Lenny's Podcast: Product | Career | Growth
00:26:45 · Lenny Rachitsky, Casey Winters
[00:26:45] S1: I've had the exact same experience. I had it, describe what I've done, it was, like, 70% mistaken. Yep. Is there anything you've found value in yet with GPT of any kind in your your work, or is it still kind of just poking around in novelty for you? [00:27:00] S0: Yeah. I've had a couple of those things where it's like, hey. How do I actually get this weird thing done? And it's been like, you know, clear bullet points, take these steps, and I'm like, oh, great. Like, this was actually really hard to find on Google. So things like that, I actually quite like it for. So that's where my head goes to, like, more confidently use it. Because, of course, I'll try it, and if it's wrong, I'll learn where So it's it's it's low risk. But it's been right on some of those things, and it's like, oh, cool. I couldn't figure out how to do that. There's something on Google Docs that I need to figure out how to do that was kinda fancy. I asked ChatGPT. They told me how to do it, and I was like, oh, great. [00:27:39] S1: I had a similar experience where I just needed a formula in Google Sheets, and I just told it, like, I need this thing, and it just gives me the actual formula. [00:27:45] S0: Yeah. That's that's so magical when it happens.
00:27:45 · Casey Winters, Lenny Rachitsky
[00:27:45] S0: Yeah. That's that's so magical when it happens. [00:27:47] S1: Yeah. I don't know. I'm not that good with sheets formulas. Shifting course a little bit, you also wrote this really interesting post on founder intuition versus team expertise, and there's a lot to it. And I think it's a really interesting topic because it's this classic discussion that startups have. How much should a founder trust their gut and how much should it be top down? Here's what we should be doing versus the team kinda bottom up, figure out what to build. And so I'd love to spend a little time here. So maybe just to start broadly, what is this... You kinda came up with a framework of how to think about when founder intuition should overrule, say, team expertise and how that changes over time. So maybe just talk about that.
00:28:25 · Casey Winters
[00:28:25] S0: Yeah. If founders are lucky slash good enough to find product market fit, They've usually built up all this intuition about their customers, about their product, and their business that are really hard to explain to others and may even be, like, subconscious. So when they start to hire people, you know, these people will come in with a lot of, you know, excitement, ideas, maybe even really relevant experience, especially, you know, senior leaders. And I've seen some founders are like, cool. I need to let these experts start to own these areas and get out of the details. And I think that's actually the opposite of what you want because none of these people know the business as well as you get. You actually need to direct them until they show you they've really got it and are making better decisions than you would. So this is not a Founder example, but I remember when I hired Erika Warren to build out our loyalty program at Grubhub. She now leads growth at at change.org. And after a month or so, she was like, dude, you're in all my meetings. I got this. And, you know, that let me know she was in a different part of the situational leadership framework than I had put her in. So I backed away, and, you know, she crushed it from there. Founders will put a lot of new leaders in that delegate bucket too quickly. It's like, oh, it's theirs. They got it. They know more than me. When founders actually know the right answer and should just tell them. And this can, of course, change. Like, in the case of Erika, you know, if you hire the right people, they they do get smarter than you. You can and should start delegating. And many founders don't notice the signals where their founder intuition has been usurped by team expertise, or maybe it's just ebbed in effectiveness over time. And and that, of course, makes sense. Right? Founders have all these different things they're dealing with, and then your employees can really dive deep in certain areas. So I encourage employees to proactively signal both directions, like, hey. I need direction from you, or hey. I got it from here. Trust me on this one.
00:30:27 · Lenny Rachitsky, Casey Winters
[00:30:27] S1: Interesting. So you're saying as a founder, the heuristic should be if you feel confident about a decision, generally, you should be clear, like, Hey, I think I know what we need to be doing here. Don't just make people feel better necessarily by just saying, Okay, you tell us what you want to do. And then on the flip side, an employee at the company, if you feel really confident about something, make it clear to the founder, like, I really think this is the right move. Is there anything more you wanna add there? [00:30:55] S0: Yeah. Well, I mean, there's obviously the feedback loop of that, of, like, you know, what happens when you do either of those things. So, you know, depending on the the founder's response to that or the employee's response to that, there's kinda different approaches, you know, you can take. [00:31:12] S1: And part of this, yeah, this cool chart of just, like, over time, the founder expertise becomes less and less relevant. And I guess is that because they just don't spend as much time with the customers because they have other stuff going on where they hire people that are smarter. And then over time, team expertise goes up.
00:31:26 · Casey Winters
[00:31:26] S0: If you're lucky enough to scale a company, there's just more and more things going on that all will reach the founder in some way, but it means more breadth and less depth on any particular issue. And the reverse is true for, you know, people you hire. Right? You're able to get really deep into things that maybe you were really deep into two years ago, but, you know, you just can't you can't stay deep in anymore. So I I I built this, you know, chart on... Or or I guess I should say table on the different phases of, you know, a startup. Right? And when you're finding product market fit, like, everything goes through the founders. Like, you cannot outsource that. And then, you know, when you start scaling the company because you found product market fit, it's the first time that founders run into this, like, classic problem of what got you here won't get you there. What got you to product market today was iterating on product and doing things that don't scale. Guess what? You found a product that works. Don't do that anymore. Make it scale. Don't come up with new products. You found the one that works. The reason I came up with this, you know, framework, originally is when I was at Grubhub, you know, we were scaling pretty nicely and and fairly organically. I I think, Mike and Matt, the founders, had intuited these phases of, like, building a company, like, pretty well. But we acquired a competitor, and, you know, I saw how that company we acquired operated. And even though they were largely in the same phase as us, they still operated like they were founding the company. Like, everything was going through the founder. And, you know, intuitively, I was like, oh, this is why we're acquiring you and not the other way around. So I think it's really hard for founders to get those signals organically, and I think it's up to us as employees to help. And, you know, the founders can listen to the signals or not listen to those signals, but that's part of why why we're here. But we should also give those signals when we're confident we really get it. Not like coming day one being, know what your sales strategy should be. You're doing it all wrong. Chances are the founders weren't doing it all wrong. They knew something you don't know about yet.
00:33:33 · Lenny Rachitsky, Casey Winters
[00:33:33] S1: What is it that you think made it such that you won and they didn't... Is it because they didn't invest... They didn't shift to scaling and delegating to their employees as much as the founder just telling everyone? Correct. Right. Like, the, [00:33:45] S0: everything was, like, not moving as quickly because everything had to go through the same person to get done. So it just allowed them to not launch as many markets, to not sign up as many restaurants, to not figure out as many, you know, growth channels, yeah, as we had done. [00:33:59] S1: Got it. So they just bottlenecked themselves, and they weren't able to move as fast because the founder thought they needed to make these decisions, and they were still the ones that knew everything. Yep. That makes me think about most companies, maybe not most, but many founders just, like, believe they have the answers. Like, they are confident they know what to do. Right. And it's rare they get to a place of like, no. I actually don't. [00:34:21] S0: Well, I would say no one gets to no no one gets to it super intuitively. [00:34:26] S1: Any advice for either as a employee at a company with a founder like that or a leader of just how to push back and help the founder understand maybe you should let go and trust people to make decisions?