Lenny's Podcast: Product | Career | Growth
00:55:02 · Jenny Wen
[00:55:02] S0: Yeah. Yeah. I remember first becoming a manager, and I think one of the pieces of advice that I either got from a course or a book or something, is like, yeah, "Now that you're a manager, you have to really prioritize your time and categorize your work." And there was this two by two of ... I don't remember what it was in it, but you essentially say, "Oh, these are the things that only I can do. These are things anybody else can do, and everything else, it's low leverage and you shouldn't do that anymore." And a lot of the low leverage things were just things that are really nitpicky in the weeds, or just literally, yes, probably somebody else could do those tasks. But when I think about leaders and managers that I respect the most, I actually think some of their best traits is that they choose low leverage tasks that they take on themselves, and that actually ends up being actually a very high leverage thing, because it's them who's doing it. So one example is whenever you have senior leaders who just test the shit out of the product, and they're just so in tune with it, and they dog food it, they repro the bugs, they spend a bunch of time with engineers sharing the logs and nitpicking and stuff like that. And I think that ends up being super actually high leverage, even though it's a lot of time, of nitty-gritty time, because it creates this familiarity with the product, which I think is really good. It also creates this vibe where it's like, oh yeah, this senior leader really cares deeply and they actually know the ins and out of the product, and they're rolling up their sleeves and they're giving this feedback and working with the team on it. And I think similarly to what I've seen is when a senior leader is able to fix a bug now. I think I've actually seen Mike Krieger before put in PRs himself, and it's really nice because it's like, okay, cool, we're all on this team together and nothing is below this person. And I think another thing that I love that's a little bit more cultural, is when somebody goes out of the way to make somebody's anniversary card or something, and vibe code them something super nice, or make them something, a super nice card, because I think it just shows that it's like an EA or somebody can put together the card, but this leader is just somebody who cares so much about their team that they put in the effort.
00:57:25 · Jenny Wen, Lenny Rachitsky
So that's something I try to embody, is choosing the seemingly low leverage tasks that are worth my time. [00:57:32] S1: Yeah, that is so interesting. What you're saying there is, in a sense, the low leverage stuff is the stuff that often has the most impact because your reports wouldn't expect you to spend time on this thing, and the low leverage ends up being high leverage. [00:57:47] S0: Yeah. And I think it's what makes your style of leadership stand out, or feel special to a certain person. [00:57:53] S1: Amazing. Another, I don't know, ritual and way of running teams that I heard about you, is you encourage team members roasting each other, which on the surface doesn't sound like a wonderful environment, but on the other hand, I hear constantly that the teams that you've built are just the happiest, the highest performing teams. Talk about, I guess, this idea of roasting and encouraging that, and just what you've learned about building awesome teams.
00:57:53 · Lenny Rachitsky, Jenny Wen
[00:57:53] S1: Amazing. Another, I don't know, ritual and way of running teams that I heard about you, is you encourage team members roasting each other, which on the surface doesn't sound like a wonderful environment, but on the other hand, I hear constantly that the teams that you've built are just the happiest, the highest performing teams. Talk about, I guess, this idea of roasting and encouraging that, and just what you've learned about building awesome teams. [00:58:18] S0: Yeah, I think it's not that I'm like, "Yo, you should roast each other." I'm not forcing it in that way or anything, but when I think about the psychological safety, and teams and people that just get along with each other, when you think about your friends, you're always willing to push the boundaries a little bit and roast them. You're roasting your friends a lot, but you actually might not be roasting your coworkers a lot, because it's all just about comfort and safety. So it's not that I'm like, "Oh, I want my teams to roast each other." But I think it can be a really good sign when the people on your team feel comfortable just poking fun at each other a little bit. And I think that also can be a good sign when folks also feel the same way about you as a leader, where it's like there's just an element of they don't fear you as much, and they feel like there's a sense of safety where if they say something, they're not going to get fired. So an example of this is, with my last team, I feel like they would make fun of things that I would say at crits sometimes, certain phrases I would say.
00:58:18 · Jenny Wen, Lenny Rachitsky
[00:58:18] S0: Yeah, I think it's not that I'm like, "Yo, you should roast each other." I'm not forcing it in that way or anything, but when I think about the psychological safety, and teams and people that just get along with each other, when you think about your friends, you're always willing to push the boundaries a little bit and roast them. You're roasting your friends a lot, but you actually might not be roasting your coworkers a lot, because it's all just about comfort and safety. So it's not that I'm like, "Oh, I want my teams to roast each other." But I think it can be a really good sign when the people on your team feel comfortable just poking fun at each other a little bit. And I think that also can be a good sign when folks also feel the same way about you as a leader, where it's like there's just an element of they don't fear you as much, and they feel like there's a sense of safety where if they say something, they're not going to get fired. So an example of this is, with my last team, I feel like they would make fun of things that I would say at crits sometimes, certain phrases I would say. [00:59:23] S1: What's an example of that?
00:59:26 · Jenny Wen
[00:59:26] S0: Oh, I would always be like, "Okay, what are next steps, and how do we follow up on this?" And then they'd be like, "Okay, what are next steps?" And they would sort of channel me in that way. Yeah, I just think it shows a level of like, okay, these people are not necessarily afraid of me, they know that they trust me, they can trust me, and then they sort of know enough about each other, and me personally and our personal lives, to be able to know where those boundaries are. But at the same time, I think the thing that you err into in that territory, is as a manager, are you friends with your reports? Which is I think a thing people tell you not to do. And so the way I think about balancing this out is you have to create this baseline of psychological safety, and people feel comfortable both with each other and with you, but you also have to make sure that they know that you have really high standards. And I think these two things can feel like they're at tension, but I think they work really well together, because it's like once you have that psychological safety, you have people trusting each other and you, applying the high standards actually I think becomes potentially easier because you can do it without fear, I think. And I sort of think about this from the approach of being a tough parent a little bit. It's like, "Oh yeah, my team, I work with them in a way where they know I'm always going to be there and I'm not just going to fire them on a whim or something. But at the same time, they also know that I want the best for them, and that I have high standards, and that I'm working with them to make the best work possible." And so yeah, that's the balance I think you just strike is like, can you create this environment of one where your team feels comfortable roasting you, but at the same time they know they have to be doing great work, and they will do great work with you.
01:01:24 · Lenny Rachitsky, Jenny Wen
[01:01:24] S1: That is awesome advice. It's interesting how often this just management style comes back, or management, good management, it comes back, reminds me of, what was it, radical candor, just this combination of caring deeply and challenging directly. And that's kind of what I hear here, is just make sure people know that you care deeply about them, but also be very direct and have high standards. [01:01:47] S0: Yeah. Yeah. [01:01:48] S1: That's so interesting. Okay. Maybe a final question. I'm always looking for interesting frameworks and methods and processes that people have found useful in their work. And I hear you're a big fan of something called the legibility framework. Talk about this, talk about how you use it, why it's so valuable.