The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude)

15:23Lenny Rachitsky:about how like there's already so much ai news to keep track of as a regular person and then actually seeing what's actually happening inside a lab is a whole new set of feeds to watch yeah yeah it's

15:34Jenny Wen:like i don't i think that is the the best ai news is probably internally if you're ever at one of

15:39Lenny Rachitsky:these companies in the slack damn yeah yeah just problem keeps getting harder just keeping keeping track what's going on okay so okay so that's part of the job what else there is still some of like

15:49Jenny Wen: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 co-work and now i want to set aside some time to think about hey what are the next like three months looks like and and where does that actually where could that actually go given where the market's at where the models are at and what could that be because I think it still really helps to visualize that and show that to the team and point everyone in the same direction 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 we're really consulting 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 and that's and that's a really fun part of my job that i think didn't exist as much

16:58Lenny Rachitsky:a few months ago are you still doing elements of the traditional design process prototyping user research uh panels i don't know just like going out and you know like the whole the whole thing

17:08Jenny Wen:you described yeah we're still doing 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 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.

17:40Lenny Rachitsky:Got it. Okay. So that's a really interesting takeaway. 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.

17:57Jenny Wen:Yeah. I think as a designer a few years ago, I would say like maybe 60 to 70 percent of it was like mocking and prototyping stuff up and then spending, you know, the last 20 or some of the last 20 or so like doing the sort of like jamming with engineers, consulting with them. And the last like 10 percent maybe doing, you know, coordination meetings, et cetera. but now I feel like the the mocking up part of it is like 30 to 40 percent and then there's that other 30 to 40 percent there that is now jamming and pairing directly with engineers and then there's like a slice I don't know how much I have left but like there's a slice of it that is now

18:40Lenny Rachitsky:like implementation as well yeah like actually building and shipping yeah 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 I want to talk about how you actually are. I see also what's in your AI stack. What tools are you using?

18:57Jenny Wen:What is in my AI stack? Well, we're going to Thropic. So we're going deep on the Cloud stack. Yeah. I am. I'm using obviously like chats, Cloud chat. And but increasingly more and more Cloud Co-Work. I've basically shifted all of my chat use cases over to Co-Work because I've been finding that. Yeah, it sort of is better at these longer running tasks. And most of the things I was asking Cloud for are these longer running tasks. And then there's Cloud Code, of course. I use it mostly 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 Cloud as well.

19:37Jenny Wen:I've been trying to actually use Cloud Code more remotely, like through both mobile and through Slack as well. It's really fun for somebody to say like, oh, yeah, this one icon's off or something. And you just at 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 yes, that's basically my stack.

20:04Lenny Rachitsky:Are you still using Figma as a designer?

20:05Jenny Wen:I am still using Figma, yes, yes.

20:07Lenny Rachitsky:Okay, I was waiting to hear. Okay, so Figma is still part of your life. Being a former Figma, is that what you all were called? Yeah, yeah, Figma, yeah. Yeah, okay. So I know there's this big debate on Twitter, are just like, is code the future of design? Do we need a Figma anymore? Do we need a design? What's your sense? Figma is still important?

20:27Jenny Wen:I mean, as a former Figma, maybe I'm biased in that way, but 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. 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 ten 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 and and push yourself to come up with a bunch of these different directions right now coding or or right now working with some of these coding tools

21:07Lenny Rachitsky:doesn't lend itself super well to that because it's super linear you get super invest in one

21:11Jenny Wen:direction and you just iterate with a lot on them for example um so i figma has been really great at just like exploring all these different options and i think it's still going to 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 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 want to like go directly to code in.

21:51Lenny Rachitsky:It's interesting you still use an IDE because in engineering, it's clearly shifting to command lines, agents, IDs are kind of moving, moving to not be cool anymore. So it's, and it makes a lot of sense. You just want to edit some CSS things, some like color stuff. And so I could see why not just telling the agent, hey, just come on, change this one hex value. Just changing it is so much easier.

22:12Jenny 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?

22:18Lenny Rachitsky:So that's interesting. I wonder if IDUs now become the useful for designers and PMs and engineers have moved on.

22:24Jenny Wen:Yeah, maybe. Yeah.

22:25Lenny 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 direction that is cohesive and is creating products we're proud of a lot of designers i think are in this boat right now i'm 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

23:03Jenny 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 should go here.

23:19Lenny Rachitsky:It's like, no, I think we should have a button here because not everybody realizes you can prompt this.

23:24Jenny Wen: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, 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 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 want to do more.

24:03Jenny Wen: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.

24:13Lenny Rachitsky:So true.

24:14Jenny Wen:Oh, man.

24:15Lenny Rachitsky:How to keep up with all our agents, our seven agents who are constantly running. Yeah. Okay, so then as a designer, we're 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?

24:46Jenny Wen:It's not that there's no designer involved. It's more just like there's it's almost like there's too much for one designer to handle. But I think with this, I think about where the features or products are that 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 i think quad co-work 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.

25:33Jenny Wen: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 going to put it out there because we believe the benefits outweigh the cons. I think that is like OK to do, especially when there is something really valuable with the product already. And it's worth putting out there. But I think the promise you sort of have to make your users is is like, hey, hey, we're going to put it out there, but we're going to iterate. We're going to take your feedback and we're going to iterate and we're going to make it better.

26:07Jenny Wen: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 is 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 your company and I think I think that's something that we've been doing pretty well and I think if there's anything anyone's listening that can if anyone's listening can take away from it it's like yeah 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.

26:55Lenny Rachitsky:The way I've heard you describe this is building trust through speed.

26:58Jenny Wen:Yeah, for sure. 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.

27:11Lenny Rachitsky:Yeah, it's clear 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 cloud code can code very quickly uh the fixes come very fast 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?

27:51Lenny Rachitsky:So we've gone through this progression of tab completing 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 CloudCode is now helping him come up with ideas and decide what to build, which is like, okay, wow, look at that. The whole product workflows, the product development process slowly get 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, do you think AI is going to get very, very good at taste, judgment, design?

28:29Jenny Wen:I think it will get better at taste and judgment and design. Yeah, like I think we might be holding on to that a little bit too much and saying like, oh, yeah, like, you know, a designer or somebody will always know the best thing to ship or the best version of this. And I but I do think AI, like AI sense of taste will get better. I think someone has to decide like what is actually going to get built and what actually matters. and when I think about people saying like oh you know like AI is just going to 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 learning is 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 They can't necessarily solve this dispute between you and somebody else.

29:28Jenny Wen: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 whatnot. There's some sort of like it's like judgment around what to do next.

29:45Lenny 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're going. 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. Like even an example you shared, like it could give these two people trying to make a decision.

30:21Lenny Rachitsky: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. So I think we're just, yeah, to your point, I think we undervalue just how good it'll get at this stuff. 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.

30:46Jenny Wen:Yeah, yeah. I think some people still have to decide, like, oh, we want to build this kind of product.

30:51Lenny Rachitsky:Or like given what the AI is 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?

31:06Jenny Wen:Does this actually make sense in the product? So I think there's that like decision making such judgment layer, which feels like maybe one day we won't have to do that. But it's it still falls on us.

31:17Lenny Rachitsky:Yeah, it doesn't make sense. It makes me think about the radiology example where there's always the sense that AI is going to take over that field of radiology and tell you what is going on. But like the human is mostly useful for signing off on the decision because someone needs to be liable if they're wrong, which isn't the best job in the world. But but that's a different game is health versus code. Yeah. OK, 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 last. lasting, uh, user interface to AI like chatbots.

31:52Lenny Rachitsky:Okay. No, no, this is just like a temporary stop along the journey, but how it's like kind of even further than just terminals. Um, do you have thoughts on just, I don't know where, 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?

32:08Jenny Wen:There will likely be a combination of both, like both UIs and interfaces that you are interacting with clicking with and and that feel like more tactile we are already seeing this and playing with this within claude like the chat but 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 click them and they are much more efficient than you know typing something to Clyde but at the same time when we 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 so my read here is like I I don't think chat is ever going away because this opened up this like new way of like infinite ways to work with the model and to sort of like talk to the computer that we just didn't have before.

33:16Jenny Wen:But I think that it will still be most direct for very specific things to exist in this UI. And I think that 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 this space where I don't think chat and maybe even like talking to the terminal is going to go away.

33:41Lenny Rachitsky:It's interesting that like with Open Claw, Clawed, Mold Clawed, all the names the innovation one of the big innovations is like another way to chat with it through WhatsApp and Telegram and SMS just like another form of chat pod but that just like that was a big unlock oh I could just chat with it through WhatsApp.

33:55Jenny 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.

34:11Lenny Rachitsky:Yeah. So Kevin Wheel, 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 talking still works. So that's why it's been this beautiful way to deal with the growing intelligence of models and it continues to work.

34:42Jenny Wen:Yeah, that totally makes sense. Yeah.

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35:24Lenny Rachitsky:Companies like Perplexity, DBT, and BuzzFeed use Omni to ship analytics their customers can trust. That's O-M-N-I dot C-O slash Lenny. Okay, I want to come back to this whole idea of management and IC. So 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.

35:48Jenny Wen:Yeah, it 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 like an org structure that sort of needed it. And now I'm actually back to doing full-time IC work. And I joined Anthopic 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, you know, I sort of want to be close to the work. and I think this feels like a really important time to do it before I like ascend the corporate ranks you know and having these like questions and doubts about like is middle management like is that safe in the future like 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 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 and being at that level but i also just really love the 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 these coin the coin like pretty equally but i think actually what being an ico across this past year has taught me is that it actually just like gave me a lot of skills that I don't think I would have gained if I was just managing throughout this year.

37:17Jenny Wen: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 that'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 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 an interesting time to be 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.

38:05Lenny Rachitsky:And so you were previously a director of design at Figma right? How big was your team like how large was your org just to give people a reference?

38:13Jenny Wen:At the max, I probably had, I think, 12, 15 designers or so. And I had a few managers as well. So it was like an org.

38:23Lenny Rachitsky:Yeah. Okay. So you've 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?

38:34Jenny Wen:I think as long as there is a team of people it helps to have somebody who is managing a team like I think there's 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 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 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 and do you see yourself going back into management long term 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 my motto there is like whatever it takes you know if it's somebody that 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 so the advice i'm hearing for people in

39:52Lenny Rachitsky: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.

40:03Jenny Wen:I think so. And I think traditionally, 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 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 to where I think in the past design has been much more like people management oriented.

40:30Lenny Rachitsky:What did you find yourself most rusty in when you went back to IC Designer?

40:35Jenny Wen:Actually like doing crits, you know, and just getting criticized. Yeah, getting criticized. You're like, oh, yeah, like it is hard to get it is hard to get critical feedback and to hear it and to hear on such a regular basis, because that's the thing you have to do as a designer is like 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 so

41:02Lenny Rachitsky:currently you're you're leading design uh slash ic designing on co-work is that right yeah awesome so boris he was on the pod recently talked about how there's like a lot of debate about what co-work 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 co-work i have

41:26Jenny Wen:it here on my monitor by the way looking at it with co-work 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's sort of like everything all at once like we were like okay

41:47Lenny Rachitsky:we're gonna we're gonna ship it soon it was 10 days 10 days of building yeah it was it was it

41:53Jenny Wen: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 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 co-work. So things like when Claude gives you a to-do list, we tried a bunch of different form factors for that.

42:26Jenny Wen:We tried a bunch of different form factors for the way it presents you different, like 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 like landed on the best form factor ever, but essentially it was like stuff that was sort of 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.

43:02Lenny Rachitsky:And it blew up the internet when you launched it, so it worked out. Is there a feature of Co-Work today that you're either most proud of or just like can't wait to fix and and improve honestly i think we're i'm just most proud of us

43:15Jenny Wen:actually just like shipping it to be honest um and putting it out there and uh yeah i don't know if there's like one specific thing yet because 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 iterating, especially on the homepage, and to make that something where it feels more like, hey, these are like tasks you can give Claude and the tasks that Claude are working on. And so that actually should be rolling out.

43:52Jenny Wen:It might already be rolled out by the time this comes out.

43:54Lenny Rachitsky:I see like this little randomizer thing where you click it and it gives you all these different ideas.

43:58Jenny Wen: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 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 i love that you shared that

44:32Lenny Rachitsky: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, OK, now we know what we want it to be. Let's build it and ship it.

44:48Jenny Wen:Yeah, I think for some reason that became like the viral thing that got taken away from all of the sort of co-work announcements is that it only took 10 days. But I think there have just been so many different explorations and people that of worked on different pieces of co-work 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 and by the way for people that don't know much about

45:26Lenny Rachitsky:co-work is like the way i think about it's like clawed with hands where you do stuff on your computer is that is what's how would you describe it just like in a sentence or two that's a good

45:34Jenny Wen:description i actually haven't heard that but i like that i might use it more often as clod with hands i also think about it as like it's like clod but clod is really good at taking all your garbage and then turning it into something nice like i think one of my favorite and like any sort of use case that i i really like out of co-work is just like giving it a folder of my stuff and And it doesn't really matter what's in that folder, but I'm able to extract something good out of it.

46:04Lenny Rachitsky:I've done that many times. 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, what do you look for that's maybe new? 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?

46:26Jenny Wen:Well, I do think working specifically in the kind of environment that I do there, there's just like a sense of like, resilience and like roll with it kind of thing 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 in 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 that T-shaped framework where it's like they're really good at like a few core skills, like 80th percentile good.

47:23Jenny Wen: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 shape or all becoming engineering shaped. 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. It's just somebody who is really good at a bunch of things. Again, a huge ask. And then the other person that's really exciting to me is in that T-shaped framework, like a deep specialist, like someone who is T-shaped.

48:04Jenny Wen:But like 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, you know, working at some of these places, like folks like these, you can sort of afford to hire them and actually bring them on board. And then my last one is probably the one that I think we're all overlooking, which is what I call the cracked new grad. 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 i think this person is really interesting right now because i think most companies are just hiring like senior talent like folks that have done things before 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

49:21Lenny Rachitsky:just like overlooking but i'm like really excited about this is awesome uh on the deep t shape deep what's an example of someone in design that has a like what's what's a skill that they're

49:32Jenny Wen:really good at sometimes there's designers who are just like really technical in a way where they could be like 50 of soft they're they're basically a software engineer like that's really interesting especially because right now like 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 but another like deep kind of like specialist he is just you know maybe they're just really good at like visual design 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

50:10Lenny Rachitsky:awesome okay and then this block shape i had mark andre said in the podcast we kind of called it the f f shape or e shape or 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 yeah yeah

50:24Jenny Wen:Yeah. And like basically, like, I don't know, if you almost had their skill set, it would it would look like a block.

50:29Lenny Rachitsky:There's so many skills that you spread out. Yeah. OK. And the correct new grad. So this is just like someone that is eager, like open minded, gritty, very smart, I imagine is a big part of it.

50:42Jenny Wen:Yeah. Awesome. Yeah. Yeah. if someone's like a new design like a young designer trying to break in trying to be successful

50:50Lenny Rachitsky:what would your advice be to them to help them have a shot at and so joining anthropic for example

50:55Jenny Wen:i would just say there's 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 going to teach you some approaches and whatnot but like the best the best kind of like cracked new grad folks I know are just like people who just like use the technology build actual things don't feel like limited by you know how little experience they might have I think that sometimes they're actually unburdened by that because 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 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 clod robot project this was like a few years ago too where they were uh just assembling robots that were running on clod and then somebody else did something where she just wanted to put googly eyes on a bus 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.

52:40Jenny Wen: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 the stuff that will make people stand out.

52:50Lenny Rachitsky:For current designers that are in a career, Austin Lee 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

53:04Jenny Wen:better other stuff 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 designers 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 well 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.

53:42Jenny Wen: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 et cetera, et cetera.

53:53Lenny Rachitsky:How good of a designer is Claude, would you say? Or Claude Code would have everyone describe? Like, would you hire Claude as a designer or is like not there yet?

54:01Jenny Wen:I don't think Claude is there yet. I don't think a lot is there yet in terms of a designer you would hire. I think it is not yet the strong generalist or the deep specialist or the crack new grad. I think it's pretty good at a first pass and presenting a bunch of different ideas to you. But nothing there quite feels like, yeah, special and hireable yet.

54:22Lenny Rachitsky:Which is good news for designers for now. 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 can it pump out amazing, novel, unique creative experiences or is this it's just never going to be that good as a human designer?

54:38Jenny Wen:I mean, it's gotten a lot better in the last year or so even.

54:42Lenny Rachitsky:So, yeah, there's a couple of management. I don't know, rituals or takes you have that I've heard from folks that you work with that I want to 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 you

55:01Jenny Wen:talking about that 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 really prioritize your time and categorize your work and there was like this two by two of like 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 I actually think some of 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 dog food it they report 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 um it also creates this vibe where it's like oh yeah the this senior leader really cares deeply and they actually know the inside of 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 to what I've seen is like when a senior leader is able to like fix a bug now you know even like I think I've actually seen like Mike Krieger before like put it put in PRs himself um and it's it's it's really nice because it's like okay cool like we're all on this team together and nothing is like below this person um and I think similar another thing that I love that's a little bit more cultural is when somebody like goes out of the way to like make somebody's like anniversary card or something and like vibe code them super nice, something super nice or make them something a super nice card.

57:14Jenny Wen:Because I think it just shows that, yeah, it's like an EA or somebody can put together the card. But this later 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 seemingly low leverage tasks that are like worth my time.

57:32Lenny 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 like the low leverage ends up being high leverage.

57:47Jenny Wen:Yeah. And I think it's what makes like your style of leadership stand out or feel special to a certain person.

57:53Lenny Rachitsky:Amazing. Another, I don't know, ritual and kind of way of running teams that I heard about you is you encourage team members roasting each other, which on the surface doesn't sound like a wonderful environment but 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 yeah i think it's not

58:19Jenny Wen:that i'm like yo you should roast each other you know 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 always sort of willing to like push the boundaries a little bit and like roast them. Like you're roasting your friends a lot, but you actually might not be roasting your coworkers a lot because you, it's all just about like comfort 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 the people on your team kind of feel comfortable, just like kind of poking fun at each other a little bit.

58:58Jenny Wen:And I think that also can be a good sign And 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. But they and they feel like there's a sense of safety where if they say something, they're not going to get fired. So an example of this is like with my last team, I feel like they would make fun of things that I would say at crit sometimes, like certain phrases I would say. What's an example of that? I don't know. Like I would always be like, OK, 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 um and they 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 they trust me they could 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 man as a manager are you friends with your reports which is I think the thing people tell you like not to do and so the way I think about balancing this out is like this creates like 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 because it's like once you have that psychological safety you have people trusting each other and you applying the high standards actually i think becomes potentially easier because you can do it without fear i think 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 going to be there um and I'm not just going to fire them on a whim or something but at the same time they also know that I want the best for them you know and that I have high standards and that you know I'm working with them to to make the best work possible and so yeah that's the balance I think you just write because 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 will do great work with you that is awesome advice it's interesting

1:01:26Lenny Rachitsky:how often this this uh just like management style comes back or management uh good management it comes back reminds me of what was a candid radical candor just this combination of caring deeply and challenging directly yeah and that's kind of what i hear here is just make sure people know that you care deeply about them, but also be very direct and have high standards.

1:01:47Jenny Wen:Yeah, yeah. Interesting.

1:01:49Lenny Rachitsky:Okay. Maybe a final question. I'm always looking for interesting frameworks and methods and processes that people have found useful in their work. And I hear you're a big fan of something called the legibility framework. Talk about this. Talk about how you use it, why it's so valuable.

1:02:03Jenny Wen:Yeah, this framework, I think I saw it on Twitter of maybe last year or something. and it was evan tana who's 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 idea is like super legible the idea is probably not that novel and somebody's already like they're already going to implement it 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 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 this most sense to people and i think this is obviously a good way for a vc to operate because you're trying to look for the opportunities that people don't see and put them out there in the world but i also think that like part of the role of the designer at least um at least 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 put it out there um and i think there's like like when i mentioned 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 co-work uh where there was this internal prototype that we called like cloud studio that i think somebody built like partway through last year um and it essentially was this like really kind of like dense powerful interface that was built on top of some agentic harness i it might have been claude code at that point in time too and it had all these like displays were 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 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 folks in research the folks building it and and just folks internally there's 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 i think that really was an example of an illegible idea and ultimately what came from it was like the skills framework um and and uh like the sort of like markdown files that sort of that instruct clod 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 work on clod co-work and i was thinking about like oh yeah what is the form factor for those things seeing that prototype and seeing the kinds of information that people found really helpful like seeing clod's plan and to-dos um seeing clod'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 cloud code work.

1:05:37So yeah, I think about like, how can designers almost be more like

1:05:42Jenny Wen:VCs in this way internally when we're looking at prototypes?

1:05:46Lenny Rachitsky:This is super interesting. I did a research project recently where with this guy Terrence Rohan and VC, actually, we looked at what are patterns across people that have joined companies very early that ended up being massive successes like Palantir and Stripe and Linear and Notion, all these companies, 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 it's like so crazy that everyone's laughing at this this is this is impossible you're never going to do this this is the craziest thing yeah why would you even think like palette like all like open ai 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

1:06:39Jenny Wen:helps pull it together 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 it's to like dive deeper and try to understand what that is yeah yeah because i think people who often gravitate towards these early ideas they can't always articulate why and it's sort of up to you to like dive deeper and understand that

1:07:01Lenny Rachitsky:that's one of that was so there's three patterns we found one of the other ones was there's just pay attention to people getting very excited about this thing even if you don't get it and it's like sounds crazy that's so interesting okay and then what was the other one oh the founders are just like top one percent was the other piece there which everyone at anthropic already so you got that one oh man jenny what a crazy time we're living through what a world how much so much change okay before we get to our very exciting lightning round is there anything else that i should have asked you that you want to leave listeners with that you want to double

1:07:37Jenny Wen:down on 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 allowed us on social but they're doing a lot of really great work and especially through this time our jobs are changing so much the team is so resilient and they're they sort of span this whole spectrum of people who are really technical and prototypy 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 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.

1:08:18Jenny Wen:Anthropic, if it sounds more exciting than terrifying, would love to connect.

1:08:23Lenny Rachitsky:What sounds exciting is getting access to these slacks or all the features being built. Yeah, that's the core benefit. 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 if they want to apply?

1:08:38Jenny Wen:Think a little bit about the archetypes that I mentioned, especially the strong generalists and the deep specialists. those folks were really excited about. But generally folks who are...

1:08:49Lenny Rachitsky:The block in the deep tea.

1:08:50Jenny Wen:The block in the deep tea. What could we be talking about? Yeah, folks who feel like they, you know, those archetypes resonate with them, but also folks that are just really excited about the technology, have been building a lot and sort of want to be on the frontier.

1:09:10Lenny Rachitsky:Amazing. Well, with that, we've reached our very exciting lightning round. We've got five questions for you, Jenny. All right.

1:09:17Jenny Wen:I'm ready.

1:09:18Lenny Rachitsky:Here we go. What are two or three books that you find yourself recommending most to other people?

1:09:22Jenny Wen:The first one is The Power Broker by Robert Caro, which is an incredibly aggressive recommendation, given that it's like 1100 pages. But I think in this era, when our attention spans are so short, I think this is actually worth reading end to end. because I think there are very few collections or memoirs where it spans through someone's entire life and you sort of see how somebody changes throughout those decades. And it's also something who's really controversial too and 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 this like long arc thinking because we're thinking so much about right now.

1:10:08Jenny Wen:So 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. The second one that I recommend to a lot of people is a book called Insomniac City, which is written by Bill Hayes, who was the partner of the scientist Oliver Sox around the time that Oliver Sox died. And it's just this like really beautiful kind of like ethereal memoir of Oliver Sox last days and their sort of love story. 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 and just like makes you think about mortality, but also like love and life and stuff like that.

1:10:52Jenny Wen:So that's one of my favorite books.

1:10:54Lenny Rachitsky:My goal here is, you know, I'm trying to create we're trying to create Renaissance humans. All of this other stuff is excellent. Cool. Interestingly, I saw Julie Zhu, famed design leader, was reading The Power broker recently i don't know what's going on over here spreading in design land okay do you have a favorite recent movie or tv show that you really enjoyed um i watched a sentimental value recently

1:11:18Jenny Wen:i watched it on a plane which is you know how how directors want you to watch their films um but it's a it's a norwegian film by the same director who did the worst person in the world i think just the the pacing the writing the relationship between the characters is just really subtle and beautiful um it's basically about this family sort of a family drama but also about this house that they lived in their entire lives it's beautiful because like the house is sort of a character so i don't know what else to say about that but that was a really good movie um and then i would also recommend obviously the pit season two item we're on that we're on that i think everybody just likes to watch people who are really competent at their jobs do something

1:11:59Lenny Rachitsky:um so yeah imagine being an actor on that show just like how much you have to learn and memorize

1:12:04Jenny Wen:all these terms yeah yeah it just also seems really fast-paced too like they do so much stuff in like one shot and there's just so much like movement and stuff like that seems really really

1:12:14Lenny Rachitsky:hard to be an actor on and i only recently realized noah wiley was in er as like a younger person and now he's like the head of this yeah yeah oh man okay favorite product you recently

1:12:23Jenny Wen:discovered that you really love cannot be co-work not one that i actually discovered recently um But Retro, I've been using it for basically two years now since it came out. And I think I discovered new benefits of it recently. So for folks who don't know about Retro, it's sort of like this small community photo sharing app in which you can only share photos from each week, from a given week, as opposed to like all time. And it basically has like none of the social media stuff. Like you can't really see like counts. It's not there's no ads, etc. but one really nice thing is now that i've been using it for two years i can now look back at each year and see like oh yeah this week two years ago i was doing this and it's become this really special way to like live through each week of my life basically wow and uh it's also a beautifully

1:13:16Lenny Rachitsky:grafted app if you're looking for building your own taste in design designers love retro i could see i could see that okay do you have a favorite life motto that you often come back to in work

1:13:27Jenny Wen:or in life yeah um not sure if it's my favorite life motto but one thing i do catch myself saying a lot is just uh it is what it is my dad says that all the time i love it yeah yeah it sounds super defeatist but i promise it's not i think just given how much stuff is going on in the world right now and especially with the industry and whatnot uh you can't control everything and so sometimes it is what it is just like brings the levity you need to move forward i went to i did a

1:13:56Lenny Rachitsky:10 day meditation retreat a while ago and I came back from it and it's like, dad, you've been right all along. This is the whole of the answer to it all. It is what it is. You can't don't cling. Don't try to change. Just it is what it is.

1:14:08Jenny Wen:It is what it is.

1:14:10Lenny Rachitsky:There's so much depth to that. I was like, OK, smarter than I even thought. OK, final question. Coming back to co-work, is there a I don't know, mind blowing use case, something just like, wow, that's so cool that coworker can do that either something you use it for or you've heard somebody using it for

1:14:28Jenny Wen:one thing i really like is just like introspection and so uh i have this this folder basically of like local notes that i have from that i use like i a writer for and i basically just like write whatever and over the years have collected it with a bunch of different notes and they span like all different things like one-on-one notes like random thoughts like kind of like tiny memos interview notes etc and my favorite like it makes it's it's cool to me is just like using co-work to like analyze that and have insights out of it actually create things out of it um so like anything i anytime i can like learn something new about myself like i love that but i think a very practical thing i did with it the other day was like along the lines of hiring i was like oh yeah i want to sort of articulate like what it is that i look for when i look for a design craft because I think actually a lot of people struggle to articulate that.

1:15:21Jenny Wen:And I just had it read through all of my notes, both like interview notes and other things that I cared about and memos and stuff like that I've written in the past. And then it made me this rubric for evaluating that. So that kind of introspection where it's like, oh, I don't even I wouldn't have realized even these things about myself that I've been putting out there implicitly. That's been really cool for me.

1:15:42Lenny Rachitsky:That is so cool. So just to make this very clear for people, you have a folder with all these things you've written one-on-ones meetings like you could do i don't know if y 'all are allowed to use granola something like that like meeting transcripts and ask it and it's like i was gonna ask what prompt you use but it's just like read all these things i've written and help me probably just like understand how i feel about what is design craft yeah basically i think it was like

1:16:04Jenny Wen:hey i have a bunch of interview notes and a bunch of notes related to design craft in this folder read it and then help me craft a like a memo slash rubric for how I assess craft in interviews.

1:16:20Lenny Rachitsky:So cool.

1:16:21Jenny Wen:Yeah.

1:16:22Lenny Rachitsky:Jenny, this was awesome. What a what a time to be alive.

1:16:25Jenny Wen:What a time.

1:16:26Lenny Rachitsky:Two final questions. Where can folks find you online if they want to reach out and how can listeners be useful to you?

1:16:31Jenny Wen:Yeah, I'm on Twitter slash X is what we're calling it these days. It's at Jenny underscore when that's probably the best place. Not really on LinkedIn as much. So that's that's the best place. And how can folks be helpful to me? Send us your product feedback, you know, like we're working on co-work or anything cloud related, really just send us your feedback. We'd love to make it better for you.

1:16:53Lenny Rachitsky:Jenny, thank you so much for being here.

1:16:55Jenny Wen:Yeah, of course. It was great chatting, Lenny.

1:16:58Lenny Rachitsky:It was wonderful. Jenny, thank you. Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.