Lenny's Podcast: Product | Career | Growth
00:33:41 · Lenny Rachitsky, Jenny Wen
[00:33:41] S1: It's interesting that with OpenClaw, Claude, Moltbot, all the names, one of the big innovations is another way to chat with it through WhatsApp and Telegram and SMS, just like another form of chatbot, but just like, that was a big [inaudible 00:33:54]. Oh, I could just chat with it through WhatsApp. [00:33:55] S0: Yeah. And it's like chatting and talking to someone is still ... We as humans are doing it, and it's a way for us to interact in a really rich way. And now we just have this other medium to interact with a computer, basically. [00:34:11] S1: Yeah. So Kevin Weil, who works at another AI lab I won't mention, he had this great point on the podcast that talking is such a beautiful way to handle every level of intelligence. We can talk to people that are very, very smart and not so smart and it's talking, and it scales so well across the spectrum. We can talk to people at 200 IQ, 300, like its talking still works. So that's why it's been this beautiful way to deal with the growing intelligence of models as it continues to work.
00:34:42 · Jenny Wen
[00:34:42] S0: Yeah, that totally makes sense. Yeah. Yeah, I have takes on this. Yeah. So this past year at Anthropic, I joined as an IC at first, and then I managed a team for a few months in an org structure that sort of needed it, and now I'm actually back to doing full-time IC work. And I joined Anthropic as an IC because I was just really excited about the kind of work that there was to be done as an IC here, but also because I was feeling like I sort of want to be closer to the work, and I think this feels like a really important time to do it, before I ascend the corporate ranks. And I was having these questions and doubts about, is middle management, is that safe in the future? Is the way that we're working actually, is this going to be a job that persists in the future? Or should I try something else and get my hands dirty kind of thing? And to be totally fair, I actually love both sides of the coin. I love managing people. I love setting up teams and being at that level, but I also just really love IC work. I was sort of a reluctant manager when I did it, and I was like, "Okay, I'll do it." So I love both sides of the coin pretty equally. But I think actually what being an IC across this past year has taught me, is that it actually just gave me a lot of skills that I don't think I would've gained if I was just managing throughout this year. Like I mentioned, the design process has changed so, so much in this past year, and I feel like I've just picked up so many hard skills that I wouldn't have necessarily had the time to do if I was just managing a team. So that's actually the best thing it's afforded me. And I think at any point if I'm managing a team again, I think it will give me the empathy and understanding of how the design process has changed. And I think that's actually a really important thing right now because the teams are working so differently. And I think it's actually pretty hard to empathize if you are not working in that way, or you're not always testing all the tools and trying stuff. But yeah, it's an interesting time to be a designer. And if I had not worked in this environment, I don't know if I would've totally understood it or knew what to do or how to guide my teams. So that's sort of what this year really gave me.
00:38:05 · Lenny Rachitsky, Jenny Wen
[00:38:05] S1: And so you were previously a director of design at Figma, right? [00:38:06] S0: Yeah. [00:38:08] S1: How big was your team? How large was your org, just to give people a reference? [00:38:13] S0: At the max, I probably had, I think, 12, 15 designers or so, and I had a few managers as well. [00:38:21] S1: Cool. And then you went back to an IC? [00:38:21] S0: It was like an org. [00:38:23] S1: Yeah. Okay. So you had the sense that middle management might not last. What's your current feeling? Do you think design management is a thing that persists long-term, or do you think everyone turns into IC? [00:38:34] S0: I think as long as there is a team of people, it helps to have somebody who is managing a team. I think there's real value in managers. It depends what the shape of the manager is and what they actually do. But the way I think about what a helpful manager is these days, is somebody who is not just, I think pure people management like, oh, just somebody to set you up, help you in your career, have one-on-ones, make sure you're feeling good at work. I think that that is not a thing as much anymore, but I think somebody who can really function as giving the team direction, as well as doing some of the people management stuff, that tied together, I think is the future of what managing looks like, at least for now. Somebody who can really engage with the team in terms of the work and giving direction there, as well as creating the environment for them to do their best work. [00:39:26] S1: And do you see yourself going back into management long-term?
00:39:26 · Lenny Rachitsky, Jenny Wen
[00:39:26] S1: And do you see yourself going back into management long-term? [00:39:28] S0: I will. I probably will. I think I really just love helping a team build the best product possible. And my motto there is, whatever it takes. If it's somebody that, if the team needs somebody to give the team direction and set up the team and whatnot, that could be me. If the team just needs somebody to execute on it, that could be me as well. [00:39:50] S1: So the advice I'm hearing for people in design that are especially managers, is you almost need to move back into IC in order to truly understand what is happening and how much it's changing, so that you can be a better manager. [00:40:03] S0: I think so. And I think traditionally, at least what I've seen, a lot of the engineering disciplines, when they hire EMs or even sometimes directors there, they actually make the EMs take a rotation for a few months and pick up a few tasks, and really understand how the technology works before they become a full-time manager. And I think design probably needs to do something similar too, where I think in the past design has been much more people management oriented. [00:40:31] S1: What did you find yourself most rusty in when you went back to IC designer? [00:40:35] S0: Actually doing crits, and just really- [00:40:35] S1: Getting criticized.
00:40:35 · Lenny Rachitsky, Jenny Wen
[00:40:35] S1: Getting criticized. [00:40:40] S0: ... Yeah, getting criticized. You're like, oh yeah, it is hard to get critical feedback and to hear it, and to hear it on such a regular basis, because that's the thing you have to do as a designer, is it's a pretty vulnerable exercise to share work and present it with your team, and then also just get a lot of critical feedback and take that all the time. Yeah. [00:41:02] S1: So currently you're leading design/IC designing on cowork. Is that right? [00:41:07] S0: Yeah. [00:41:08] S1: Awesome. So Boris, he was on the pod recently, talked about how there's a lot of debate about what cowork should be, and there's all these big ideas and he's like, "In the end, let's just make it like a terminal, basically, in the product, and just kind of a fancy terminal." Is there anything you could share about just the process of landing on where you landed for that experience of cowork? I have it here on my monitor, by the way, looking at it. [00:41:29] S0: With Cowork specifically, we have had a bunch of different prototypes internally of what that could look like. And it's one of those things where we tried a lot of things, and then I think we weren't really sure when it was actually going to be ready to ship. And then it was sort of everything all at once. We were like, "Okay, we're going to ship it soon." [00:41:53] S1: I think it was 10 days, 10 days of building.
00:41:53 · Lenny Rachitsky, Jenny Wen
[00:41:53] S1: I think it was 10 days, 10 days of building. [00:41:53] S0: Yeah, it was definitely longer than that overall. It was 10 days to get it from what we had internally to something that we were ready to ship externally. So we'd been building it for a while, but we weren't really sure about the actual form it was going to take. And so the way it got there is actually, there was a lot of different other explorations that we had internally on top of different agent harnesses and whatnot. And we just had prototyped little parts of the different interactions that ended up in cowork. So things like when Claude gives you a to do list, we tried a bunch of different form factors for that. We tried a bunch of different form factors for the way it presents you different multiple choice questions. We tried a bunch of different ways to teach people what the use cases are and whatnot. And I don't know if we landed on the best form factor ever, but essentially it was stuff that was already working internally that people liked, that we just thought we were going to get some more signal on by releasing it. So I think forcing ourselves to release it within that 10 days that we did, it was just sort of like, whatever we had, let's put it out there and then let's go out there and iterate from there, which is what we're doing. [00:43:02] S1: And it blew up the internet when you launched it, so it worked out. [00:43:05] S0: Yeah. [00:43:06] S1: Is there a feature of Cowork today that you're either most proud of, or just can't wait to fix and improve?