E35: “Shifting from control to empowerment” with Alisa Cohn, #1 Startup Coach in the world at the Thinkers50 Marshall Goldsmith Coaching Awards

Powerful at work radio Episode 35 welcome to Powerful at Work Radio, the podcast for professionals who see their work as a calling. I'm your host Rosa Ponce de Leon and together we'll explore how people can position themselves to make a real difference with their work. We will cover topics ranging from leadership to emotional wellness to a true power looks like and everything in between. If you're ready to do work differently, tune in and join the movement. Now, let's get after it. Alyssa Cohn was named the top Startup Coach in the World at the Thinkers50 Marshall Goldsmith Global Coaches Awards in London. Alyssa has been coaching startup founders to grow into world class CEOs for nearly 20 years. A one time startup CFO, strategy consultant and current angel investor and advisor, she was named a Top 30 Global Guru and has worked with startups such as Venmo, Etsy, the Wirecutter, Mack Weldon, and Tory Burch. She has also coached CEOs and C suite executives at enterprise clients such as Dell, Hitachi, Sony, IBM, Google, Microsoft, Bloomberg, the New York Times, and Calvin Klein. Alyssa is a sought after speaker and has keynoted events for Companies such as IBM, PwC, Dell, Standard Charter bank, and Citi Inc. Named Alyssa one of the top 100 leadership speakers. Alyssa is a guest lecturer at Harvard and Cornell Universities, Henley Business School and the Naval War College. Marshall Goldsmith selected Alyssa as one of his Marshall Goldsmith 100 coaches, a gathering of the top coaches in the world. She is the Executive Coach for Runway, the incubator at Cornell NYC Tech that helps postdocs commercialize their technology and build companies. She serves on the board of the Cornell Advisory Council. She has coached public and political figures including former Supreme Court, Chief justice of Sri Lanka and the first female minister in the transitional government of Afghanistan. Her articles have appeared in hbr, Forbes, and Inc. She has been featured as an expert on Bloomberg tv, the BBC World News, and in the New York Times. A recovering cpa, she is also a Broadway investor in productions which have won two Tony Awards and and is prone to burst out into song at the slightest provocation.

Alyssa, so good to see you. How are you this morning?

I'm great. It's so great to be here with you. How are you?

I'm good. Okay. So you're launching a book here coming up in October and it's a very relevant book to our discussion, so I can't wait to hear about it.

Well, let me tell you all about it. It's called From Startup to Grown up Growing your leadership while growing your Business. And it has to do with you, the entrepreneur, building yourself. So it's drawn into three sections. Managing you, managing them and managing it, managing the business. And for all of us, no matter where we are in our journey, we have to think about those dimensions inside of business. Managing yourself, managing others and managing the business overall. And I think that's important for all entrepreneurs and really all practitioners.

And I love the simplicity of how you're breaking this down into three pieces. It's like the three legged table, you can't not have one. And so let's jump into the part where I think most entrepreneurs, they have a really good grasp on their craft and they're really good at executing when it comes to that. But maybe building the teams, they realize that their leadership isn't as strong as they thought. Can we tackle that a little bit? What are the biggest issues that you see there?

Totally. I mean, that's really why I wanted to write the book, is that it has to do with, you know, entrepreneurs and founders don't think about what it takes to build sustainable company. So you have any entrepreneur, any founder, great at their craft, maybe she's a product person, maybe he's a sales guy, or maybe that they are really excited about disrupting some space or building a whole new category, that's fantastic. And they have the passion about building that category. That's great. But then over time, it's no longer you tinkering with 10 other people or you being able to communicate to just 20 people around you. It's about having to build your own chops in, your own skills as a leader to grow. And those don't come naturally to anybody. What I say in my book is that leadership is an unnatural act. We all have to learn aspects of leadership. Otherwise the thing that you want to do, which is build a sustainable product through building a sustainable business, won't be able to happen.

I've never heard of leadership called an unnatural act. So let's talk about that because I think you're absolutely right. I think there's so much to leadership that challenges us and pulls from us and it comes from working with different people and then obviously challenges of the business. But it does force us to step aside and say, it's not about me, I need to transition or grow or adapt. So can you talk a little bit about that?

Yeah, definitely. The reason I focused on managing you first, so it's managing you, managing them, managing the business. You got to manage yourself. So that means understanding yourself and understanding your triggers. Because when you're managing them, you are going to get Triggered because people are frustrating. They understand you and they don't understand what you think you just said, whether you said it or not. But like they are going to be frustrating because that's how people are. When you're managing a whole bunch of people, they won't all be on the same page. Now, anybody might get impatient. Anybody might think, I'm just going to do it myself. Anybody might think this is like you're not doing a good job. What I want to tell you is the truth, which is this is not working. But all leaders have to step back and think, where am I, where am I going and how am I going to get there? So the person who's not doing a good job, you actually have to compliment for the things that they are doing, right? So they can hear you say the things that you need them to change and fix. People who are frustrating, you can't let your frustration and irritation show because that's going to shut them down, especially you as the leader. So you need to control yourself, which is unnatural, and find a way to pick your spot. And even in the middle of sort of pressured situations, it's a lot of work.

I think those triggers are very common. If you're not paying attention, if you don't expect yourself to get frustrated, frequently that you're not going to be ready to not show it, or if you're not managing your emotions leading up to this, where am I, where do I want to be and where do I want to get and have a realistic path or a realistic strategy? I think the outbursts of your emotions or your frustrations are going to be maybe not easy to manage.

Not easy to manage. Especially because we are not always aware of our problems and our little issues that then trigger us. And also because startups are extreme workplaces, they are like a pressure cooker. So you don't have time to step back and reflect and really think about what am I trying to do here. You just react. You add that to the fact that you're working hard, really hard all day long. Maybe you didn't eat lunch. And so also what's going on with you is you're kind of hangry, right? You're hungry and you're angry. Those things we think, oh, it doesn't matter. It matters. So taking care of yourself is also a very important element of handling having.

Emotional self control and those things. When, like I said, I'm hearing you say this, most people what might say, that's just one more thing I got to do, how critical it is to do that one more thing.

Yeah, that is the one thing you need to do. Everybody else can do those things around you. That's the thing you have to do. You as the founder, you as the leader, any leader. Your job is to be a role model. Your job is to orchestrate the work of others. Your job is to motivate and support the people around you doing the work. If you have 10 people on your team, I don't care how smart you are, your two hands and one brain are nothing compared to their 20 hands and their 10 brains. And that multiplies over time. Right. About how big your. Your system is. Right. So it multiplies. So you have to figure out that your job is to orchestrate the work and then organize yourself that way. And then to your point earlier, that's not so easy to do. When you were the one who was always great at engineering, you were the one who was sort of the product visionary. You're great with salespeople or with customers. That's fantastic. But your job now is to manage and to lead, and that's the set of skills you need to develop.

And do you think there's a time there to maybe grieve that disconnect because you're letting go of the thing you love and you're giving it to other people? Here, have my baby. I trust you with this baby, and I'm just gonna let go. How hard is that? And is there a time that we should realistically assign to grieve that loss?

Oh, that's a yes, first of all. Yes. You get it.

You get is really hard.

You know, I worked with a CEO, and he was. He knew himself to be. And everyone knew him to be a product CEO. You know, he's really into the product, and he be caressing and honing and sculpting and fine tuning the product. And that's wonderful. But over time, he really didn't have time to do that because he was busy orchestrating the work, and he had to really hand off all of the product to the new product lead he brought in. And by the way, that was so hard for him. And he kept letting it go and taking it back and letting it go and taking it back. And the work of coaching was to help him and the head of product get on the same page so that he could then give it up. And then to your point, that was not a happy day. That was a sad day, a grieving day. And I think part of coaching is to help people deal with their feelings, grief, which we don't talk about. Right. Like grief, like sadness, like anger, so that they can go out and be the emotionally even killed leader that's needed for the company.

So good. And I think we need to also make room for some disappointments too, because the vision of the new product manager in your example, may not he. He's not going to carry it out. Not may not. He's not going to carry it out in the way that you would do it. And so you have to like, totally not only disconnect from the role, but not assign emotions in response to the thing that is so different than what you would have done.

It's so true. Because at scale, there's no longer your ability to be a craftsperson at that kind of level of minute detail. At scale, by definition, there's a lot of things that are going to be imperfect. You've got to tolerate that imperfection and to your point, live with disapp. That's not quite the vision you wanted it to be.

And it could be better. I compare things to a teaching that I heard on someone that was in theater, Shakespeare theater, for a long time, and he talked about bringing all the actors together. And everybody knows every Shakespeare play, they haven't changed. But yet everyone is uniquely different and great in its own way. And because you bring these different people with different talents, you kind of let them fall into their own. And eventually, once it goes into live presentations, it's wonderful. But I think in the example here, yeah. The person could, could come up with something great.

Yes. That's the upside. I love that you just said that. That is the upside is that you're like, well, it's not mine anymore. I'm giving it over to you. I spoke to a founder recently and she said, I now throw out ideas like this is my idea. And then people will say, how about this instead? And she realizes that's actually much better. And so what's beautiful is your ability to let go of your baby and have others imprinted and co own it with you. And oh, by the way, in the best moments, that turns out to be a better experience, a better product or a better baby.

And do you think, I don't want to leave this conversation just yet, but it occurs to me, does everyone need to be a CEO? If you're the product person and you're not ready to let go, might it be better to find a home for that product that you can still be the lead on the product?

Sure. You know, I think that's really a very powerful question. Like when I sort of the note went from founder to CEO or the idea from startup to grown up. The very first section is, hey, do you want to be the CEO? Like be honest. Because not everybody wants to be the CEO. So what that means is you may want to lead your company of 10 people or 20 people or even 100 people. And then over time you may realize I don't want to give up product or I don't want to give up engineering or whatever it is. You can find somebody to come in and be the CEO and run the team and let you still do what you want to do. There's no problem with that. I talked to a founder a few weeks ago and he said, I figured out that I am really great to the 20 million mark. And then after that this is not my thing, I'm a starter and that's what I want to do. It took him three or four times to figure that out as all of us in our self awareness. But I think it's very powerful to recognize that not every founder has to be the CEO and not every CEO of a 50 person company has to be the CEO of a 5000 person company. Self awareness is the key on that.

That's so good because I think that scaling and growing is such a natural part of building a company. And having that self awareness comes in critically once you start hitting your benchmark, especially if you're doing a great job. So at what point you said this particular ex. It took them three times. At what point do you start having those conversations with people?

Me as a coach?

Yeah, sure. Or just in your experience, when is the best time to bring that up so that people listening can maybe have an idea of something they need to tackle down the line.

Oh, I see. Well, to be honest with you, in real life that tends to happen because of problems like a time we're talking about it or someone's thinking about usually too late. So to everyone who's listening out there, I invite you to really think about what are your values, what are the most important things to you? And if you're starting a company or you're even elevating yourself into any level of leadership, are you sure that leadership is what you want to do? Because if what you want is frankly status and power, there are other ways to get that. If what you want is control, you can think about the ways to get control of without necessarily being the leader or the CEO. Because you have to think about am I prepared, willing and able to think about the needs of others to grow rapidly and to learn Maybe some boring things that I don't really want. Like I really. That are. Don't come naturally to me. If you're not up for that journey, you might want to think about whether or not you want to be the CEO or the leader. If you are up for that journey, recognize that you have a lot to learn and throw yourself into learning that.

You know, that's so good because especially when you said control, I totally reacted and I caught myself. But I find that so many leaders are controlling. And there's a place for quality control, and there's a place for having those controls, and they're very necessary, but not in the leader. Because I think when you have a controlling leader, it totally kills innovation and creativity and independence of thought. We've all probably experienced that at some point.

Totally. Because at that point you're controlling and people kind of wonder, well, if you're here to do my job, then what am I supposed to be doing? And the worst case is when people resign but don't tell you so. They're just taking up space and they're going through the motions, but you're not getting their hearts and minds anymore.

Right. And it's just killing everyone. I mean, there's no satisfaction for that employee. They're unfulfilled and it just becomes a cancer in the company.

Exactly. So you just think about, how do you go from control to empowerment? Control is normal for a founder who. How else would you ever decide to start a company if you didn't think you could control something and if you didn't have a little bit of ego around it and didn't think you were right? You have to have that healthy sense of, I can do something. But at some point, you quickly have to shift from control to empowerment and then hire the right people to empower and train and coach and guide the right people so you can empower them.

Let's talk about that. Because you're talking about hiring the right people. Team building is huge. Even if you're just building a team inside of another team or empowering, empowering people, that maybe you're handed a team, but you need to make some changes. Yeah, let's talk about that.

Well, I think, first of all, you need to recognize that you're managing a team and not individuals. So that means that, yes, you need to manage the individuals as individuals, but you need to think about their output as far as a team. So what that means is you want to think about, well, what is the makeup of this team? What are the strengths and weaknesses of this team as a whole. Is Sarah playing in a spot where she's her highest and best use? Is Eddie playing in a spot where it's his highest and best use? And are they then contributing to the overall work? That's the kind of assessment you need to do. And then I think it's really important to be clear with people about what's working and what's not working. So the way you earned the right to do that is to build a strong relationship, to show people you have their back and to act as an ally to them, to support them, ask them at their weekends, but also put them in positions to succeed and then over time to recognize, hey, I think you're fantastic. Hopefully that's true. And you're doing these great things really well. Hopefully that's true. And if you would switch from doing this to that, that would make it even better. That's the best kind of feedback. Because people think you have my back. There's a reason you're telling me this and I can improve.

I really love that. And in training young people to take on those roles of telling people the truth. Yeah, sometimes that's really hard for people. And always, first of all, if they are good, are you paying attention to the right things and giving them real focused feedback? Not general stuff like I'm paying attention. I noticed A, B and C that you're really good at and you really excel at this. But then what about when they're not doing well? What can you say to that?

Well, that's very difficult. So back to actually leadership is an unnatural act. We adults don't feel comfortable giving other adults feedback. Right. So your point about like, it's uncomfortable. Yep, it's uncomfortable. So then step back. Are you trying to help this person build her career or not? You are. You're the leader. That's your job. So then if they're not doing anything well, you might want to search your heart. How did you make this mistake in hiring them? Or if you received this person from somebody else, might be like, okay, so where do we go wrong here? And kind of like think about that. But then you need to be very clear. Here is prescriptive, it's specific. Here's what I need from you. Here's what you're actually doing. Here are my specific suggestions. So I'm trying to think of a good example. It might be a product manager who is always late with the product and also not getting buy in from the other stakeholders. I mean, that is exactly what you're supposed to do as A product that's like bad performance. Okay. Like, where'd we go wrong? So then it's about sitting down with the person and seeing. Do you recognize that your job is to both be on time with the product and to get input from the other groups? Maybe she didn't know that. Tell her that these are also not skills that you needed to get advanced training in. Right. This is not med school. Right. You could really just do this with your basic interpersonal skills. So then there's a question of I don't ever have time. I don't have enough time. Okay, great. Let's help you with time management. Or they're. They don't get back to me when I ask them questions. Okay, good. Let's talk about how you build your relationship with them, how you do be a better communicator. What you need to do is escalate things in time if that's what's necessary. You get down to the level of prescription with them to help them be more successful. If they then can't do it, a second conversation is maybe they don't want to do it.

Yeah, that's true. That happens. And it doesn't have to be a bad thing. If they tell you that that should be a win. Like, great, we came to an understanding. Awesome. How can we help you exit?

Exactly, exactly. There are probably other roles and by the way, if it's a good person, you can even refer that person. You can even do a recommendation for that person who you think would be a great salesperson or who would be a great. In this case, they actually might be a good admin type or even a junior product manager, but they can't run the whole shift themselves. That's okay.

That's beautiful. And so going back to the idea that you're orchestrating as a leader, you're talking about setting people to win, playing to their strengths in the right positions. And so how easy it is to have that clear sight picture of the strategy and of what's actually getting done versus where are the holes that I need to plug in or that I need to add support to.

Yeah, well, it's really hard. That's why you have to try. Right? That's what you should be doing rather than kind of shaping the product or calling yet another non strategic customer. So the answer is that you really want to have a dashboard that shows you. Here are the most important things we're working on inside of this company. Early stage, it needs to be proof of concept, engagement of users, those kinds of things. Later on it needs to be a revenue goal. At some point you got to get customers to pay for your product. And so it needs to be a revenue goal of some, some way. Then you need to think about internal efficiency. So you have to think about what are the right metrics that I need to have, which may be different from the metrics you cared about a year ago. Are the people that I'm dealing with, do they understand those metrics? Are they able to deliver those metrics and what are we missing? So when you compare people like this one has great people skills and this one has great execution skills, let's pair them together and have them work together, that is really great. But ultimately that team needs to be able to deliver those metrics. And wherever you're missing, you've got to figure out how to train or fill in the skills you're missing.

That's really good. And is creating this a one person show or is. Is there a perfect amount of people to be involved in this development of this big picture?

Well, right, so the answer is not too big.

Right.

But also not just you. Right. So you is your blind spots and your conviction. I was just reading this about, I think it was Clif Bar that when he was creating Clif Bar, he and his mom were making the recipe and he was fooling himself. This is actually pretty good. No, really, I'm eating it. It's pretty good. And he'd share it with his biker friends and he'd be like, this is terrible. This is bad. You're only relying on your own point. You're going to get clouded because you're like, I'm so sick of this. I want to do this. But if you've got 100 people weighing in, that's not a good idea. You've got to have a small group of trusted people who have actually insight. Right. Significant feedback and opinions and that they're relevant about what you're creating and they can help you think about what the top, what those key, what the key metrics are.

So it sounds like that's another mini team that you have to form of its own.

Always. We're always forming. I mean, I think everybody should also have a personal advisory board. Right. That's a challenge group. And that also shows them your. Shows you your potential and is able to circulate around you, which is separate and apart from your company.

Right, Right. So good. So good. And have you done both? It sounds like being a personal advisor, I mean, gosh, you've done everything. Personal advisor and being, being that Member of the team that helps develop those strategies.

Oh yeah. Well, also back in, back in my old days, I was the CFO of a startup and the head of judging those startup. And so in that sense I was like around the table on the topic of like, how are we building this company? I've certainly been on personal advisory boards for other people and I also have my own personal advisory board. And it's like, you know, formal and not formal. But we, none of us can do it ourselves. All of us need other people to challenge us, to support us, to show us a portrait of how we don't already see ourselves.

And what I was going to get to as a follow up question, is it the case that most people are really good at one and not the other or vice versa? So the difference between the person who challenged the personal development of the CEO and looks at potential and then the person who's actually helping with the strategy and the measures and all those things, I don't know.

But it's definitely true that one person never has the whole package. Right? Like, so you want to have a variety of opinions and a variety of skills because people are lopsided by definition. I've never met a perfect person. I don't think you have either. No.

And I wholeheartedly agree that no one person has it all or can see everything. And that's why we need teams.

Exactly. That's right.

So going back to your book, as we start to wrap up here, what was your biggest inspiration to writing this book? And is the fact that times are changing and possibly we're seeing big changes to big corporations where people are leaving to being entrepreneurs. Is there a place for that conversation?

Oh, definitely. I mean, I've been writing this book because I've been coaching within startups for like 20 years. And so I've seen this movie for over and over about the pitfalls, the predictable pitfalls that founders fall into. At the same time, this book is relevant now more than ever because I think we're seeing a massive influx into entrepreneurship. So people, founding companies, people becoming solopreneurs, people realizing that even inside of a corporation, they have to beef up their own entrepreneurial skills. Because really we're all entrepreneurs and we're all the CEO of ourselves.

Absolutely. So good. I couldn't have said it better. Thank you for that. And where might we find your book? Because it's not launched yet, but it's coming.

I know. Well, keep checking my website. Alyssacon.com will give you all the up to date information and it'll be available for pre order probably in the summer because those how these things go. And also subscribe to my newsletter where you will get many announcements about my upcoming book Beautiful.

And you have another project coming up too here in the near future.

Oh, that's right. Well, speaking of solopreneurs, I'm also doing a program with my colleague Dori Clark and we specifically are helping coaches and consultants learn to build their businesses, learn to get more clients, learn to sell, learn to charge what they're worth. Because you can be the best coach in the world. But if you want to stay a coach, you need to build sustainable coaching practice. So you need to learn the skills of sales and marketing to be able to do that. That's with W. Thanks.

So good. That's definitely necessary and I hope our listeners will take advantage of these opportunities to connect with you and look forward to this wonderful book that's coming out in October.

Amazing. Thank you so much.

Thank you.

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