Lenny's Podcast: Product | Career | Growth
00:53:51 · Tom Verrilli
[00:53:51] S0: Yeah. Funnily, that's become most of my career. Actually, I've worked for three founders in a row who are all very product-minded and whatnot. I've got two, which is a blessing actually. In general, I try not to double up. If Grant or Logan, our founders are on a thing, probably doesn't need me. What's the advantage of an extra layer? I think jokingly one of the PMs on the team has referred to it as the two dads problem where you've just got two people issuing conflicting instructions, or somebody wants to review and then you do all this work to present it to me, and then you go back and it gets a different thing. So my first thing is if Grant or Logan are on it, I check that they're watching it, they're accountable for it, and I step out. So there'll be long periods of time where fully half my team can be working on something, and I couldn't tell you day-to-day where it is because it's with Grant, it's with Logan, and that's totally fine. I don't have to be across all of the things they're doing. We just need to make sure that there is somebody doing that bar raising. So we spent much time doing that alignment. I think the second one is, ultimately, if you are a product leader in a founder-led company, you have to understand it's not your company, it's theirs. And you just find the right balance of, hey, are you open to feedback on this? Have you made up your mind? Are you open to a push on this? And you just find that rhythm working with folks. Generally speaking, there's a reason that founder-led companies do so well in our industry. The insight required and the kind of customer intuition to make the thing in the first place and work tends to be really important. And then I just view my job as making sure that we've got coverage on the places where our founders are.
00:55:28 · Lenny Rachitsky, Tom Verrilli
[00:55:28] S1: Awesome. So a couple things you've learned here for building, and I think in consumer, this is especially important, is counterintuitively to how maybe people think things should work, you're finding that the best teams, companies, products end up coming from top-down, founder-led, almost micromanagement is a dirty word to a lot of people, but it's basically being in the weeds is, in spite of how people may feel, this actually ends up being leading to better stuff, better [inaudible 00:55:56]. [00:55:55] S0: Top-down works well if leadership is good enough to be in the weeds and be specifically correct. I think where it falls apart is where you don't actually know ground truth and then you attempt to manage people from above. And that's where I think the term micromanagement comes from. Otherwise, if you're working from the same data and you have it, I don't know a junior engineer or an entry-level designer who isn't stoked to sit there and work alongside the CPO or the CEO and ship something because you're just unblocked. There's no alignment meetings, there's nothing to do. I also find that you can give way better feedback if you're literally in the detail. And I think the nuance is just like, how do you make sure you can do that in enough places? There's never been a better time to attempt to be in the detail on things because you can literally query it in real time.
00:55:55 · Tom Verrilli, Lenny Rachitsky
[00:55:55] S0: Top-down works well if leadership is good enough to be in the weeds and be specifically correct. I think where it falls apart is where you don't actually know ground truth and then you attempt to manage people from above. And that's where I think the term micromanagement comes from. Otherwise, if you're working from the same data and you have it, I don't know a junior engineer or an entry-level designer who isn't stoked to sit there and work alongside the CPO or the CEO and ship something because you're just unblocked. There's no alignment meetings, there's nothing to do. I also find that you can give way better feedback if you're literally in the detail. And I think the nuance is just like, how do you make sure you can do that in enough places? There's never been a better time to attempt to be in the detail on things because you can literally query it in real time. [00:56:40] S1: I think that's such an important nuance here. The story told is so powerful, this idea of Grant just, okay, I'm going to clear my day. I'm going to spend time going deep on this stuff. That feels like a very necessary ingredient for someone at the top to be making micro decisions. Because to your point, if they don't have all the details, they're not making a decision out of real data.
00:56:40 · Lenny Rachitsky, Tom Verrilli
[00:56:40] S1: I think that's such an important nuance here. The story told is so powerful, this idea of Grant just, okay, I'm going to clear my day. I'm going to spend time going deep on this stuff. That feels like a very necessary ingredient for someone at the top to be making micro decisions. Because to your point, if they don't have all the details, they're not making a decision out of real data. [00:56:58] S0: And we can do that because, as I said, we plan what we're doing and then we allocate, and then we're dividing and conquering. So he's probably trying to nail three or four most important things at a time. And he's the CEO. He's going to call the ball and say, these are the four things I own right now. And I'm going to be like, "Great, I'll be over here then." And then within those, what am I doing with the rest of my day that is more important than nailing the five things I've said we'll get done this half? If it's anything other than maybe hiring, standing meetings, any of that stuff, you can just clear it and set the tone for the team that until we understand it, we can't do anything else. [00:57:34] S1: Say somebody is looking for a CPO role or a first PM role, they're kind of similar, basically working for a founder. What would be your advice for them to land in a place where they're happy and not just super frustrated by this kind of middle layer where they just don't actually have any agency?
00:57:52 · Tom Verrilli
[00:57:52] S0: Yeah, I mean, I think the first thing you've got to work out is why do you want it? There's this idea that the CPO's job, you get to decide all the roadmaps and all those things, and I've got bad news for you. That's not strictly true. But I think it also comes down to spending some time with that person to work out how do we jam on a topic? How do they like to get pushed? How do they not? And then you spend a lot of your time calibrating. So before I joined Whatnot, I think Grant and I had five or six different coffees where we talked about how do you get this type of team to move? How do you work on those things? And then I obviously went through a series of interviews, and actually came down to LA where Grant and Logan were based at the time, and spent a whole day with them just in a room, going through a couple different problems, talking through different things in the roadmap, just really getting into it. And I tried through that to be my most ordinary self as opposed to interview self, if that makes sense. Because you got to ask yourself, do I really want to spend my whole time having this discussion and this debate? But I like being a CPO or a product lead because in a lot of ways what I'm doing is I'm helping translate that vision and that intuition into reality. And then there is an art to learning how to push somebody without competing with them. And I think a lot of the times I've seen the CPO CEO relationship go badly. It ends up with the CPO is competing with the CEO for vision and they end up at loggerheads. And I think that's not your job.
00:59:17 · Lenny Rachitsky
[00:59:17] S1: I want to ask more about that, this art of pushing back and nudging things in a direction. Is there one trick or one tip you might share with folks to be good at... Because a lot of people deal with execs and they're always trying to get them to agree to what they want.