219: Leading the Charge: Alisa Cohn on Mastering Leadership to Propel Your Business Forward with Alisa Cohn

Today I have the great pleasure of speaking with one of the top executive coach, Alyssa Cohn. She wrote From Startup to Grownup. We're going to learn a lot of concrete tips that we can apply in our business to grow our business and to grow our leadership. Enjoy the conversation with Alyssa Cohn. Hello and welcome to a new episode of the Business of Meaning podcast. And today, another rock star. She is the coach for senior executive in a large organization. She did TedX. She wrote a book From Startup to Grown Up. My friend, Alyssa Cohn. Alyssa, thank you so much for being here today.

Thank you for having me. Eric, it's so great to see you.

I've been waiting. You know, you're very busy and obviously my calendar as well. But I was always telling you before we start recording, I love speaking with people like you who have so much experience and so much stories that just by listening to you I'm learning something. So no pressure.

It's good to learn from each other.

That's right. Now, before we get into the book and some of the question I have, can you let us know how did you get to doing what you're doing now?

Yeah.

And also how you get all those rock star in the industry to basically support you and vouch for you. And you're also one of the top 100 coach that been selected by Marshall.

Goldsmith, the guru of coaching.

Yeah, exactly. Yeah. And so tell us a little bit about your journey.

Sure. So I was at PricewaterhouseCoopers doing consulting. I was on the so called fast track program. Five years to partner and I really thought my life was set. You know, it's like the Joseph Campbell quote, if you can see your path all the way through to the end, you are following someone else's path. And indeed I could see my path all the way through to the end. And I really woke up one day and thought, I hope I get the flu so I don't have to go to work tomorrow. And I woke up the next day, or actually 18 hours later I woke up, or didn't wake up, but I came down with the flu and my boyfriend at the time had to rush me to the emergency room. And I was down for the count for like two weeks. And in that two weeks I thought, wow, this is not for me. Like no mas. Like I'd rather be a waitress, I gotta figure this out. So I looked around, looked around, what do I want to do? And then I met a coach at a conference and she was speaking to the Vol. I was volunteering at this conference. She Was speaking to the volunteers and I'm thinking, can I leave? But then she speaks to the volunteers and I'm like, what is that? I want to do that. It was like violins played. I knew that was me. I saw myself in her and I followed her around at the conference and she told me to take coach training, which I did. And I wanted to become a coach, but I was super, super young to be an executive coach. So I joined the startup world and I was a CFO of one startup and the head of strategy of another startup. And that all imploded in the 2000s. And I thought, okay, I'm become a coach now. And so on Friday I said to become a coach, and on Monday I became a coach. You know, it's been one foot in front of the other for 24 years.

And then you worked for DraftKings.

Yeah.

Etsy, Venmo, Dell, Hitachi, IBM, Google, Pfizer. I mean, all those names.

Yeah.

So I know you decided in three days to become a coach, but how did you build your brand and how did you people recommend you and start working for those larger brands?

Yeah, it's a good question because it's also like, how do you get your start? Right. So like 20 years in, it's like easy now for people to hire me. Right. But when I was just a nobody just starting, what do you do? So I did everything. I was really, I really hustled. I didn't draw a com breath for like five years. But what I did was I did everything. Like I coached clients for free and decided that I was going to teach at adult ed. And I was very passionate because, you know, I was a CPA and I been a cfo. So I have a strong business background, a strong money background, and I just had this sense that like people over complicated personal finance. So I, I designed and taught a course at the Boston center for Adult Education on money. And so I was doing this like, intense course. I didn't even realize, like, I was like doing like a human encounter session in this course. I had a friend who was a coach and she called me and said I was about to leave for teaching this class and she called me and said, hey, how you doing? I said, I'm great, Joyce, but I gotta go, I gotta teach this class. And she said, oh, well, what's new? I said, hey, not much new. I gotta go, I'm going to teach this class. What class? It's about money. I gotta go teach this class. And she said, oh, you're a cpa, right? I said, yeah. She said, one of my clients, emc, is looking for someone to teach in their business acumen program. Would you be interested? And I'm like, I got plenty of time to talk to you about this.

You were late teaching that class that day.

Exactly. I'm like. And I was late for. Exactly. I was late for class because I knew that if I could get into a large company like emc, which got bought by Dell, you know, about five or six years ago, but if I could get into a big company like that, I would absolutely, like, work my way into leadership curriculum, which I did. So I taught business acumen for a period of time, then I taught leadership, and then they realized I was a coach. And then I started coaching executives inside of emc. And that gave me a very big credibility reservoir and experience reservoir. So from there, lots of things happened. The clients I had been coaching for free recommended me to others, and then they paid me. And the people at EMC who I coached left emc, went to another company, and they brought me in there. And that's how these things spiral. You have to keep, you know, basically the goal or the secret to entrepreneurship is keep going and keep trying. And the secret, certainly to being a solopreneur is try everything. Because only 1 out of 10 things is going to work out. But the 1 out of 10 things that works out works out really well.

Are you still a solopreneur or you have a team or.

I'm a solopreneur. I have a tiny, tiny team, but I also bring in. I bring. When I work inside of larger companies, I coach a number of people and I will often bring in other coaches to coach with me.

Got it.

So.

So I just want to make quickly a comparison with the people I'm helping.

Yeah.

Which business owners in the meetings and event industry? Most of us. Starting with myself. When I start my first business, solopreneur, you find a client, you have a project. Great. And you are executing the project, and then at the end of the project, shoot, I need to find another client. And then you find another client, and then you back in the weeds of organizing the project itself.

Yeah.

It's like an Amsterdam wheel.

Right.

How are you coping with that or how you break, obviously, after 23 years, I'm sure you have recurrent client, but let's say the first five years, how do you develop the business and avoid the trap of being always into this amster wheel of doing a project and finding a new client and finding the project, finding, et cetera, et cetera yeah, good question.

Very common issue in coaching as well. Everyone who's like, let's say, a solopreneur. And I would say the answer honestly is elbow grease. Hard work in the sense that I coached my clients. When I began to have clients, I coached them and then I did things like asking them for referrals. I'd find out about all the networking. I was in Boston at the time, all the networking events going on in Boston, and I would go to them, I would attend them. I found various different opportunities to speak for free, and so I would speak for free. So is it hard to coach, let's say three or four clients in a given day and then also take time out to go out and speak and then come back or speak in the evening or go out to events? Yeah, it's hard. It takes planning. It takes stamina, it takes hard work. It takes determination. And for me, I had all those things. I have all those things. And I guess I would say that if you don't have those things, it is very challenging to build an actual business. So you sort of. You're stuck in the onesie twosie. But you've got to sort of plan your week so that you make sure that you are coaching or doing your business, working in the business and then working on the business at least 30% per week. Another suggestion I have for everybody is write articles. You can start writing articles on LinkedIn and getting people to, you know, to know about you because. And to comment on your LinkedIn posts and to you also. You can use those to build your brand, to go write for additional publications like I write. I now write for Forbes and for Inc. And Fast Company and hbr. And you know, that takes like working your way into it, being on podcasts like we're doing now. There are all those different ways to get the word out, and you've got to pick the ones that are gonna work for you. And then you have to enact them consistently, week by week, month by month. Wow.

A lot of discipline, grit.

Yes. For all of us, right? That's what it takes.

Absolutely. Yeah. In every industry, you have the thought leader. The people are very well known. Obviously, if you're a coach, Marshall Goldsmith is the reference or one of the references. There are thousands of thousands of coach around the world and I'm privileged to speak with one of the protege of Marshall Goldsmith. How did you get to that?

Yeah.

So for those who are listening, you have like this big smile.

It's. As it happens, we are recording this on the 18th anniversary to the day that I met Marshall Goldsmith. Okay, yeah, here we are, April 22nd. And here's what happened. I was wintering in San Diego. I was living in Boston. I thought, I'm going to winter in San Diego. That's what I'm going to do. And I was reading one of these books by Marshall Goldsmith, and I saw on his website that he had an 818 area code. And I thought, that's San Diego. I can't believe it. I'm going to find that guy. So I tried to network, tried to network, tried to network, couldn't find him. Nobody knew him. Okay. I sent him an email, and I just said, marshall, I would love to meet with you. I appreciate your work. I would love to meet with you, even if it's for a very short time, even if we have to schedule in the future. That's all I said. A week later, I heard back from him, and he said, call this number to set it up. So I did, and it was. It happens to be. I was wintering in San Diego, and I was going to go back to Boston literally two days later. And I went to his home in Rancho Santa Fe, California, and he greeted me at the door, took me on a tour of his house, his remarkable home, and then took me on a walk around a pond he has there. And I later found out he took everyone on this walk around the pond. And at some point, he said to me, how can I make your life better? I did not realize that was like a Marshallism, that Marshall just said that kind of thing. And I was like, oh, what do I say? So I said something like, well, I just want to spend more time with you. Because he had been talking about spending time or whatever. We walked back to his house, and I realized that even though he's the big mentor, I got to step up here. So I said, well, Marshall, how can I make your life better? And he said, well, there's a project you could work on with me. And I was like, yes, I will do that. And then he said, but it's in New York because he thinks I live in San Diego. He didn't quite get that I was just there for, like, for the winter. He said, but it's in New York. I said, perfect. I live in Boston.

Oh, you didn't say, okay, I'll move there for you?

No, no, I didn't. It just all worked out. Something like, things worked out. And he said, okay, wait for. Send me your resume and wait for instructions. I was like, okay. And two weeks Later I was in the executive dining room with the COO of UBS with Marshall and her, and we worked together shoulder to shoulder for two years. And you know, Marshall's been a mentor and a bright light and a dear friend for almost two decades.

That's wonderful.

Yeah.

One thing you said that he said, call this number and you did. It's fascinating to me that in terms of follow up and talking about anybody in sales, this is the most critical thing, the most easiest thing to do and. And I'm the first one to procrastinate. That's the thing that people don't do. Yeah, they open the door, they get the conversation, and then they don't do the follow up. What is happening in the mind? How could people overcome that? And is this something also that you see in the executive room or is it only something for entrepreneurs?

No, it's a really good question. I mean, a lot of times people don't follow up because of fear. Right. They have their excuses, they have their disorganization, they have whatever. But really it has to do with fear. And are you willing to step across that threshold? And I would just say for me, I can procrastinate too. I much more in the past and now, now I'm very much like, what the hell? What's the worst that could happen? You know, So I kind of tell myself that. But it's easy to be afraid of crossing that threshold. And I think everyone needs to develop the right disciplined self talk which is like, what the hell, what's the worst that could happen? Or what are you so afraid of? Or you know, one step at a time. And these kinds of things help everybody do the important thing. Another mantra I have for myself is successful people do what unsuccessful people don't feel like doing. And I love all those little phrases that help you take action.

Successful people do what unsuccessful people fear.

Don't, don't feel like. Don't feel like doing. Wow. Yeah.

So true. And especially when you're a solopreneur or when you start, I mean, you're accountable to yourself. And as one, one chapter, so many chapter. But there's one sub chapter in your book, the first part, managing you. You start up yourself when you said your best tool is a mirror.

Yeah.

Can you explain that?

Yeah. You know, for all of us. Well, yes, that is the name of the chapter. And I also would just say I have a rap music video on YouTube. I wrote and performed it on YouTube. It's called the work is in you. And that's because the work is in you. And that's the same thing, is that you have to look in the mirror to see what is going on with me that is causing these results or preventing my own success. How am I complicit in the conditions I say I do not want? And that the willingness you have to go there, the willingness to have to be honest with yourself and then unstick yourself from the thing that is preventing you from being successful, that will help accelerate your success. But I mean, the whole, for all of us, you know, you probably accountable to yourself. That's true in large corporations, too. You know, when I work inside and I work with CEOs of large public companies or family businesses or whatever, they'll often say, how can I hold my people accountable? And really, the first question is always, well, how are you holding yourself accountable? Right. It's always that way.

Yeah, absolutely. And I love that. The parable of the mirror. Always say that there's only one person you're reporting to, the only judge is the person you see in the mirror.

Yes.

When you look today in those executives, the challenge that people have, is it the same as it was before the pandemic, or did the pandemic change the way people look? I'm hearing a lot of people feel alone. And obviously the people I'm coaching, the business owners, they feel alone, they're overwhelmed. Is this the same in the executive room and things have changed or not at all?

Well, no, I think change of things have changed quite a bit since the pandemic. I think it's much harder to build culture. I think that if you had some slips in your management hygiene, those were not as important as they are now. When you have to manage people remotely, your management hygiene has to be pristine. The way you give feedback has to be pristine. There's been a lot of unrest in the world, and that, I think, has put people on edge. People have trouble working things out among themselves. You know, colleagues have trouble working things out among themselves because they're much more. More likely to be remote. And all of those things weigh on CEOs and weigh on executives and weigh on leaders. And then you add to that the normal stress of running the business, and then you add to that the normal feelings of it being lonely at the top because it's lonely at the top. That's all those things are, I think, right now, sitting on the heads and the shoulders of leaders.

It is indeed lonely at the top. And you obviously cannot share any of your doubts or thoughts internally. So obviously there are people like you that can be shared. Do you see also an emergence of small group of CEOs kind of mastermind that they're coming together and not only keeping themselves accountable, but more being able to share their concern?

Yeah, totally. I mean, YPO really, you know, I think pioneered that Vistage or tons of groups like that. I mean the group that we met through MMT is a, is a place to create community where people can let their hair down. So everybody, leaders, but everybody have to find trusted communities where they can be comfortable being themselves in a safe space. There's actually a lot of interesting businesses coming out of there of this right now. Like a lot of sort of facilitated peer groups that are now, I think emerging from the need for people to find community and to solve the loneliness epidemic.

And you're talking about building culture. Now obviously when you have 30 people company, there's a certain way of doing it. But when you are an exact and large firm, how do you build culture? More importantly, how you maintain culture. And I remember I won't name the name of the company, but it's easy to find out. I would go to that client and in the lobby behind the reception, you had the credo of the company that was written. Okay. And quite frankly, nobody was even knowing it or let alone, but not following it. How do you instill the importance of values and culture in an organization? And how do you make sure that it's not only once, but that people are really living and breeding?

Totally. It's a great question. And I think it is harder when people are remote and hybrid. And that means you have to try harder. So step one in whether you're in person or remote is really be intentional about the culture you want to create. So it's not just those nice platitudes. You call them values on the wall. I call them platitudes. Right. That are on the wall that no one cares about and pays attention to and also that are so generic. Be authentic or be in high, have integrity. Right. And like, what does that really mean? So actually thinking through, and here's a good way to think about this, who are the most successful people at our company and what makes them most successful? And then between us leaders, who are the least successful people at the company and what makes them not successful, that's a good place to start to really intentionally design your culture. Then you've got to create statements like values or statements or culture statements so people understand what's expected of them. Then you as a CEO have to make sure that your leaders are Actually engaging with those statements, really reinforcing them. And then another tactic for you is to on a quarterly basis have do awards of some sort or do shout outs of some sort on a regular basis inside of a slack channel or something. But like at a quarterly, all hands to really talk about this person embodying the values. It's so great, here's what they did so that you really make it a self reinforcing and generative process. That is one way that you're going to be able to at least have a chance of having everyone understand what the culture is and understand what their expectations are of them and then do those things, enact those things on a regular basis.

Talking about safe space. You know me a little bit, I always say there is no safe space. There are safe people that create an environment for that. And part of it is to have difficult, delicate conversation. And I find out that most of the time people say, especially those who say we need to be able to have difficult conversation, as soon as you start a difficult conversation, they going ballistic or they're gone. So can you explain the framework that you have for people to have difficult conversation in the business?

Yes. Well, first of all, I have in the back of my book in the Appendix 14 Scripts to Help everybody here have common difficult conversations. Like how to fire someone, like how to announce layoffs, like how to deliver bad news, how to tell someone you're not promoting them, those kinds of things. And by the way, I have more on my website, alyssacon.com forward/scripts and you can get five additional scripts to help you have delicate conversations. But in terms of a framework, number one, you need to really set yourself up as an ally, because you just said it. They're not safe space, but there is safe people, right? So first of all, you have to be a manager that people can be safe with, which means you're not out to get them, you're out to support them. You see their challenges, you're there to help and to guide and to mentor. So when you act like an ally to your people, like you really care about them and have their back to some extent, you can say anything to them and they will take it in the right way because you have shown yourself to be a trustworthy person, then the second step is to be clear about the goal of the conversation. Because sometimes managers put off the conversation and put off the conversation, then they throw the whole kitchen sink into this one conversation and it's too much to process. It's not clear what the change is that you want Right. So if you want to have somebody understand a certain situation, understand difficult feedback that you have to give them, make behavior change. It might be in the case of you didn't get the promotion, it's to inform them of why and help them feel good about the situation. Whatever it is, be clear on your goal. The third step is prepare. Write out a little script for yourself. Get your mouth around the words. Practice a few times, because in the heat of the moment when the conversation gets maybe tense, the words that your best intention is going to go out the window. So having a little script and then making sure that you leave them with hope, assuming you want to keep them. Right. Hope for the future. Because that is going to again reinforce this allyship that you have with your people as a manager. That's actually your sacred trust, your sacred. You're not supposed to be like grading them or telling them they did good or not good or constantly correcting them. That is part of the job. But the overall job is to help them see their greatness and enable them to do the best work of their lives.

And the best work of their life means that you also doing regular feedback. Definitely once a year. And once a year now, many people are gone already.

Yeah, the once a year model is kind of terrible, right? As in back in February, you did this thing like, wait, what? It's so stupid. You need to give people constant feedback. But again, it's got to come from a place from. I like to say to my managers, the leaders that I coach, I'm wasting my breath on this because I see greatness in you. If I didn't, I would not bother giving you this difficult feedback. And that is the truth. And so that's the kind of the tone you need to take. And then being specific in feedback is very helpful. Being as behavioral, as process as possible and also not, you know, like a lot of times leaders will wait either for there'll be silence or violence. Right. So the silence is, I'm not going to say anything. It's fine. I'm not going to say anything. I'm not going to say anything. And then violence is, I can't believe you always do this. And it's like the person doesn't even know, like, whoa, where'd this all come from? So that is a challenge for managers to really lean into having the delicate conversations. And I promise you either pay now or you pay more later.

Absolutely. And pay more later is even more expensive.

Yes, definitely.

The last company I started here in North America and Latin America, actually of the Expansion. It was a SAS company. Took me some months to come to create an environment where people realized that when I was asking them what they thought, I meant really to understand what they thought, and I was not asking them to tell me what they think. I want them to say, and second, to disagree with me, and I will ask them, and please disagree with me. And finally, it started always with one and then the other. Oh, okay. I disagree with him and I'm not out. So it really means what he's saying. In the environment you're working with the large organization, do you see cultural differences that are impacting the way people are managing others and the way they're managing difficult conversation?

Yeah, definitely. If you. By culture, you mean like national cultures.

Yes. I'm from Belgium originally, and now I'm in the US So I obviously clearly see that. Is this something, especially in America, where, you know, you have people from all over the world. Do you see that? Or it's just like the culture of the company is basically taking over and erasing the individual country culture?

Well, it's kind of both, because it's an amalgam of both things. So I would say that American culture overall and tech culture is, I would say, at times, overly polite. Right. People want to be collaborative. They want to be overly polite. Right. And they don't always say what there is to say. And then, funny enough, I've coached a number of Dutch people who are known for being blunt.

Boom.

Yeah, exactly. And also I coach a number of Israeli clients who are also known for being blunt. One time we were talking, I was talking with an Israeli guy about he'd actually been the founder of this company that got bought by a larger company. And so, like, sort of just helping coach him in terms of the integration. And we talked about this cultural thing that Israelis have around interrupting. And I said about how when he interrupts, it kind of connotes this to different Americans. Da, da, da. And he said, even the way you frame that, Even the way you frame it, you call it interruption. Right. Even that is culturally biased. I was like, wow, thank you for enlightening me. That's really helpful to see. And I understand you see that. And as you may know about Israelis in particular, but certainly an interrupting culture, they just think that they're saving everyone time. I already know what you're going to say. I'm going to save you some time, and let's move on. And God bless, because there's nothing wrong with that per se. The only problem is if it's, you know, butts heads with other people inside of the company. I also I worked with Hitachi and that Hitachi, of course, intersects a lot with Japanese culture, which is that people don't typically say no. You have to read between the lines to understand that the answer is no. Right. So that's also challenging for people to kind of interpret. All of us have to be anthropologists of our own culture in our own situation.

Absolutely. I mean, you say it overly polite. Always remind me first time. Basically completely moved to the US over 10 years ago and asking direction, I was driving one of my daughter to sports and said, I'm trying to get to that place, should I go left or right? And the person went, I'm not sure. I said, okay, I understand you're not sure, but would you go left or right? I'm not sure. You know, I got annoyed. Okay, but pick something that would you go on left or would you go on right? No. Until I realized that I'm not sure means I don't know. So why don't you tell me you don't know? I'm not sure.

That's hilarious.

Elisa, I know that you know your time is counted and unfortunately, with the format of the podcast, although I spent hours listening and talking with you, this is not possible now. But I'd love to go to one last topic. Today. You say, like those animals that you shouldn't feed after midnight. You say, embrace your inner gremlin and how you using imposter syndrome to drive you forward. And I definitely interested, and I would have been even more interested in the past or so, but I know that something like imposter syndrome is for everyone. So how can we use imposter syndrome to drive us?

Yeah, great question. So, first of all, just to define imposter syndrome for people who haven't heard the term, it's the feeling that you've accomplished everything in your life because of luck, but your luck is about to run out. It's the feeling of being found out that you're a fraud after all. And it is very, very debilitating for people because, you know, you can imagine what it's like. And by the way, I know you, whoever's listening to this, I know you can imagine because 95% of high achievers have at some point in their lives experienced imposter syndrome. So whoever I'm talking to right now, that probably means you. So this is very normal, and it can be very debilitating because you've got it in your head over and over, like, oh, oh, I'm A fraud, they're going to find out. And what's helpful is to acknowledge and recognize that voice in your head, like, oh, yeah, this thing comes up when I'm about to step over a new threshold, when I'm about to take on a new challenge, and to feel like I have something on the line. And so even though I understand that it's scary, I want to remind myself that who I said I wanted to be in the world was somebody who took on new challenges, somebody who can grow, somebody who does exciting and ambitious things. So the gremlin in your head that's telling you that you're not going to be able to do it is kind of like an invited guest. And when you get to that point, you kind of think about that with curiosity, like, huh, I wonder what I'm so afraid of. Writing in your journal is very helpful to think about what you're afraid of. And the last thing I'll say is I'm going to give you a tool to use to handle your own imposter syndrome, which is to create a highlight reel. So a highlight reel is a sort of a set of your best of moments, the thing, the places in your life, the times in your life where you overcame challenges and really succeeded. And when you write down four or five or six of those challenges, like physically write them down, it'll help you remind yourself of your greatness. And that's going to help you overcome the gremlin in your head to get over the next threshold, to thrive in the next exciting challenge.

That's wonderful. So self confidence plays a role as well. And I always use that example in terms of, you know, self confidence and the way you present yourself. If you have somebody on a scale from 1 to 10 that can deliver 5, in Belgium, we would always do I can deliver 3 because they're very unassuming people. And in France, they will say, I can deliver seven or eight. And here in the US I see it somehow. The guy who's running the daily and the corner doesn't even have a passport. I've never been out of the United States, but he has the greatest deli in the world.

Yeah.

And so the way you portray that, I'm sure you see that when giving your example of Itachi and Japanese culture and American culture. It's kind of interesting.

Yeah, definitely.

We are hopefully going to see each other sooner, but if not. And I'm not going to use the champagne question in a year, but when we see each other again in a year in an MMT conference, Until then, how can I make your life better?

Oh, that is so sweet. Well, I appreciate very much you sharing the story on your podcast and continuing to spread the gospel of coaching and, you know, from Startup to Grown up, which is my life's work, it's my passion and my life's work. So thank you already for what you've done.

Wonderful. How could people get in touch with you?

Well, as I said, you can go into my website and you can download my five scripts to help you with delicate conversations and one to make your life better. Alyssacon.com forward/scripts. You can also follow me. Well, you can buy my book on Amazon which is called From Startup to Grownup. My podcast is also called From Startup to Grownup and you can find me on all the socials. Alyssa Cohn A L I S A.

C O H N Alisa, thank you so much.

Thank you so much, Eric. It was great.

Alisa, thank you so much for sharing your experience and some of the stories with me today. And congrats again to being one of those top executive coach that large firms should and can count on to get better people and better leaders. Ladies and gentlemen, if you want to connect with me, please follow me on LinkedIn or go to the website eventbusinessformula.com There's a lot of resources you can use in your business and if you have any question, please reach out to me. Thank you very much.