CEO

“The other element that served me well was just refusing to specialize. I thought if I could learn all the skills that would allow me to combine them to work on the most important things versus only work on the thing I knew how to work on. And that definitely l…”

“You as a PM perhaps are fixated as you are dealing with this launch or this project, you are fixated on the execution level, which is what does it take to get something done? And how can I do it? How can I hit the next milestone? Those are all the things we ar…”

“So that's why it has to be a small team that reports to outside of EPD. It can't report to the head of engineering, head of product or head of design. Can't. It's gotta go outside, usually directly to the CEO.”

“There's a metaphor I like to use when I give PMs advice on where to work within a company, which is there's like the eye of Sauron, which is the number one most important thing to the CEO at that time. And my advice is often don't avoid that thing usually, but…”

“100% of VC is a salesperson. Cause they're selling LPs to give them money and they're selling CEOs to take their money in exchange for equity. Like that's the job of a VC. All the analytics, all the data and the, this and the, that, those are just like updatin…”

“If somebody else is ghostwriting all their stuff, it shows.”

“With leadership roles, you don't get put on a pip, right? Like if a CEO loses confidence, it's over immediately.”

“When I looked after I did this work for a few years, I looked back and I was like, which were the ones where, which were the engagements I did where like, I can see it. And it just, the narrative is like really this true north star for everything. And it was a…”

“The one thing I say is like, it's this one story that the CEO uses To drive success in, in marketing, sales, but also product, that it becomes like a North Star, strategic North Star for product roadmap, for fundraising, for recruiting, really everything.”

“If you're joining a company and the CEO does the role that is your functional area of expertise, it's probably the area where you'll learn the most because they're hopefully world-class at it, but also when will you, you'll be the most frustrated at times beca…”

“Anyone who's looking at that and like, dear CEOs or whoever who are like, now I can lay off half my workforce. That's not what this is about, right? It's not about taking a task and cutting your time in half because now what we've enabled is your ability to do…”

“I think the CEO should be basically the chief product officer of a product or tech company. And the CEO is not the chief product officer. Then I don't know if they're a product or tech led company.”

“So I don't think it's a tactical prioritization product manager call. It really is a product strategy call, and the conversation that needs to happen Is between say the head of product and the CEO or even like the leadership. If I gave you a hundred focus poin…”

“The nervous system of an organization is a reflection of the nervous system of the CEO.”

“If you're not spending 20% of your time in sales and 20% of your time in recruiting, you're failing as a founder. You need 20% of each. 20% in sales and 20% recruiting. Nothing else really matters at some level as a CEO, maybe not as founders, but as CEOs.”

“The big unlock for me was realizing that you can achieve all the same things using different strengths. Like you can be an amazing CEO being very loud, charismatic, visionary. You could also be a great CEO being very quiet and thoughtful and deliberative and w…”

“I work with a lot of founders, CEOs, and senior executives who are dyslexic. Very, very, very common, especially for CEOs.”

“So let's say you have let's say you sell it into CFOs. Don't pitch your CEO for that podcast, pitch your, you know, get a CFO and then pitch your CFO for that podcast. I'm very for companies hiring. Folks are hiring for the roles that they sell into. It helps …”

“In fact, I would say that it actually makes it very hard to be a founder if you've been a great CEO, because you've turned into this sustainer versus destroyer or creator, right?”

“A lot of CEOs have done well because they follow the dharma of the founders quite well. They have not diluted the dharma of the founders who have Started these companies and managed to sustain that.”

“Bringing them under one house allows you to optimize for the whole as opposed to optimize for the function. And if you can find a leader that is effective at that, I think you can get a lot of value out of it. And honestly, the second thing is it provides a tr…”

“The first one is that the CEO goes alone to the meeting. I need the headlight on me. I don't need any distractions. I don't need my team members. I don't need anything else in the room, just me.”

“In a small place like a startup, The hard decisions will always go to the top. Now, if the CEO does not make that hard decisions, the result is always the same. The top performing people would leave. They would leave because they don't want to be in a place th…”

“What I, what I'd say to everyone else is, like, make sure you just have a mind meld with the CEO before you decide to take the job. Like, spend a day together. Like, understand how they think and how they operate and whether you're gonna work together in a way…”

“I think when you do minus one to one, it's really hard unless the CEO says, I don't care about, you know, how the company performs for the next two years. We're going to go for it. If you want to keep the site, keep growing and the experience keep growing, car…”

“And the more senior you are, Lenny, the longer it is. If you're a CEO, it's going to take you a long time, unless you happen to be the CEO of Chipotle, who just became the CEO of Starbucks.”

“Most CEOs are really bad at planning, and that's because there's this little known secret in the Bay Area. Most CEOs never run a business before.”

“In a lot of professions like in sports or, you know, math or chess or certain academic fields, like you kind of peak in your twenties or thirties. CEO is not like that. You can kind of go your whole life and still not be like a master.”

“Everybody's got strength and weaknesses, but as CEO, like, you know, both your strengths and your weaknesses are massively amplified. And a lot of blind spots in your personality can become huge cultural dysfunctions in the company.”

“Most CEOs, most companies can't even successfully do that and just like engage in like this sort of pulling future profits forward at a discount or even defecting on partnerships that would be much more long-term valuable.”

“All the CEOs in the world, if you would ask them, have you nearly died already? And they will tell you yes. And then the next question would be how many times? And they will tell you multiple times. And if they are not, that means that they are simply too earl…”

“No CEO ever gets their executive team right on the first try.”

“And if you don't, if you disagree with it, like, you probably shouldn't be working in that company.”

“When you're reporting to the CEO and like as a chief product officer, the big mistake that people make is they think that the game is all about getting what is inside their head and like influencing the CEO, influencing the people around them to make it so. An…”

“What is what much more helpful than understanding what your CEO thinks is I think understanding how your CEO thinks.”

“And I've just found that hiring CEOs is like, you're, they're an elephant and you're the rider. They're going to go wherever it is that they want to go. And so listening incredibly carefully to people's words and their experiences, because generally people wil…”

“When tiny buys a company, we generally just leave them alone. If they already have management in place, we say nothing changes. You know, no one should know that any, that we've even bought them. Obviously people know that, but really like there should be no c…”

“I think the way I've come to think about it is that the product manager is responsible for the whole team thinking like a CEO, if that makes sense. So if the product manager takes that on as their sole responsibility and says, I'm the mini CEO, I think about t…”

“Most CEOs or most executives are incredibly disconnected from the actual AI adoption taking place in, in, inside their companies.”

“There, no, from this day on, no credit will be given for predicting rain, only credit for building an arc. And I think that's more true for CEOs than anybody. You know, you have to build an arc. Like, it doesn't matter, like, if you predict you're gonna fail, …”

“The idea that you're going to take somebody who doesn't, who isn't world-class at marketing and make them world-class, and you don't know anything about marketing is a dumb idea. It just doesn't work.”

“If I have the ideas about what your department should do next, if I, you know, am kind of pushing you to kind of move your organization forward, then that's no leverage. What's leverage is if you're telling me what you should do and how you can push the compan…”

“All the things that you perceive that are happening to you that are bad, you know, be it like the systems against you or somebody undercut you or racism or sexism or this or that or the other is very small compared to like, it means a lot if you believe it, yo…”

“CTOs tend to be skeptics. They're, they love facts. They seek knowledge. They want depth of awareness and understanding, and they also like to be self-sufficient. This is a total generalization, but I've seen this pattern over and over again. The CEO is the pe…”

“Two people owning a goal is no one owning a goal. One person owns the goal. Who is it? It's not you as the CEO. It's someone that works for you.”

“If you're sending an email and the first person on the email is the assistant and the fourth person on the email is the CEO, you've probably done it wrong.”

“Like wanting to be liked, I don't think is a good feature of a CEO and wanting to be the best place to work probably isn't the right way to go.”

“I think CEOs and everyone dramatically overrates their ability to interview and overrates their gut feeling and underrates a really high quality blind reference.”

“So I spend most of my time these days coaching very fast growth CEOs. They all are kind of like that. They're all in kind of a state of perfection, perpetual, Dissatisfaction, but in a positive way. One of the things, by the way, I like about the current crop …”

“And I've been surprised at how humble this generation is of CEOs. And I think of my generation of CEOs as being, I don't know, I wouldn't, humble wasn't the first word that would come out of your mouth when you describe kind of my generation, but this generati…”

“Although I actually do think PM is a mini CEO. Like I think people keep saying you're not, but I think you are.”

“The other thing people don't do is they don't control the time of which they have a conversation. CEO wants to hop on at six o'clock in the morning, get your ass up, get that presentation and go. You need to say, I'm not available at that time. I'm in, and you…”

“The more success you have, the more complacent the organization tends to get in the single role for the CEO is offsetting that complacency. So, to the point, the more success you have, the better you're doing, the more complacency naturally kicks in. And unles…”

“My experience is that your company is only going to go as far as your CEO goes in AI, and it's not something you can delegate.”

“A lot of the times I've seen the CPO CEO relationship go badly and ends up with like the CPO is competing with the CEO for vision and they end up at like loggerheads. And I think, you know, that's not your job.”

“If nobody's got data, it's just two opinions. The CEO's opinion is going to win. And like, that's okay. Check your ego at the door, get to the answer.”