214 Alisa Cohn: CEO Startup Coach & Author of From Start-Up to Grown-Up

I am unwilling to give up that.

I will start over from scratch as many times as it takes to get where I want to be. I want to be you just want.

To make sure you will get knocked down, but just make sure you don't get knocked out. Knocked out.

So your only choice should be go focus on what you can control, control, control. Hi everyone and welcome to the Kara Golden Show. Join me each week for inspiring conversations with some of the world's greatest leaders. We'll talk with founders, entrepreneurs, CEO and really some of the most interesting people of our time. Can't wait to get started. Let's go. Let's go. Hi, everyone, it's Kara golden and we're here on the Kara golden show and I have my next guest who is a friend from a great group that I'm a part of called the List and her name is Alyssa Cohn and she is the global CEO of coach and author of the fantastic brand new book that I have right here called From Startup to Grown up, which was incredible. I finished it a couple of weeks ago. I wrote to Alyssa right away and I said, oh my God, I have to have you on the podcast because it was so relevant, especially for me having grown my own startup company. And she's just got so much wisdom and so much experience and inspiration to share with all of us. So I'm thrilled that she is here today. So as I mentioned, she is also the global CEO coach, and she started out in kind of a unique way and in the startup world, but not too dissimilar to many other people who didn't really know that they were kind of going to be focusing on entrepreneurs and startups. She was at PwC, which is one of the big four accounting firms, and then feeling the itch, she went into the startup world. Her successful coaching career has worked with many, many C suite executives and founders and Fortune 500 companies, including people from many companies that you would recognize, but also does incredible workshops for companies like Venmo and Etsy and Microsoft and Google and you name it. So Alyssa was named the number one global guru for startups in 2021 and the top startup coach in the world at the 2019 Thinkers50. And I mean, just so many accolades here. She's been, has had amazing press, so you may have also heard about her. But again, this book, everyone definitely has to pick this up. So, so, so incredible. So welcome, Alyssa.

Thank you so much for having me. Karen, thank you for that wonderful introduction. I really appreciate it.

Absolutely. So I always go back to the Beginning. So you're growing up. Did you know that you would end up doing what you're doing today? Being in finance, being in the startup world, coaching some of the top influencers and, you know, inspirational leaders of today's time? Talk to me a little bit about that.

Well, I would say this. I don't think that anyone, you know, at 4 years old or 8 years old says, I want to be a coach. Right? Like, I don't see that happening. But I will say, when I was 14 years old, I remember having a conversation, a very intense conversation with a friend of mine and we both said, what would you do if you didn't have to worry about money and you could do for a living without having to worry about money? And the answer, my answer to the question was have intense conversations. So that's what I would do if I could do anything. And now I'm a coach. And the good news is that what I do for a living is have intense conversations because I love real talk and I love deep conversations and I just love, you know, hearing people's stories. So in some ways that was what I knew I wanted to be when I was a kid.

That's awesome. And did you feel like you had people around you who were pretty intense? I mean, who were, you know, making you think more? How do you do that? I mean, how do you have these intense conversations? Maybe you're growing up in a house that doesn't want to ask questions like, how do you do that?

That's a very insightful question. I think it's a combination of two things. I think I grew up in a house where we did not necessarily have deep conversations. And then in the contrast, I grew up in a youth group. So my youth group was called Young Judea and it was a quote unquote, peer led youth group when I didn't even know what that meant. But I did know that at 13 years old, I was facilitating conversations, intellectual discussions with my peers about, you know, Jewish topics, but also social issues topics and social action topics. And so that's where I think I got my love for intellectual curiosity at an early age.

Very interesting. So one of the roles that I, when I was doing my research, I saw that you were the chief of staff for the provost at Northeastern University. And so was that your first role? Right out of my school, My second.

Job, My first job out of school was I worked with international exchange students and I was a manager. I helped place kids in the US and then my second role was to be chief of staff to the provost at Northeastern.

That's amazing. What did you learn in that role?

In the first role, I learned a lot about crisis management and context switching, I'll tell you that. And in the second role, actually, this is really the bottom line of how I became a coach or the genesis, how I became a coach, which is that we did strategic planning when I was chief of staff to the provost. And the facilitator was amazing, the person who led strategic planning. And I was so inspired by her and the way she handled groups and the way she sort of dealt with even defensiveness and difficulty. And then the second thing is that the provost said at some point in this process, you can't manage faculty because they have tenure. And even I was pretty young, but even then I thought, huh, it can't be that people will only do what you want them to do because otherwise you'll fire them. So that kind of set me off on a course to understand why do people do what you want them to do in service of the organization or sadly don't.

Sure, totally makes sense. Super, super interesting. So you went on, totally switched gears at this point and went into PwC. So what was kind of the thinking there?

Yeah, so I was at business school. And at business school I was one of like 20% of other women. And it was a lot of guys who had done engineering and also, you know, sort of they were into investment banking. And so I got all turned around in business school because that's what felt like success. So I focused on accounting and strategy and finance. And I went, I got recruited to do this Advanced Development Program, PwC, where they took a small number of people and put them on the so called fast track to partner. I had been a journalism major. I had to go to math camp before I was even allowed into business school. So for me I was like, wow, I could have, you know, it's like something to prove in terms of like, I can do hard things and I can do that analytical stuff. But also I thought, well, my path is set five years to partner. I'm good. It felt like a validation. I was young and I was still finding myself even coming out of business school. But it felt like a validation, like, you're going to be okay and it kind of validates that you've got this degree. So I kind of left behind me that interest in people and organization in service of what looked for the moment like success.

So interesting. But at PwC, obviously you're working with a lot of different companies as you were moving up and what was kind of the biggest thing you learned from that experience.

You know, PwC was a fantastic experience. And as the years go by, I realize more and more what a fantastic experience it was. I did plenty of audit hours, and it's not all I did, but I did audit hours. And by the way, auditing is a really good learning device. You learn what to look for, you learn if something doesn't quite make sense, you learn to ask questions. It's actually very helpful. And then I also learned about how do you work quickly, form a team? You know, my engagement teams, we had to form teams quickly, execute quickly, and then leave and go form a different team. So I learned a lot about how to be great at group dynamics with an initial team, with a new team.

That's awesome. Were you focused on any certain industry at PwC?

Middle market. So I worked with an integrated set of middle markets, which is why, again, because I was in this program and also because I was in this integrated services business line, that's why I got to see so many things. I did exit strategies, HR strategies, marketing strategies. I helped prepare a company for ipo. So I got to see a lot of things while I was there.

That's awesome. When you ended up then leaving and going into the startup world, what kind of prompted you to do that?

Well, I had a moment of truth, which is that I woke up one morning and I thought, I hope I get the flu so I don't have to go to work tomorrow. And I know other people can relate to that. But then I got the flu. So 18 hours later, I was rushed to the emergency room and. And I got the flu. And they were like, you can't go back to work. So I was like, down for the count for two weeks. And in that period, I just thought, this is not it. I gotta figure out what it is if this is not it. Because it just felt too. The firm ultimately felt too big for me. And I just felt like I couldn't make my mark. And in my mind's eye, I kept thinking, to make a difference. That's what I wanted to do, to make a difference of the work of my hands mattered. And so I kind of set out to think about what that was going to be. And I looked into financial planning because I thought, oh, I could help somebody buy their first house or send their kids to school. I looked into a bunch of things, but ultimately I met Two things happened at the same time. I met a coach, and I'm like, what's that I want to do?

That was Your first Interesting. Yeah, yeah.

I saw myself in her and I also thought, well, I'm too young to be a coach. That's not going to happen. So it was the time of kind of the heyday of the first startup bubble and the dot com world. I got involved with them. I got recruited to first one.com as a head of strategy and the second.com as a CFO and ultimately the general manager. And so luckily for me, I was both taking coach training and learning about coaching along with actually building my leadership skill. So as a CFO and as an executive at the table, I began to sort of understand what it takes to run a business and what it takes to lead people. So when that all imploded, I felt much readier to become a coach.

So interesting. So leaving more traditional, you know, everything from working at Northeastern University to being at PwC, were you ready to go into a startup? Like, did you feel like you had your own kind of stuff to learn? I think that I always share with people in growing the company I founded. Hint was, you know, you think, for example, that people have amazing experience that is totally relevant. But I think that culture is also kind of shocking to people who come from large companies. Right. And they're walking in. And to some extent, I think being in a startup is, some days it's by the seat of your pants. Right. You don't. I mean, you've got hopefully strategic planning and you're trying to figure out exactly what's going to happen next year, but you're also nimble enough to be able to make decisions that can be advantageous. Right. To your company. And that happens all the time. Tell me about your thoughts on that. Because I feel like there are so many people I meet along the way that are approached me and said, I love that you're doing a startup. I've had amazing experience. How do I transition into that? What if they transitioned? I have a friend of mine who actually was at Deloitte for years where she transitioned into a startup and had an amazing opportunity. And after a year she's like, this place isn't for me. And I was like, maybe it was just that one versus actually, but I feel like there's this culture, culture thing that a lot of people just don't really realize is challenging for so many.

Very challenging. Actually, it's a very timely question because I just wrote an article for the Harvard Business Review on how to get a job at a startup if you're a seasoned executive. Right. So how to make that transition and step one is recognize what you're getting yourself into. Right? Because just like you said, you know, my first startup, it can only be described as it was chaos. It was just chaos. And I was quite daunted for a period and thought I had made a horrible mistake. And so it took me a while to figure out how to operate inside of quote, unquote chaos and to realize that as an early employee, my job was to make sense of chaos. Now, luckily for me, I'm a very proactive person. I enjoy jumping in, I enjoy taking on kind of more than my remit, and those skills served me well in all my experiences at startups. But I think it's a good point that people who come from a structured environment where things are really well laid out, with a lot of resources, where you kind of have a sense of like this is my job and this is someone else's job, don't do very well in especially an early stage startup.

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I think so much about this because as a coach, I'm listening to people, I'm helping give tools and I'm also teaching people. So why? Because leadership is not natural. We are not born with these skills. Right. The skill of leadership requires you to have difficult conversations with the adults around you. The truth is very little prepares you for that. You don't have difficult conversations with your friends. You don't give feedback to your friends. As you're growing up, most of us were in an environment, we grew up in an environment where conflict was hard to have. Either you didn't have conflict, either you had screaming matches. So the idea of how do you have productive conflict does not happen naturally. It's a learned skill. And in addition, what I also would say is that when I look inside of organizations, sometimes you as a leader have to give someone confidence that they can do it. Even as they're screwing up. Even as they're screwing up. Right. So that's quite unnatural. And so all the things that you need to do I think are important to first of all be self aware and see what your natural blind spots are, what your natural swing is, what your natural tendencies and what the natural things that kind of drive you crazy. And then at times overcome them and do something very different from what is natural to you. And that is the journey and growth of being a leader.

I think too, this idea of failure is okay along the way. Like actually, as I always tell people, as long as it doesn't cost you a lot of money. Right. It's or the company a lot of money. I mean, the key thing is, is manage failure along the way that I think that there are things that you, you know, you need to try, otherwise you're not going to be able to be successful in situations. But you have to manage risk. And so.

So true.

Yeah. And teaching that as a leader, I think, is, is something that I find actually the more experience people have, the more educated they are, I think you're much less likely to take those risks. So I really, really loved reading you talking about that because I really think it is leadership is unnatural to so many people. And being able to kind of push that thinking over to other people too, and give feedback too, is definitely front and center for anybody. I know that that is a great leader today. So what is one common mistake that you think leaders are making today?

Well, there's so many that come to mind. One common mistake that all leaders make, I think all the time is forgetting that they're the expert on their intention, but everybody around them is the expert on their impact. And what that means is when a leader speaks and then is misinterpreted, the leader can be, oh, I didn't mean that. Well, it doesn't really matter because the hundred people you just communicated to or the thousand people you just communicated, that's what they thought you meant. And so recognizing that you don't always come across that the way you need to. And that also people, most leaders and certainly most founders can often think like, well, I'm just me. I'm just me being me. But especially as you grow in the company, just being you is not really what's appropriate because they see you as the boss, as the leader, as a CEO. Also, as you get bigger, they see the need for you to be a little more formal in your approach. And I think that very often, especially entrepreneurs, but really all leaders kind of miss the mark in recognizing how they need to shape themselves as a leader as the company grows.

Definitely. So what you shared on the Tim Ferriss podcast, which you were on, I loved that episode, by the way you shared the tactic you all always utilize, no matter who the client may be. Do you remember that?

Is it 360 feedback?

Yes, that's it. So talk to us about 360 feedback.

Well, so that is the antidote, right? So if you're the expert on your intention and everybody else is around you is the expert on your impact, what that means is you need to really get an understanding of your impact so you can marry your intention with your impact. Which means you need to find out from the folks around you what's working about your style and then what's not working and what you don't see about your style. And that's going to help give you a roadmap for the ways you need to adapt your style to help you be more a successful leader and a more successful, you know, steward of the business.

So interesting. I'm constantly reading about how leaders handle meetings because I think meetings are always this, you know, some people, especially people I see who come from large companies that, you know, standing meetings are all, they're all part of everyday life every week life, even on zoom meetings as well. And I think one of the things that I really liked that you talked about in the book was what you suggest at the end of every meeting. And I think also, like, should you have meetings overall? Like, what is your thought on that to share with everybody?

Well, first of all, I stand alone because I love meetings, as I said on the Tim Ferriss show and as I said in the book, but really I love the potential of meetings because to your point, most meetings are kind of gloppy. They happen all the time. We don't even know what we're doing here. So what I like to really help my clients understand is like, seriously, what's the purpose of this meeting? Why are we having this meeting? What will be done? What will be good at the end of this meeting, which is not true right now? Will we all know something? Will we have made a decision? Will we all have an understanding of where we stand on something? And so if you get really clear about that, you're going to have a much better meeting. And then at the end of the meeting, what you're referring to is three questions I like to use to end the meeting is, are, what did we decide here? Who will do what by when and who else needs to know? And if you can answer those questions at the end of the meeting, you probably had a pretty good meeting because you in some way advanced the game. And also the results of that meeting are going to in some way live past that meeting. People are going to do stuff, people are going to know stuff. And so I think that's a good way to measure if you had a good meeting and also a good way to take action after the meeting.

So what if you're a manager, you're involved in a meeting, you've got your senior people in the meeting that have called the meeting, and basically you just go to the meeting because you're told that you have to go to the meetings. How do you reset? How do you share that? This is a total waste of my time for any people out there listening to this. Maybe you've been in this situation and, you know, you just show up because that's what you're supposed to do, but maybe you don't have the courage to say what you're saying. What would you suggest to those up and coming leaders that maybe are in this type of situation?

That's a great question. And also it is a thing that happens so often. We get an automatic pilot. So I'm supposed to go to the meeting. So I go to the meeting. I think there are two things to suggest. The first is if you're not comfortable, and I can understand why you're not comfortable announcing in the meeting, you know, sort of, why are we here? Why do I need to be here? You can pull someone aside and say, you know, I see that we have this regular standing meeting, or I'm always invited to this kind of meeting, I'm happy to come. I just want to understand better how we're thinking about this meeting, how this sort of drives us forward, what the purpose of the meeting is. Should I prepare in a different way? When you start gently, just asking questions, examining what's going on around here, everyone has the insight, oh, at least maybe we need to change. And maybe I won't even say, you don't need to come, but maybe we don't need to have this meeting. Right? Maybe this could be done by email. So I think politely questioning and gently questioning brings things to the surface. And I also think, the second way I was thinking is that if you're in the meeting and you realize that this is just kind of this rote situation, there's nothing wrong with your suggesting, let me just check in at the end of this meeting, where do you think we're going to be? Or some other question. And your tone really matters because if you say that in a gentle way, in a calm way, and in actually a very curious way, because maybe there's a plan, a method to the madness that you're not aware of, that will help everybody raise to the surface the questions we're having about the meeting.

So interesting you have some Amazing people on the back of the book, I was just looking at the Seth Godin talks about. This book is a breakthrough and should be essential reading for anyone who is ready to lead and make a difference. Highly recommend. You know, I would say that it's not just for CEOs and leaders. I think I talk to so many people who would love to do their own startup down the road or tomorrow. And I think that this really gives you a great indication of, you know, what's coming because I think so many times people think it's just about having a great product, it's just about raising money. It really is about inspiring and leading a team. And I really do believe that great leadership goes hand in hand with a company doing well as well. Like, I think that it's, you know, once in a while you find companies that have sort of, you know, had a hockey stick of some sort, but then it's eventually found out that there's other, you know, things going on in the company that I think are, that really goes back to leadership more than anything else. Do men and women lead differently?

I think that we have this notion, I think we think about this in terms of notion of energy, the notion of the feminine energy versus the so called masculine energy. There is a sense that there are times that women will be more collaborative, more maybe inquisitive, maybe more bringing people along and able to be more neutral when they're giving feedback, as in asking questions, and that the male energy may be more dictatorial. I guess my experience is that I have seen plenty of men actually not always be as decisive and directive as they should be, really. And I've seen plenty of women be extremely decisive and directive in their leadership style. So I guess for all of us, we need to learn to blend those two energies. And I think that everyone has the opportunity to look at their leadership style and see which part of that is missing. Because the truth is that the most collaborative leaders are often the least decisive. And the most decisive and directive leaders have trouble, trouble bringing people along. So I guess my, my message to everybody is we need to really be aware of your style and blend the styles.

I love it. Well, so much great information here. Everybody go out and get this book. And Alyssa, thank you so much. Where do people find out more about you and your workshops and overall, I mean, like you said, you write for Harvard Business and you obviously the book and so many other amazing tidbits that I've read that you've shared. But where's the best place for people to find out all about that.

People can come to my website, which is alyssacon.com, a L I S A C-O-H-N.com and you can come there and you can download what I have a tool for you which is five scripts to help you have difficult or delicate conversations and one to make your life better. So in the appendix of my book it's these 14 scripts to have delicate conversations, which is how do you have a one on one, how do you have a career conversation? How do you give people difficult feedback or announce bad news or all sorts of other things? And people love those scripts. So I have additional scripts on my website that you can download and you can say hi through my website or through LinkedIn.

They're terrific. By the way. Everybody should definitely subscribe to that as well. I downloaded it and I got lots of great tools out of it. So it's really, really terrific. Well, thank you so much Alyssa and thanks everyone for listening. We're here every Monday and Wednesday with amazing, amazing leaders like Alyssa where we can all learn so much. So definitely subscribe. If you have not subscribed to the podcast, Give us all 5 stars on Apple and Spotify or your favorite platform and follow me on all social channels as well as Alyssa. But my social channels are karagolden with an I. And finally, if you haven't picked up a copy of my book Undaunted, do that. And also a favorite flavor of hint. Definitely pick up a case of that too on drinkhint.com or on Amazon or your favorite local store too. So thanks everyone. Goodbye for now and have a great week. Before we sign off, I want to talk to you about fear. People like to talk about fearless leaders, but achieving big goals isn't about fearlessness. Successful leaders recognize their fears and decide to deal with them head on in order to move forward. This is where my new book, Undaunted comes in. This book is designed for anyone who wants to succeed in the face of fear, overcome doubts, and live a little undaunted. Order your copy today@undauntedthebook.com and learn how to look your doubts and doubters in the eye in a Achieve your dreams for a limited time. You'll also receive a free case of hint Water. Do you have a question for me or want to nominate an innovator to Spotlight? Send me a tweet aragolden and let me know. And if you like what you heard, please leave me a review on Apple Podcasts. You can also follow along with me on Facebook, Instagram, Twitter, and LinkedIn Aragold Golden. Thanks for listening.