105 From Startup-up to Grown-up with Alisa Cohn

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On today's show, we sit down with Alisa Cohn, who is named the number one startup coach in the world at the Thinker50 Marshall Goldsmith leading Coaches Award in London. She was also named one of the top 30 global gurus for startups based in New York City. She coaches startup CEOs, co founders, other startup executives, and board members all over the world. She also coaches senior and emerging leaders from Fortune 500 companies. Her clients include Venmo, Foursquare, Envision, Etsy, the Wirecutter, sold to the New York Times, Pfizer, Novartis, Dell, Hitachi, IBM, Calvin Klein, and many, many more. On today's show, we talk about how can praise be your secret superpower when measuring performance? What should be measured? How does the CEO manage their board? What should one do when their co founder can't keep up? What is the CEO megaphone effect? And much more. This is an exciting episode filled with a lot of amazing information that I'm sure you're going to want to listen to multiple times. Without further ado, let's start the show. Enjoy.

Welcome to the Silicon Valley Podcast with your host, Sean Flynn, who interviews famous entreprene venture capitalists and leaders in tech. Learn their secrets and see tomorrow's world today.

Now, I'm super excited about today's episode. I'm sitting down with Alyssa Cohn, who was introduced to me by Jeffrey Wolman, who I've met through a CEO coaching group here. Now, Alyssa is a top, top global CEO coach. I can't tell you all the accolades she's won our audience. Everyone here should be amazed and very happy for today's interview. But enough of me talking, let's get right into it. Alyssa, can you tell our audience a little bit about your career up until this point?

Yes. First of all, Sean, thank you for having me. I'm so excited to be spending the time with you. So I'm an executive coach. I've been an executive coach for about 20 years. I work with CEOs and other leaders to help them really think about where are they, where are they going and how are they going to get there. Before that, I was the CFO of one startup, the head of strategy of another startup, and I was also a strategy consultant. And before that, I was in the nonprofit world. So I had kind of a checkered past until I found my love, passion, and vocation of coaching.

Now, how important is it for a CEO to be able to take feedback, to be able to be coached, the.

Truth is that learners win when you're a leader, when you're the CEO, especially if you're the CEO of a startup, your whole job is to be learning rapidly, adapting rapidly. So what that means is you're taking feedback all the time from the environment, from your customers, from your board, from mentors and advisors of yours, and then certainly from the people around you who are the consumers of your leadership. So the idea is that, hey, if I think about what does the customer want and then adapt my needs to the customer, really you have internal customers as well. And the consumers of your leadership are the experts on how you show up and how you're motivating them. What I always say to CEOs is you are the expert on your intention. Everybody around you is the expert on your impact. And marry intention with impact is part of really the joy and the goal of leadership development.

Now, speaking of the CEO's impact with what's around them, what is the CEO megaphone effect?

So the CEO megaphone effect is the fact that when you are the CEO, and this is really especially true when you're the founder CEO, your suggestions are orders, your observations are orders, your inklings and your brainstormed ideas are orders. And certainly your orders are orders. So what that means is you as a CEO have to realize that whatever you say, even if you think you're whispering it, it is coming out in a megaphone, directed at the people that you're dealing with, your employees, your other executives. And they're going to go off and do that thing whether or not you wanted them to. And it's important for you to realize that you have that multiplying effect, that voluble effect, the megaphone effect. When you're the CEO now, you said.

You had been, or you do work with a lot of startups. Now, many of these startups, what the CEO is facing is probably the first time in their career they've actually ever done any of these things. How common is it for them to have the imposter syndrome? How would they get over that? How would you address it?

It's just normal to, as you say, address things for the first time and feel like an imposter. I mean, when I think about the founders that I work with, I just talked to a founder today and he said, I've been a serial entrepreneur. This is his third startup, and this is the biggest he's ever gotten. His other two were acquired when they were smaller. And he said, I've never really had a job in corporate America. I had a job for two years, and then I immediately became a founder. I didn't really get a lot of education on what it is to lead and how to lead. And so he recognizes that every new stage that he's in kind of puts him in a spot where he's never been in before, where there's no playbook. He's had to really deal with the imposter syndrome that he's come up against. And I would sort of think about it differently for in my book, I interviewed Susie Batiz, who's the founder of Poo Pourri, and she said, I don't have imposter syndrome. I am an imposter. Right. Because I've never done this before. And that gives people permission to have never done that before either. And they've got to find various ways to invent the right answers for themselves while maintaining confidence, even in the face of a normal sense of being an imposter.

I guess while they're trying to find out more about themselves, is that something where they should allocate a certain number of hours every day or how do they go about finding out more about themselves to grow into what they're doing or actually above what they're doing to the next steps?

Right. That's the whole point. You can't just devolve into what you're doing now. You have to evolve into the sort of the company that you're going to create. So when you start a company of 10 people and then 20 people, and then 50 and then 100 and then 500, then 5,000, you have to realize that your job is to adapt rapidly, just ahead of the curve of that scale. What that means is you have to set aside time for sure, for reflection, for journaling, for recognizing your triggers and what sets you off, for recognizing what shows up that makes you feel demotivated, that makes you feel drained. And then also a360 feedback is very helpful so that people around you can weigh in on what's working and not working about your style. Because the truth is that a founder, a CEO, as you grow and the company changes around you, you're going to have to communicate differently. So at first, when you've got 20 people in the company, you're all in the same room. You can casually just share your thoughts. When you're 100 people or more, you have to have formal all hands. People aren't going to necessarily hear what you're saying. In the all hands, you have to make sure you have leaders around you who are repeating the critical messages. So People understand what's going on. They're all staying in sync together. As you continue to grow, you have to continue to adapt your style around communication and around leadership. It's about seeing what's working now and not what worked last week. So the playbook that worked last week may not be working now. And you have to be constantly adapting.

As the CEO, how would you get feedback or know that last week's playbook isn't working this week, and this week's playbook isn't going to work next week?

So one way to do that is to make sure you have people around you who will tell you the truth. So one CEO I know, he says the price of entry to this meeting, the leadership meeting that he has, is to share with me bad news. So that means that people get used to sharing bad news with him. And what that means is if what he just did in the all hands doesn't work, didn't work, or if he's sort of thinking about if he's messaging something in a certain way and it's not resonating with people, that executive in the leadership meeting feels empowered, in fact obligated to say, hey, this thing that you're doing is not working. The way you are handling this kind of casually is not working. Or maybe you're handling something too formally and that's not working. Also, it's important to have skip levels throughout the organization so people get comfortable with you, so that people are willing to give you bad news, even about yourself, when it's necessary.

Now, most of our listeners are either VCs, but a huge part are entrepreneurs. You just said skip levels. A lot of these people have only had companies with four or less employees. What are skip levels?

So skip levels have to do with. When you're the CEO, you have an executive team, a leadership team who reports to you. And let's say that's like six people or eight people. They have direct reports, too. So your job as a CEO is to have every once in a while, touch bases with the people who report into your executives and maybe even the people who report into them. So you get to know the people, your employees, not just your executives, so they feel a bond and a connection to you, so you can really show up as the energizer, as the founder, as the inspirer, and also that they get comfortable with you and they can share things that are not working in the company without feeling too intimidated.

Okay, now in your book, you also mentioned praise is your secret superpower. Can you go into detail what you mean by this?

Thank you, Sean for mentioning my book. My book is called From Startup to Grownup and it has to do with that journey of going from founder to CEO. What I find with founders is that founders are extremely self motivated and self determined. They're not looking for praise from the outside world and they're often not getting praise from the outside world because what they're doing is often bucking conventional wisdom. Therefore, they may not be attuned to how important praise is. The other thing about founders is very often they are never satisfied and even self critical and they're always striving for more. They're looking for more from their employees also. So they forget that their employees who are not founders need praise. They need to know that their efforts matter. A lot of research has been done on what motivates people and the thing that motivates one of the top things that motivates people is seeing progress, seeing the impact of their work. And when you're a founder and you're in the middle of building a company, millions of things going wrong, things are going wrong all the time. And also you don't always know if you're winning because it's like, well, we got that customer, but we need so many more customers. Or we had that win of some sort, we built that product and we released that product, but we don't really know how that product's going to do. And then moving to the second product. There's a lot of questions and confusion inside of a startup. You as a founder have to find ways to merchandise progress for your team, show them the progress they're making, and then praise them for little things and big things so that they feel good about their contribution. When I say little things, I have a story in the book about an employee handing something to the founder and the founder going, uh huh, receiving it and thinking, I talked to him later thinking that was good, but not saying that was good. So the employee goes back to his desk and he's like, it didn't seem like he was happy with that. I'm not sure, what did I do wrong? And spending an hour trying to fix this perceived mistake, which wasn't a mistake. But since he got no reaction and no positive reaction from the founder, he's thinking, maybe something's wrong. And then equally when employees don't see the bigger picture, we launched this project, we launched this product, we were able to get these customers, we got this much revenue, people aren't sure, well, is that good? Are we on track? And founders have to Signal their people and give them signals of that progress they're making. So it's about praise, it's about pointing out good things and progress, and it's about showing people the path to victory.

Now, how much of that would you say is the culture of the business or the company?

Culture is a big topic and for me it's one of my favorite topics because people think that culture is like, be nice to each other or be honest. No culture has to do with the embedded systems that we use and the rituals we use to, for example, celebrate success, showcase wins, even help support each other as employees, give each other positive feedback and positive praise. And those are the kinds of things that if they're embedded inside of the life of companies instead of the day to day, through practices and through rituals, can actually get you so much more discretionary effort from your people. So that's the thing. It's not just like, oh, it's nice to do. It actually gets you more from your employees because they're motivated more, because they realize they're making progress and that their efforts are appreciated. I think it's a really important element to embed into your culture.

Now, do investors, do venture capitalists, do they look at a culture of a business before writing a check or is that just the thing of it'll get fixed later?

Venture capitalists and investors are increasingly understanding the value of people. So people make up the culture and I think they're increasingly understanding that a founder or two or more founders who have an understanding that it's important to build a team and have the right people around you and it's important to embed in them this culture, the culture of discretionary effort and a unique selling proposition. I think they recognize that a culture is distinctive for companies and helps great people stay when things are bad. And also even when things are a little bit out of control and when good people stay at a company, the company is more likely to do better. I think enlightened venture capitalists are seeing the business value of culture creation. I think founders probably for that reason are also understanding it more now too.

I'm just curious, side question, do you think that there's a lot of talk of ESG investing and that do you think they're going to have a culture category with ESG in the future? Or how much do you think culture outside people are going to really ask questions? I'm only going to invest in a company with good culture.

That's an interesting question. I mean, I don't think that culture is going to be ESG investing is an arm of maybe a train of thought or philosophy which I think is still being defined. I don't think it's going to be about investing in culture in the same way, but I do think that there are well known toxic cultures that investors are uncomfortable being associated with and I think they've gotten caught and are uncomfortable being associated with them. I think this notion of wanting to make sure there is a comfortable culture, an inclusive culture, is going to maybe be an increasing priority for venture capitalists and also for all investors. I'm not sure if I see it as its own category. It's hard to measure what's a good culture and what's not a good culture. I also think that the most important part of culture is that it's distinctive, that people understand what they're joining and they're self selecting into a culture that will help keep them satisfied for a period of time.

One thing that was very interesting, a quote that I remember it had something to do with if there's a discrete job, do some research and figure out if it can be done without hiring someone new, that was it, more or less. But could you talk about this?

What happens with startups is that they start keeping track of things in a bit of a piecemeal way and maybe a sort of by hand way, which means that they keep track of customers, for example, on a spreadsheet. And by the way, that's great at first and especially when you think about lightweight systems and also about minimum viable product and let's do this kind of lightweight. I think that makes sense. Over time you've got a bunch of customers and maybe you've got more than one product and that manual entry on a spreadsheet is no longer going to work because first of all it's impossible to keep up with it. And second of all, it's like, well, where's the spreadsheet? So you want to have a centralized system where everyone can go to look for the information. And then you don't need five people doing that manual data entry. You need a system that's going to create that or that's going to be able to be the caretaker of that. And there's a lot of different examples that start off manual or let's say labor intensive and that over time, as you create systems and processes that people can follow and playbooks that people can follow, which makes it easier with time, and then also implement technology tools and automation tools and other things, obviously you're going to be able to hire fewer people. But you have to recognize as a leader, it's time to now implement these processes and systems and tools and it's not time to hire one more person. That's an important part, certainly important part of scale, and it's important part also of hiring the right people at the stage where you're ready to build those systems. You don't want to hire then a doer, someone who's going to figure it out, a scrappy early stage startup person. You want to hire someone who's going to step back and think, well, what do we actually need here and how can we squeeze more juice out of this lemon?

I like how you talked about the doer versus the more specific, focused person. Talk a little bit about that for our audience. I think our audience is all doers.

To be honest, a doer, especially if I think about early stage employees and if I think about one of the companies I work with now, super early stage, they hire proactive, excited, enthusiastic people who are figure it outers like, wow, let me try to figure this out. And they don't have best practices. They have their intelligence and common sense and that's great for early stage. And then as you get more mature, you want people who are going to come in and build those practices that bring in the best practices from other places and build the right structure, the right tools, the right processes that they know work that they've worked with in other companies and that are going to work here and people are going to be able to get in alignment with them. I guess I would say that you definitely want to bring in different kinds of people at different stages of your company. You want to sort of build scrappy, you want to have scrappy doers early stage and then you want to have more specialized builders later stage. By the way, those people need different things from you as the leader. They have different priorities. The early stage people also can sometimes be almost like primal startup people, which is amazing. You've got your people who come in a little bit later, who are. They're more like employees. They're more like, where's my 401 and where's my career development and where's my health insurance? And they want to get from a job the kinds of things that we expect from that certainly in the US and so it's a different set of priorities and different desires. And so therefore different leadership style and different things are going to make them happy and satisfied inside of the company.

So as a company grows and roles change, what happens when a person that used to be on a team becomes a manager, or someone that was a manager might get demoted and just put on the team. How did.

It's hard, but it's a celebration. We promote people from within. This person is on a team of five people or eight people or whatever it is. The manager left or something happened or we decided we needed to have a different manager. We're taking one of these peers and promoting them to manager. That's fantastic. And it can be a little awkward because these people were all peers on Friday and on Monday, they're the manager. The end of my book. I have a number of scripts for delicate conversations. And those scripts are helpful for, like, what do you say when this sort of awkward thing happens or this difficult thing happens? And one script I have is for a manager, a new manager, to say to the team that he used to be a peer of. You know, I'm the manager now, right? I know you know that maybe it's going to feel a little awkward, but what's really important to me is that you know that I'm here to learn to be a great manager. I want to be a great manager for you. Why don't you give me some input about the things that you're hoping I do and you're hoping that I don't do. I also really want to take responsibility for your career development, and I'm going to make mistakes as I go, so please forgive me. So that's the kind of script that you can use if you're being promoted from peer to manager. And it's just going to address the elephant in the room, which is someone else didn't get that job and they wanted it, or it's so awkward that you were going out with us on Friday and now you're the manager and do we have to treat you differently now? That's one side of the scenario. The other side of the scenario is really hard. It does happen that sometimes person and a company will get promoted to be a manager, to be a leader, and they were a great engineer or they were a great marketer or whatever it was, but actually they're not a great manager. And they're not being mentored. They don't really know how to do it. They may not have a natural inclination and the person that put them in that role probably made a mistake. So now the question is, what do we do with that person who used to be a fantastic individual contributor? Well, if it's possible, you can have the conversation with that person to say, listen, you were great as an individual contributor and as you stepped into this manager role. I see there's ways in which it's not really a fit. What I'd like to do is have with you an important conversation about how we're either going to solve these question marks and development needs with you as a manager or possibly change your role back to where you were really successful and thriving. Well, how do you see it? Because that's an important two way conversation. There are times that that manager realizes that she doesn't want to do it. And so that's really helpful to bring it up. I'm a lover of the truth. I'm a lover of straight talk. And I think it's just really important to be able to have these direct conversations, which are also difficult.

Okay, now what happens when you have that beginning team? Those five people, they're all buddies. They all start at the same level. But as the company grows, the CEO realizes my buddy from college may not be the best cto. We might want to bring in someone else to be be that position and then actually manage him. And what happens to that? The good old boys or we started this together. When more seasoned people are brought in, when there's real money now involved, that.

Is a difficult conversation to have. There's no question. And also what I think happens is that founders and CEOs don't contemplate it. They sort of start this company with their five buddies and it grows to 30 and it grows to 100. And it's all great. And they don't ever contemplate that there's going to be at the beginning, there's going to be a time where, to your point, that CTO can't scale where they need to go. My advice is, first of all, when you hire your friends, you're bringing on added complexity. On the one hand, it's great because you know this person and you've been through the trenches in college or whatever over your first couple of jobs with this person. But on the other hand, you're sort of putting your friendship at risk in some ways because now you're in a professional environment and they might expect you to be the same old person joking around. And that might even be true in the first year or two. But when the stakes get higher, what's helpful is if you've had a conversation with your friend which lays out, hey, we're friends and I'm so excited you're joining this company. I just want you to know that it may mean that we're not going to be able to hang out in the Same way that we've used to. We have to be more careful about, more mindful of that. Because I don't want people to think like I'm giving you special treatment as my friend. And also there's going to come a time where we're going to be successful, I hope. And what it's going to mean is I'm going to bring in more seasoned executives who have done this before. So when that happens, that's going to be good news, not bad news. And I'm going to want to bring in somebody who can mentor you and grow you where you want to go in your career. But I do want you to know that at that time, I probably want to bring in someone more senior. I want to make sure that I tell you that now so it doesn't come as a surprise for you in two years.

That is a harsh conversation to have.

Well, you think it's harsh? It's hard.

No, it's honest.

I think that founders, early stage founders, live to enlightened ones say to me, as successes having been acquired or having gone ipo, they say when I don't have that conversation with anybody coming in, then it sets up a difficult conversation two years from now, three years from now, whatever from that event. When I have that conversation, although you say it's hard, it then prepares the mind for when that happens, which inevitably, if you're successful, it will. With many people, maybe not everybody, but with many people, I agree with you, that's a hard conversation. But I also say, well, pay now or pay later. To me, the difficult conversation you have three years from now is the price you pay. When you don't pay the price.

Nice. Okay, let's go back to when someone becomes a manager, gets that step up. What are the roles? What should a manager do? What should they perform?

A manager, really their job. First of all, what a manager needs to do is have a psychological transformation. It used to be about the manager's like the person who's the manager. It used to be about your contribution. You shipped the product, you created the spec, you finished this sort of section of the project, whatever it is. But as a manager, you have to take your satisfaction and your excitement from the successes and the wins and the completion of the contributions of your team. So you have to really shift what even makes you happy. And that's confusing for people because they're used to, again Friday they were the individual contributor and on Monday they're the manager. And they're not quite ready to support and empower other people. They're still in the mindset of doing it themselves. So number one, it's a psychological transformation you have to make to realize that your success comes from the success of others. Number two, it's about seeing yourself as a conductor, not as a doer. And so you want to help unstick roadblocks, you want to help people think through systems, want to help people mediate grace based in roles and responsibilities. You want to coach people and give them feedback so they can be their best and they can do the best work of their lives. And also it's tactics of management. You have to learn how to delegate, you have to learn how to run a meeting, you have to learn how to have one on ones which support and empower your people. Those are the things that the mindset shift and the heart state shift. And then also just the tactics of knowing how to. How do you delegate without getting in the way of somebody? How do you empower people but still have checks and balances on what they're doing? How do you correct people without making them feel bad? All those things are the life's journey and the life's work of being a great manager.

You mentioned how to measure things without making them feel bad. Let's go a little bit deeper into that performance. What should be measured? How should it be measured?

Yeah. So first of all, it's really helpful to have clear goals. And I know that sounds kind of obvious, but in the fog of war inside of a startup, you don't always have clear goals, especially when you're still trying to do proof of concept or even when you're later stage, you're trying to get maybe as much revenue as you can. You're not thinking, we have a goal we're shooting for. So first of all, it's about having clear measures. I tell a story in the book about how a CEO and founder I worked with his sales team, starting at five people, they were trying to get all the meetings they could, all the qualified meetings they could, which is great. But over time their job was about to go ipo. Getting ready to go IPO is to be more predictable. So they had to bring in a sales leader who understood how to create predictability in their revenue and really turned out to be not as many meetings as you can, but really very clearly. Four meetings a month leads to for every one of their sales reps leads to the enough closing by the end of the quarter to meet their revenue targets. So there what you have to measure is the number of qualified meetings per month for anybody building A product. It's about how do you really be clear about we're launching on Xstate so we have the milestones along the way. First of all, it's about having those clear goals and talking with people so they understand their goals and then bad things happen, things get in the way of goal achievement. It's about coaching and helping people correct mistakes and also looking at mistakes with curiosity, with a mandate to learn. Having people understand that their first job in making mistakes is to learn from them, be interested in them and to continue to grow and learn and correct their mistakes. When mistakes keep happening, then there's a discussion around are you the right fit for the role? Is it something you really want to do? And then over time it becomes increasingly clear if bad things keep happening and they're not achieving their goals and they're not trying, this may not be the right person for the job. But well before that it's just very helpful to create an environment where people feel safe and people feel able to be open with you, the manager and with there are other people around them about mistakes that got made and how to fix them. And that's how you create a learning environment, a learning culture and ultimately that's how you win.

So I'm kind of curious about that with if there are mistakes that continually to happen, is that how quick the company is growing? And what I mean by that is if this company's in hyper growth and they're making mistakes in a three month span, is that similar to a company that's growing slower where the mistakes are made over a six month span? How does, I'm just thinking how does growth affect time allowed for mistakes?

I think the question is how high are the stakes of mistakes when you're in a customer facing bug, when you're selling to customers and you have a product, I'm picturing a B2B company that I work with and they have a product and downtime is really not acceptable. Also if there's a problem, they want immediate customer support, which understandably. So the question is, does the customer support team achieving that high standard? And honestly there's very little room for error there because if you make a lot of mistakes there, you're going to lose customers. And that's the lifeblood of your company. Have you put the right person in that job? Are you really finding the right leader for that who understands the stakes and can coordinate a group of people where even if mistakes are made, still you kind of do what you need to with customer service. And the second thing I would say is that certainly with hyper growth, people are all called upon to reprioritize all the time, work fast and hard. And also new people are coming on board all the time who need to be indoctrinated into the culture and the processes. So it's easier to make mistakes, it's easier to have misses. And I think that that's a little bit the name of the game and you have to build in tolerance for that. But most importantly, you want to try to build in the right onboarding structures, the right tools for people to use and the right backup plans and contingency plans in case something keeps happening over and over.

And going back to your book, there's a lot of terms in your book. Some are kind of commonplace, others I. It was the first time ever hearing them when I read them.

Oh, like what?

Well, I'm just going to name a few because I'm secretly plugging an interview coming up. You mentioned things like Coin Model, Rose Thornbud, and okrs. Now, all our listeners that have listened to our intel series and we got a couple of new interviews in the pipeline for some intel alumni network VIPs. So stay tuned with the OKRs. But Alyssa, can you talk about some of these terms?

Well, the coin model is a model for feedback, which I invented, and I call it the coin model because you want to gain currency with your people. And it's a way to give feedback that can hopefully the point of giving feedback is not to make someone feel bad, it's not to vent. It is specifically to activate change in people. So COIN means. COIN is C, O, I, N. C is for context, which means when you're in a meeting or when you're having these kinds of interactions, it's kind of the where and the when. And then O is for observable behavior. So it's not. You get defensive. It's not you always do this. It is specifically in the meeting. I observe that when someone has a different point of view, you shut down. Observable behavior is you fold your hands and you look down and then you don't say anything else for the rest of the meeting. So I is the impact. So it's context. Observable behavior I is for impact. The impact is that everybody in the meeting feels a little uneasy and open conversation gets shut down and then N is for next step. So therefore I want you to be aware this behavior does show up for you in meetings. And I'm curious how you think you'll be able to stop it. Or may I ask you to stay open and engaged even when someone challenges you and to recognize that actually meetings are for challenge. So that's the coin model of feedback. And what I hope it does is it helps people really unpack what the behavior is. And it really is tuned to helping people improve, not just to vent and make people feel bad. The Rose Thorn bud is a connecting exercise. When you're starting a meeting or even in a one on one or really anytime, you can do a very lovely instant connection with people by just exchanging Rose Thorn Bud. So a rose is something I'm excited about, I'm happy about, something that's going great. A thorn is something difficult that's going on, something that's not great, like a bad thing. And a bud is an emerging possibility. If you say you're Rose Thorn bud and the other person says they're Rose Thorn bud, suddenly you've connected. Suddenly you actually know a lot more about this person. And you can restore or feel empathy and closeness in the relationship. That's a good thing. That makes people feel connected at work. But also once you have more connection with people, you can have a better conversation, even by talking about difficult things.

Fantastic. And we're going to save okrs for a future interview for the intel people. But I got to ask, with all your experience with all these companies that you've worked with, after a while, is it possible to kind of predict in the future problems that might arise? And if so, how would you go about handling them today before they even come about?

Yes. So I'm great at pattern recognition. In fact, some of my clients think I'm psychic. Someone says, oh, he's going to quit. I go, he's not going to quit. And then he doesn't quit. And they're like, how did you know? I'm like, I don't know. I could just tell that guy wasn't going to quit. That guy's too happy here. He likes complaining. That's why you think he's going to quit or whatever. Or when I initially meet a CEO, they will sometimes tell me about Frank. Oh, I have this issue with Frank and we work it out. And then another session or two, they talk about Frank. And then I realized that we're going to spend a lot of time on Frank and ultimately we're probably going to part ways with Frank. I've seen that movie before and I think that's what's going to happen because in part they're asking me for permission to fire Frank. By the time I get there, they probably needed to Fire Frank for like a year, but they haven't done it. I'm here to show up. And by the way, I have been known to be a little bit aggressive sometimes, like, well, it's not working out. We need to terminate this person. And I don't mean to be that way, but I think sometimes we tolerate behavior that's not acceptable and then everyone's got to go around this difficult person in the organization or a well meaning person who's just not doing their job and we can't get them to do their job and then we're sort of quiet about it and we shy away from it. I can predict that probably we're going to part ways with Frank and I can even predict that the CEO is unpacking what's going on with me. And I see my role as someone who can surface difficult topics. So not so much that I'm like, oh, we need to fire this person, but let's surface all the problems and let's understand all the impacts of what's going on and the expensive nature of having this person in the middle of everything and how toxic it becomes.

Okay. Now, speaking of difficult situations, what about a CEO managing their board?

There are a lot of fantastic board members that I have met who are super engaged, brilliant, super strategic, and Most of the CEOs I work with have a reasonable board, which means it may not be perfect, but it's good, well intentioned and there are pretty good dynamic. But there's enough cases of the opposite of that. So in the book I review all the different dysfunctional personalities of board members, but ultimately it's your board. You got to deal with it. So number one, recognize that when you take money from an investor, you're buying yourself a long term relationship and a long term board member. And just be aware, make sure it's the kind of person you want to have on your board. Many VCs are that and also you as a CEO need to take charge of this board. So the way I relate to that in the book is that your board is like another direct report and you've got to relate to them to help get the best out of them as a group. And so you want to create good dynamics and informal relationships and good feeling and camaraderie on the board. And also for you to have strong one on one relationships with your board members so they know how to help you so you feel comfortable sharing what you need to share with them. And so ultimately it was a good dynamic with the board.

I feel like I'm just asking you questions. Where this tough situation and that tough situation, another tough situation. What happens when your co founder can't keep up with you?

My philosophy is let's try to anticipate problems in advance. So when you have a co founder, I think it's very helpful to do what I call a co founder prenup to sit down and have a conversation with each other about your strengths and the other person's strengths and about your values and the other person's values and the image of the company that you want to build and what's going to happen if we have conflict together. And those kinds of things help you make sure that you are working with a person who, for example, wants to grow in the same way that you want to grow, wants to have the kind of outcome that you want to have. If you've done that work and then if you've also talked openly about what happens if one of us is not growing as fast as the other and not keeping up, what do we do about that? To your point before, that's a hard conversation to have, but it lays the table for in the future if that ends up happening now, if it does happen and you haven't had those conversations, it's once again the time to sit down with your co founder and say, here are my observations. My observations are, for example, I'm working 10, 12 hours a day and trying to hold this part of the company together. And my observation is that you're not putting in the same kind of intensity as I am. And the impact is that the teams that you're responsible for aren't producing as much as we need to or you need to grow as a manager. And I don't see you doing that. Which means that the team underneath you is feeling uncared for. There's like gossip going on, there's conflict with the other team. You're not laying in, you're not leaning in. And those are the conversations you have to have with your co founder, which have to do with do you want to learn these things? Because co founders are special. That's your business partner. You've been through the trenches with this person. And also we give allowance for co founders to be the person who has not done this before. You bring other people in, they've done this before. You're a co founder and you have not done this before. So how can I support you in growing more rapidly? It's really hard. And this only breeds resentment when your co founder is not growing, not keeping up, and then you have to figure out what do you want to do about it. Sometimes co founders are very happy to say I'm not up for this growth. I would much rather have a more experienced leader come in and mentor me and show me how to do it. I'd like to report to somebody else. That would be totally fine and a good outcome actually, if that's what people have to really figure out what they want. Part of what I also in the book Early Stage or the early chapter of the book is having the self awareness to know what drives you and what triggers you and how much you want to learn and how much you want to learn about being a leader and building an enterprise as opposed to just learning more of your craft, whether that's product or marketing or technology.

Now we have just a few minutes left, so I really want to pack in the questions while there's still time. So I'm combining a couple right now.

Oh boy.

Can you be a good CEO if you're not able to fire someone, not able to stand to the board, not able to give directions to people senior of your age, can you still be a good CEO? And with all your experience coaching CEOs, what's the one trait that you've seen to determine or to kind of, kind of sway you that this is going to be a successful CEO?

I hate to say it depends. I mean, you've just given me a pretty difficult version of the CEO. So the CEO who can't manage the board can't fire anyone or hold people accountable sort of can't manage. I would say do you really want to be the CEO? However, if you want to be the CEO and you're great, let's say with customers and maybe with the vision and maybe even inspiring in large groups, if you have a strong COO who can do those things with you, you could still be the CEO. It's really about finding the right partner or the person who can come in and be your right hand and step in for your weaknesses. If you are self aware enough to recognize that and humble enough to bring that person in, I think that will work. Put it that way, that will work. And your second question is, what is the most important trait? There are so many important traits. I'm going to talk about two. It goes without saying that perseverance and drive and I'm going to win no matter what and we're going to get there and one foot in front of the other and these problems cannot get the best of me. That is one important trait for all founders to have. If you think about company survival and then I guess I would say openness to feedback. So humility relating to openness to feedback. Because what that does is that showcases your desire and ability to learn. And I think that the biggest trait that CEOs need to have, founders who need to grow them into CEOs need to have, is your ability to learn. And that's about taking in feedback and recognizing, experimenting with style and being vulnerable and screwing it up and getting mentorship. But it's all focused on how do I learn.

Fantastic. And last question, if anyone wants to find out more information about you, your book, what's the best way to go about doing it? And your book at the very end had some scripts to it if you want to. You mentioned it before, but talk a little bit about that as well. I think our audience would really enjoy it.

Sure. Well, thank you. So first of all, people can come to my website, alyssacohne.com, a L I S A C-O-N.com and actually on my website I have a number of additional scripts you can use for difficult conversations or delicate conversations. And that's what I have in the appendix of the book, which is about 11 scripts that you can use with. I include the co founder prenup in that. I include scripts that you can use when you have to layer an employee, a more senior employee onto an existing employee. Scripts you can use when you have to announce layoffs, scripts you can use when you have to give bad news. Scripts you can use to share back the 360 feedback that you got and what you learn. Scripts you can use to have one on ones with your employees. All those kinds of things. My clients find them very helpful to be able to get your mouth around the words.

Alyssa. I really enjoyed this episode. I'm sure our audience is going to listen to it multiple times. There is so much good quality information here. And with that, I want to thank you for taking the time today to be on the Silicon Valley Podcast.

Thank you so much, Sean, for having me. I loved it.

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