Episode 169: Alisa Cohn, From Start-Up to Grown-Up

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Motivated to Lead podcast helping you become a better leader. I'm your host, Mark Klingsign. Hi everyone. Thanks again for joining us for our podcast this week. My name is Mark Klingsign with SEMA Partners. Each week we interview leaders and they share lessons learned from their careers. Our goal is to help you become a better leader. This week we're happy to have join us. Alyssa Cohn Alyssa is an executive coach who has worked with C suite executives at prominent startups such as Venmo, Etsy, DraftKings, the Wirecutter, Mack Weldon, and Tory Burch. She's also worked with Fortune 500 companies including Dell, IBM, Microsoft, Google, Pfizer, Calvin Klein, and she is an author From Startup to Grown up, which is a new book which has won the 2022 Independent Press Award. She also is a creator and host of podcast of the same name. She's a frequent keynote speaker. Magazine Inc. Magazine named Alyssa one of the top 100 leadership speakers and she was named the top startup coach in the world at the Thinkers50 Global Coaches Awards and the number one global guru for startups. She has some great thoughts she's going to share around leadership and some things that she's learned in her career and working with executives. Looking forward to today's conversation with Alyssa. It's great to have Alyssa joining us. I appreciate you taking time out of your, your busy schedule to talk to us today.

I'm so happy to be here. Mark. Thank you so much for having me.

Yeah, well, I guess can you give us just a little bit of your story we won't take. I know you could go, go on for hours talking about kind of your, your journey, but would love to get just an overview for our audience, kind of how you've gotten to where you are today.

Sure. Well, journey is right. I would say that I, when I was in business school, I went to business school originally in order to sort of examine and see why people do things in service of the organization or sadly don't. And once I was in business school at Cornell, I got all turned around and I exited. I ended up focusing on finance and accounting and strategy and exited into PricewaterhouseCoopers and the Fast Track program. Five years to partner. Ooh la la. And I thought, all right, that's it. My life is set. And I think a lot about the Joseph Campbell quote that I love this quote. It says, he says, if you can see your path all the way through to the end, you're following someone else's path. If your path only becomes clear Moment by moment as each foot touches the ground. And that was definitely true for me because I saw my path all the way through to the end. And then I woke up two and a half years in and I thought, this is not it. Right. And so I had kind of a big moment of truth where I thought, I hope I get the flu, so I have to go to work tomorrow. So indeed I got the flu. 18 hours later I was rushed to the emergency room and I got the flu. And I just thought, this can't be no mas. Like I would rather be a waitress. So I had to figure it out. And luckily for me, my then yogi boyfriend dragged me to a conference that we were going to volunteer at, Body and Soul conference. And I there met a coach who spoke to the volunteers. Her name is Cheryl Richardson. And I was like, what is that? I want to do that. And so I followed her around and I just found my, my path and that was it. And then definitely had put one foot in front of the other for 22 years.

Well, if you were able to, and I like to ask this question on the front end of the conversation, if you were able to go back and talk to that 22 year old and give her some coaching, how would you coach her?

You know, in general, my advice to my younger self is always calm down, it's going to be okay. And it's only later in life that I've even been able to approach taking that advice myself.

You wrote, and I think this was in the forward, you said leadership is an unnatural act. And we've got a lot of new leaders, kind of up and coming leaders, but kind of unpack that a little bit as far as what you meant by that statement.

Yeah, well, you know, in my book from Sharp to Grown up, it's the journey of founder to leader, but it's really the journey of all leaders, all new leaders, as you say. And one of the insights you have to realize is that you have to learn how to do doesn't just happen. It's not natural. And the reason is because if someone is screwing up, you kind of want to tell them they're screwing up. But sometimes as a leader, you have to give them confidence and praise them. You don't normally give feedback to your friends or feedback to your family, but nonetheless, when you're in the business world and you're the leader, you have to give feedback to people. You've got to deal with them when they don't want to hear your feedback. So those, for those reasons and many more you have to sort of learn the unnatural act of leadership in order to be successful and grow as a leader.

In the book From Startup to Grown up, it's looking at as far as kind of the founders, but it has a lot of great advice for people that maybe are not entrepreneurs, but they're, they're leaders in companies and definitely encourage everybody to pick up a copy. You talk about as far as that there's different, different aspects and I think you start that correctly, that you have to learn to manage yourself before you manage others. But talk a little bit about that. Just some of the things that new leaders could be doing as far as to again, get kind of the right lens as far as to look at themselves.

Yeah. The reason is because when you're sort of wondering how to handle a difficult employee and you're kind of gearing up and thinking about having difficult conversations with them, there's something in the way for you that hasn't allowed you to do what you need to do for the past days, weeks, months or sometimes years. As in have the right conversation with this person. I want to help you build the tools to do that. But first we have to look at yourself. It always starts with you, but you have to figure out what is going on inside yourself has prevented you from taking action on these situations. Some ways to do that are, you know, for me, and I say in my book, reflection has to become reflex. You have to be able to journal and really get to the power of why, what's in my way, what am I thinking and feeling, what's energizing me, what am I afraid of? That's one aspect of managing yourself. It's about building your self awareness, kind of measuring yourself. I have a few scales in my book where I talk about, you know, sort of how do you communicate? Are you a communicator and you're gregarious and you're brainstorming all the time, or are you kind of keeping your cards close to your vest and not talking? And there's other continuums as well. You have to assess yourself on that. Equally importantly is you've got to really dig into what are the psychological and emotional components which are getting in your way. Like a lot of people suffer from imposter syndrome. A lot of people are just, you know, sort of overly anxious. So mining those things and getting to the heart of the matter and then building the skills and tools to help you manage yourself is the only way you're gonna have the capacity to grow as a leader.

So when you're Sitting down with, with a founder who maybe has, has moved into that, you know, by, by default, they're the CEO and they, they may or may not be the best leader for, for the company. How do you, what do you say to somebody who I, you know, I had a great idea, I started a company, and how do you help them figure out, are you the best leader to kind of take it forward?

Yeah, well, that's a very sensitive question. I mean, when you start a company, you're the only leader, so you better be the best leader. You have to be the best leader, right? Because you're the only leader. And until a certain point of the company, you're actually not a leader. You're a founder. And that requires you to get people on board no matter what, get funding, get people to connect to your vision, understand your vision, and then rally around your vision. It also means you got to jump in and do stuff over and over, and you got to hire people who are also ready to do stuff. It's only in the years that follow where you have to decide, do I want to be the leader who steps away. You know, Dennis Crowley is one of my former clients. He's the CEO and founder of Foursquare. And he said this before my book. He said, at first you give away the boring stuff, like who wants to do the budget meeting anyway, right? And then you give away the stuff that, like, you know, you kind of disappoint, you have to give it away, you know, the marketing stuff, and then you have to give away product. And you don't want to give away product, but to become a leader and have the company grow and have you grow, you have no choice but to give it away. At some point, you, the founder, have to decide, am I willing and able to give away all the fun stuff in order to do the job of, like what I call cranking the machine of running the company. Those are actually two different skill sets. And you have to search your heart to decide do you really want to learn what you need to learn to do that aspect of it.

So as you're, you're looking at new leader, what are some of the big blind spots that leaders tend to have? What are the areas that they tend to over and over. And I'm sure you've seen it repeated. You've done this with hundreds of founders and startups. Leaders talk a little bit about that. What are the common things that people miss?

Yeah, without a doubt, one of the common, I think the most common is that you are the expert on your Intention. Everybody around you. Founder is the expert on your impact. And leadership development in part really requires you to marry intention and impact. People don't realize that they come across in a certain way. You know, they're only inside of themselves. They're not, they're not with themselves. So they don't realize that they're coming across a certain way. Maybe a little bit too forceful, maybe at times, times sometimes kind of snippy. They don't realize people are kind of afraid of them because they're new employees. And then they're like thinking, oh, this is the big CEO, this is the big founder. And they're just like, oh, the founder's like, oh, I'm just me. Like, why would anyone be afraid of me? So all those things have to do with self awareness and awareness of their situation. That is the most common thing I would add. You know, with founders and with all leaders, you have to realize your suggestions are orders, your brainstorms are orders, your inklings are orders, and your orders are orders. And just becoming aware of that is another common blind spot.

I've heard it, it said by, by leaders that you have to be careful, especially when you're, you're in charge of a meeting, that you don't offer all of your thoughts on the front end of it. How do you coach as far as leaders as they're, you know, either moving into a new situation or they have their first team around them, what are some tips that they can do to, to be a better leader and in meetings and getting, you know, the team to, to kind of rally around.

Yeah, the first thing about meetings is to be clear what the purpose of the meeting is. Right. So it's like you bring people into the meeting, you're like, we're going to talk about all these things. You've got to be per, you've got to be purposeful and clear what the outcome you're looking for in the meeting and then drive the meeting to that conclusion. As you know, I have a whole chapter on meetings, so I'm obsessed with meetings. And just to say that one of the aspects of you as the leader is to get clear on what your role is in the meeting. So sometimes your role in the meeting is to actually get what everybody else wants to, what they have to say, as in actually understand where everybody else is on this topic, whatever it is, what their point of view is. If you jump in and you give your point of view first, you're tainting the entire meeting and everybody's going to want to follow along with your point of view. Many people are anyway. And so it's really important if you really genuinely want to get people's point of view that you've got to be quiet to let them all speak. Also, what happens very often in my experience, I have a founder who is constantly asking me or had been asking me, why don't they participate in meetings? As in why am I the only one speaking in meetings? And I asked them for their input and they just clam up. So I observed a few meetings of his and the answer is because he jumps into fill in silence and he tells everyone what they think, what they should think. He tells everyone what he thinks and then he's wondering why there's an awkward silence when he asks for their input because he hasn't given them the space in the room to actually bring themselves to the table. So it requires self management to be able to really come to terms with what it takes to lead meetings.

So when you're, you're looking at a leader that is hiring maybe the first executive team, what are some things that you encourage them to do? And again, what are you, as far as you're coaching them, what are you telling them that they should be looking out for as far as hiring that first staff?

The first exact. Yeah, well I've just been discussing this with the founder. So it's very top of mind. Basically you've got to really think about what are the jobs to be done. So people will say, oh, I want a CFO who is experienced and knows how to, you know, run the finances of a company. And I'm like, well that's very unspecific. Like what specifically are you looking for in terms of the jobs to be done by this individual? Like that's really important for you to get a handle on. Because for example, for a cfo, you might want that CFO to really be great at helping you achieve the right gross margin. Or you might, that might want that CFO to be very operational and be very great at running with the OKR system or whatever the systems of the company. Those are two very different CFOs. So you've got to get clear about what your expectations are for the jobs to be done and what are your top three priorities and then what are the cultural attributes you're looking for too? What happens? People hire people who are smart but not collaborative, or collaborative but not proactive, right? So then things don't get done the way you wanted to get them, wanted them to get done. So you got to think about what am I actually looking for in terms of building a culture around here? It can't just be smart. It's got to be some version of, let's say, proactive, be able to hold themselves accountable. How do you, the CEO, expect to be managed? Do you want them to be constantly telling you what they're doing? Do you want to assume they're just doing it? Not. Not check in with you, whatever that is? It's very helpful for you to get that in your mind's eye. And then when you interview the candidates, you want to look for very specific evidence that they bring those cultural attributes and also those specific experiences in jobs to be done so that you know what you're getting. What happens is people don't think about that specifically. They don't think about that clearly and with enough, let's say, structure. And then they hire someone and they're wondering, oh, I didn't hire the right person. Like this is, they're not doing what I wanted them to do. And then I would add, most importantly is you have to also think about how you onboard that person, because that's a critical part of hiring, too.

You've worked with a number of companies that are now well known that they were that in that startup phase, and now they've grown to be household names. Talk a little bit about the CEO as a talent magnet. What, what do you see that the, you know, talk about hiring and just things to look for. But how do you attract, as far as talent and what do you see as characteristics and the CEOs that are able to build those teams that attract, you know, the. The right talent?

Yeah, the CEOs who can attract the best talent are tenacious, are focused on talent, and are building a culture and a brand that people want to attach themselves to. And I absolutely think that the CEO needs to be a talent magnet, because what's going to happen for sure is whoever you hire on your executive team, early days are not going to be with you necessarily on the way to, you know, the bigger company. And so you've got to be, in your mind's eye, constantly be on the lookout for people that you can recruit and bring to the team to add in, to fill in the gaps, to be the right people right now. And you, the CEO, are the ones who. The ones who cares the most. And you, the CEO, had the most credibility to attract the right people to the team.

I think one of the things, and you have a chapter that talks about managing the board. I think that's one of the roles that new leaders, maybe they haven't had the responsibility and working with the board. Talk a little bit about that, the mindset and what do you see as far as new CEOs mistakes they make and what would you encourage them to?

Yeah, so what I say is that you should treat the board like another direct report. Like, wait, what? Because they manage you well. Yeah, but you've got to manage the board and you've got to put the time and effort into managing them the way you have to manage a direct report. So you've got to assess the strengths and weaknesses of your board members. And I have in my book a taxonomy of the board members that you may encounter as you, as you build your startup, some of which are, most of which are kind of, you know, interesting characters, let's say. And if you kind of get a sense of the strengths and weaknesses of each board member, you've got to think about how do you build board culture? How do you build the expectation that we're all working together? Because that's going to help you. If they're working together, it's going to help you ultimately run the board and build the company. And then also what are the expectations back and forth with your board about how much information to update them with, when to have board meetings, really understanding their expectations, and you also completing and sharing your expectations. Strong communication is always the right answer. And setting clear expectations so people are not surprised is also very helpful.

What do you say to somebody who maybe gets sideways with a board? I'm sure you maybe have coached a few CEOs that maybe things have kind of derailed. Is that possible to get, get back on track and once.

Absolutely. I mean, there's a story in my book that I tell about one of the most dramatic experiences where the CEO, basically the board member told him, if you don't replace yourself as CEO, then right then, then I'm going to be off the board. Right. I'm trying to get you fired. Basically, like, okay, that's really intense. So he had to really swallow hard and both swallow his pride. Let's say the CEO as well as really determine what's going on around here. There's a reason my board member is saying that. So I've got to get over my hurt feelings, over my ego, over my defensiveness and ask the question, why is he saying that and what do I really need to do? So he kind of had to eat humble pie and fly out to, you know, the location of this board member and have the conversation without getting all upset and Bent out of shape. The board member himself, not being a softie, right? So not being himself, an enlightened guy, but he had to listen to what he was saying. And ultimately, because he listened, because he heard, because he then started adjusting his behavior, the board member not only agreed to stay on the board, but also actually offered and was effectively mentoring him. That's because he was able to get over the drama of, you know, this guy doesn't like me. This guy's crazy. And turn it into something positive and powerful for his own development.

I love to ask executive coaches some of their favorite questions just to help people get back on track and maybe come up with some solutions on their own. What are some of your favorite questions that you like to.

When I'm coaching.

Coaching? Yep.

Yeah, I'm very. I'm very coachy. In fact, my. My clients will mimic me, and my. I have one client in particular. They're so used to me doing this. So when they ask me a question, one of my favorite questions is, what do you think? As in, what should I do? What do you think you should do? That's so coachy. Right. And then also they'll then say, I don't know what to do. And then I'll say, well, what if you did know? Right. That's really just holding space and being a placeholder for, calm down and think about it for a minute. Right. You know more than you think. Also, I love the question, what would you do if that weren't a problem? As in, like, oh, we do have. We're struggling with this problem. This problem. This problem. And they get so mired in the problems that they forget that actually there's a bigger picture here. There's a bigger vision and a bigger picture. So I like that kind of question, too. And I like the kinds of questions which are just kind of deep. As in, like, what is that like for you? What does that feel like? The reason that managers and leaders should use questions like that is like, some employee will come. This is a problem, or they'll be disruptive or defensive and being defensive. Usually if they're defensive, you get defensive, and then you get defensive, they get defensive. But if they're getting all defensive, you could say, gotcha, I didn't mean to make you defensive. I'm wondering what's going on with you. And then it just kind of ratchets it all down because then they may share what's going on with them, and that'd be really powerful.

I was listening to your podcast with Tim Ferriss, and Encourage everybody to listen to it. It's. I told, told you. It's. It's a long podcast, two and a half hours, which he's got long form but great, great information and stay till the end. You've got some great scripts that I think will be helpful for people. But talk about the importance. And I think you've done this with. I think you've coached him as far as personally and, and he talked about an exercise where you went out and gathered feedback as far as. From those that work with him. And you've done this with a lot of the executives talk about that exercise and the importance of getting, getting feedback and honest feedback and stuff that you maybe, maybe don't want to hear and just the importance of that.

Yeah, the importance of 360 feedback is to illuminate blind spots as well as to really see the impact of what you're doing, which is not working as in the bad stuff you're doing, as well as to really see what gifts you're bringing when you do the good stuff you're doing. And it's all of those things. And so what I do with all my clients is I go out and I get 360 feedback and I ask people around them, what are his strongest strengths, what he seems to get better at, and what specific behavioral suggestions do you have for him to make him a better leader? And then I debrief that with my client and you know, two of one, they all get defensive and annoyed and upset. I don't blame them. And then we calm down and then I help them make meaning out of it and create a plan to help them capitalize on their strengths and work around their weaknesses.

What are some other things that you think are important for a leader in that first, you know, few years to whether, you know, personal development or whatever that would help them to, to get on, on the right path as far as in their leadership?

Well, I think personal development is the name of the game. I think you have to think about what's going to enrich me. So, you know, how. What do I need to read in terms of leadership books or what do I need to read in terms of like getting a handle on myself books? I personally am very Buddhist. I've read a lot of meditation books or that's kind of a moxy moron, right? But I have read meditation books, but I've also listened to and really done my own work, my own inner work on meditation and kind of pursuing some spirituality. You need to have something that you can hold on to it's also getting clear on your values. What's the most important thing to you? I really believe in a strong both morning routine as well as just an overall fitness program. Everyone should be on a fitness program. It really helps you with your stress and it's sort of anxiety and it's also just healthy for the body. It helps you cognitively. So those are the kinds of things that I think everyone should be doing. But I certainly think if you want to be an effective leader, you need to have something like that in place.

So you talk about need to read books. What books do you recommend? Again, put your book on the list for our listeners, but what are some other books that you encourage people to read?

I really love Crucial Conversations by the folks who did Vital Smarts. They have a whole bunch of now crucial conversations. Crucial Conversations, crucial confrontations. The influencers change anything. And I'm sure I'm missing one, but those are all very practical and helpful tooly books about how to build your influence, about how to have difficult conversations, which is so important for people. I love the Patrick Lencioni series, especially Five Dysfunctions of a Team I think is excellent in terms of thinking about a model and a framework for leadership. And I love the Leadership Challenge by Kouzis and Posner, which is a big, thick yellow book, but it really talks about kind of the importance of how you build credibility as a leader.

So outside of work, what do you like to do to recharge? You mentioned a couple things, but what are your, what are your passions and what do you do?

Well, one of my passions is fitness and I, I'm obsessed with kettlebells. And so I. You can follow me on Facebook or Instagram and you can see my irregular regular videos of me and my exploits with kettlebells. I also I've created a rap music video about executive coaching that was my pandemic project. It's called the work is in you because the work is in you. You can find it on YouTube. And I also love Broadway theater.

Well, any parting advice for a new or up and coming leader that you think would be helpful as they're starting their journey?

Keep going. Build resilience. Build a morning routine. Find mentors. Find a coach, whether informal or formal, and keep going. One thing I will quote Jeffrey Pfeffer on. He is a Stanford professor and very big on the topic of power and influence. And he said something which was so simple, which I think is important for all of us. You're going to screw up the most important way for you to be successful in doing what you want to do is to build the resilience to try again and keep going.

Great advice. How would somebody learn more about your work? And definitely going to check out your wrap.

Thank you.

But how would they find out more about you?

Sure. Well, you can look me up on the Internet. You can go to alyssacon.com backslash startup and find out more about my book. You can download five scripts for Delicate Conversations and one to make your life better at alyssacon.com forward/scripts. And you can also find my podcast, also called From Startup to Grown up, wherever all podcasts are found.

Great. Well, let's say I wish you continued success as as you continue to help leaders grow and definitely looking forward to your next book. I know you, I think you said this book took you 10 years at least in the process and so I'm sure you've got another one in that you're going to start thinking about writing maybe, right?

Yeah, maybe. We'll see. Thanks, Mark. I really enjoyed the conversation. Thank you so much.

Absolutely. Thank you for listening to the Motivated to Lead podcast. Please subscribe on itunes. You can also see a video version of this interview@ motivatedtolead.com this podcast is brought to you by SEMA Partners, helping you find your next great leader.