense of, like, that is my path. Yeah.

That is so outside the box. Like, it's so outside the box of the box of the box. Right. To coach someone, because there's so many different avenues you could go, I'm sure.

Definitely. Yes.

Well, and if you think about it, people hire personal training coaches if they want to, like, improve their physical, you know, body. Why wouldn't you hire a professional coach to. Or personal coach to help you? I mean, that's like one of the biggest parts of your. Like, your entire life is right. You know, professionally, mentally, like that whole piece of it.

Yeah, totally. Yeah. I mean, that's the thing, is that people will sometimes say to me, even just like, socially, like, oh, yeah, I keep trying. I've tried for years or whatever, but unfortunately, people try in ineffective ways. They don't have all the tools. And I'll speak for myself as a coach and some of my amazing colleagues, we just have a lot of tools, and we can really help Shortcut. The shortcut. The process wow.

Well, sign me up. I need to exercise my brain more.

Well, how can people get in touch with you? And we're going to add this on the show notes as well. What are the best ways for people to reach out or contact you? If you know they want coaching or if a company like a CEO is watching this and they want to reach out to you?

Sure. Well, you can definitely go to my website, alyssacon.com a l I s a c o h n dot com and you can also download I told you about my difficult conversation silica conversation scripts. So on my website, I have five additional scripts to handle delicate conversations and one to make your life better. So that's Alyssa Cohn.com/scripts. And then people can also find me on LinkedIn and on Twitter at Alyssa Cohen, I'm in all the socials.

Okay, great. Alyssa, this has been so informative in our short amount of time that we've had together. Thank you so much. Can't wait to hear TED talks from Italy and all the the things coming up. That's so exciting.

And until next time, Live Bold.

I'm Jerry P. Tok, CEO of Radio Influence. I just wanted to take a quick moment to say thank you for downloading and subscribing to this podcast. There are a lot of people behind the scenes here at Radio Influence that work hard to keep you entertained day in and day out. If you'd like to get involved and advertise on this program or you have some show ideas that you'd like to see us add to the Radio Influence family, please email us@contactadioinfluence.com we all have crazy schedules, so the fact you took time out of your busy day to let us entertain you for a while means a lot. Without you, the listeners, we wouldn't exist. So thank you again for downloading and subscribing to this show. Don't forget to check out radioinfluence. Com to see what other shows we also have to offer. All of Radio Influence's programming can be found on Apple Podcasts, Stitcher, Tunein, Radio, Google Play, and of course, radioinfluence. Com.