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 with an, 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 that I want you to notice.

 Welcome to in depth, a new show that surfaces tactical advice, bounders and startup leaders need to grow their teams, their companies, and themselves. I'm Brett Berson, 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@firstround.com

for today's episode of in-depth. I'm thrilled to be joined by Alyssa. Alyssa is an executive coach. Who's worked with companies ranging from Etsy, Venmo, and InVision to the wire cutter, Google and IBM, even counting folks like Tim Ferris among her client list. She's recently summed up her over 20 years of coaching experience in her new book from start-up 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 leaners 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. 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 establish CEO. But it's also a great lesson 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 to 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 asked 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 are the consumers of your leadership are the ones who are able to weigh in on how your leadership is landing because you, the CEO of the expert in your intention and everybody around you is the expert on your impact. So it's leadership effectiveness is definitely impart 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 in, 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 may be 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, 

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.

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 creates a lot of good culture in that company where people are learning. 

 Looping back when you're running 360 feedback processes. And you mentioned this at a very high level.

Obviously one of the things you do is sit down in this case may be 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? 

 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 be 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 wanna do is say, well, what does that look like? 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 is 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 move to development opportunities.

And that's what I really dig in. So they might say he's not collaborative. 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. 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 is 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 feed 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 the truth in the feedback than anyone is giving? And doesn't 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 themselves. 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 ahold of him when I need him. And I said, okay, well, tell me more about that. Well, I tried to text him, I try to email him. I need him and he doesn't get back to me. I don't know why. And 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 those stakeholders said to me. So I said, well, is that the way he is that when you bring something up to him, he 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 off.

 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, Hmm, how come they 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're 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 once they most often, but I would say half the time, maybe it a little more than half the time they don't fall on their commitments.

And I think that's endlessly interesting and also shows me how silly 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 10 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.

 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 is 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. I personally bring the skill of interviewing to the table and also the patients I'm endlessly fascinated with why, and I bring a lot of patients 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 input, but there's also a lot of other things calling it 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. 

 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 360 process 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 type of thing and not just a written 360 or talking at the end of a one-on-one.

 I definitely agree with that. I think there's something so powerful in the conversation and then 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 talked 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 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'd 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.

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 a reaction, which is not fair and is 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 the 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.

 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 six 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 CEO's 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 deeply rooted in the way that they behave or see the. 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.

So 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 is eating at a Wednesday at three 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. 

 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, give him no positive feedback.

It 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. 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 does 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 it, my executives and maybe some other people are getting from me. At least two or three words of praise per week. So I'm running 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 want 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 and 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. 

 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 like 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 may be the way that you implement or action on it? 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 conference. 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 there'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 others. Is 

 your advice in terms of actually how to make change very similar or are 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 blind sides. And also, it was kind of like, well, what am I doing here? So it 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 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 an, 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.

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 know that. 

 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.

Alisa Cohn has nearly 20 years of experience in executive coaching at companies like Etsy, InVision, and Google. Here, she shares advice for getting better feedback and actually enacting change on the journey from scrappy founder to seasoned CEO.

How to grow from founder to CEO: Advice from exec coach Alisa Cohn

Advice for getting better feedback and actually enacting change on the journey from scrappy founder to seasoned CEO.