Jenny Wen, Claude head of design: Why design process is dead

Why non-deterministic AI states can't be cleanly pre-mocked anymore: Anthropic shipped Claude Cowork in 10 days by pairing with engineers, not mocks.

Jenny WenguestLenny Rachitskyhost

Mar 1, 20261h 17mWatch on YouTube ↗

EVERY SPOKEN WORD

80 min read · 16,235 words

0:00 – 4:23
Introduction to Jenny Wen
1. JWJenny Wen
  This design process that designers have been taught, we sort of treat it as gospel, that's basically dead. You as a designer actually, like, do not have the time to make these beautiful mocks anymore.
2. LRLenny Rachitsky
  A big part of the design role now is helping engineers and teams execute, not just telling them, "Here's the design."
3. JWJenny Wen
  A few years ago, 60 to 70% of it was mocking and prototyping, but now I feel the mocking up part of it is 30 to 40%.
4. LRLenny Rachitsky
  You're better off not blocking that, letting them cook.
5. JWJenny Wen
  It's not just designers who are feeling like, "Oh yeah, we have to keep up with engineers." I think even engineers are like, "How do we keep up with ourselves?"
6. LRLenny Rachitsky
  How to keep up with all our agents, our seven agents we're constantly running.
7. JWJenny Wen
  The result of engineering changing a bunch is that design is sort of forced to change. We used to go off and make this two-year, five-year, 10-year vision even. Now it becomes a vision that's three to six months out and isn't necessarily creating this beautiful deck, but sometimes just creating a prototype that points people in the right direction.
8. LRLenny Rachitsky
  Boris on the podcast recently was saying Claude Code is now helping him come up with ideas.
9. JWJenny Wen
  We'll get better at taste and judgment and design. We might be holding onto that a little bit too much.
10. LRLenny Rachitsky
  Where will human brains continue to be valuable?
11. JWJenny Wen
  At the end of the day, someone has to decide what is actually going to get built and what actually matters. Someone still needs to be accountable for the decision.
12. LRLenny Rachitsky
  What do you now look for when you're hiring designers?
13. JWJenny Wen
  There's probably three archetypes of folks that are really interesting to me right now.
14. LRLenny Rachitsky
  Today's guest is Jenny Wen. Jenny was head of design for Claude, is now leading design for Claude Cowork. Prior to that, she was director of design at Figma, where she led the design teams behind FigJam and Slides. She was also a designer at Dropbox and Square and Shopify. And what I love about this conversation is that Jenny is living in the future of where design as a profession is heading, and she's here to give us a glimpse into what that looks like and how much things are gonna be changing for designers. It is pretty wild and extremely interesting. A huge thank you to Noah Levin and Emily Lin Hasham for suggesting topics and questions for this conversation. Don't forget to check out LennysProductPass.com for an incredible set of deals available exclusively to Lenny's newsletter subscribers. Let's get into it after a short word from our wonderful sponsors. This episode is brought to you by Mercury, radically different banking loved by over 300,000 entrepreneurs, including me. I switched to Mercury from Chase over a year ago, and it is such a profoundly better experience. It's like an actual product person built a bank versus a banking person building a product. It is fast, it's elegant, it is super easy to set wires, to track my spending, to set up triggers to move money around when accounts get low. We moved all of our invoicing to Mercury, and it is such a smoother experience than anything else we've tried. It's also really easy to grant people on your team just the right amount of access to help take work off your plate. It's free to get started, no in-person visits, no minimum balances. The product also flexes to all sizes of company, from startups to large enterprises. Just visit mercury.com to learn more and apply online in minutes. Mercury is a fintech company, not an FDIC-insured bank. Banking services provided through Choice Financial Group and Columna Members FDIC. This episode is brought to you by Orkes, the company behind Open Source Conductor, the orchestration platform powering modern enterprise applications. Modern systems are built on microservices, APIs, and event-driven architectures. But legacy automation tools can't keep up. Siloed low-code platforms, outdated process management, and disconnected API tooling break down under real-world scale and constant change. Orkes Conductor provides a production-grade orchestration layer for coordinating microservices, APIs, data pipelines, human tasks, and agentic workflows with deterministic control flow, retries, observability, and governance. Built for enterprise scale, Orkes supports visual and code-first development with built-in compliance and reliability. Through a built-in MCP gateway, AI agents handle reasoning and decision-making while safely accessing existing APIs and internal systems as MCP tools. This enables agents to operate across enterprise environments and scale from demos to production, orchestrating systems, agents, and humans together to deliver smarter outcomes faster. Learn more at orkes.io/lenny. That's O-R-K-E-S dot I-O slash lenny. Jenny, thank you so much for being here, and welcome to the podcast.
15. JWJenny Wen
  Yeah, excited to be here.
16. LRLenny Rachitsky
  I've been looking
4:23 – 6:33
Why the traditional design process is dead
1. LRLenny Rachitsky
  forward to this conversation because I spent a lot of time on this podcast talking about the future of software engineering, how much that role is changing, uh, the role of product management, how much that role is changing. I haven't spent a lot of time on how design is changing. Clearly, it is also changing in a really big way, and you have such a front row seat to where things are heading. Uh, I also know you have a lot of very strong opinions about where things are heading. So, uh, there's a lot of stuff I wanna talk about. I wanna just start with this, just this broad question. How is the design process changing with the rise of AI?
2. JWJenny Wen
  It's changing a lot. Um, I, I think it's still also got a lot, a long way to go in terms of the way it's changing. Like, I think we've actually seen, you know, engineering, um, change a lot more in the, in the past little while than design actually has. But I think the result of engineering change a bu- changing a bunch is that design is sort of forced to change. Um, and so I think some context around this is I, I did a talk at a conference in Berlin a few months ago in September, and I called it, like, Don't Trust the Design Process, where I basically just said, like, "Hey, you know this design process that designers have been taught where you go and you go off and you do a bunch of research and discovery, and then you, like, diverge, you converge, diverge, converge?" And it's like this process that we sort of treated as gospel and, and tried so hard to preserve, and we were like, "Trust the process." That is... That's basically dead. Uh, I think it was sort of dying before the age of AI, but given now that, you know, engineers can go off and spin off their, like, seven Claudes, [laughs] I think as, as designers, we really have to let go of that process. And I think that's the big thing that's changing.But I think even in the past three to four months since I did that talk, that talk actually starts to feel pretty... It, it kind of feels outdated to me, which is a little embarrassing. But especially with the big shift of, like, Opus 4.6 and a bunch of folks just, like, really discovering and using Claude Code over the holiday break, um, I think we're seeing this, like, force to change our pro- process happen even more. The, the way
6:33 – 10:00
The two new types of design work
1. JWJenny Wen
  I sort of see it now is, like, there are basically two types of design work, and design work is kind of, like, becoming really stratified in this new wor- in this new world. Um, so there's, like, the first one which is really just, like, supporting the implementation and execution. So this is the one where, you know, engineers are using their seven Claudes to, to create all these features, and anybody can, like, put an idea out there. And you can just, like, talk about an idea, and somebody, usually actually an engineer because they're still better at implementing this stuff than we are, they will just make a scrappy version of it, and you can try it out. And you as a designer actually, like, do not have the time to make these beautiful mocks anymore or to, like, kind of lead in this way. And then I think there's, like, the second kind of work that feels also really important, which is, like, creating the sort of vision or direction for things. Um, this one feels like the hardest to make time for, and it's still... It's one that, like, we, we still did before, but I think the shape of it's very much changing. 'Cause I think we used to go off and say, "You know, we're gonna do this design vision. We're gonna go off and make this, like, two-year, five-year, whatever, 10-year vision even, and we're gonna, like, point us towards something." But the way that the technology is changing now, like, we actually don't know... [laughs] We don't know what's gonna happen in two years. There's too much changing, and it usually becomes a vision that's, like, three to six months out and isn't necessarily something that is, like, creating this, like beautiful deck that's, like, beautifully story-told. It's sometimes just, like, creating a prototype that points people in the right direction. And I think this kind of work is, like, still really important in this world because in a world where people can spin off their seve- seven Claudes, make whatever features they want in any dire- in any kind of, like, direction or, or in implementation, you need to point them towards something, and in order to make sure that we're all making something that makes sense together and is also done in a way where it's, like, efficient, right? Like, if we're all working towards something that has one greater cause, it's, like, much more efficient to do that than, than just random things. Um, so that's, like, the big shift that I'm seeing, and I think I have opinions about it now. But ask me in, like, three months, and it might actually change even more.
2. LRLenny Rachitsky
  So what you're saying here is it's not like, uh, you or the design field is like, "We need to change." It's engineering and the fact that you can build so quickly just forces, uh, the role of a designer to change. Because as you said, engineers can just ship, ship, ship, ship, ship. And what you're finding here is, like, you're better off not blocking that, letting them cook, as they say. And, uh, and then there's kind of this mode of helping them along a- as they ship, bring it together, make sure it all kind of connects, guide them a l- a, a little bit.
3. JWJenny Wen
  Yeah, I think so. Yeah, I don't think there is, like, one unifying voice that's like, "Designers, we need to change right now." But there... Yeah, there is sort of, like, the, the follow-on effects of engineering tooling really changing. I think we'll probably see design tooling change in this next year or so as well. But i- a lot of it right now is trailing that. And I think it's also really empowering for us, too, because as designers, we also now have access to a lot of these coding tools, and we can be a part of the process in a way where we're implementing stuff. Like, it's like I'm, I'm, I'm doing a lot of las- last mile stuff where I'm implementing all the polish and, like, a- a- and, and sort of, like, working with engineers really closely to get the feature across the line, um, and also prototype stuff in actual code as opposed to, like, relying
10:00 – 13:00
How widespread this shift will be
1. JWJenny Wen
  on engineers to do that again.
2. LRLenny Rachitsky
  How true do you think this, this is at all companies, at, say, AI companies, non-AI companies? You know, someone may be hearing this, okay, Anthropic, Claude. Like, okay, it's like they're at the bleeding edge, for one. Two, it's, like, developer-y a little bit. But I think people might be feeling, "Okay, I... This is not gonna happen at Salesforce. This is not gonna happen at, I don't know, ServiceNow, wherever." So I guess does... Do you feel like this is where all teams are heading, or is it mostly AI bleeding edge companies? How widespread do you think the design process shift is gonna be?
3. JWJenny Wen
  So the talk that I did last year has weirdly been, like, the most resonant talk that I've done. And I... So I think it's something that people are starting to feel across the industry where they're like, "Oh yeah, we can't do the old design process anymore. You know, we are using tools like Claude Code and, and v0 and whatnot to, to start to spin up prototypes." And PMs are starting to spin up prototypes and stuff like that as well. So I think there's something there emerging. But the other interesting observation with that talk, too, was there was actually also a decent amount of, like, backlash. Like, people were... People clearly have invested their entire careers in learning, teaching, using this, like, really stable design process. And they were... I think there was a lot of, like, discrediting, like, "Oh yeah, like we can't do without discovery. We can't do without these pieces of process." So I think there is still a, a piece of the industry that is not quite there yet in terms of this way of working, if that makes sense.
4. LRLenny Rachitsky
  Yeah.
5. JWJenny Wen
  Yeah.
6. LRLenny Rachitsky
  And a big part of this is, like, you could argue... Like, the question is what leads to the best, most successful products in companies? And you could argue it's spending time doing discovery, user research, mocks, iterating, beta testing, or it could be just engineer ship stuff that's okay, not amazing, good enough. We learn, iterate, build, iterate. Is your sense that that second path is... Not only is that just, like, what everyone's doing, but that actually leads to the better product at this point?
7. JWJenny Wen
  I think you sort of have to choose and use your discretion as to, like, when to actually ship something. But I think the, the ability to execute, try something out, and try it with, like, real data, um, and, and a real user's, like-Kind of mindset in the product. I think that does lead to a better product, especially as we're all working with these like new developing AI models that are non-deterministic. You can't, you just can't, you can't mock up all the states, you know? And you can't theorize, and you can't even make, uh, like a clickable prototype with it. You sort of have to use the alpha models underneath, and you have to sort of see people try it out with their use cases. Because with these models, like you discover... You can design them for different use cases, but you don't... You have to discover use cases as you see people using them. So yes.
8. LRLenny Rachitsky
  The other thing I always hear, and building on what you just said, is just you don't know what people will do with AI. You don't know how good it'll be at certain things, the non-deterministic piece of it. So you can create these amazing mocks of what it might be, and then people use it in a completely different way, which is where Cowork came from, and probably
13:00 – 18:45
Day-to-day life as a designer at Anthropic
1. LRLenny Rachitsky
  even Claude Code at the beginning. And so, so what's it, what's it just like to be a designer at Anthropic? Just like give us a day in the life of working at Anthropic, uh, in, at the center of the storm.
2. JWJenny Wen
  A good amount of time at Anthropic is actually just like catching up on what people... What's happening at the company. I think this is the company where... I, I've worked at a few other companies around this size, where I think there's just a lot of like information and a lot of things going on, but I feel really compelled to keep up with it. You know? Like, there's- there's stuff that is like model developments on the research side, and then at any given time, there are just so many different teams prototyping and trying different ideas out, and there's a bunch of different like g- code names and stuff like that. And a lot of time, I'm just like trying to navigate and figure out what those, what those projects are. Because I think I'm just trying to spot and see like, hey, what's coming up ahead for me? Um, because there's stuff from both the research team, but also some of our like labs teams that are tr- that are closer to research and trying out and prototyping stuff. And then there's just like stuff I want to try out, you know? Like, we have a bunch of like... We have a bunch of prototypes and products internally that we can use, and I am just curious and I wanna try those things out. And then I think there's also a lot of folks who internally have a lot of insights and opinions on where the industry's going, and some of those are just like really interesting to read because a lot of these are like philosophical debates or directions of the company and stuff like that. And yeah, I feel like I just wanna keep up with these things, whereas I think at a normal company, I'm like, "That's fine. This is stuff that's happening outside of my reach. I don't, I don't really care as much." Where here, I think it's both the volume and the kinds of things that are happening that I'm like really interested in keeping up with. Um, and then aside from that sort of keep up, like that's not a huge part of my job, but I do think it's a really interesting part of it.
3. LRLenny Rachitsky
  Well, it connects to the point you made earlier, a big part of the design role now is helping engineers and teams execute, not just telling them, "Here's the mock, here's the design." It's helping them stay on track, helping them connect ideas, create a cohesive experience as it's happening. So that makes sense.
4. JWJenny Wen
  Yeah. Yeah. Yeah, and I think part of it is just curiosity, you know?
5. LRLenny Rachitsky
  Mm-hmm.
6. JWJenny Wen
  Like, it feels like I have this front row seat to so much-
7. LRLenny Rachitsky
  Yeah
8. JWJenny Wen
  ... that's happening in the industry. And so a lot of it is like, yeah, our Slack is a goldmine [laughs] you know? Like, I'm just excited to re- to read through the things that people are working on and they're saying.
9. LRLenny Rachitsky
  I never thought about how like there's already so much AI news to keep track of as a r- regular person, and then actually seeing what's actually happening inside a lab is a whole new set of-
10. JWJenny Wen
  Yeah
11. LRLenny Rachitsky
  ... feeds to watch. [laughs]
12. JWJenny Wen
  Yeah, yeah. It's like I don't-
13. LRLenny Rachitsky
  Oh, my God
14. JWJenny Wen
  ... I- I think that is the, the best AI news is probably internally if you're ever at one of these companies in the Slack.
15. LRLenny Rachitsky
  Damn.
16. JWJenny Wen
  Yeah.
17. LRLenny Rachitsky
  Yeah.
18. JWJenny Wen
  Yeah.
19. LRLenny Rachitsky
  It's... Just problem keeps getting harder of just keeping, keeping track of what's going on. Okay.
20. JWJenny Wen
  Yeah.
21. LRLenny Rachitsky
  So okay, so that's part of the job. What else?
22. JWJenny Wen
  There is still some of like the traditional like let me think about what's happening in the, in the future and let me like make some designs for that. That's something that, for example, this week I've allotted some time to where I'm like, "Okay, cool." Like, we have been in a lot of like execution mode for Cowork, and now I wanna set aside some time to think about, hey, what do the next like three months look like? And, and where does that act- where could that actually go given where the market's at, where the models are at, and what could that be? 'Cause I think it still really helps to visualize that and show that to the team and point everyone in the same direction. Um, and then I also spend a bunch of my day just jamming on stuff with engineers. Like, a lot of it is just a conversation or like whiteboarding or going through something that they built and giving them feedback on it and being a designer in that kind of way where we're like consulting. Um, and then I spend a part of my day in code, you know, like polishing, implementing stuff. Sometimes what happens is an engineer and I have worked through something and they've implemented a first version of it, and I, I just go in and polish it with them. Um, and that's, and that's a really fun part of my job that I think didn't exist as much a few months ago.
23. LRLenny Rachitsky
  Are you still doing elements of the traditional design process? Prototyping, user research, uh, panels? I don't know, just like going out and in, you know, like the whole, the whole thing you described.
24. JWJenny Wen
  Yeah. We're still do- I think we're still doing all of that to some extent. Like, we, we have a user researcher on the team who is putting together, uh, both like traditional studies as well as surveys, and the whole team is reading that, that, the, the, those studies and that feedback. We are still, we are still prototyping stuff. We are still... I'm still mocking stuff up. I think it's just I have a wider set of tools now, and I think the proportion of time I spend doing each thing just has changed.
25. LRLenny Rachitsky
  Got it. Okay.
26. JWJenny Wen
  Yeah.
27. LRLenny Rachitsky
  So that's a really interesting takeaway.
28. JWJenny Wen
  Yeah.
29. LRLenny Rachitsky
  It used to be that was a huge... Like, I guess what would be the pie chart of what your life was before, where it's like traditional thinking, planning, prototyping, mocking, research, and then just like feedback and execution, and now today?
30. JWJenny Wen
  Yeah. I think as a designer a few years ago, I would say like maybe 60 to 70% of it was like mocking and prototyping stuff up, and then spending, you know, the last 20 or so- some of the last 20 or so-W- like doing the sort of like jamming with engineers, consulting with them, and then the last like 10% maybe doing, you know, coordination meetings, et cetera. Uh, but now I feel like the, the mocking up part of it is like 30 to 40%, and then there's that other 30 to 40% there that is now jamming and, and pairing directly with engineers. And then there's like a slice... I don't know how much I have left, but, [laughs] but like there's a slice of it that is now like implementation as well.
18:45 – 20:03
Jenny’s AI stack
1. LRLenny Rachitsky
  shipping.
2. JWJenny Wen
  Yeah, yeah.
3. LRLenny Rachitsky
  Amazing. So kind of following that thread, what's in your AI stack? What do you, as a designer... I know you're a manager and I wanna talk about how you actually... Or IC also. What's in your AI stack? What tools are you using in your role?
4. JWJenny Wen
  What is in my AI stack? Um, well we, [laughs] we're Philanthropic so it's-
5. LRLenny Rachitsky
  Of course
6. JWJenny Wen
  ... we're going deep on the Claude stack.
7. LRLenny Rachitsky
  Yeah.
8. JWJenny Wen
  Um, I am, I'm using obviously like chats, uh, Claude Chat, and the... But increasingly more and more Claude Cowork. I, I've basically shifted all of my chat use cases over to Cowork, um, 'cause I've been finding that, yeah, uh, it, it sort of is better at these longer running tasks, and most of the things I was asking Claude for are these, these longer running tasks. And then there's Claude Code, of course. I use it mostly in the, with, with VS Code in the IDE because I'm usually tweaking front end stuff, and it helps to just like be able to see the code and then talk to, to Claude as well. I've been trying to actually use Claude Code more, uh, remotely, like through m- both mobile and through Slack as well. Um, it's really fun for somebody to say like, "Oh yeah, this, this one icon's off," or something, and you just @ mention Claude and Claude does it, and then you pick up the PR and it's done. That's been really, really fun too. And yeah, I think that's just like... I think we're a fully Claude house here. So [laughs] yes, th- that's basically my
20:03 – 22:25
Why Figma still matters for exploration
1. JWJenny Wen
  stack.
2. LRLenny Rachitsky
  Are you still using Figma as a designer?
3. JWJenny Wen
  I am still using Figma, yes, yes.
4. LRLenny Rachitsky
  Okay.
5. JWJenny Wen
  Yes.
6. LRLenny Rachitsky
  I was waiting to hear.
7. JWJenny Wen
  Yes.
8. LRLenny Rachitsky
  Okay, so Figma's still part of your, your life.
9. JWJenny Wen
  Mm-hmm.
10. LRLenny Rachitsky
  Uh, being a former Figmate, is that, is that what y'all were called?
11. JWJenny Wen
  Yeah, yeah, Figmates.
12. LRLenny Rachitsky
  Okay.
13. JWJenny Wen
  Yeah. [laughs]
14. LRLenny Rachitsky
  Yeah, okay. So I know there's this big debate on Twitter just like is code the future of design? Do we need, like, many more... Do we need a design? What's your, what's your sense? Figma still important?
15. JWJenny Wen
  I mean, as a f- as a former Figmate, I, I... Maybe I'm biased in that way, but I, I, I think there is still... Like, when I use Figma I'm like, "Yes, this is what I should be using," and it still fills a very good gap for me. Um, I think a lot of that is actually just like, one, is exploring a lot of different options. I think that's a really important part of the design process, to be able to just think about, like, eight to 10 different ways to do something. Um, I think the best design happens when you're able to just like throw a bunch of ideas at the wall and curate and just like a- and, and push yourself to, to come up with a bunch of these different directions. Right now coding or, or right now working with some of these coding tools doesn't lend itself super well to that. Because it's super linear, you have to super invest in one direction, and you just iterate with Claude on them, for example. Um, so I, uh, Figma has been really great at just like exploring all these different options, and I think it's still gonna exist that way to some extent. And then I think there's like really fine sort of visual and interaction details that are also really great to, to, to be able to just try out in Figma. Again, it's a lot of different directions, but it's micro directions. It's being able to think about, like, different typography or, or styles. Having those in a canvas where you can just explore that specifically is still so, so helpful and is not something that I always wanna like go directly to code in.
16. LRLenny Rachitsky
  It's interesting you still use an IDE because in engineering it's clearly shifting to, uh, command lines, agents, IDs are kind of moving, moving-
17. JWJenny Wen
  Uh-huh
18. LRLenny Rachitsky
  ... to not be cool anymore so it's... And it makes a lot of sense. You just wanna edit some CSS things-
19. JWJenny Wen
  Yeah
20. LRLenny Rachitsky
  ... some like color stuff, and so I could see why not just telling the agent, "Hey, just come on, change this one hex value."
21. JWJenny Wen
  Yes. [laughs]
22. LRLenny Rachitsky
  Just changing it is so much easier.
23. JWJenny Wen
  Yeah, it's really annoying to be like, "Can you change this to this class?" When you can just go in and change it to a different class.
24. LRLenny Rachitsky
  That's interesting. I like [laughs] to wonder if IDEs now become the useful for designers and PMs, and engineers have moved on.
25. JWJenny Wen
  Yeah. Maybe,
22:25 – 24:19
Advice for working with engineers
1. JWJenny Wen
  yeah.
2. LRLenny Rachitsky
  Okay. So a lot of your time you spend working with engineers giving them feedback, kind of nudging them in the right direction. There's a sense I feel of just like, like your advice is like let go. Don't feel like you need to be this gatekeeper, but there's this piece of, okay, help them move in a s- direction that is cohesive and is creating products we're proud of. A lot of designers I think are in this boat right now of just like, "Oh my God, I can't keep up with all these engineers shipping stuff all day." What's something you learned about just either how to help your engineers get better at design so that it just ends up being better, or just kind of keeping on top of this and not going crazy?
3. JWJenny Wen
  Whenever I do work with engineers on projects and it's more on like a consulting basis, I do just try to explain, you know, why I'm thinking a way that I'm thinking to help them like extract principles as opposed to me just being like, "No, I don't think this [laughs] should go here." It's like, "No, I think we should have a button here because not everybody realizes you can prompt this. Um, and, and here's an example where it comes from research and whatnot." So I also just like try to point engineers to our design system and stuff like that in code because right now Claude is like writing a lot of the code, and it's like not always, it's not always like picking up stuff in the design system and whatnot. So as much as I can sort of equip them with stuff that they can use in the future without me, [laughs] that's helpful. And then on your point of trying not to go crazy, I think it's hard. You know? I think it's really hard right now. And I, I, I see this a lot from actually both engineers and designers where it's like now that we're sort of capable of doing so much we wanna do more. Uh, and, and so I think it's not just designers who are feeling like, "Oh yeah, we have to keep up with engineers." I think even engineers are like, "How do we, how do we keep up with ourselves right now?" So that's something I'm hearing a lot.
4. LRLenny Rachitsky
  [laughs] That's so true.
5. JWJenny Wen
  Yeah. [laughs]
6. LRLenny Rachitsky
  Oh, man. How to keep up with all our agents, our seven agents-
7. JWJenny Wen
  Yeah
8. LRLenny Rachitsky
  ... we're constantly running.
9. JWJenny Wen
  Yeah.
24:19 – 27:35
How to maintain craft, quality, and trust in the AI era
1. LRLenny Rachitsky
  Okay. So then as a designer, where in this profession craft and great experience and quality and trust are such a core part of the job to help instill that in the products, because that in theory leads to really successful products and companies. How do you just think about maintaining craft quality trust as your products are just shipping a thousand times a day and you're not able to stay on top of them and there's no designer involved?
2. JWJenny Wen
  It's not that there's no designer involved, it's more just like there's... It's almost that there's too much for one designer, uh, to handle. But, um, I think with this, I think about where the features or products are the-- like where they are sort of in the cycle of adoption versus like kind of early preview. So for example, like we sometimes will launch things and we will say, "Hey, this is a research preview. It's, it's early, it's gonna have a bunch of these flaws." And, and we caveat that a bunch. And I think Claude Cowork is actually a good example of this, where we labeled it a research preview and we put it out there knowing that, hey, this is like similar to our models. You know, this is the worst it's ever gonna be, but we're gonna put it out there because we believe, you know, internally we've tried it a bunch and there's something really powerful here that some people will benefit from. It might not yet be the easiest to work with, it might not be the highest quality, it might have some issues with it, but we're gonna put it out there because we believe the benefits outweigh the cons. I think that is like okay to do, especially when there is something like really valuable with the product already and it's worth putting it out there. But I think the promise you sort of have to make your users is, is like, "Hey, we're, we're gonna put it out there, but we're gonna, we're gonna iterate. We're gonna take your feedback and we're gonna iterate and we're gonna make it better." And you have to sort of commit that, you have to show that to the world. You have to respond to people's feedback, and you have to show that you are continuously shipping and improving it. Because I think the way that you really lose trust around quality and releasing something early is if you release it early and then nothing ever happens. That, that is what... something that degrades a brand. But whenever you put something out early, like it's, it's possible to do that and like maintain the brand of, of your company. And I think, I think that's something that we've been doing pretty well. And, and I think if there's anything anyone's listening that can... if anyone's listening can take away from it is like, yeah, we're, we're continuing to do that. And, and I think that is actually really fun for me as a designer because you put something out there and you actually learn and you get feedback about it immediately and you know what to do next.
3. LRLenny Rachitsky
  The way I've heard you describe this is building trust through speed.
4. JWJenny Wen
  Yeah, for sure. It's, yeah, it's building trust through speed, but also just like making people feel like they've been heard and that we're fixing things based on what they're trying to use it for, and their feedback is actually appreciated and used.
5. LRLenny Rachitsky
  Yeah. It's clear when, when the labs launch stuff, and y'all are very good at this, everyone on the team is tweeting and just like responding to tweets and comments and, and then shipping, "Hey, we fixed this yesterday and this is happening." So there's a clear sense of this is just today and we know this is broken and we will fix it. And, and then because Claude Code can code very quickly, uh, the fixes come very fast.
27:35 – 31:38
Will AI ever have “taste”?
1. LRLenny Rachitsky
  Okay. So another big question that people are asking that I ask a lot on this podcast is around just like what skills become valuable? And like another way I've been thinking about it, Lex put it this way recently, is where will human brains continue to be valuable as AI gets smarter? So we've gone through this progression of, uh, tab completing Ella segments of code to 100% of code is written by AI now, like it's crazy, to now AI is reviewing its own code. Boris on the podcast recently was saying Claude Code is now helping him come up with ideas and decide what to build, which is like, okay, wow, look at that. Look at it go. The whole product workflows, the product development process slowly getting eaten up by AI. So the question is just like, where will human brains still be useful, at least until we have super intelligence? Do you think like A- do you think AI is gonna get very, very good at taste, judgment, design?
2. JWJenny Wen
  I think it will get better at taste and judgment and design. Yeah. Like I, I think we, we might be holding on to that a little bit too much and saying like, oh yeah, like, you know, a de- a designer or somebody will always know the, the best thing to ship or the best version of this. And I... But I, I do think AI will, that like AI sense of taste will get better. At the end of the day, someone has to decide like what is actually going to get built and, and what actually matters. And, and when I think about people saying like, oh, you know, like AI is just gonna build this software for us, a lot of the hard parts of building software are actually like not building it, you know? If you think about the hardest times that you've had at work, Lenny, it's probably things like, oh, you and some other person like disagreeing about like what should go into this feature or what shouldn't go into this feature. And those things still feel like, yes, AI can weigh in, but it can't necessarily solve this dispute between you and somebody else. And so there is something about like deciding what actually goes into the things we build, which I guess is taste in some way, but maybe not taste in like the way we think about like aesthetic taste or, or whatnot. There's some sort of like, it's like judgment around what to do next.
3. LRLenny Rachitsky
  Just watching how quickly AI had took over coding, which I think a year ago, definitely two years ago, most people are like, "I don't think so. I don't think AI will get this good," and that the best engineers in the world trust it so much they're not even looking at the code anymore. Like that's where we've gone. It just made me reevaluate all these assumptions I've had about, okay, AI will never be as good as really good PMs, designers at judging what is great and deciding what to build. But I'm just like starting to think, I think it will get there. [chuckles] Like even an example you shared, like it could give these two people trying to make a decision, here's all of the data you need to make a decision and here's why this is the right answer and just press yes, press one, and I'll go ahead and build it.
4. JWJenny Wen
  [laughs] Just show me, yeah.
5. LRLenny Rachitsky
  So I think we're just... Yeah, to your point, I think we undervalue just how good it'll get at this stuff. S- okay, so your sense is it'll get better, but your sense is we'll still need awesome designers to be involved, awesome PMs to help make these decisions. Engineers, of course.
6. JWJenny Wen
  Yeah. Yeah. I think someone will still have to decide, like, "Oh, we wanna build this kinda product," or like, given what the AI's presenting us, like someone still needs to be accountable for the decision. You know, the same way that like even though Claude can write all this code for you today, it is still an engineer who's accountable for, like, does that code actually work? Does this actually make sense in the product? So I think there's that like decision-making/judgment a- layer which feels like maybe one day [laughs] we won't have to do that, but it's, uh, it still falls on us. Yeah.
7. LRLenny Rachitsky
  It doesn't make sense. It makes me think about the radiology example where there's always the sense that AI's gonna take over that field of radiology and tell you what is going on.
8. JWJenny Wen
  Mm-hmm.
9. LRLenny Rachitsky
  But, like, the human is mostly useful for signing off on the decision-
10. JWJenny Wen
  Yeah
11. LRLenny Rachitsky
  ... 'cause someone needs to be liable if they're wrong. Um, which isn't the best job in the [laughs] world.
12. JWJenny Wen
  [laughs]
13. LRLenny Rachitsky
  But, uh, but that's a different game is health-
14. JWJenny Wen
  Yeah
15. LRLenny Rachitsky
  ... versus
31:38 – 35:33
The future of chatbot interfaces
1. LRLenny Rachitsky
  code.
2. JWJenny Wen
  Yeah.
3. LRLenny Rachitsky
  Okay. Another ongoing question in AI and design is just, like, it feels like chatbots and terminals are just like... Like, I don't think anyone expected this to be the lasting, uh, user interface to AI. Like chatbots, okay, no, no, this is just like a temporary stop along the journey, but now it's [laughs] like gone even further in just terminals.
4. JWJenny Wen
  [laughs]
5. LRLenny Rachitsky
  Um, do you have thoughts on just, I don't know, where, uh, like do you think there will be a next step of how we interface with AI, or do you think chatbots and terminals are, are mostly where we end up?
6. JWJenny Wen
  There will likely be a combination of both. Like, both UIs and interfaces that you are interacting with, clicking with, and, and, and that feel, like, more tactile. We are already seeing this and playing with this within Claude, like the chatbot. Um, so we recently released a bunch of these widgets that let Claude sort of elicit and ask you questions and also show you, you know, things like the weather and stocks and whatnot in interactive ways. And I think those have had a really good reception because people still like to see UIs and touch them and, and click them, and they are much more efficient than, you know, typing something to, to Claude. But at the same time, when we le- really leaned into this, like, chatbot paradigm, like I think that just gave us this whole world of flexibility that we didn't get with these sort of like baked-in UIs. Um, so my read here is like I don't think chat is ever going away because this opened up this like new way of like infinite ways to, to work with the model and to sort of like talk to the computer that we just didn't have before. But I think that it will still be most direct for very specific things to exist in this UI, and I think that what will probably happen here is that a lot of those UIs will be generated more and more often by the models as opposed to something that we're, like, hand-coding each instance. But I think we... Yeah, we're in the space where I don't, I don't think chat and, and, and, and maybe even like talking to the terminal is, is gonna go away.
7. LRLenny Rachitsky
  It's interesting that like with OpenClaw, Claude, ModelBot-
8. JWJenny Wen
  Yeah
9. LRLenny Rachitsky
  ... all the names, the innovation- one of the big innovations is like another way to chat with it through WhatsApp and Telegram [laughs] and SMS. Just like another form of chatbot, but that, just like that was a big unlock. Oh, I can just chat with it through WhatsApp.
10. JWJenny Wen
  Yeah. And it's like you... Like, chatting and talking to someone is still, like, you know, we as humans are doing it, and so... And it's a way for us to interact in a really rich way, and now we just have this other medium to like interact with a computer basically.
11. LRLenny Rachitsky
  Yeah. Um, so Kevin Weil, uh, 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 IQ. It's talking still works, so that's why it's been this beautiful way to deal with the growing intelligence of models, is it continues to work.
12. JWJenny Wen
  Yeah, that totally makes sense, yeah.
13. LRLenny Rachitsky
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35:33 – 41:00
Moving from director back to IC
1. LRLenny Rachitsky
  Okay. I wanna come back to this whole idea of management and IC. So, so you've spent... You've kind of put yourself back into the IC role in a lot of ways. Talk about that and if you think that's just like a thing design managers need to be doing.
2. JWJenny Wen
  Mm-hmm. Yeah, I have takes on this. Um, yeah, so this past year at Anthropic, I joined as an IC at first, um, and then I managed a team for a few months in, in like 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 'cause 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, you know, I, I, I sort of wanna be close to the work and I, I think this feels like a really important time to do it before I, like, ascend the corporate ranks, you know? [laughs] And, and I- I was having these, like, questions and doubts about, like, is, is middle management, like, is that safe [laughs] in the future? Like, are, are... Is, is, is the way that we're working actually... Is this going to be a-... job that persists into the future or, or should I, you know, try something else and, like, get my hands dirty kind of thing? Um, and to, and to be totally fair, like, I actually love both sides of the coin. Like, I loved, I love managing people. I love, like, setting up teams, um, um, and, and being at that level. But I also just really love IC work. Like, I was sort of like a reluctant manager when I did it, and I was like, "Okay, I'll do it." Um, so I love both sides of this coin, the coin, like, pretty equally. But I think actually what being an IC across this past year has taught me is that it actually just, like, gave me a lot of skills that I, I don't think I would have gained if I was just managing throughout this year. Um, like the design... 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. Um, so that's actually the best thing it's afforded me. And I think at any point if I'm, like, 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, yeah, 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, like, not always, like, testing all the tools and trying stuff. But yeah, like, it's, 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 have totally understood it or, like, knew what to do or how to guide my teams. So that, that's sort of what this year really gave me.
3. LRLenny Rachitsky
  And so you were previously a director of design at Figma, right?
4. JWJenny Wen
  Yep.
5. LRLenny Rachitsky
  How big was your team? Like, how large was your org, just to give people a reference?
6. JWJenny Wen
  At the max, I probably had, I think, 12, 15 designers or so, and, and I had a few managers as well. So-
7. LRLenny Rachitsky
  Cool. And then you went back to IC
8. JWJenny Wen
  ... it was like an org. [laughs] Yeah.
9. LRLenny Rachitsky
  Yeah. Okay. So you had the sense that middle management might not last. What's your current feeling? Do you think management... design management is a thing that persists long term, or do you think everyone turns into IC?
10. JWJenny Wen
  I think as long as there is a team of people, it, it helps to have somebody who [laughs] is managing a team.
11. LRLenny Rachitsky
  Okay.
12. JWJenny Wen
  Like, I think there is, uh, there's, like, real value in managers. It depends kind of, like, what the shape of the manager is and what they actually do. But the way I think about, like, of what a helpful manager is these days is somebody who is not just, like, I think pure people management. Like, oh, like, just somebody to sort of set you up, help you in your career, have one-on-ones, make sure you're feeling, like, good, [laughs] good at work. I think that that is kind of not a thing as much anymore. But I think somebody who can really function as, like, giving the team direction as well as doing some of the people management stuff, like, that tied together I think is the future of what managing looks like, at least for now. Um, like somebody who can really engage with the team in terms of, like, the work and giving direction there, um, as well as, like, creating the environment for them to do their best work.
13. LRLenny Rachitsky
  And do you see yourself going back into management long term?
14. JWJenny Wen
  I probably will. I probably will. Like, I, I think I, I really just love, you know, helping a team, like, build the best product possible, and my f- my motto there is, like, whatever it takes, you know? If it's somebody that... If, if, if the team needs somebody to give the team direction and, like, set up the team and whatnot, that could be me. If the team just, like, needs somebody to execute on it, that could be me as well.
15. LRLenny Rachitsky
  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.
16. JWJenny Wen
  I think so. And I think traditionally, um, at least what I've seen, a lot of, like, the engineering disciplines, like, when they hire EMs or even sometimes, like, directors there, they actually make the EMs, like, take a rotation for a few months and, 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, like, people management oriented.
17. LRLenny Rachitsky
  What did you find yourself most rusty in when you went back to IC designer?
18. JWJenny Wen
  Actually, like, doing crits, you know? Um, and just realizing-
19. LRLenny Rachitsky
  Getting criticized.
20. JWJenny Wen
  Yeah, [laughs] getting criticized. You're like... Oh, yeah. Like, it is hard to get, uh, 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, like, you... 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 a- and take that all
41:00 – 46:06
The 10-day build of Claude Cowork
1. JWJenny Wen
  the time.
2. LRLenny Rachitsky
  Hmm.
3. JWJenny Wen
  Yeah. [laughs]
4. LRLenny Rachitsky
  So currently you're, you're leading design, uh, slash IC designing on Cowork-
5. JWJenny Wen
  Mm-hmm
6. LRLenny Rachitsky
  ... is that right?
7. JWJenny Wen
  Yeah.
8. LRLenny Rachitsky
  Awesome. So Boris, he was on the pod recently, talked about how there was, like, 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, 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.
9. JWJenny Wen
  I... With Cowork specifically, we have had a bunch of different prototypes internally of what that could look like. Um, and it's one of those things where we tried a lot of things, and then we... I think we weren't really sure, like, when it was actually going to be ready to ship, and then it was sort of like everything all at once. Like, we were like, "Okay, we're gonna, we're gonna ship it soon." Um-
10. LRLenny Rachitsky
  It was like it was 10 days, 10 days of building.
11. JWJenny Wen
  [laughs] Yeah, it was, uh, it was l- it was definitely longer than that, like, overall. It was, like, 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, like, the actual form it was gonna take. Um, and so the way it got there is actually there was a, 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, um, 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, uh, presents you different, like, multiple choice questions. We had tried a bunch of different, um, ways to teach people what the use cases are and whatnot. And I don't know if we, like, landed on the best form factor ever, but, uh-Essentially, it was like stuff that was sort of already working internally that people liked that we just thought we were gonna get some more signal on by, 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, [laughs] let's put it out there, and then let's go out there and iterate from there, which is what we're doing.
12. LRLenny Rachitsky
  And it blew up the internet when you launched it, so- [laughs]
13. JWJenny Wen
  [laughs]
14. LRLenny Rachitsky
  ... it worked out.
15. JWJenny Wen
  Yeah.
16. LRLenny Rachitsky
  Is there a feature of Cowork today that you're either most proud of or just, like, can't wait to fix and, and improve?
17. JWJenny Wen
  Honestly, I think we're... I'm, I'm just most proud of us actually just, like, shipping it, to be honest, um, and putting it out there. And, uh, uh, yeah, I, I don't know if there's, like, one specific thing yet. 'Cause, like, I think when, when you work on something and you work on it so long, especially as a designer, you're like, "I don't know if I..." Like, you know, I... All I can do is see flaws in it. But I think there's a lot of stuff that I'm excited about. Like, we have been, uh, iterating, especially on the homepage, and to make that something where it feels more like, hey, th- these are, like, tasks you can give Claude and, and that tasks that Claude are working on. Um, and so that actually should be rolling out. It might already be rolled out by the time this, this, this comes out.
18. LRLenny Rachitsky
  I s- I see, like, this little randomizer thing where you click it-
19. JWJenny Wen
  Mm-hmm
20. LRLenny Rachitsky
  ... and it gives you all these different ideas.
21. JWJenny Wen
  Mm-hmm. Yeah, yeah, yeah. And then so when you actually start to work with Claude on stuff, it feels more like a to-do list. Like, it feels more like these are things Claude's lo- working on. Um, these are things that Claude needs your attention on. And I think there's a, just a, there's an opportunity here to make it feel much more like this, like, shared to-do list between you and Claude. So excited to iterate on that. And then I'm also excited to think more about, uh, yeah, like, what is the actual true form factor of this? Like, is it stuck in the screen always? Or how does this sort of, like, reach out to the different surfaces that it's working with?
22. LRLenny Rachitsky
  I love that you shared that it wasn't just 10 days to do this thing. There's, like, these numbers that people throw out there, "We build it in 10 days," and your point is, like, there was time spent thinking about what direction it should go and prototyping, mocking, trying stuff. And then it's like, okay, now we know what we want it to be. Let's build it and ship it.
23. JWJenny Wen
  Yeah. I think for some reason that became, like, the viral thing that got taken away from all of the, the sort of Cowork announcements is that it only took 10 days, but I think there, there have just been so many different explorations, uh, and people that have worked on different pieces of Cowork that, yeah, it was, it was not just 10 days. And there's a lot of different people involved. It's, it's one of those things where it's like the, the idea kept coming back, and it's, like, never the right moment, or there's, like, different variations of it, and then all of a sudden it's the right moment, and it feels like, oh, so obvious all along. But there was a long, long journey to get there.
24. LRLenny Rachitsky
  And by the way, for people that don't know much about Cowork, is, like, the way I think about it, it's like Claude with hands-
25. JWJenny Wen
  [laughs]
26. LRLenny Rachitsky
  ... for you to do stuff on your computer.
27. JWJenny Wen
  Yeah.
28. LRLenny Rachitsky
  Is that... Is... What's... Well, how would you describe it, just, like, in a sentence or two?
29. JWJenny Wen
  That's a good description. I actually haven't heard that, but I like that. I might use it more often as Claude with hands.
30. LRLenny Rachitsky
  [laughs]
46:06 – 50:44
Hiring: the three archetypes
1. LRLenny Rachitsky
  Okay. Coming back to managing and being a manager and the role of a designer, I want to talk about hiring for a little bit. So seeing how much is changing in the role of a designer, h- what do you look for that's maybe new? Like, what do you now look for when you're hiring designers that you think is really important for them to be successful in this new world?
2. JWJenny Wen
  Uh, well, I do think working specifically in the enviro- the kind of environment that I do, there, there is just, like, a sense of, like, resilience and, like, roll with it kind of thing, um, that I think is really important. Because, yeah, so much is changing around us, and you have to be really willing to adapt, to try out new methods, to try out new tools, and learn stuff as opposed to just, like, be stuck in the old processes and the old ways. Um, but then I think about also there's probably three archetypes of folks that are really interesting to me right now. Um, and I think these folks were already interesting to me before, but I feel like is, in this era feels especially important. Um, so the first one I would call is, like, strong generalists. Um, so not just, like, regular generalists where they're, like, kind of good at a lot of things, but, like, people that are, like, almost, like, block shaped, you know, in that T-shaped framework where it's like they're really good at, like, a few core skills, like, 80th percentile good. I think this is, like, pretty rare and hard to hire for, to be honest. But I like this because the design role we've already seen is kind of, like, stretching and spanning, right? Like, we're all becoming more PM shaped, we're b- all becoming engineering shaped. Um, and so if you already have strong skills in a few different buckets, it's really easy for you to sort of, like, flex around and expand your, and expand your role. So that's really exciting to me, is just somebody who is really good at a bunch of things. Again, a huge ask. Um, and then the other person that's really exciting to me is in that T-shaped framework, like, a, a deep specialist, like someone who's is T-shaped, but, like, the, the, the tip of the T probably is, like, goes down farther than most other people. So folks that are maybe, like, the top, you know, like, 10% of the industry and whatnot. Again, super hard to find, and I feel very lucky that, like, w- you know, working at, at, at some of these places, like, folks like these, you've... you can sort of afford to hire them and, and, and actually bring them on, on board. Um, and then my last one is probably the one that I think we're all overlooking, which is what I call the craft new grad. [laughs] Um, it's just somebody who's, like, early career and, uh, feels kind of, like, wise and experienced beyond their years, but is also just, like, very humble and, and, and very eager to learn. And I think this person is really interesting right now because-W- uh, I think most companies are just hiring, like, senior talent, like folks that have done things before, are, are super experienced. But given how much the roles are changing and what we're expected to do is changing, I think having somebody who almost has, like, a blank slate and is just, like, a really quick learner and is really eager to learn, um, new tactics and stuff like that and doesn't have, like, all these baked-in processes and rituals in their mind, that's super valuable. Um, so I think those are the folks that I think a lot of us are just, like, overlooking, but I'm, like, really excited about.
3. LRLenny Rachitsky
  This is awesome. Uh, on the deep T shape, what's an example of someone in design that has a... Like, what's, what's a skill that they're really good at?
4. JWJenny Wen
  Sometimes there's designers who are just, like, really technical in a way to where they could be, like, 50% a soft- They're, they're basically a software engineer. Like, that's really interesting, especially 'cause right now, like, a, a lot of it is... At least for us, it's like, you know, you're working with- directly with the model, so it can... It helps when you have just, like, deep engineering expertise. Uh, but another, like, deep kind of, like, specialist T is just, you know, maybe they're just really good at, like, visual design or, or just, like, designing icons or something where things like that, given that everybody can, anybody can make anything, you know, having that deep specialist slant feels like, oh yeah, they can really help differentiate the things that we're building.
5. LRLenny Rachitsky
  Awesome. Okay. And then this block shape. We had Mark Andreessen on the podcast. We kind of called it the F, F shape or E shape where there's, like, multiple T things. Sideways F, sideways E, I guess. Is that what you're describing where there's, like, many things you're really, really good at?
6. JWJenny Wen
  Yeah. Yeah. And, like, basically, like, I don't know, if you almost had their skill set, it would, it would look like a block, you know, like, instead of a T.
7. LRLenny Rachitsky
  'Cause there's so many skills that, like-
8. JWJenny Wen
  Yeah. Yeah
9. LRLenny Rachitsky
  ... the Ts spread out. [laughs] Okay.
10. JWJenny Wen
  Yeah.
11. LRLenny Rachitsky
  Okay. And the crack new grad. So this is just, like, someone that is, uh, eager and, like, uh, open-minded, gritty-
12. JWJenny Wen
  Mm-hmm
13. LRLenny Rachitsky
  ... very smart, I imagine is a big part of it.
14. JWJenny Wen
  Yeah.
15. LRLenny Rachitsky
  Awesome.
16. JWJenny Wen
  Yeah.
50:44 – 54:42
Advice for new and senior designers
1. JWJenny Wen
  Yeah.
2. LRLenny Rachitsky
  If someone's, like, a new design- like, a young designer trying to break in, trying to be successful, what would your advice be to them to help them have a shot at, at ends up joining Anthropic, for example?
3. JWJenny Wen
  I would just say just, like, build a bunch of stuff. Like, try a bunch of stuff out, build, build actual things. I, I think that is... That can feel... I don't really know what the state of, like, design education or education is these days, but at least from, like, back when I was in school, like, everything was very, like, theoretical and like, "Here, we're gonna teach you some approaches and whatnot." But, like, the best, the best kind of, like, crack new grad folks I know are just, like, people who just, like, use the technology, build actual things, uh, don't feel, like, limited by h- you know, how little experience they might have. I think they're, sometimes they're actually unburdened by that 'cause, like, we have expectations of ourselves after being in industry for so long, but they actually don't, and they sort of feel like anything is possible. And so just, like, building a bunch of stuff and, and sharing it with people and finding a community of folks that, uh, that also do that. Um, yeah, I think my, my one call out here too is, like, I went to a school that started something called Socratica, like, much, about a few years after, actually a while after I graduated. And basically, their whole thing is, like, building stuff and showcasing it almost like a science project. And I think there's just been a really cool movement there of folks who just, like, build things and do things. Like, for example, somebody built this, like, Claude robot project. This was, like, a few years ago, too, where they were, uh, just assembling robots that were running on Claude. And then somebody else did something where she just wanted to put googly eyes on a bus [laughs] in Boston or something. And there's just, like, a sense of, of both, like, agency in terms of like, "Yeah, we can just do stuff," but then also this community where people were just trying and building things and sharing things with each other. So whatever that looks like, given the, you know, the school that someone's from or graduating from, yeah, doing that kind of stuff is, is, is the stuff that will make people stand out.
4. LRLenny Rachitsky
  For current designers that are in a mid-career, awesomely senior, do you think you need to get technical and learn to code, at least build? Or do you think you could be really successful and just not lean into that and get better at other stuff?
5. JWJenny Wen
  I think it definitely helps to maybe not, like, learn how to code so much that, that, uh, you know, you're building something from scratch. But I... It does feel like more and more of the designer's vocabulary right now is implementing some stuff. I wonder, though, as, you know, the, the models, both the models and the products get better, if, like... We'll... I mean, we probably will continue to, like, move up the abstraction layer and layers, and you won't have to actually know how, you know, each, a single line of code will work. But I think what I would say is, like, start to bring that into your, like, toolkit, the coding tools. Whether or not it's like you're actually becoming technical, I think any designer should just be really aware and, like, know how to use the tools that are at hand as opposed to maybe, like, learning and, like, going off and, you know, learning React or, or et cetera, et cetera.
6. LRLenny Rachitsky
  How good of a designer is, is Claude, would you say? Or Claude Code, whatever you want to s- Like, would you hire Claude as a designer, or is, like, not there yet?
7. JWJenny Wen
  I don't think Claude is there yet. I don't think Claude-
8. LRLenny Rachitsky
  Okay
9. JWJenny Wen
  ... is there yet in terms of a designer you would hire. I think it is, it is not yet the strong generalist or the deep specialist or the crack new grad. I think it's, it's pretty good at a first pass and at presenting a bunch of different ideas to you, but, uh, nothing there quite feels like, yeah, special and hireable yet.
10. LRLenny Rachitsky
  Which is good news for designers for now.
11. JWJenny Wen
  Yeah. [laughs]
12. LRLenny Rachitsky
  That it sucks at this for now. And I'm so curious to see how good it could get at this. That's, like, such a big open question, is-
13. JWJenny Wen
  Mm-hmm
14. LRLenny Rachitsky
  ... can it pump out amazing, novel, unique, creative experiences, or is there s- it's just never gonna be that good as a-
15. JWJenny Wen
  Yeah
16. LRLenny Rachitsky
  ... as a human designer?
17. JWJenny Wen
  I mean, it's gotten a lot better in the last year or so
54:42 – 57:52
The value of “low leverage” tasks for managers
1. JWJenny Wen
  even, so yeah.
2. LRLenny Rachitsky
  There's a couple management, uh, I don't know, rituals or takes you have that I've heard from folks that you work with that I wanna touch on. One is that you have this hot take that low leverage time for managers is just not a thing, that there's a lot of benefit you can get out of things that people consider low leverage. Can you talk about that?
3. JWJenny Wen
  Yeah. Um, yeah, I remember, like, first becoming a manager, and I think one of the pieces, like, 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, uh, like, to really prioritize your time and categorize your work." And there was, like, this two by two of, like... I, I don't remember what it was in it, but you essentially say, like, "Oh, these are the things that only I can do. These are things anybody else can do, and everything else, you know, like, it's low leverage and you shouldn't do that anymore." And a lot of the low leverage things were just, like, you know, like, things that are really nitpicky in the weeds or just, like, literally, yes, probably somebody else could do those tasks. But when I think about, like, leaders and managers that I have respect the most, um, I actually think some of the, the, their best traits is that they choose, like, 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. Um, so one example is, uh, whenever you have, like, senior leaders who just, like, test the shit out of the product and they're just, like, so in tune with it, um, and they dogfood it, they repro the bugs, they spend a bunch of time with, like, engineers, like, sharing the logs and, like, nitpicking and stuff like that. Um, and I think that ends up being, like, super actually high leverage, even though it's a lot of time, of, like, nitty-gritty time, because it creates this, like, familiarity with the product, which I think is really good. Uh, it also creates this vibe where it's like, oh yeah, the, this senior leader really cares deeply and they actually know the ins and the product, and they're rolling up their sleeves and they're giving this feedback and working with the team on it. Um, and I think similarly, too, what I've seen is, like, when a senior leader c- is able to, like, fix a bug now, you know? [laughs] Even, like, I think I've actually seen, like, Mike Krueger before, like, put, put in PRs himself. Um, and it's, it's, it's really nice 'cause it's like, okay, cool, like, we're all on this team together and nothing is, like, below this person. Um, and I think simil- another thing that I love that's, like, a little bit more cultural is when somebody, like, goes out of the way to, like, make somebody's, like, anniversary card or something, um, and, like, vibe code them super ni- something super nice or make them something, a super nice card, 'cause I think it just shows that, yeah, 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. So that's something I try to embody is, like, choosing the, like, the l- the seemingly low leverage tasks that are, like, worth my time.
4. LRLenny Rachitsky
  Yeah. That is so interesting. Like, what you're saying there is, in a sense, like, the low leverage stuff is the one, is the stuff that often has the most impact because your reports wouldn't expect you to spend time on this thing, and there's a l- like, the low leverage ends up being high leverage.
5. JWJenny Wen
  Yeah. And I think it's what makes, like, your style of leadership stand out or feel special to a
57:52 – 1:01:45
Why the best teams roast each other
1. JWJenny Wen
  certain person.
2. LRLenny Rachitsky
  Amazing. Another, uh, I don't know, ritual and kind of way of running teams that I heard about you is, uh, you encourage r- uh, team members roasting each other.
3. JWJenny Wen
  [laughs]
4. LRLenny Rachitsky
  Which on the surface doesn't sound like a wonderful environment, but, uh, 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.
5. JWJenny Wen
  Yeah. I think it's not that I'm like, "Yo, you should roast each other," you know? [laughs] Like, I'm not, like, forcing it in that way or anything. Um, but when I think about the sort of psychological safety and teams and, like, people that just get along with each other, like, when you think about your friends, you know, you're, you're always sort of willing to, like, push the boundaries a little bit and, like, roast them. Like, y- you're roasting your friends a lot, but you actually might not be roasting your coworkers a lot because you... It's, it's all just about, like, comfort and, and safety, right? 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, uh, the people on your team kind of feel comfortable just, like, kind of poking fun at each other a little bit. Um, and I think that also can be a good sign when folks also feel the same way about, like, you as a leader, where it's like there's just an element of, like, they don't, they don't fear you as much, [laughs] but they... and they feel like there's a f- sense of safety where they, if they say something, they're not gonna get fired. Um, so an example of this is, like, with my last team, I feel like they would make fun of things that I would say at crit sometimes, like s- certain phrases I would say. Um-
6. LRLenny Rachitsky
  What's an example of that?
7. JWJenny Wen
  I don't know. [laughs] Like, I... Oh, I would always be like, "Okay, like, what are next steps?" And like, "How do we follow up on this?" And then they'd be like, "Okay, like, what are next steps?"
8. LRLenny Rachitsky
  [laughs]
9. JWJenny Wen
  Um, and, and they would sort of channel me in that way. Yeah, I just think it shows a level of, like, okay, these people are, like, not necessarily afraid of me. They know that, uh, they trust me, they can, they can trust me. Um, and it's, it's... And then they sort of, like, know enough about each other and me, like, personally in our personal lives to be able to, like, know sort of where those boundaries are. Um, but at the same time, I think the, the, the thing that you sort of err into in that territory is, like, are you, as your ma- as a manager, are you friends with your reports? Which is, I think, a thing people tell you, like, not to do. And so the way I think about balancing this out is, like, this creates, like, the, the... You have to create this sort of, like, uh, baseline of psychological safety and people feel comfortable both with each other and with you, but you also have to make sure that you, they know that you have really high standards. Um, and I think these two things can feel like they're at tension, but I think they're actually... They work really well together. 'Cause 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.
10. LRLenny Rachitsky
  Mm-hmm.
11. JWJenny Wen
  Because you can do it without fear, I think. Um, and I sort of think about this from the approach of, like, kind of like being a tough parent a little bit, you know? It's like, oh yeah, like, they... My team, I work with them in a way where they know I'm always gonna be there, um, and I'm not just gonna fire them on a whim or something, but at the same time they also know that I want the best for them, you know? And that I have high standards and that-You know, I, I'm working with them to, to make the best work possible. And so, yeah, that's a balance I think you have to strike is, like, can you create this environment of one where your team feels comfortable, like, roasting you, but at the same time, like, they know they have to be doing great work, and they, and they, they will do great work with you.
12. LRLenny Rachitsky
  That is awesome advice. It's interesting how often this, this, uh, just, like, management style comes back... Or management, uh, good management, it comes back, reminds me of, what was it? Candid rad- radical candor.
13. JWJenny Wen
  Mm-hmm.
14. LRLenny Rachitsky
  Just this combination of caring deeply and challenging directly.
15. JWJenny Wen
  Yeah.
16. LRLenny Rachitsky
  And that, that's kinda what I hear here, is just make sure people know that you care deeply about them, but also
1:01:45 – 1:07:22
The legibility framework
1. LRLenny Rachitsky
  be very direct and have high standards.
2. JWJenny Wen
  Yeah. Yeah. Exactly.
3. LRLenny Rachitsky
  That's so interesting. Okay. Maybe a final question.
4. JWJenny Wen
  Okay.
5. LRLenny Rachitsky
  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.
6. JWJenny Wen
  Mm-hmm.
7. LRLenny Rachitsky
  Talk about this. Talk about how you use it, why it's so valuable.
8. JWJenny Wen
  Yeah. This framework, I think I saw it on Twitter of m- maybe last year or something, and it was Evan Tana, who is a partner at SPC, uh, he's a BC. So it, it basically is this, like, two-by-two. I don't think it, like, got so much attention, but I, once I started seeing it, I, like, actually couldn't stop thinking about it. So, um, on the two-by-two, he basically has, like, founders. Like, founders can be either illegible or legible, and then ideas can either be illegible or legible. Um, and basically he was saying that, like, okay, if, if both the founder and the idea is, like, super legible, the idea's probably not that novel and somebody's already, like... They're already gonna implement it or, or, or do it, and you're actually not finding something new. Um, but then where it gets really interesting is where, like, the idea itself is illegible. And by illegible, he means, like, oh, it's sort of, like, really f- you know, on the frontier. People might not get it yet. Or, like, the way it's being told, it just doesn't... It's not, like, being told in the, in the, 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 tr- trying to look for the opportunities that people don't see a- and put them out there in the world. But I also think that, like, part of the role of the designer, at least, um, at least at, at a, at a frontier lab at Anthropic, is kind of spotting the ideas that are illegible and trying to understand what's there and how to take that and, like, transform it, whether it's through storytelling or whether it's through, like, the actual UX and the form factor, and, and, and, and put it out there. Um, and I think there's like m- like when I mention, you know, going through Slack and, like, looking at all the stuff that people are making, like, that's kind of what I'm doing. I'm trying to see, like, oh yeah, what are the ideas that are really... That, like, there's, like, some energy there around, but, like, might not make sense yet that, that are worth me, like, thinking about more in my work. There's, there's one good example, actually, that, like, ties to Cowork, uh, where there was this internal prototype that we called, like, Claude Studio, that I think somebody built, like, partway through last year. Um, and it essentially was this, this, like, really kind of, like, dense, powerful interface that was built on top of some agentic harness. I, I, I... It might've been Claude Code at that point in time, too. And it had all these, like, dis- displays where it's showing you, like, all this knowledge and all these skills and, and things Claude was doing and, like, previewing its outputs. Um, and I think to a designer, I looked at it and I was like, "This is, like... I don't know what's going on. I don't really get it." Um, but then I sort of saw the, the folks in research, the folks building it, and, and just folks internally, there was just a lot of energy around it, and I was like, "Cool, like, I think there's, like, something here, but I just don't understand it yet." And I think that really was an example of an, an ille- an il- illegible idea. And ultimately, what came from it was, like, the skills framework, um, and, and, and-
9. LRLenny Rachitsky
  Mm.
10. JWJenny Wen
  ... uh, like, the sort of, like, markdown files that sort of, 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, like, you know, the folks working on this prototype extracted that out of it. But when it did come to working on Claude Cowork and I was thinking about, like, oh yeah, what is the form factor for this thing? Seeing that prototype and seeing the kinds of information that people found really helpful, like seeing Claude's, um, plan and to-dos, um, seeing Claude's, like, context and the files that it was, it was going through. Like, those kinds of things are things that I ended up pulling out of that prototype into Claude Cowork. So yeah, I think about, like, how can designers almost be more like VCs in this way internally when we're looking at prototypes.
11. LRLenny Rachitsky
  This is super interesting. I did a research project recently where, uh, with this guy Terrence 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, um, Linear and Notion, all these companies. Like, people that have joined many of these companies early, what were they looking for? And one of the factors was the idea is so, is, like, so crazy that everyone's laughing at this. This is, this is impossible. You're never gonna do this. This is the craziest thing ever. Why would you even think, like, Palant- Like, all these... Like, OpenAI actually was one of them, just, like, some research lab doing some stuff. So, so it's interesting that... And it's not like every time this will work, and it's not like every crazy idea that sounds, makes no sense will be good. But I think what you're saying is pay attention to stuff that's, like, interesting to you and isn't totally clear. Maybe you can be the person that helps pull it together.
12. JWJenny Wen
  Yeah. Yeah, that, but also, like, if there is some energy around it, but I don't quite under- always understand what the energy is-
13. LRLenny Rachitsky
  Mm
14. JWJenny Wen
  ... is to, like, dive deeper and try to understand-
15. LRLenny Rachitsky
  You're like, "Cool"
16. JWJenny Wen
  ... what that is. Yeah.
17. LRLenny Rachitsky
  Got it.
18. JWJenny Wen
  Yeah. 'Cause I think people who often gravitate towards these early ideas, they can't always articulate why.
19. LRLenny Rachitsky
  That's so interesting.
20. JWJenny Wen
  And it's sort of up to you to, like, dive deeper and understand that.
21. LRLenny Rachitsky
  That's one of... That was... There, so there's three patterns we found.
22. JWJenny Wen
  Yeah.
23. LRLenny Rachitsky
  One of the other ones was-
24. JWJenny Wen
  Ooh
25. LRLenny Rachitsky
  Pay attention to people getting very excited about this thing, even if you don't get it.
26. JWJenny Wen
  Mm-hmm.
27. LRLenny Rachitsky
  And it's like, sounds crazy. That's so interesting. Okay.
28. JWJenny Wen
  Yeah.
29. LRLenny Rachitsky
  And then what was the other one? Oh, the founders are just like top 1% was the other piece there, which everyone at Anthropic already is, so you got
1:07:22 – 1:17:24
Lightning round and final thoughts
1. LRLenny Rachitsky
  that one. Oh man, Jenny, what a crazy time we're living through. What a world.
2. JWJenny Wen
  What a crazy time.
3. LRLenny Rachitsky
  How much, so much change.
4. JWJenny Wen
  [laughs]
5. LRLenny Rachitsky
  Okay. Before we get to our very exciting lightning round, is there anything else that I should have asked you that you wanna leave listeners with, that you wanna double down on?
6. JWJenny Wen
  Um, I think I just want to call out, uh, the Anthropic design team, um, and shout them out, uh, just because it's a team of folks that are just really humble, and they're not always the loudest on social, but they're doing a lot of really great work. And especially through this time where our jobs are changing so much, uh, the team is so resilient, and they're, they sort of span this whole spectrum of people who are really technical and prototype-y to all the, all the way to folks that are really high craft and, and, and delivering stuff that's, that's going out the door and is fabulous. Um, and we are hiring throughout the year, so I just wanted to call that out. If I didn't scare you with the way that we work internally at Anthropic, if it sounds more exciting than terrifying, um, would love to connect.
7. LRLenny Rachitsky
  What sounds exciting is getting access to these Slacks where you have all the features being-
8. JWJenny Wen
  Yeah. [laughs]
9. LRLenny Rachitsky
  ... built and-
10. JWJenny Wen
  Yeah, yeah. That's the core benefit
11. LRLenny Rachitsky
  Let's talk to super intelligence right now and tell me where I should invest. I'm just joking. And then in terms of hiring, is there anything specific that people should think about to, if they wanna apply?
12. JWJenny Wen
  Think a little bit about the, the archetypes that I mentioned, especially the strong generalists and the deep specialists. Those folks we're really excited about. Uh, but generally-
13. LRLenny Rachitsky
  The block-
14. JWJenny Wen
  ... folks who are-
15. LRLenny Rachitsky
  The block and the deep T.
16. JWJenny Wen
  The block T. The block [laughs] the block and the deep T. Um, what could we be talking about?
17. LRLenny Rachitsky
  [laughs]
18. JWJenny Wen
  Uh, yeah, folks who feel like they, you know, they, those archetypes resonate with them, but also folks that are just really excited about the technology, have been building a lot, um, and, and sort of wanna be on the frontier.
19. LRLenny Rachitsky
  Amazing. Well, with that, we've reached our very exciting lightning round, [thunder] and we've got five questions for you, Jenny, on your end.
20. JWJenny Wen
  All right. I'm ready.
21. LRLenny Rachitsky
  Here we go. What are two or three books that you find yourself recommending most to other people?
22. JWJenny Wen
  The first one is The Power Broker by Robert Caro, which is an in- [laughs] which is an incredibly aggressive recommendation given that it's a hu- it's like 1,100 pages. Uh, but I think in this era when our, our, when our attention spans are so short, I think this is actually worth reading end to end. Um, because there... I think there are very few, like, collections or memoirs where it spans through someone's entire life and you sort of see how somebody changes throughout those decades. Um, and it's also somebody who's really controversial too, and it's, it's nice to sort of like read a really nuanced view of somebody, Robert Moses, and I think we just lose out on some of the, this like long arc thinking 'cause we're so much, we're thinking so much about right now. So, uh, it's just an important reminder that careers are long and is also really good for kind of understanding how somebody just gets things done really well. So, Power Broker. Um, the second one that I recommend to a lot of people is, uh, a book called Insomniac City, which is written by Bill Hayes, who is, was the partner of the scientist Oliver Sacks around the time that Oliver Sacks died. And it's just this like really beautiful kind of like ethereal memoir of Oliver Sacks' last days and their sort of love story. Um, I think this has like very little to do with the stuff on your podcast, Lenny, but it's just like, it's just a book that I really love, um, and just like makes you think about mortality, but also like love and life and stuff like that. So that's one of my favorite books.
23. LRLenny Rachitsky
  My goal here is in, you know, I'm trying to create, we're trying to create Renaissance humans.
24. JWJenny Wen
  Mm-hmm.
25. LRLenny Rachitsky
  So all of this, uh, other stuff is, uh, excellent.
26. JWJenny Wen
  Cool.
27. LRLenny Rachitsky
  Interestingly, I saw Julie Zhuo, uh, famed design leader, was reading The Power Broker recently. I don't know what's going on over here.
28. JWJenny Wen
  [laughs] Yeah.
29. LRLenny Rachitsky
  Spreading in design land. Okay. Do you have a favorite recent movie or TV show that you really enjoyed?
30. JWJenny Wen
  Um, I watched A Sentimental Value recently. I watched it on a plane, which is, you know, how, how directors want you to watch their films.

Episode duration: 1:17:24

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Introduction to Jenny Wen

Why the traditional design process is dead

The two new types of design work

How widespread this shift will be

Day-to-day life as a designer at Anthropic

Jenny’s AI stack

Why Figma still matters for exploration

Advice for working with engineers

How to maintain craft, quality, and trust in the AI era

Will AI ever have “taste”?

The future of chatbot interfaces

Moving from director back to IC

The 10-day build of Claude Cowork

Hiring: the three archetypes

Advice for new and senior designers

The value of “low leverage” tasks for managers

Why the best teams roast each other

The legibility framework

Lightning round and final thoughts

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