Lenny's Podcast: Product | Career | Growth
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.
01:02:03 · Jenny Wen
[01:02:03] S0: Yeah. This framework, I think I saw it on Twitter, maybe last year or something, and it was Evan Tana, who's a partner at SPC. He's a VC. So it basically is this two by two. I don't think it got so much attention, but once I started seeing it, I actually couldn't stop thinking about it. So on the two by two, he basically has founders. Founders can be either illegible or legible, and then ideas can either be illegible or legible. And basically he was saying that, "Okay, if both the founder and idea is super legible, the idea is probably not that novel, and somebody's already like, they're already going to implement it or do it and you're actually not finding something new." But then where it gets really interesting is where the idea itself is illegible. And by illegible, he means, "Oh, it's sort of really on the frontier, people might not get it yet," or the way it's being told, it's not being told in the way that makes the most sense to people. And I think this is obviously a good way for a VC to operate, because you're trying to look for the opportunities that people don't see and put them out there in the world. But I also think that part of the role of the designer, at least, at least at a frontier lab at Anthropic, is spotting the ideas that are illegible, and trying to understand what's there, and how to take that and transform it, whether it's through storytelling, or whether it's through the actual UX and the form factor, and put it out there. And I think when I mentioned going through Slack and looking at all the stuff that people are making, that's kind of what I'm doing. I'm trying to see, oh yeah, what are the ideas that there's some energy there around, but might not make sense yet, that are worth me thinking about more in my work? There's one good example, actually, that ties to cowork where there was this internal prototype that we called Claude Studio that I think somebody built partway through last year, and it essentially was just this really kind of dense, powerful interface that was built on top of some agentic harness. It might've been Claude Code at that point in time too. And it had all these displays where it was showing you all this knowledge and all these skills and things Claude was doing, and previewing its outputs. And I think, to a designer, I looked at it and I was like, "I don't know what's going on.
01:04:33 · Jenny Wen
I don't really get it." But then I sort of saw the folks in research, the folks building it and just folks internally, there's just a lot of energy around it. And I was like, "Cool, I think there's something here, but I just don't understand it yet." And I think that really was an example of an illegible idea. And ultimately what came from it was the skills framework and the markdown files that instruct Claude on how to do something. So that came out of that specific prototype. That was not something I was directly involved in, and that was more of, the folks working this prototype extracted that out of it. But when it did come to work on Claude cowork and I was thinking about, oh yeah, what is the form factor for those things? Seeing that prototype and seeing the kinds of information that people found really helpful, seeing Claude's plan and to-dos, seeing Claude's context and the files that it was going through, those kinds of things are things that I ended up pulling out of that prototype into Claude cowork. So yeah, I think about how can designers almost be more like VCs in this way, internally when we're looking at prototypes.
01:05:46 · Lenny Rachitsky, Jenny Wen
[01:05:46] S1: This is super interesting. I did a research project recently with this guy Terrance Rohan, a VC, actually, we looked at what are patterns across people that have joined companies very early that ended up being massive successes, like Palantir and Stripe and Linear and Notion, all these companies. People that have joined many of these companies early, what were they looking for? And one of the factors was the idea is so crazy that everyone's laughing at this. "This is impossible. You're never going to do this. This is the craziest thing. Why would you even think ... " OpenAI actually was one of them, just some research lab doing some stuff. So it's interesting that ... And it's not like every time this will work, and it's not like every crazy idea that makes no sense will be good. But I think what you're saying is pay attention to stuff that's interesting to you and isn't totally clear. Maybe you can be the person that helps pull it together. [01:06:41] S0: Yeah. Yeah. That, but also if there is some energy around it, but I don't quite always understand what the energy is, it's to dive deeper and try to understand what that is. [01:06:41] S1: Got it. [01:06:52] S0: Yeah. Because I think people who often gravitate towards these early ideas, they can't always articulate why. And it's sort of up to you to dive deeper and understand that.