Top Startup Coach: Why Your Team Won’t Tell You the Truth (And How to Fix It) | Alisa Cohn

Most workplaces, right, large companies, small companies, are filled with 4th graders and 6th graders acting out.

You hear about Steve Jobs and Elon Musk's management styles and they get amazing results. What is the bar of aggressive good and aggressive bad?

Isn't that the million-dollar question, right?

Yeah. What are some things that you would advise founders prior to 3 years ago that you've changed your mind because of AI?

It used to be like overhiring was kind of normal. I think overhiring is no longer acceptable. Do your fucking job.

So excited to have Alyssa Cohn here. She's one of the leading executive coaches for founders and leaders at places like Google, Microsoft, Venmo, Etsy, Glean. The list goes on. And she's an expert in scaling leadership during turbulent times, which before AI might have just been associated with growth, but now it's like every week is turbulent.

It's a tornado.

Yeah, it's a tornado. I feel like very, very prescient to have you here.

I'm so excited to be here, really, truly, to be in your office and to find out more what you guys are doing.

Yeah, I think I've spoken to your Delphi more than I've spoken to you. So it's good to have—

That's great.

The real person here.

Yeah.

And I want to start with a topic that has been top of Silicon Valley mind for the last 2 years, which is founder mode. Founder mode has given founders and leaders way more permission to get in the weeds, And I'm curious, what has Silicon Valley and founders most misunderstood about the concept of founder mode and where it could potentially go wrong?

Yeah, I love that question. So of course, we all know that founder mode is like this thing that Brian Chesky talked about and Paul Graham popularized, which is around kind of getting in there more with your hands as a founder. And I actually think that's fantastic. I think that's actually essential and fantastic. And in the age of AI, what I'm finding the best founder mode is, is that founders are actually building the thing they want their team to build, at least as a demo and a prototype, in order to show them. And actually, there's nothing more powerful than being like this. This is what I want. Lead by example. Well, both. Let me show you what I want in a very working prototype kind of way. But also, to your point, lead by example. I'm getting in there with the tools. I'm pushing myself to think differently, right? So kind of love that about founder mode. I think that— and I would also add that even aside from the age of AI, The idea of founder mode is I care, I'm the spiritual leader, I'm directing the team, and it's, I think, super important for the ability to zoom in when something is super important. But equally important, and this is where founder mode can go wrong, it's important to be able to zoom out when it's like, okay, the team has it, it's all working. It's not 100% maybe the way I would do it, but actually the team maybe has better ideas than I do. And so their ability to kind of let the team run with something. Is the only way it's going to scale and that the team is also going to thrive. And I think that founder mode can go wrong when it does substitute for either I can be a micromanager or worse, I can be a jerk. And those are bad executions of founder mode.

And have you had examples since the term got popularized of founders that you've worked with where they reacted to that and them getting in the details was very good? And then them getting details was very bad. Like, any specific examples?

Sure. I mean, there's one founder I work with. And I would say that as founder mode— I'm going to just be really sort of circumspect about this. But as founder mode has sort of became more in her mindset, she was able to take something that was strategic and kind of stuck and move it forward.

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And the team also didn't like the new mode. So there was a whole bunch of dialogue around like, you're micromanaging. And I think to some extent, I think she was micromanaging. I think that there was a way in which she was not giving enough direction. It was a little bit like, I think founder mode can also go wrong when it's like, do this, now do this, now do this, as opposed to, wait, wait, wait, wait, wait. Here's where we're going.

Mm-hmm.

Here are some of the things that I see along the way. You may have better ideas, but this is what I see. I wanna make sure that we're on the same page and up to speed. So please update me on a weekly basis, or let's have a meeting to check in on this, as opposed to kind of a daily, like, directive, which I always call, like, question, answer, question, answer. And I think that is where she got gummed up on founder mode. And I think others do too, because again, it is— I think one thing about founder mode in many of these, like, leadership dualities is like, actually it's good until it's bad. Or there are two, let's say it's two sides, right? Some of it's good and some of it's bad. And your job as a founder is the wisdom to know the difference.

Constant balance.

Constant balance and constant course correcting.

Yeah.

Right? Balance is an interesting way to put it because it's like on the whole balance, but sometimes you're in it and that's not balanced. And sometimes you're out of it and that's not balanced. But like, it's the, I think it's more like the tension between the two and the wisdom to know when and the ability to course correct when you realize you've gone in the wrong direction.

Yeah, I feel like a lot of founder mode, you said, is care and setting a high bar for excellence. How have you seen founders increase the bar for excellence without, again, being like, do this, do this? How do you set what does good look like without being micromanaging?

It's very challenging, obviously. And I think actually it comes down to hiring the right people, hiring the people that you have the right mindset with, that have the right same work ethic as you do, that have the same kind of vision of what excellence looks like. And then hiring for the qualities around being so-called strategic. But what that really means is ability to kind of see the bigger picture and then bring it down into execution. Ability to be a problem solver and not just a— not a problem finder, but a problem solver. So if you find people like that, you as a founder have a lot easier time. It's always like—

Mm-hmm.

It's like, how do people say to me all the time, how do I motivate my people? You hire self-motivated people and then you let them motivate themselves, right? And then you're kind of giving some direction and nudges along the way and getting on the same page. But I think it's just so important that you understand kind of the bar you're looking for when you even hire people.

Yeah.

At the same time around excellence, right? I think it's just constantly also like showing the bar, showing the vision, showing even the direction and narrating for people where we're going. Because you gotta picture your people in the backseat of the car. You're in the front seat of the car and you're driving and you can see ahead of you, but people in the back, They don't see everything. They just see what they're doing. They see, like, they can't really look out the window. Even if they do, they see a different view. And that's not bad. That's literally their job. And so your job as a founder and as a leader is to help them see the future and also help them track progress as they go. Because if you're just the kind of person who's like, do this, it should be better, it should be better, it should be better. Well, then who wants to work for that?

How have you seen as a result, not just the founders, but the best teams and cultures reinforce That excellence? You know, when someone is obviously a demonstrator of excellence versus someone who's not a demonstrator of excellence, how do you have— is it like reward punishment? Is it accountability? Like, how do you have a culture that reinforces itself?

You know, I think the key to that is the team ability to say what's true, right? So like creating— this is not so easy to do, right? But it's creating a culture which is the ability to say, hey, I think that could have gone better. Can we talk it out? Or, hey, that could have gone better. I think maybe you needed help. Do I need to help you in the future? Or that kind of dialogue, which is not about blame, but it is about open and easy discussion about things that are going well, things that are not going well. And it's the opposite of what I always call a polite culture. And when I say polite culture, it's like never a compliment 'cause it's really just like, everything's great.

You're too nice.

Yeah, it's a too nice of like everything's just actually great. And then meanwhile, there are some companies and there's, I just wanna say these are not my clients, but there is a company that I do work with, it's a partnership with, and they are so polite. They are so polite. Like, you gave me that water. Like, oh, here, have some water. Oh, thank you so much for the water. Oh my God, that's amazing that you gave me the water. Like, I'm kind of exaggerating, but that's kind of how they are. And I'm sorry, but the company's going downhill. They just are. Again, not a client, to be clear, not a client. But definitely you observe an overly polite culture, which I think is correlated also with just low performance.

So how— what's the answer to being overly polite? Is it to being mean? Or like, how do you prevent nice from being destructive?

Right, exactly. So by the way, You can, you know, this is where I love actually Kim Scott's book, Radical Candor.

Radical Candor.

Right? Which is really about, I care enough to tell you the truth. So first of all, you start with a baseline of hiring people who want for good and have good work ethic and excited about the thing and are self-motivated. And then you help them along the way by giving them clear direction, giving them feedback, giving them positive feedback. This is going great. I love it. Here's the milestone. We all could achieve the milestone. All these good things. Like, it's all like, there's actually a lot of good things happening. And then when things are not so great, It's that the team is empowered to be able to say, hey, that didn't go well. We were 2 weeks late with the launch. Let's— not even the leader, but like, let's debrief, like a person on the team, and see how we could have gotten— we could get that better and what we can learn from that.

Yeah.

So it's the idea of being a learning culture and also that you can talk about things which are kind of matter of fact, build great relationships with people so they can have those dialogues together so that it's not about blame and mean. It's about straight talk and truth and most importantly, learning. And if you think about that in your life, there are probably people in your life That you can say anything to because trust is so powerful, right?

It's not about ego or who's hurting who. It's collective rise.

Right. Exactly. Right.

And let's say you're coaching a new founder client who is coming maybe from a polite or nice culture. They've been avoiding hard conversations. They've been avoiding giving hard feedback. How would you coach them to have a difficult conversation with someone who's underperforming in a way that sets the bar high without being too nice?

Right, exactly. So that is also very normal because it's not just like a founder coming from a polite culture. It's a founder being raised in an environment where we don't are uncomfortable with conflict, right?

Mm-hmm.

So that's like a starting point that people have their own baggage around culture, around conflict. I totally get that. But it's also like, it's really saying, is your job and goal to give this person difficult feedback to make them feel bad? Usually not, right? The goal as a founder, as a CEO, as a leader is to have excellence in the company, to get to our mission, to do the thing, right? To win. And so along the way, what you need is people doing their jobs. And there are inevitably times people are not going to do their jobs or they're misguided or something and they need help and support and they need feedback. If you think about it in the context, this is not for anyone to approach someone to say, I'm going to have a mean conversation or a tough conversation. It's more like, actually, that's your job to get things on track. That's the starting point around motivation.

That's the job.

Yeah, that's the job. You tell yourself, actually, Scott Bilski, the founder of— he's a really well-known founder in New York.

Yeah, I love Scott.

Yeah, Scott's great. Wait, what was the name of his company? How come I forgot it for a second?

Behance.

Yeah, Behance and sold to Adobe. And he's on my podcast and he said, I had to finally tell myself, like he had a lot of issues with conflict and having difficult conversations.

I've read his book, The Mess in the Middle.

It's amazing. It's amazing. And he said, I had to tell myself, do your fucking job. And that's really what it comes down to. You gotta do your job. But then what do you do? You gotta plan out the conversation. What's my goal? My goal is never to make someone feel bad. It's to excite action, to ignite action. Give people the context of, here's what happened in the meeting, in the situation with your peers, whatever that is. The observation is that your peers are not up to speed on what you're working on. The impact, I impact, is that they are confused and also they're kind of annoyed at you. And so the next step is something we have to figure out together, but the ultimate goal is how are you going to keep your peers up to speed? on this thing or whatever it is. And so it's not about like you're a bad person. It's about you're doing a good job, you wanna do a good job, and in this context, it's not working.

Yeah.

So how are you gonna change it? And you can do that in a calm way and actually in a polite way and a supportive way, but you do need to tell them. Otherwise, what's gonna happen is it's gonna be a toxic environment with the peers, and that's not gonna get us to our mission. So that's how I think a lot about addressing difficult conversations. Yeah, it's hard to say, But if you don't say it, it's much harder for the company.

And then how do you end those meetings in a way where there's a clear feedback loop on the other side, where there's compounding?

What do you mean?

Like next steps. This is what we're going to do to improve.

Yeah, so the next step is— I mean, I think in an ideal state, you as a leader would say to your person, so what do you think is the next step? And they might say—

Not being prescriptive.

Right. Well, right, there you go, because it's a dialogue, right? Well, I think I should keep my peers up to speed. Great. That's a great next step. But it might also be, What's the next step? I'm not sure. And there might be because something you didn't know is, I don't even know what, like I can't get ahold of a lot of my peers. Like, oh, that's really good to know. So for a next step, it sounds like what we need to do is bring everyone together to kind of reset expectations of the way you're gonna work together. Okay, great. So that's the dialogue around next step, but it does have to be a next step. What I think a lot of founders and CEOs and leaders do is they give the feedback like, well, I gave the feedback, but we didn't make an agreement.

There was no alignment.

There was no, yeah. Then there was no agreement about what this person was going to do differently. And so that definitely goes wrong because it's like, oh, I keep telling you and telling you. And by the way, the notion of like, not so much mean, but let's say tense, difficult, is about how I keep telling you this and you aren't changing. And now I'm frustrated, understandably.

Yeah.

Right. But the question always is, well, did you get a commitment around change? Did you actually agree what was going to be different? And in that context, you then have something to go back and say, hey, we had this conversation. You told me you're going to do this differently and you didn't. What happened? Yeah.

What if there's a disagreement behind what the root cause of the issue is?

Yeah. Then you get to talk it out. Because that's the whole thing, like you're not keeping your peers up to date, do that. They're like, well, now hang on, wait a minute. I've been trying to keep my peers up to date, but somehow they're not responding to me or picking it up or whatever, or they hear what I want to do, but they don't like what I want to do, so they want to do their own thing. Oh, wow. Thanks for telling me. That's fantastic. Now we have to have a discussion with the team as a whole, just as an example. So either way, the point about root cause, like getting to root cause, is part of the point about dialogue. And you will never get there if you don't approach having those difficult conversations.

So we talked about how to turn nice to maybe not mean, but more direct.

Direct, yeah.

What about the opposite end? You hear about Steve Jobs and Elon Musk's management styles, and they get amazing results.

Yep.

What are things that can often turn wrong if you're too aggressive? Like, what is the bar of aggressive good and aggressive bad?

I know. By the way, isn't that the million-dollar question, right?

Yeah.

I know. Because let's talk about Elon Musk. You know, Steve Jobs, we only have his myth. So I feel like we're very far away from how he really was. And we all think and know, and theoretically I think, that he grew as a leader, right? People would say that. Elon's right here in front of us playing out in the news. And people are working with Elon, and you hear a lot of their chatter. So I think, first of all, I would just say that— I'll just talk about Elon for a second. Again, I don't know him. And so I'm just kind of responding to press accounts and whatnot. You have to appreciate that he's a first principles thinker.

Yeah.

And you have to appreciate that he's there in a sleeping bag by himself helping you work through the problem and kind of considered himself like cheap Chief problem solver. You have to appreciate all that. If a founder comes to me and says, but Elon Musk does, it works for him. I would always say in the nicest possible way, Elon Musk is once in a generation. I suspect that you're not going to get that glow.

Do what works for you.

Right, exactly. But I did work with a founder once and his team was on the verge of mutiny because he was so critical, constantly critical. Nothing was good enough. He did all the things. He worked super hard, the hardest one in the office. He was a genius at fundraising. He was doing all the things. He hired a great team. And he was so critical of them that they couldn't take him. So by the way, there are consequences of that, right?

Yeah.

So it's not like this is not my rule. This is their rule. They were on the verge of mutiny and about to quit. And that's when he hired me to help him understand what's the problem of just being— I just have high standards, right? But it turned out he hadn't done the work around Building the right culture, building the right community around—

And trust.

Trust, 100%. Even like positive feedback, what is going well. And then what he really didn't do is set a clear vision and agenda. So they were all doing the best they could and it was never good enough because he was never clear on what he really wanted.

What that meant.

Yeah. So setting clear goals and objectives, acknowledging you don't know what they are, thinking like, wow, it's kind of like out here, let's figure it out together. All of those kinds of things help you be not so critical. But I would just say the last thing is that Many founders are themselves super driven and self-critical. And so the other thing is to really look inward to see what's the inner voice that I'm giving myself saying, and how is that showing up in the outside world?

That usually manifests externally.

It does. It always does. And, you know, they say about the founders, right? Chips on shoulders, like, you know, chips in pockets, right? And I think that's really true that a drive for founders often comes from that like sense of dissatisfaction and it's great and it has to be tamed.

Yeah. How, like you said, in the early stages, that drive and the chip can be a green flag.

Yeah.

Are there any traits, let's say you were a VC and you're like, oh, this is a trait in an early-stage founder, green flag, but that trait is a red flag for later-stage founders? It makes them the bottleneck.

Yeah, I think it's, I think, really hard to see this in the beginning because you don't know how someone's going to grow. And I think investors who say they can see it, I would just say I think that there may be a little bias in their sample size and whatnot. However, if you are a big control freak as an early-stage founder, that's fantastic. That's wonderful. You're in it. You're focused. If you can't then let go appropriately, we're talking about zoom in and zoom out, you'll just never scale. You just won't.

Yeah.

If you're the kind of person that's almost overly charismatic, and that can be fantastic, you then— we've seen this with like WeWork and other kind of companies like that, it's like the charisma is bringing you along and you're building a cult around you. And there's good in that. And then ultimately, that doesn't sustain a long-term business.

Yeah. Yeah. So tell me about charisma and where that breaks. Where does charisma break?

I mean, it's— I think it breaks when you're— you're— so when people can't tell you the truth. And you have such a reality distortion field and you're not right, then you're bringing people off a cliff and no one is there to say, we're going off a cliff, or like, this doesn't make any sense, or the team's not with you, or this isn't like, this is no longer kind of pinned to reality. And I think, so let's say, quote unquote, over-charisma. It's also people wanna please you and they want your approval. And all of that can turn toxic.

How would you coach a founder who maybe has a culture where people are afraid to disagree? What do they do in meetings to say, hey, let's flip this around. Let's un-Adam Neumann this.

Let's un-Adam Neumann this. But that's what you just said is exactly right. Let's flip this around. You can't come to this— everyone wants to be in the executive team meeting. Everyone wants to be at the big table in the executive team meeting. It's like this big thing. And it's like the cost of admission, the price of admission for coming to this meeting is telling me something I do not want to hear. So it's like, Sometimes a team, by the way, again, it's like, what kind of team is this? You look at a situation, you've got to just deal with things situationally. If you have a founder who's very critical and focused only on what we haven't done, what we haven't done, or not what we have done, then a great starting point of that meeting is let's do good news. Let's do milestones and good news around the table. Let's take 10 minutes to do that.

Yeah.

And then we can have our meeting. But with a founder that might be not getting the bad news, it's like, let's start with bad news. Okay, what do I not want to hear? Start with bad news. Go around the room. And if you can't give me on a regular basis something I don't want to hear, I'm kind of wondering, are you involved? Like, what's going on that you can't give me some bad news? Because I'm sure there's bad news happening. If everything's perfect. Yeah, if everything's perfect, why are you here? Right? So it's like, it's like very helpful to just be open to that. The other thing is, if you as a founder want feedback and people aren't giving you feedback, I'm looking at your team, if you're not giving— if they're not getting feedback, You can also say, what suggestions do you have for me to make me a better leader? They can say, oh, nothing. It's so great. Okay, good. Then if you keep on a regular basis saying, well, what suggestions do you have? How can I be better? They might have 1 or 2 suggestions and then you can say, thank you so much. It's really helpful, and you try to implement a few so that people learn that when you get suggestions, you don't punish, you actually reward.

Yeah. Earlier you talked about the founder being the driver in the driver's seat that sets the vision. How do you think about how much a founder should communicate the thinking behind the vision? Because part of the founder job is also to protect the team.

Yeah.

But also, you need to explain enough to show the work that you've done to justify your reasoning behind a strategy.

Yeah.

So describe the delineation between overcommunication and just the right amount of communication.

There is never overcommunication. There's never overcommunication. Not really. In that context, now there's other things, right? piggyback on what you said. But in general, it's like, here's the vision, here's the historical context, right? The founders, like, the best founders are the best historians. Like, I understand my space.

Yes.

I've done deep in this. Connect all the dots. Connect all the dots. I've talked to 20 people. I know what we're doing. I have a point of view on this. I'm open to your input, but I have a point of view on this. All that's fantastic. And this is the vision. This is why it's going to be so great, including, you know, the world hasn't caught up. The world hasn't caught up yet. Right? So it's like we are continuing this path and we're going to have the world— the world's going to catch up. And here's why I think that. Right? So that's actually super helpful. And you can almost never overcommunicate that. I think the problem does come because founders are ideas generators. And so if you're generating idea after idea after idea, there's a lot of problems with that. First of all, the team can't handle it. First of all, they don't know if it's— should we do this? So we're doing this now? Not? And you feel like we got 20 things to do. You're like, no, we only have one thing to do. Well, you keep giving us 20 things. No, I'm just talking, right? So it's very helpful to remember this is what has to be the focus. The second thing is, if indeed you are having all these ideas that we should be trying out, at some point you don't have the management capacity to try out all those ideas. And your job to, quote unquote, protect the team is definitely focused on, I'm going to keep my ideas to myself. I'm going to tell my trusted friends and colleagues, maybe my co-founder, maybe my AI, whatever. But I'm not going to tell the team because it's going to be distracting for them. And so that's how you want to think about it.

What are some things that you would advise founders prior to 3 years ago that maybe does not relate anymore? You've changed your mind because of AI on management, leadership. Are there any things that you've really had to question? Is this right still?

I mean, I think I was very moved. This is not about AI as much as I was really moved and I recognized the truth in founder mode. And I think that coaches, HR people, professional managers are all trained to be like, delegate, you should be delegating. And the only thing I would say is that I always had an asterisk to myself. Like, I would always— so I would talk to— I would be working with the founder and I would be doing 360 feedback. Do you know what 360 feedback is? You talk to folks all around.

I did it.

Okay, you did it. I want to hear what you found out.

I found out a lot.

We're going to get to that in a second. Okay. But I talked to the HR person. This always happens, and I say, "What? How should get better?" Da da. And I say, "Oh, he's delegate more." Okay, tell me more. He's to trust them and delegate more. Then I would say, "Great. Can he trust them?" And then the HR per this is like so red red for me. She would say, "Oh, I don't know." Like, okay. Well, if you don't know, then what do you mean trust them? Like what? Say more, right? It's just such a meme. And when Founder Mode came out, I myself was like, I know, that does feel right.

Yes.

That does feel right, that actually delegating everything all the time and that being the goal doesn't actually make sense. And professional managers do a lot of work around massaging and smoothing things out. So I think that was a big shift for me. And I personally felt more empowered around, I'm not sure delegation is the right idea, right? Like, just to say that. I think in the age of AI, The notion of— I think it used to be like overhiring was kind of normal. I think overhiring is no longer acceptable.

It's done. Right.

Yeah. You just can't. Like, you need to use the tools to help you at least do a better job of figuring out who you want to hire and what capabilities they need. And certainly use the tools to drive efficiencies. I think that— I'm not saying that's a change that I felt, but that's a change in companies that I think everybody needs to internalize. For sure.

So I imagine a lot of the founders that you coached that started companies before AI are like, oh my God, our entire business model is done. Our product can be vibe coded in a second. Our strategy doesn't work anymore. There's no more quarterly planning. It's weekly planning now. How have you seen that transition done most effectively from like, hey, we can predict the future, to now nothing is predictable and we need to be more nimble?

So Everything you just said, so true, times 100. And first of all, everybody has to just get really connected, make a friend of reality, right? Reality has won 100% of the time. So it's like, oh, I wish it weren't true. No, no, no. And the founders I work with pretty much are ready to embrace reality. It's people they work with who are unready to embrace reality. And so it's more about, you know, they're ready, willing, and able to start. I won't even say pivot, but I will say like, look and see what we have. And then figure out how do we now adapt in the face of AI? Do we have to adapt our product, our service? Do we have to add a different product? Do we have to pivot completely? I don't know. But, like, that is something you need as a founder to look at 100%. And the more challenging thing has been bringing the team along. Because you've got, even in a startup, 100 people, 1,000 people, whatever it is, you've got comfortable people doing the thing. And you've brought in people who are really comfortable doing the thing. And now the thing is no longer relevant. And so they don't like that. I don't blame them. I don't like it either. And you've got to get them on board with it's no longer true. And one of my, like, sayings is, it's not my truth. I'm reading it in the Wall Street Journal just like you are.

Right.

It's not— this is not my rule. Like, look around you and see what's happening. So you've got to bring people along in that way. A lot of them are not just candidly going to be equipped to make that adjustment. You've got to be straight with them about explaining what's involved in that adjustment. By the way, there's never been a better time for self-study. If you get somebody out there who's like, I have no idea what this is, but I'm going to spend the weekend learning it, I'm like, I love you. You should go anywhere. You should definitely keep that person because that person is focused on their own learning and taking initiative. But really making the case for the people on the team that things are different, we need to think differently, we need to have our workflows different, we need to change our ways of working, that has been very challenging. Interestingly, all my clients and all my colleagues and friends and everybody I know has often said, they've often said it's even more challenging for the engineers because they've had to change their way of working and they're entrenched in a certain kind of way.

For sure.

But it's certainly true I mean, every single industry, every single company I work in, startups and not startups, is being transformed in a way that it feels unstable. And so, like your point about it's no longer quarterly planning, it's kind of weekly planning or monthly planning.

You're flexible.

Yes.

You just got to be not attached.

Not attached. Exactly. Agile. But then you as a founder have to kind of still hold on to what is true. So I think it's very helpful to be like, What is up for discussion? What is adjustable? And what is never gonna change?

Yeah.

Yeah.

So there is a benefit to the self-study thing.

Yeah.

Anyone can learn anything. I found the negative, the reverse of that, is because you can learn anything, you think you can do more.

That's true.

And so there's less focus.

Yeah.

How have you seen the best CEOs, one, keep people focused and honest on what they're actually good at?

Yeah. I mean—

Because AI can make you feel like you're good at things when you're not.

I know. Do you know, that hasn't been the biggest issue. The issue has more been that people are really reticent and hesitant to try to use AI to its fullest and to push themselves, I would say.

So you would actually say the opposite approach, they're not doing it enough?

I think they're not. I think on the whole, they're not doing it enough. And I think A CEO, a founder would be delighted to have somebody come and say, I'm doing all these things, you know, like, and it's working really well. And then I think just like any partner, let's look at it together. It's really helpful when you are sitting with someone and you're saying, let's look at that work product on the other side of the table. We're here on this side of the table looking at that work product, which is over there, and let's now assess it. And then, you know, it's like quality.

It's the conversation.

Yeah, it's just a conversation.

Yeah. Do you have a framework for the shift from I'm involved to delegation? Where it's like we've built trust, now is a good time for delegation.

I think it's a journey. I think it's a total journey because—

It's not a one-time thing.

No. I think another thing I've changed my mind on is this notion of a 90-day onboarding plan. I just had Tene, the founder of Whisper, on my podcast. I was surprised to hear it was from him, But it resonated with the same kind of advice as the CEO of Databricks, which is, I spend a lot of time with people early on. Like, I spend hours every day with this new person, especially a high-level executive, so that I can share context.

Mm-hmm.

And Greg Gallant from Muck Rack told me that it's like, you're the expert on sales or marketing or whatever that is. I'm the expert on muckrack. And so we want to come together.

The intuition, vision.

Exactly. How we got here, the skeletons in the closet. I don't want to tell you, like, don't do that because we tried it before. But I do want to tell you all the ways we tried that before. So when you try it this time, you should try to do it differently, taking that into account. And that is such a vast shortcut. And a lot of traditional executives don't like it. Because they're like, why are you in my shorts? I know what I'm doing. And I'm sort of sympathetic, but I think it's super helpful. to spend time and energy getting someone up to speed. We spend so much time and energy hiring people, and this onboarding thing is like 90 days and leave them alone. No, no, no. It needs to be hours per day touching in. So the question is, after a week or 2 or 3 of that, you got trust with this person. Hopefully. If you don't trust, then you know—

It's a different problem.

Yeah, exactly. But you have trust with this person, and you're also seeing the way they act, and you're seeing the way that like, oh, we talked about this thing 2 days ago and now it's fixed, or Oh, they brought me these 5 problems based on this discussion that we had. Oh, they're listening. I love that. And then they resolved 3 of the 5 problems already. And here are the 2 left. Oh, I feel trusting of this person. But it's just experience, right? Yeah.

What's the hardest thing you've had to coach a founder through, both for you and them? I want to depict how dark it can get.

What happens with founders is they aren't taking care of themselves. They just aren't. They're working a lot of the time. This may be less true now because I think we're more in like a physical fitness culture.

Yeah.

But certainly like 5 or 10 years ago, it was not true that founders were taking care. It was like a badge of honor, like, I'm not getting any sleep, whatever. And that is a disaster and really leads to depression. And then the second thing is, of course, they need to go see a therapist or somebody who's a specialist to help them really deal with their feelings. And there's one or two cases where the founder quit. Like, it was like, you know what, this is not making me happy. This is terrible. It's not good for me. And there are some cases where they were able to kind of get out of it by taking care of themselves, by, you know, some of the—

Internal work seems to be—

Yeah, the internal work, but also spring, right? Sometimes actually it's like the weather is really bad and they're staying— oh my God, one of them staying in his apartment the whole time because he's just working the whole time and the weather's so bad in New York, right? Which I get. And you need to have the self-awareness to be like, okay, I need to Get outside at least once a day, right? That kind of stuff. I think I would say that people would be amazed at how much the physical matters more than we really give it credit for.

Yeah, it seems obvious, but sometimes you just have to experience it for yourself.

Yes, it seems obvious, right?

Until you hit a wall.

Yeah.

You coach founders to do the internal work.

Yeah.

Should founders be coaching their teams to do the internal work as well?

Well, I think so. That's my religion, right? The internal work is my religion. I think that everybody can benefit from doing the internal work. I think most people need partners and somebody to help with the internal work, whether it's a coach or a therapist, even like just a journal. I think everybody without the internal work, most workplaces, right, large companies, small companies, are filled with 4th graders and 6th graders acting out. I just think that that's my observation. And I think if people do their internal work, that means kind of healing their 6th grader And coming into the world as— coming into the workplace in their best self more often. And I think that's better.

So you think the founder should serve as a bit of a therapist sometimes?

No, I don't think the founder can serve as a bit of a therapist. I think any engaged leader should be a safe space for people. And you can say like, hey, I noticed you're a little quiet. Are you okay? Or being willing and able to engage in like, oh, this is going on with my family or my whatever, whatever. You're like, oh, That's rough. I'm sorry. And be a good listener.

Yeah.

But do I think that most founders have the inclination, the time, or the skills to really help people go deep and do that healing? No. But I think it's like, listen, I care about you. I care about you as a person and in service of this company. And what I think you should do is do some internal work. It seems like maybe you should talk to a therapist. Maybe you should do more journaling or find practices that are going to help you resolve some of these things. And the way it shows up is, an example, in a workplace you often have people, a few people who are just defensive. Like no matter what you say, they're defensive. Or it might be if you give them feedback, they shut down. Oh, I'm so terrible. It's so bad. They shut down. And you're like, no, I'm just asking you to change a little bit of this thing. You don't have to overreact. These are examples. Or then you have 2 people who can't work out a pretty simple topic because one or both of them have to always be right. Wow, what's going on there? In all of those cases, that's obviously not a fully healed, fully formed human being. There's something that's unfortunately getting in the way. They mean well, but it's something getting in the way. It'd be really helpful to explore that and try to resolve it because it's going to make you happier. Oh, by the way, it's going to make you a better employee.

Assuming there are a lot of founders watching this episode that may not have the privilege of having your time, they will have your Delphi's time. Oh, yes.

My Delphi's time.

What is a question or situation that maybe you think founders are afraid to ask? They're afraid to ask for help on, that you encourage them to feel comfortable asking your Delphi?

Please ask my Delphi how to handle imposter syndrome. Because imposter syndrome, severe self-doubt, these sort of feelings of significant doubt or I'm going to become a fraud are rampant in the startup world. And also, it's true that, like, 95— I don't know how to get statistics, but like 95 100% of enormously successful people at some point experience deep imposter syndrome. And the problem is they can't tell anybody because it's like such a shameful thing. So please ask my Delphi, please, how to handle imposter syndrome, and you will get a lot of tools about how to handle imposter syndrome, including challenging, really getting it attuned, tuning in on the thoughts, the actual thoughts that you're having, and challenging them with evidence. Number 2, creating a highlight reel, which is about times you overcame challenges to remind yourself of your greatness when you kind of Forget about it. And certainly number 3 is about finding your support group of people who remind you of your greatness on a regular basis. And all of those things repeated one at a time on a regular basis will help you overcome normal imposter syndrome that will then help you flourish and build companies because we need your talents and we need you in the world building companies and creating new things. And that's what creates our world so great, makes our world so great.

Great answer, and it actually brought a follow-up question.

Okay, great.

As a founder, I feel like every month you're doing something for the first time.

Yes.

Again, and especially as the company grows, whether it's design, pricing, brand, Series B, all these things.

Yeah.

What's your thoughts on— some version of it is fake it till you make it.

Yeah.

Some version of it is like manifestation, like act the part before you have to become the part. And some people just like accept that you're a beginner and be humble.

Yeah.

What strategy have you seen be the most effective?

All of the above.

All the above.

All the above. Because fake it till you make it is great until it's like toxic fake it till you make it. Then it turns into, again, this toxicity. But I think it's about reminding yourself that you've overcome challenges before and that you can do hard things. Then really internalizing, I can do hard things. I'm the person that can do hard things, which means you stand up straight and you then project. Then you think about and you visualize, you manifest, What would this meeting look like if it came out great? What would this situation be if it came out great? And really think about that and enter the space with that input. And then also, yeah, don't lie. Like in the sense of, I haven't done these kinds of things before. I'm learning all the time. People love a learning culture, especially in startup world. People love somebody who's willing and able to do the reps and do the work. And I think being honest about that. So I think it's about all the flavors of that.

Yeah.

And kind of fine-tuning what's gonna work when.

I love that.

Yeah.

Thank you so much.

You're welcome. Thank you. Oh my God, this is so fun. Yay. Yay, all of us.

Thanks for tuning in. If you enjoyed today's episode and want personalized advice from Alyssa, head to the link in the comments or description to ask her digital mind on Delphi.