Growing from founder to CEO: Executive coach Alisa Cohn on how to get better feedback

Checking in with people to see if they've noticed your change is extremely powerful. It's probably the most useful way to get people to change their perception. Because as a coach, I worked within a large company and when I first showed up, the CEO told me a story about some executive and the way he had done a certain thing. Five years later that CEO was telling me the same story about that same executive. So I would say to all the CEOs out there, the best way to make sure that people are observing the changes you're trying to make is to point them to them, to ask them if they've noticed the change, to ask for specific suggestions on how they can make this change more rapidly, more consistently, how it would be better for that person, and then do that and then ask again. Because that really cues and signals to people. I'm trying to make these changes and I want you to notice.

Welcome to In Depth, a new show that surfaces Tactical advice Founders and startup leaders need to grow their teams, their companies, and themselves. I'm Brett Burson, a partner at First Round and we're a venture capital firm that helps startups like Notion, Roblox, Uber, and square tackle company building firsts. Through over 400 interviews on the review, we've shared standout company building advice, the kind that comes from those willing to skip the talking points and go deeper into not just what to do, but how to do it. With our new podcast, In Depth, you can listen in to these deeper conversations every single week. Learn more and subscribe today@first round.com for today's episode of In Depth, I'm thrilled to be joined by Alyssa Cohn. Alyssa is an executive coach who's worked with companies ranging from Etsy, Venmo and Invision to the Wirecutter, Google and IBM. Even counting folks like Tim Ferriss among her client list, she's recently summed up her over 20 years of coaching experience in her new book From Startup to Grown up, which just came out this week. It's a great read on how founders can scale their leadership as the company grows, and it's full of tips on how to manage yourself, collaborate better with others, and stay focused on what the business needs from you. In our conversation today, we really focus on what founders and startup leaders can learn from Alyssa's experiences as a coach. We start by getting into self awareness and how tough it can be for executives to truly get candid feedback. Alyssa is a true expert in the art of conducting 360 feedback, so it was great to get her perspective on the right questions to ask and how to get at the root of what people are actually saying in their feedback. We also spend a lot of time talking about what to do with what you hear from why not every piece of feedback is useful to her tips on how to actually enact change and incorporate feedback you've received into your day to day routine. Alyssa also shares why she's such a big believer in closing the loop by regularly checking in with others to see if they've noticed any improvements. Next, we tackled the most common opportunities for growth that she's seen time and time again in her coaching practice, from communication and decision making to how the CEO's own personality is often unconsciously reflected in the company culture. We wrap up by covering how to have effective conversations about layering and letting people go, as well as the reflection ritual that she recommends every founder incorporate into their daily routine. I think this episode will be super helpful for those who are making the transition from scrappy founder to established CEO, but it's also a great listen for any startup leader who's struggling to give away their Legos and looking to get better. I really hope you enjoy this episode and now my conversation with Alyssa. I'm really excited to have you joining us and to have this conversation.

Me too.

One place that I thought might be interesting to start is the topic of self awareness and I think it's particularly tricky in the context of founders and CEOs. And I think as you spend a lot of time thinking about self awareness, getting feedback, growing at the rate that the company is growing, and being able to operate in a way that is consistent with what the company needs at any given point in time. So I'd be interested to talk about if you're the CEO of a company, it could be a 10 person company or 500 person company. How do you think about understanding and figuring out what you're actually doing well and in what ways you need to grow and what tends to be hard about that?

Well, I'll answer the first question first. So the best way to really get insight on what you're doing well and what you need to improve on is 360 feedback. So as a coach I do a lot of 360 feedback where I ask the folks around the executive what's working, what are her strongest strengths, what are her development opportunities, weaknesses, blind spots, obstacles, and what specific behavioral suggestions you have to help her be a better leader. So that is like where the consumers of your leadership are the ones who are able to weigh in on how your leadership is landing because you, the CEO, are the expert in your intention, and everybody around you is the expert on your impact. So leadership effectiveness is definitely in part, about marrying intention with impact. So that's the way you get, like, an insight onto what's going on around you. And I guess I would say if you don't have a coach doing that with you, and for you, it's just very helpful to set up the right relationships with the folks around you so they can offer up suggestions on a regular basis.

I'd love to come back to your role as a coach in terms of pulling this information out of, in this case, maybe an executive team or something like that. But outside of that, to the second point, if you are the CEO and you want to create the dynamic or the structure or rituals or what have you to get that feedback, can you share more about how you go about doing that? And I think in any sort of potentially hierarchical relationship, there's challenges to that in terms of getting direct and clear feedback.

Definitely. And the challenges grow as the company grows, and maybe you become more important in the eyes of the people who didn't used to know you. So the challenges just get harder on that. So I think the way to think about that is to, first of all, really proactively seek out suggestions on a regular basis. So sometimes it's, what do I need to get better at? And people don't want to tell you, but if they are able to just offer a suggestion, that can make people feel safer. And when you ask over and over and over again, you kind of communicate and signal, I'm serious, that I really want that. And that could be from your executive team. It could be from folks one or two levels down. It could also be from people who have been with the company a long time, so they knew you when it was just 10 people, and so they have a different kind of relationship with you. And then the opportunity and the way to do that is to reward that behavior. It could be that they publicly say, you know, I got this feedback from Brett, and I got this suggestion, and I'm going to start doing that. And I really appreciate that, Brett, that you shared that. If the CEO will share that in a public forum and recognize that feedback is appreciated, suggestions are appreciated, and that we're all learning here. It does a lot of things. It helps people feel safer giving feedback and suggestions, and also it showcases that we in this company are all learning together. So then it creates an environment where people are expected to be learning. They don't have to know everything or be Perfect to be great at their jobs. And that also a lot of good culture in that company where people are learning together, looping back.

When you're running 360 feedback processes and you mention this at a very high level, obviously one of the things you do is sit down, in this case maybe virtually with folks on the executive team when you get together with those people. Let's say you're working with a CEO, it's a 200 person company, and you're talking to his or her VP of marketing. What are the questions you're asking? What are you trying to learn in that time to be able to translate it into useful feedback?

First of all, I'm trying to establish rapport very quickly because I want to make sure they're able to tell me the uncomfortable things or the things that they're not quite sure if they should bring up. So I really spend time trying to make people feel safe and letting them know this feedback is confidential and that I'm not going to say who said what. So I'm going to give the comments and the feedback back to the CEO, but I'm not going to say who said what. And that also if there's any inklings or observations they have, it's a good time to share them all in service of the CEO being a better leader and ultimately the company being more successful. So I really frame it like that. And then what I talk a lot about is when they say, well, I think he's a great strategic thinker, then what I want to do is say, well, what does that look like for you? What do you mean by that? Strategic thinker is like one of those examples that can mean a lot of different things to a lot of different people. So my drilling down and asking specific questions about does that mean that person's a long term thinker? Does that mean this person sees around corners? Does that mean the person is proactive? Which sometimes that's what strategic thinking means to people. And then once I get an understanding of the clarity of what they're talking about, then we move to development opportunities. And that's when I really dig in. So they might say he's not collaborative enough. And so then I would say that's great. What do you mean by that? Well, and that might be he's always interrupting or he has one on ones with people and doesn't share the information with the rest of us who need to know it. Those kinds of things. And then I will ask sometimes about the specific questions that me and the CEO have decided are helpful. So for example, what's his communication style like? Or how does he influence others? Or do you think he's more external facing or more internal facing? And what does that balance look like? And do you think it's the right balance, those kinds of questions? And then again, I kind of keep digging in for specifics. And then what I like to do at the end especially is to ask for specific behavioral suggestions. Because again, if we're thinking about someone being more collaborative, just as a good example, what that looks like to everybody is very different. So I want to get their specific idea of what does collaboration look like. In this case, it might be he should let everybody know once he's made a decision, he should ask for everybody's opinion inside of the executive team before he makes a decision, that kind of thing. And then I feel all of that back to the CEO anonymously and we go through it. It's really important to say the CEO doesn't have to and often doesn't take all the suggestions that come out of this process, but it's very helpful for that person to have a roadmap of what his direct reports and other folks around the company want to see from him as a consumer of his leadership.

Two things popped into my head. One is how do you think about about the truth in the feedback that anyone is giving and does it matter? One of the things that I've found as I've explored this topic over many years, is that a lot of times someone's feedback is more a reflection of themself and sometimes their own challenges or opportunities, more so than whatever the actual piece of feedback about that person. Does that matter? Or all feedback should be treated the same and it doesn't matter effectively how reflective it is of reality.

First of all, I totally agree with you. Very often feedback is a reflection of the person's concerns or their own, let's say, issues and shortcomings. I think what's powerful there is that I don't ask one person, I ask eight people or 10 people or 12 people. And so themes definitely emerge from talking to a good sample size of people. Recently somebody said to me, I can't get a hold of him when I need him. And I said, okay, well, tell me more about that. Well, I try to text him, I try to email him. I need him. He doesn't get back to me, I don't know why. And then I say, okay, that's great. So have you addressed that directly with him? No, I haven't. I said, okay, how come is he not accessible. Like, are you concerned? Are you afraid? I just don't want to get into a confrontation. That's what the stakeholder said to me. So I said, well, is that the way he is, that when you bring something up to him, he'd get into a confrontation? He said, no. I bet he would take it pretty well. I just feel a little uncomfortable. I say, okay, great. Well, let me ask you to do this. I'm talking to the stakeholder here. If you want to take on a challenge, I would invite you to give this feedback to him directly and to see how that goes, if you feel safe doing so. And I tell you that, Brett, because very often, as the coach, I am definitely the receptacle of a lot of concerns and issues and topics that actually they could raise to the CEO directly. But for many reasons, they don't. Going back to what we said earlier about sort of the hierarchy and part of, I think, of my role in being in the system is to help people have more direct conversation and feel safer having the right conversations one on one.

That makes a lot of sense. How often do you find that people then go and have that conversation?

About half the time. So then it's like, how come they didn't do it the other half? You know, I think about that endlessly. People will make commitments to me, for example, I'm very into, like, when are we going to do what and who's going to do what by when? So I'll say, great, so when do you think you'll be able to do that? Oh, by next Friday. Okay, great. Do you mind sending me a note just to confirm that you had that conversation? I'd really be curious about how it goes. And most often people commit. I won't say most often, but I would say half the time, maybe even a little more than half the time, they don't follow up on their commitments. And I think that's endlessly interesting and also shows me how at least some people in that environment relate to commitments.

So I want to talk about that specific idea in a second. Something that I've noticed is we've tried all sorts of different feedback mechanisms. 360 reviews written, I asked for feedback, et cetera, and I have found what you do in terms of having a coach or an external person interview people, the quality of the feedback is not incrementally better. It's five times better, it's ten times better. Do you think it's that there's something in terms of a good interviewer is able to disarm someone and allow them to share more openly or if you agree that the quality of feedback tends to be better. What's the why behind that?

First of all, I definitely agree with you. I've had actually very, very accessible CEOs who do ask for feedback and get feedback. They say to me, just like you said, this is so much more direct and even so much more actionable and it's clearly better quality of feedback. I'll speak for myself. I was a journalism major in college and I did journalism a little bit after college. And I do think that I personally bring the skill of interviewing to the table and also the patience. I'm endlessly fascinated with why and I bring a lot of patience into, well, how come this and why that and what does that look like? And tell me more about that. And what's another example? People sense that I'm interested, not that I'm grilling them. So speaking for myself, I think that that is a skill also. I make sure to make time in a busy day. Any executive like you is probably processing a number of different things, a lot of different things, and they want to make time for this. But there's also a lot of other things clawing at their attention. And when I come into a system to do 360 feedback, that's all I'm focused on. And so I sort of make sure that we have enough quality time to do it. And I think there is something about telling a third party which is just different from telling you to your face.

Yeah, I think that last one is really interesting. I also wonder whether there's something about to your point in terms of asking great questions or being in conversation with a third party about someone else that elicits a different type of feedback than even an Anonymous survey or 360process where you're sitting down and writing. And maybe it also creates space to your point. You're on the calendar, you have a half an hour or an hour. I don't know how many people spend a true hour or more writing feedback for their, in this case CEO. I would assume it forces someone to just spend more time reflecting. And my advice, because I've seen how transformative this is, is that more CEOs should be doing this TYP thing and not just a written 360 or talking at the end of a one on one about it.

Oh, I definitely agree with that. I think there's something so powerful in the conversation and in the chemistry between the person asking and the person who's weighing in. And I think that the prompt questions in real time are very helpful for people to really examine. Yeah. What's going on? I think the other benefit of, you know, when I'm a coach and I walk into an organization and I talk to eight or 10 or 12 people, I get a really strong view of what's going on. It's not just about the CEO, it's like, what else is going on around here and what is the culture like and what are people experiencing and what's in the way of getting work done and what's helping get work done. And I think that just being in conversation about that is very helpful for the whole company. I guess I would also say somebody writing their feedback, even, even if it's verbatim comments and they're writing and they can write whatever they want, they feel differently when they're able to share with another human being this is what's really going on. And I think it leaves the stakeholder, assuming it's a relatively healthy situation, it leaves the stakeholder, the executive I'm talking to, feeling also better themselves.

One of the things you talked about a minute ago is you do this process and maybe have somebody like a coach do it, maybe you're doing some version and trying to get high quality feedback yourself and you get all this feedback. As a CEO, how do you think about advising a CEO on what feedback to spend time focused on versus not now, or it's not valid feedback or not useful feedback. What does that process look like?

It's such a good question because I think that CEOs are under the mistaken impression that they have to take all the feedback all the time. And first of all, it's a slow process. It doesn't just like, here, do this, okay, good job. I get a lot of feedback. So it takes us some time to digest it together. And many CEOs, I won't say all, but many, maybe most, have some sort of reaction. We first have to deal with the reaction, which is not fair and it's not true, and you know, different kinds of defensiveness or guardedness and we have to deal with that. But at some point they pretty quickly move to the topic at hand. And so we look at it together and then we process it together. And I think the most important thing I can do is I can ask them, CEO, what does this look like from your point of view? Can you see this? Can you understand the impact they're having? Because they have a certain experience of what is going on and maybe the reality of the situation, like, oh, they don't understand because I'm just trying to make sure that everyone does the same thing or they don't understand all the pressures on balancing. That's absolutely true. But their perception in this case is reality and we have to deal with the reality of their perception. And so my question to the CEO is usually, what do you think is going on? What do you think is concerning and that you need to really take a look at inside of all this feedback? And then what are some areas that you recognize are maybe not the most important things? And to your point, we can put them off until later or you may never do them because you think they come from the less mature executives on your team. So we talk through all of that and then make a decision about what the CEO is going to move forward and start doing on that point.

An area that I'm endlessly fascinated with is how a CEO, founder, executive, et cetera, actually makes change. And I think one of the challenges with feedback, and again, some of this stuff could be behavioral, some of it could be very tactical, et cetera. What winds up happening, I think more often than not is somebody says thank you for the feedback and they genuinely mean it. In this case, they agree and they want to action on it. But then you follow up in 6 months or 12 months and you see if there's been a meaningful change. And the answer is in most cases, no. And I'm curious what you've noticed about that. And maybe when you think about the CEOs that have been able to change and evolve and take this feedback and grow, what are they doing? Because I often think it's difficult because a lot of the things that come up in this type of feedback amongst an executive team or for a CEO is often quite different, deeply rooted in the way that they behave or see the world. And so a lot of it is not. The number one thing that would be so incredible is if they would respond to my email faster. A lot of the media stuff is like a deep part of the way that somebody behaves. And so it's very hard to change or even if you understand and agree with the feedback. The inertia of the week or day or year oftentimes I guess, keeps you from doing anything. It's like the difference between knowing that you need to change the way that you eat for your long term health, intellectually knowing that, and then you follow up with what somebody's eating at a Wednesday at 3 o' clock in the afternoon. And those two things are often at odds with one another. And so if somebody wants to increase the chance that they're able to take this feedback and really implement it, really change and grow as a CEO, what advice would you give them?

I'm going to answer the question as a coach, but I want to say that everyone can do this without a coach. So the first step is to say, okay, I accept. I give in. I accept. It's true. So a really good example is a CEO I worked with who was extremely critical and never gave positive feedback. So that's a double bind, because it's both. People are feeling like they can never please him and they can never win. It's never going to be enough. And also, there's no, like, pat on the back to make up for that. It made for a very difficult, difficult working experience and didn't help make forward motion. So that's a good example because actually, to your point, it was pretty deeply rooted. He had grown up in an environment with a father who did not give him a lot of positive feedback, gave him no positive feedback, and was very critical. And we bring this with us into the workplace. We identified this as an area, and he really wanted to be a great CEO. He also recognized that this was something that was negative from his childhood. He was bringing to the company. He didn't want to. He really wanted to make a change. So step one, decide you want to make a change, and then step two is really set a goal. What is that change going to look like? So is it going to be that at the end of a number of months, people are going to experience you as someone who gives positive feedback? Okay, great. So what's going to cause that? Well, making sure you give positive feedback and then checking in with people to see if they've noticed what's changed. So how do you make sure you give positive feedback? Well, you can actually write it down. Like, you can actually say to yourself, okay, my goal for myself this week is to make sure my executives and maybe some other people are getting from me at least two or three words of praise per week. So I'm writing on a spreadsheet and make sure I follow that up and then do that and then check in in a couple of weeks. Like, hey, I heard from Alyssa that I wasn't giving enough positive feedback. And it's really important to me that I give positive feedback and that we have an environment where people can enjoy each other and work well together. So I wanted to let you know that's what I'm working on. Have you noticed a change? Now? The first time you tell them that they may not have noticed a change, but now they're on the lookout for that kind of change. And so you keep doing it. You make sure you have a spreadsheet or your calendar or whatever is going to keep track of positive feedback. You keep activating it over and over again. You check in with people and over a very short period of time, you'll be able to both change the reality and also the perception. And that's part of what change has to do with.

What are other examples that come to mind? I assume maybe you find when you're doing this work with high potential CEOs that there's a power law of feedback in the sense that there's a handful of things that come up. You've written about and thought a lot about this dimension of positive feedback versus criticism. Are there other common opportunities for growth that come up that maybe the way that you implement or action on it looks a little bit different?

So sometimes there's the two sides of the same coin. So it might be the person, maybe he never engages in conflict. And so that's an area that needs to be changed. He needs to be able to tell people that this isn't good, or that he needs to be able to hold people accountable and engage in difficult conversations more readily. Or on the other side of that might be a CEO who can be overly direct and actually make people feel bad because she's telling them regularly again what they're doing wrong all the time and not what they're doing right. So it's two sides of that communication. I think what also comes up is decision making. So needs everybody to weigh in before she makes decisions or makes decisions on her own without consulting other people.

Is your advice in terms of actually how to make change very similar or is there any other tools that people can leverage?

I think that it's similar, but I'll talk about decision making. So it might be that she makes decisions without consulting others and that leaves them both blindsided. And also it's kind of like, well, what am I doing here? So kind of demoralized. The thing to do there is very similar in terms of set a goal. I'm committing to make sure that other people are involved in my decision making process. And then you really have to work with the other people and say what should our decision making process be and how should we decide on different kinds of areas and who should be deciding and on the areas that I should be deciding, how much input should I get from you all and when that might be in the Executive team meeting. It might be in one on ones. It might be only the people who are involved with that area need to weigh in. But one way or the other, make a decision with your executive team, how you're going to bring more people in and then activate that over and over. And then checking in with people to see if they've noticed your change is extremely powerful. It's probably the most useful way to get people to change their perception. Because as a coach, I worked with a large company, and when I first showed up, the CEO told me a story about some executive and the way he had done the certain thing. Five years later, that CEO was telling me the same story about that same executive. So I would say to all the CEOs out there, the best way to make sure that people are observing the changes you're trying to make is to point them to them, to ask them if they've noticed the change, to ask for specific suggestions on how they can make this change more rapidly, more consistently, how it would be better for that person, and then do that and then ask again, because that really cues and signals to people. I'm trying to make these changes, and I want you to notice.

How do you think identity fits into this process of gathering feedback, prioritizing, and actioning on it? One of the things that I've been endlessly interested in is, and you talked about this a few minutes ago, in terms of maybe the way that you received feedback or criticism or what have you as a child, impacts the way that now you're the CEO of this company and you're receiving or giving criticism. And when you look at the why behind people's behaviors, I tend to think that a lot of times it comes back to identity or how does this person perceive themselves. And so an example is I work with someone, and if you look at the quality of the meetings that they're taking on a weekly basis, it's too variable and overall too low. And when you poke at it, I think the actual reason for that is that this person identifies as someone who is helpful to others, wants to do the right thing, is a good person. And if I believe I'm a good person, I believe a good person is accessible, oftentimes says yes. And that's actually why all these meetings that maybe this person shouldn't be taking shows up on their calendar. And so what I noticed is that when I've given feedback about the quality of meetings, it's not actioned on in a way that, okay, great, I'm going to go change because it's so deeply rooted in their own identity. And so I assume they would have to shift their identity first for the behavior to shift to ultimately make that change. But I'm curious how you think about identity and the stories that we tell ourselves about ourselves and how that fits into the way that we grow and evolve in this case as a CEO.

I think it's very astute, actually. And we all have identities we bring into the workplace. And if I'm thinking about a CEO who had trouble hiring, and so it was very strange because actually he was fantastic at raising money and he had a lot of conviction and a lot of passion, but for whatever reason he had trouble hiring. So coaching is really about having deep conversations and really sitting there and really finding out what's going on. And he had a lot of reasons, but really it turned out that his identity had not caught up with being the CEO of a fast growing company. His identity was still, I wonder if I should leave my job and start this startup. Really. He was still in that space in some ways emotionally. And he was concerned about. He was fine telling the investors the story, but he was not fine telling human beings that they should leave their safe job and come and work for this little rickety ship that he had. And that's how he saw himself and that's how he saw the company. And so I do think that our identity plays into things quite a bit, actually. But I would also say that the way to resolve that is both outside in and inside out. So we can think our way into a new way of acting, but we can also act our way into a new way of thinking. And I think that is actually, to me, one of the real superpowers of a great CEO who has to adapt that quickly. They have to realize, on the one hand, I don't want to do this and I'm concerned and get at the root of the problem, but that doesn't always solve the problem. Sometimes it's okay. I'm recognizing your point about taking two low quality meetings. I'm going to step back, I'm going to shift my filter about the kinds of meetings I'm taking. And I'm really uncomfortable. I don't like it, it makes me uncomfortable. But I'm going to do it anyway as I upgrade my identity in a certain way to, in this case, to maybe somebody who is really precious with his time as compared to trying to be very helpful.

Are there other examples of how you shift your identity through just behaving in a new way that you might be able to explain or share.

There was one on the topic of conflict, which I think would be that CEOs who would not say they're uncomfortable with conflict, but always shy away from conflict. And their identity is probably based in their childhood about we didn't talk about difficult things. We kept them under the covers. And so it's like impolite and uncomfortable to have straight talk or have conflict. And so that identity is probably pretty rooted. And so that person has to practice having conflict, even though that really makes them quite uncomfortable. I think another example is, let's say, a product CEO who grew up in the product space, grew up maybe in the elegance of product and engineering, and still sees herself that way. And so she doesn't want to sort of take on the mantle of authority or decisiveness, and she wants to maybe have a collaborative environment. We're all weighing in just like we. We used to when we were working together in the product and engineering world. And that's her identity. And so she has the opportunity to be more decisive and declarative and maybe have conviction as the CEO, even though it makes her very uncomfortable.

I'd be interested to hear how you think about how all of this fits into the culture and or needs of the company, in the sense that a lot of feedback is culture or company dependent. You may have a culture that tends to be much more direct. You might have a culture that tends to be maybe much more gentle in the way that they think about feedback. And it gets into this broader question of I tend to think that there isn't a particular CEO archetype that always thrives. It's that the CEO has to be right fit to the company, just like the culture has to be right fit to the company. We like to tell ourselves stories that there's one type of great CEO. But the thing that I've always realized is that when you spend time with lots of different successful CEOs, people do things in all sorts of different ways. People have strengths that are very different, and oftentimes those are the things that are needed for that specific company at that point in time, not just generally. And so you think about a few CEOs that are super successful, and each one of them is very, very different. Larry Page is very different than Marc Benioff. And I'd argue that both of them, and maybe the companies are just expressions of themselves, were tremendously successful and their own skill set was right fit to the thing that the company was doing and the culture of the company. And so as a CEOs collecting feedback or deciding how to behave. How does the culture or norms of the company fit into how that CEO should grow or evolve?

First of all, I totally agree with you that you can be a successful CEO with all different behaviors, all shapes and sizes. You can be loud, you can be soft, you can be charismatic. You can be maybe not as charismatic. I think that a CEO who starts a company is in some ways creating a culture that is a reflection of of her or him and without necessarily being conscious of it. Unless co founders have been very deliberate about deciding what culture they want to have. Mostly though, they just start and they hire a bunch of friends or people they know and they get started. And I think that very often they will unconsciously hire themselves. There's a CEO I work with who did individual sports and without knowing it, he hired a whole executive team, all of whom had done individual sports and not team sports. And so in some ways the culture was a reflection of that in terms of they were more individuals than team oriented. And I think that again, without always being aware of it, they hire people they feel comfortable with and the culture kind of springs up. Now I think that very often the focus of the company, like Salesforce and Google are obviously very different focused companies. I think that probably the CEO feels a connection to a certain style, a certain company and a certain product and service. And so it kind of makes sense that that whole thing will shape itself around the CEO. But I think over time the company has to grow and you as a CEO need to bring something different than what you had originally. So I think that you might, if you're a quiet CEO, you might need to bring much stronger and extroverted communication skills if you are the CEO who's more external focused. At some point, as a company's growing, there are growing pains, you're going to have to focus more internally. So I think that you as the founder need to be self aware enough to realize that the company requires something from you and that if you don't, I think the culture just grows around you and it's not always a good fit for the company you're trying to build, especially when you're starting to scale.

What are the warning signs or early indicators that someone might need to grow or change and maybe it's different than their normal behavior. And to your point, totally makes sense that a company is basically going to be a reflection of the founder, particularly in the early days, for all the reasons that you outlined, which are normal. We often spend time with people that are similar to ourselves, depending on how you think about it, there's a lot of benefits. You tend to be more intuitively aligned with people like you, and so you don't need to get into first principles arguments all the time. There are definitely benefits to creating a team, and then the team is effectively the company in your image as a founder. But to your point, as you really grow, you often don't need to be the opposite of who you are in your innate steady state, but you need to grow in certain ways. And outside of just capturing feedback, are there other early warning indications that, you know, maybe you're innately very hard charging, for example, and that was very helpful in the way that the company in whatever the product that the company was doing, but that now you might need to change or evolve in some way?

Yeah, I think that there's an early warning when people start to leave and they talk about the pace being too much and the hard charging being too much, or hard charging also sometimes goes along with goal shifting, and that can be crazy making for people. So either they're communicating to their leaders and managers this is too much, or they're actually starting to quit. That's a good warning sign that we need to take a second look. Also, it's not direct feedback, but it's sort of culture surveys at a certain level in the company. I think early on culture surveys, I have mixed feelings about them, but as you start to scale, I think it's super important to get a handle on what people are saying and how they're feeling. And so that kind of snapshot can be very helpful to give you that indication. And then I think that very often the founder will have this primal energy and intense energy and work all the time. Again, to your point about hard charging, and if the founder tries to get in tune with what's going on and really be still a little bit and see what's going on, the founder will notice people don't seem to be as engaged as they used to, or they don't seem to have the same energy as they used to, and I wonder why. And then it would be really helpful for the founder, the CEO, to go and talk to a few people and say, I'm feeling this, Are you experiencing this? Are you feeling this? And then they can hopefully open up a dialogue about it again. That goes back to making sure that you've created safe space for people to really tell you what's going on, I.

Guess to sort of put a bow on this first section of topics. Going back to changing and evolving and growing as a CEO. I think one of the tricky things is that when you start a company and you go from 0 to 1 and then 1 to 10 and things are working in the company, you can often be overconfident or close minded to a certain extent in the sense that, hey, I helped do this entire thing and it's working and so let's just keep doing this. How do you help somebody figure out that they actually do need to change in some way? And it's sort of the classic what got you here won't get you there. But I think it's really magnified specifically in startups because it's so hard to get a company to go from zero to something that's really working. And so it would be normal to think that you're particularly great and wow, this company is growing 10 times this year. There's something very peculiar about fast growing venture backed technology companies in that it's so hard to do the thing. And once the thing is really growing, one is that it's very easy to be overconfident and two is I always come back to the idea that it's hard to know if something is working because of something you're doing or in spite of something you're doing. In software businesses, when something's working, it can often be in spite of the way that a CEO in this case is behaving. They may be exceptionally critical of their team and put people down and the company is still growing exceptionally well. And they will tell themselves I should keep behaving the way that I'm behaving because the company's growing like crazy. But they don't realize that the company's growing in spite of the way that they're behaving, not because of the way that they're behaving. I'm curious if anything comes to mind or if a CEO doesn't immediately get that they need to change, what is the journey that they need to go on or what is the transformation that needs to happen such that they realize that hey, maybe there is an opportunity here to do something better or grow or change.

A few tools come to mind. So when I start with a CEO, I will often say, what's the end game here? And I would say most often they do not say the end game is to cash out and be rich. They say the end game is to build a legacy, or the end game is to create wealth for all the employees here, or the mission of the company is to make everyone's life better in a certain way. So if there Are things going on in the company that are, like you said, the company is successful despite these issues with the CEO. What I help them do is to think about the three to five year vision or the ten year vision of who they want to be and what the end game is and shifting it not to, oh, you have problems here, but into, well, you said you wanted this and you said this is the kind of person you want to be. How do you need to show up differently today to achieve that 10 year vision of who you want to be and what you want this company to be? So that takes it into a different or reflective realm. And if it's the kind of person who's reflective and wants to have that conversation, then that's very enticing and opens up different pathways for people. The second thing is I always ask my CEO and founder CEOs to go talk to other founders because that's where the wisdom is. They could be peer founders, they could be a number of years ahead of them, obviously even, you know, older and more successful. And I think they learn so much from that exposure and it helps them think differently about their current state because the peers and the mentors can help show them where the pitfalls may be a year or two or three down the road. And obviously when founders talk to other founders, that's in some ways the most convincing. But Brett, the last thing I would say is that sometimes, until there's a fall, that person is going to have this sort of overconfidence or hubris or whatever you want to call it for a while. But if it's built on ground where what got you here won't get you there, ultimately there will be a fall. My job is to try to intervene before there's a fall, to help the founders see that they need to make those changes before there becomes a massive problem in the company.

So, switching gears slightly, one of the interesting things I would assume that you experience is that you spend a lot of time sitting down with CEOs and they're interested in potentially working with you in some way. And I assume you're asking them questions about what's going on. Do you find that the content of those conversations and what, what's top of mind and what CEOs are struggling with tends to be more similar? Or is it a lot of snowflakes that tend to be quite unique?

I think that it's different flavors of similar situations. Typically when I'm talking with somebody for the first time, I guess it falls into two camps. It's mostly there's something going on, as in, I'm having some issues inside of the company, I'm concerned about some things we're not getting the results we want or something like that. Sometimes it is I'm a first time founder and I don't know what I don't know or sometimes I'm a second time founder and I don't think I did it right the first time. But if I think about especially the first bucket, my experience is that it's most often a people problem that they are not dealing with and it's causing some issues. So like we're behind on our product roadmap. Great. Okay, great. What happened? What's going on? And then I'll understand the role has outgrown the existing product leader and they haven't had that conversation or feels like in general we're getting a lack of results around here. Okay, great. Who's running the cadence of your goals process and your executive team process? Oh, almost no one or somebody who just sort of came in to plug the hole. Oh, okay. So it looks like we're missing a person, we're missing a skill set inside of the company. So those are the kinds of things that I tend to identify in the first conversation I have with people. And actually when I first talk with somebody, just to let you know, I try to do a little piece of coaching in that first conversation so we can test each other's styles. But also because I'm really interested in what's going on around here and can we take a step forward in just a half an hour or 45 minutes? And can I myself get down to the place where I can actually make a difference for somebody in a first discussion?

What does that look like? Or can you tell us a story about when you felt that maybe you really clicked and that sort of little taste of coaching resonated?

I would say just last week I had a conversation, initial conversation with a first time CEO. So she had incredible pedigree, McKinsey background and large company background. And it was a remote team, which is not unusual these days. And her company had grown very quickly, much more quickly than she had anticipated. And now they were at around 60 people again. It felt to her like overnight. And I said, what's going on? Because there's a reason you called me. So we did a little piece of coaching and the coaching was, I don't feel like I'm showing up well for the team. So I said, okay, tell me more about that. What do you mean by showing up? So what we talked about was how she doesn't always feel herself like an executive because she's so busy herself putting out fires and being a doer. She's not showcasing herself as an executive, as a leader. Okay, so what's the impact of that? Well, the impact of that is that people are in some ways not engaged and in some ways also confused. There's a lot of new people. We're all remote. We don't know how to engage with each other. And so things are breaking down because of confusion. Okay, so they need more communication from you. Yes. So tell me about the regular all hands you have or executive team meetings you have. Oh, I don't really have regular all hands. Oh, okay, great. So we quickly set up for her a cadence of all hands and executive team meetings. And then there's still this issue of I don't feel like I'm showing up as an executive. Okay. So I helped her think about how do you put five or 10 minutes in before at least those meetings and maybe before other key meetings where you step away from your to do's and you remind yourself of what, however that's going to help you make a way to remind yourself that you're the CEO and they are all looking to you for leadership. Not for this task list that you're working on, but specifically for leadership. And then how will that change the way you show up and the way you communicate? Communicate. So she loved that we talked about specific phrases she could use and that whole thing took about 35 minutes.

Can you tell us a story about maybe when there was like organ rejection and it was clear this wasn't going to work?

I had a conversation even just last year, you know, again, it's the same thing for me. So great. So let's take a little step forward on some piece of coaching. And we talked about, in this case it was hiring. So he was saying it's not working. The hiring process of music is not working. We're behind on our hiring. Okay, great. So every time I asked him a question, like I would say, how have you thought about your pool? Oh, our pool is great. We have everybody, you know working on this. We have two recruiters working on this. We have all points bulletin. Okay, great. So have you talked to your HR person to think through how you could make some changes here? Our HR person comes from this great background and she's doing a great job and she's doing the best she can. And it was just this feeling. I can't remember the whole conversation, but it was this Feeling of closed door. So every time I asked a question, there was no interest in pursuing that or thinking about that or reflecting on that. And also I kind of had the feeling of, we've already thought of that, we've already thought of that. So I have to say it's not like, oh, this person wasn't reflective. But I do know that for whatever reason, my style wasn't landing with this person and, and it wasn't opening up a partnership. And what's really important in coaching is to have a partnership where we can have an easy dialogue back and forth and that we're both co creating a situation and that just didn't feel possible in this situation for whatever reason. And again, I just want to say, like I would say, oh, he was so closed, but maybe the chemistry wasn't there, maybe he's not a closed person, but it felt like a closed door to me.

One of the things that you mentioned as you were talking about a couple of these stories, and I think this comes up all the time and it's something you've also spent a bunch of time on, which is the job of the CEO in terms of getting the right people on the bus and figuring out who at any given point in time should stay and who should leave. And the common advice is that people don't fire fast enough. And I also think that managing talent is one of those tricky things that for whatever reason requires you to screw up profoundly before you're able to take that advice. I'm always interested in there's a difference between somebody intellectually understanding a piece of advice and actually implementing it. And so I think people understand intellectually the concept of it is natural to let someone go too late. And yet unless they do that many times, they often won't be able to make that change. And I'd be interested in what you've learned or what advice you tend to give CEOs around how to develop that muscle.

Brett, that is a very hard problem. And you're absolutely right. First of all, most CEOs come late to the saying about firing fast and also about as soon as, you know, you should fire someone, it's a year too late. And actually, surprisingly, CEOs themselves come late to that expression. I think that the way to help people get over that and to take action more quickly. And by the way, it is a very difficult situation, especially if you're a founder and you've grown up with these people and you've gone to their weddings or they've come to your weddings or You've really been in the trenches with them and they got you to here. They're the people who got you to here. It adds a whole other layer of difficulty.

I would just say the other thing I've been intrigued by is there's Also, as a first time CEO, of which many of the best CEOs are first time founder CEO, you're doing a tremendous amount of learning on the job. And so I think it would be natural to then give people the benefit of the doubt that they have to do a lot of learning on the job. And it can often lead to you giving people a pass because a lot of times people don't think they're the world's greatest CEO and then they're like, my head of marketing is not where I need them, but let's develop them and support them. And so you have this odd duality of you're on your own growth journey relative to maybe someone else on your exec team.

It's so true. I talked to two co founders one time and they both were really emphatic. Like we are growing and learning so much, we don't know what we're doing. We have to give grace to the people around us to give them the leeway also to figure it out. Which to your point, that's a very common thought. I look at that differently. I think you have so much to learn, you want to surround yourself with the people who have a lot to teach you. The other way I approach this is as much as possible, I'm into facts and data as much as possible. What does this role require? So in like the head of product, for example, it used to be you had one product and your head of product was great at managing the product managers for this one product. But now you have five products and this head of product doesn't have the vision or the operational skills and maybe the understanding of how these things all fit together to be the head of product for these five products together. So let's step back. What do we actually need in this person? We need them to be able to manage multiple priorities, be able to be a peer with your increasingly senior executive team. We need them to be able to manage people and manage operationally in a shifting priority situation. Those are some examples of the things that you actually need in this role. Okay, great. So does your existing person have those skills? And if you're being honest and unemotional, the answer is no, this person doesn't have those skills. Then it's the hard discussion about how emotionally you're Going to get to the right place to fire someone or to make a change in the role, at least to change that person who actually means well and is doing their best, but is not ultimately able to perform that function.

What does a good conversation look like between a CEO and in that case, the product leader?

I think the conversation starts with feedback. I think it's important to recognize that your job as CEO is to make sure this person is getting that feedback sooner rather than later. As in the years go by and now we're running three products and I'm noticing that you're having trouble shifting priorities, maybe even this head of product. You're playing favorites with the folks who you used to know very well and you seem to appreciate them more. And you need to make room for the rest of the people on the team. Also, we're missing some deliverables here. So that's kind of the first conversation that might go on for a little while. And then the conversation is, I'm really alarmed because I can just see that we're going to continue to get better. And what I need you to do is to improve your skills in being more of a peer of the executive team and having more conviction over your point of view. Also managing your team in a more comprehensive way and having a more built out strategy for how all these products fit together. So I really need you to take seriously the fact that those changes need to get made and I'd love to know how you want to do that. So do you want to get a mentor? Do you want to go to training? Do you want to just step back and create your own plan one way or the other? I just want you to know that I need you to make those changes. So that is the direct conversation that you have before what I would call the pre firing conversation. If we're going to talk about firing, there's a difference between layering and firing, of course. But if we're going to unfortunately terminate this person, then the conversation looks like, listen, we've had a lot of discussions about the way things are going. I really need you to recognize that the way it's working is not working. And either you need to figure out a way to get this whole situation back on track, or I'm sorry to say we're going to have to part ways. I can talk with you about that a little bit, but ultimately that's where I'm headed and I need you to know that. So then when you have to have the termination conversation, you know for a fact that you've Given this person, every chance that you've given this person a lot of feedback and now it's time to just say, listen, I just don't think it's working. It's time for us to part ways.

You touched on a related idea, which is the idea of effectively layering someone. And I think it's such an interesting area because it comes up all of the time and it seems exceptionally hard to implement in the sense that you have somebody that was fantastic, they are unable to scale to whatever you need them to do in this new role. So the classic example would be you have a head of marketing or a marketing lead. Early on it's a 20 person company, now you're 100 people and you have to hire a VP of marketing, CMO, whatever term you want to use, you would love that marketing lead to stay, work underneath this person and continue to be an amazing contributor. That is value very, very, very hard to do, particularly if that person wants that top job. And then oftentimes they can be demotivated and I think more often than not they end up leaving, sometimes in a positive way and sometimes in a negative way. But if you were to give someone a playbook, that would enable them to increase the probability that that person would stay and be highly productive. What are the contents of the playbook?

I think it does start with communication early and it's sort of like you're beginning to see we're going to need to bring in, let's say a more seasoned head of marketing. And you know that this person's probably going to want that role. Hopefully you know your people. And so I think it starts with a conversation which is, let's talk about your career aspirations in general. By the way, I think that inside of startups, people from the CEO to the leaders and the managers don't do enough sitting down with the people and talking about their career aspirations, which helps you get to know your people, helps you get to know where they want to go, and then helps you proactively tell them, by the way, if that's where you want to go, I'd like you to see you build these skills. So hopefully you're having some of those conversations and that's part of the playbook. And then ultimately it's like, okay, well we need this person now. You're not ready yet. And hopefully you've built a good relationship with that person and you understand what their career aspirations are and you know they're going to be disappointed. But you could also say, listen, I'm back to Facts and data. We need somebody who scaled before. We need somebody who's going to bring us to where we want to go. And so what I want to do is go and find the leader who's going to be able to lead us there and also is going to be a great people leader for you so you can continue to build your skills here. I hope you stay with us and ultimately you're probably going to go someplace else at some point in your life. I hope this person's going to help you build your skills to get that role in the future. And again, to be very clear about the specific skills that you're looking for with this person so that they understand they haven't met that mark. And then also help them put together their own career development plan, either self study or with their own manager or with a mentor to help them accelerate their own learning, get where they're going. Just last week I had a conversation with someone who had gotten layered with a very well known Silicon Valley company. And I said, tell me about that. Were you upset that you got layered? He said, no, we had a leader who left. It was a very difficult situation because all of us were then reporting to the CEO and we did not know how to navigate together. Somebody did a power play and it was really chaotic and difficult. And ultimately when they brought in this leader, I was relieved. He is a fantastic leader. He's always got our back. He makes me feel like I'm learning and I could not be happier. We think about the sad stories with layering, but sometimes it's like such a relief. Oh, thank God. I have this great leader who just came in.

When you think about the very best and most effective CEOs that you've had the chance to work with or study, what are the types of things that they are doing? The rituals, the habits, the questions that they're asking? Are there touchstones or specific questions that they should reflect on?

If I think about seeing around corners, what some of the CEOs I work with, they have a practice of, what am I missing? Or what's the counter example? Like what's the counterfactual to what I think is going to happen? And I think that's a very powerful tool to say, like, what if I'm missing something here? I'm very encouraging of all my CEOs to reflect. And that has to do with how you show up day to day. So reflection, like midday reflection of what energized me the most today? What has depressed me or drained me this much today? What Am I thinking and feeling and what should I do now? I think helps you shift in the middle of your day and maybe do that hard thing that you've been putting off or take maybe a bolder step than you might. So I think resetting yourself by doing some journal prompts, either in the morning or the middle of the day or at the end of the day is very helpful. And then I would add, I interviewed for my book Susie Batiz, who's the founder and former CEO of Poo Pourri, and I also recently interviewed for my podcast Sadie Lincoln, who's the founder CEO of Bar3. And they are both incredible examples of fearless conviction on following intuition and kind of doing it their own way. I encourage leaders even more so, to tune into that intuition and find ways to balance the intuition with facts and data. And I think setting aside time to journal even five to 10 minutes a day, helps you tune into your inner voice and helps you tune into your intuition, which tells you things which are going on around you. Doesn't mean you should make every decision based on intuition. It doesn't mean you should not take into account facts and data. But I think that is an element that we, in the busyness of day to day, we sort of push aside and I think proactively making time for that, either through journaling or Also, I just spoke to a CEO three days ago who said I meditate one hour a day religiously and I never would have predicted this, but answers to questions I've been really struggling with come to me in my morning meditation. So one way or the other, it has to do with stillness and letting that voice have some space and then also marrying it with what you're seeing around you.

Awesome. Well, thank you so much for spending this time with us. This was great.

Thank you, Brett. I really enjoyed.