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

0:00 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. A big part of the design role now is helping engineers and teams execute, not just telling them here's the design. 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 percent. You're better off not blocking that, letting them cook. 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? How to keep up with all our agents. Our seven agents who are constantly running. 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. And your vision even. Now it becomes a vision that's three to six months out and isn't necessarily creating this beautiful death, sometimes just creating a prototype that points people in the right direction. Boris on the podcast recently was saying Claude Code is now helping him come up with ideas. We'll get better at taste and judgment and design. We might be holding on to that a little bit too much. human brains continue to be valuable. 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. What do you now look for when you're hiring designers? There's probably three archetypes of folks that are really interesting to me right now.

1:20 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 Fig Jam and Slides. She was also a designer at Dropbox and Square and Shopify. And what I love about this conversation.

1:37 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 No Eleven and Emily Lynn Hasham for suggesting topics and questions for this conversation.

1:56 Don't forget to check out Lenny's productpass.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.

2:20 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 make 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 Column NA members FDIC. This episode is brought to you by Orchis, the company behind Open Source Conductor, the orchestration platform powering modern enterprise applications.

3:11 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. Orca's 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, Orcas 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.

4:07 Learn more at orcus.io slash lenny. That's O R K E S dot Io slash Lenny. Jenny thank you so much for being here and welcome to the podcast. Yeah, excited to be here. I've been looking 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.

4:31 uh the role of product management, how much that role is changing. I've been 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.

4:46 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 want to talk about. I'm gonna just start with this just this broad question. How is the design process

4:57 Changing with the rise of AI. 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 the change a lot more

5:12 in the in the past little while than design actually has, but I think the result of engineering changing about 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

5:34 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.

5:50 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 clods. I think as as designers we really Have to

6:05 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 kinda feels outdated to me, which is a little embarrassing. But especially with the big shift of like Opus four six and a bunch of folks just like really discovering and using Cloud Code over the holiday break. Um, I think we're seeing

6:28 This like force to change our pro process happen even more. The the way 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

6:45 Supporting the implementation and execution. So this is the one where you know engineers are s using their seven clods 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

7:09 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

7:26 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 old. 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

7:47 No. 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

7:59 This like beautiful death 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 second seven clods, make whatever features they want in any direct in any kind of like direction or

8:18 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 But has one greater cause, it's like much more efficient to do that than Than just random things.

8:36 And 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. What you're saying here is it's not like Uh you or the design field is like we need to change. It's

8:50 Engineering and the fact that you can build Just Forces. uh the role of a designer to change. Because as you said, engineers can just ship, ship, ship, ship, ship.

9:00 And what you're finding here is like you're better off not uh blocking that, letting them Cook as they say. And uh And then there's kind of this mode of helping them along at as they ship. Bring it together, make sure it all kind of connects.

9:13 Guide them a little bit. 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.

9:29 In this next year or so as well. But 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

9:46 I'm I'm doing a lot of last mile stuff where I'm implementing all the polish and like 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 on Engineers to do that again.

10:02 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, clawed, 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 like okay, I this is not gonna happen at Salesforce. This is not gonna happen at

10:20 I don't know. Service now or ever. So I guess does do you feel like this is where all teams are heading? Is it mostly AI? bleeding edge companies. How widespread do you think the design process shift is gonna be? So the talk that I did last year. has weirdly been like

10:36 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 Clod Code and and B0 and whatnot to to start to spin up prototypes and PMs are starting to spin up prototypes and stuff like that as well.

10:57 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 Where people clearly have invested their entire careers. In learning, teaching, using this like really stable design process.

11:15 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 the 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. Yeah. Yeah. And a big part of this is like you could argue, like

11:31 The question is what leads to the best, most successful products and companies. And you could argue it's spending time doing discoveries, or research, mocks, iterating, beta testing. Or it could be Just engineer ship his stuff. That's okay. Not amazing. Good enough. We learn, iterate, build, iterate.

11:49 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. I think you sort of have to choose and use your discretion as to like when to actually ship something. But I think the

12:02 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.

12:20 You can't you just can't we 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 Yeah, for 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.

12:42 So yes. 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 a certain thing is the non deterministic piece of it. So you can create these amazing mock of what it might be and then people use it in a completely different way. Which is where Cower came from and probably even Claude Code at the beginning.

13:01 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 the at the center of the storm. A good amount of time. Ananthropic is

13:15 Actually just like catch 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 uh 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.

13:32 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

13:45 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 try 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

14:07 We have a bunch of prototypes and products internally that we can use and I I'm 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

14:21 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 I feel like I just wanna keep up with these things, whereas I think in a normal company I'm like It'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 that'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, but that's not a huge part of my job, but I do think it's a really interesting part of it. Well, it connects to the point you made earlier, or a big part of the design role now is

14:57 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. Yeah. Yeah. Yeah. And I think part of it is just curiosity. You know, like it it feels like I have this front row seat to so much of happening in the industry. And so A lot of it is like, yeah, our slack is a gold mine. You know, like I'm just excited to r to read through the things that people are working on and they're saying. I never thought about how like

15:24 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 Yeah, yeah. It's like I don't I I think that is the the best AI news is probably internally if you're ever at one of these companies in the Slock. Damn. Yeah. Yes. Just the problem keeps getting harder. I'm just keeping keeping track of what's going on. Okay, so okay, so that's part of the job.

15:48 Well. 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 wanna set aside some time to think about hey, what are the next like Three months looks like and and where does that actu where could that actually go given where The market's at, where the models are at.

16:15 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. 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.

16:38 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

16:48 We're 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.

16:59 Are you still doing elements of the traditional design process? Prototyping, use it research, uh panels, I don't know, just like going out and in, you know, like the whole the whole thing you described. 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

17:17 uh both like traditional studies as well as surveys and the whole team is reading that that the f 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

17:33 I have a wider set of tools now and I think the proportion of time I spend doing each thing just has changed. 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

17:49 traditional Thinking, planning, prototyping, mocking. research and then just like feedback and execution and now today. Yeah, I think as a designer a few years ago I would say like maybe

18:04 Sixty to seventy percent. Of it was like mocking and prototyping stuff up. And then spending You know, the last

18:13 twenty or s some of the last twenty or so. Like doing the sort of like jamming with engineers, consulting with them. And then last like ten percent maybe doing you know, coordination meetings, et cetera. Uh, but now I feel like the the mocking up part of it is like thirty to forty percent.

18:29 And then There's that other thirty to forty percent 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 like there's a slice of it that is now like Implementation as well.

18:43 Mm. Yeah. Like actually building and shipping. Yeah. Amazing. So kinda 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 are I see also.

18:55 What's in your AI stack? What tools are you using in your role? Well, we we're phantropic, so it's we're going deep on the Claude Stack. Yeah. Um I am I'm using obviously like chats. Uh quad chat and the but uh increasingly more and more quad co work. I I've basically shifted all of my tat use cases over to Cowork, um'cause I've been finding that

19:17 Yeah, well 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 Clog code, of course. I use it mostly in the with with B S 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.

19:37 I've been trying to actually use Claude Code more Uh remotely, like through m both mobile and through Slock 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 at mention Claude and Claude does it and then you pick up the PR and it's done.

19:54 That's been really, really fun too. And Yeah, I think that's like I think we're all fully clawed house here. So yeah, so that's basically my stock. Are you still using Figma? I am still using Figma. Yes, yes. Okay. I was waiting to hear.

20:09 Okay. So Sigma's still part of the your your life. Uh being uh former f figmate, is that is that we all we're called. Yeah, yeah, fig mates, yeah. Yeah. Okay. So I know there's this big debate on Twitter just like Is code the future of design that we needed. Like many more do we need to design? What's your

20:25 What's your sense? Figma's still important. I mean as a f as a former fig mate. I'm I'm maybe biased in that way, but I I th 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

20:48 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 and push yourself to to come up with a bunch of these different directions.

21:02 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 had super invest in one direction and you just iterate with Claud. on them, for example. Um so I

21:16 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

21:38 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. It's interesting you still use an IDE because in engineering it's

21:54 Clearly shifting to Uh Command lines, agents, IDs are kind of moving moving uh to not be cool anymore. So it's and it makes a lot of sense. You just want to add it some CSS to 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.

22:12 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. So that's interesting. I wonder if I D U's now become the Useful for designers and PMs and engineers have moved on. Yeah, maybe. Yeah. Okay. So

22:27 A lot of your time you spend working with engineers, giving 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

22:41 Move in a s direction that is cohesive and is Creating products for product. A lot of designers I think are in this boat right now just like Oh my God, I can't keep up with all these engineer shipping stuff all day. What's something you learned about just either how to help your engineers Get better at design so that

22:58 Mm it just ends up being better. Or just kinda keeping on top of this and not going crazy. 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.

23:16 As opposed to me just being like, No, I don't think this 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 out. engineers to our design system and stuff like that and 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.

23:43 In the future without me? Uh 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 want to do more.

24:02 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. So true. Oh man. How to keep up with all our agents. Our seven agents we're constantly running. Yeah. Okay, so then As a designer. Where in this profession craft and

24:23 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.

24:35 How do you just think about Maintaining. Craft quality. Trust. As your product or just shipping a thousand times a day.

24:43 And you're not able to stay on top of them and there's no designer involved. 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.

25:01 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. I think Quad cowork is actually a good example of this, where we labeled it a research preview. And we put it out there knowing that

25:26 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 s some people will benefit from. It might not yet be the easiest

25:40 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.

25:52 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.

26:10 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 uh something out early, like It's it's possible to do that and like maintain

26:31 the brand of 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 the uh can if anyone's listening can take away from it is like, yeah, well we're continuing to do that. And and I think that 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. The way I've heard you describe this is building trust through speed.

26:58 Yeah, for sure. It's yeah, it's building trust to 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. Yeah, it's clear when when the labs launch stuff and y'all are very good at this.

27:17 Everyone on the team is tweeting and just like responding to tweets and comments and And then shipping, hey, we fixed this yesterday, this is happening. So there's a clear sense of this is just today and we know this is broke and we will fix it and And then because

27:31 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

27:43 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 El segments of code. to a hundred percent of code is written by AI now. Like it's crazy.

28:01 to now AI is reviewing its own code. Boris on the podcast recently was saying Cloud 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 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.

28:23 Do you think like A Do you think AI is gonna get Very, very good at Taste judgment design. I think it will get better at taste and judgment and design. Yeah. Like I I think we We might be

28:38 holding on to that a little bit too much and saying like Oh yeah like You know, a d 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's 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.

28:59 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 actually like not building it, you know? If you think about the hardest times that you've had at work letting it's probably things like Oh, you and some other person like disagreeing.

29:16 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

29:32 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. Just watching how quickly

29:47 Yeah, I 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

29:57 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.

30:13 and deciding what to build. But I'm just like starting to think. I think it will get there. Like even in the 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. So I think we're just yeah, to your point, I think

30:33 We undervalue just how good it'll get at the stuff. Okay. It'll get better. But your senses will still need awesome designers. to be involved.

30:44 To help make these decisions engineers, of course. Yeah. Yeah. I think some of them will still have to decide, like, oh, we wanna build this kind of product. Or like given what the air 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 engine who's accountable for like does that.

31:05 code actually work. Does this actually make sense in the product? So I think there's that like decision making slash judgment air layer, which feels like Maybe one day we won't have to do that, but it's uh it still falls on us. Yeah.

31:20 example where there's always the sense that AI is gonna take over the field of radiology and tell you what is going on. But like the human is mostly useful for signing off on the decision. Guess someone needs to be liable if they're wrong. Um Which isn't the best job in the world.

31:35 But uh but that's a different game as health versus code. Yeah. Okay. Another ongoing question in AI and design is just like it feels like chat bots 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.

31:56 But now it's like gone even further and just terminals. Yeah. Um Your thoughts on just I don't know where it 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? There will likely be a combination of

32:10 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 chat.

32:25 But um so we recently r 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 they'll save that really good reception because Mm. People still like to see UIs and touch them and and click them and they are much more efficient than, you know

32:48 Typing something to to Clyde. But at the same time when we le really lean to this like chat bot. 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 Tata's ever going away because this opened up this like

33:07 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 will probably happen here is that A lot of those UIs will be

33:26 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

33:37 And and and and maybe even like talking to the terminal is is gonna go away. It's interesting that like with OpenClaw, Claude, Moglot, all the names. The innovation one of the big innovations is like another way to chat with it through WhatsApp and Telegram and SOS. Just like another form of chatbot, but that was just like that was a b unlock. Oh, I could just chat with it through WhatsApp. Yeah. And it's like you like chatting and talking to someone is still Like you know, we as humans are doing it. It's a 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. Yeah, um so Kevin Wheel uh

34:13 who works at another AI lab, I won't to mention He had this great point. On the podcast that Talking is such a beautiful Way to handle

34:24 Every level of intelligence We can talk to people that are very, very smart and not so smart and it's talking. And the scale so well across the spectrum. We can talk to people at two hundred IQ three hundred, like it's talking still works. So that's why it's been this beautiful way to deal with the growing intelligence of models as it continues to work.

34:42 Yeah, that totally makes sense. Yeah. This episode is brought to you by Omni. Many product teams today are in the process of debating how to ship AI analytics. The hard part is obvious. Having an LLM guess at SQL in production is a huge mess and just a bad idea. Omni takes a different approach. They have a semantic layer built in, so that when you embed their analytics, the AI actually knows your business definitions, not just your raw tables. You can test queries, validate the reasoning, and lock down permissions before anything hits production.

35:15 If you want AI analytics in your product, without building the whole stack from scratch, check out omni.co slash Lenny for a free three-week trial. Companies like Perplexity, DBT, and BuzzFeed use Omni to ships their customers can trust. That's O M N I. dot co slash letting Okay. I'm gonna come back to this whole idea of management and I C.

35:38 So So you've spent you've kind of Put yourself back into the I C 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. Mm. Yeah, I have takes on this. Um yeah, so this past year at Anthropic, I joined

35:54 As an IC at first, um, and then I managed a team for A few months in in like an orchestructure that sort of needed it. And now I'm actually back to doing full time I C work. And I joined on topic. As an IC,'cause I was just really excited about

36:11 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 want to 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, and and and having these like questions and doubts about like

36:30 Is is middle management like Is that safe 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.

36:47 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 and being at that level. But I also just really loved I C 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 it would Being I see 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 ha 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.

37:29 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

37:43 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 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.

38:05 And so you were previously a director of design, I think, right? How big was your team? Like how large was your Org just to give people a reference. At the max I probably had I think twelve, fifteen designers or so, and and I had a few managers as well.

38:21 So, I think that's a good thing Yeah. Okay. So you've had the sense that middle management might not last. W 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? I think as long as there is a team of people, it it helps to have somebody who is managing a tea. Like I think there is I there's real value in managers.

38:43 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

38:56 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 I think that That is kind of Not a thing as much anymore. But I think somebody who can really function as like

39:09 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.

39:36 And my f my motto there is like whatever it takes, you know, if it's somebody that's if you 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 design that are especially managers is You almost need to move back into I see.

39:57 in order to truly understand what is happening and how much it's changing. So that you can be a better manager. 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.

40:18 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. What did you find yourself most rusty in when you went back to I C designer? Actually like doing crits, you know?

40:37 Um and just getting criticized. Yeah, 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 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 and and take that all the time. Mm.

41:01 Yeah. So currently you're you're leading design uh slash I C 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 cowork should be and there's all these big ideas. And he's like, in the end, let's just make it like a

41:17 uh 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 it here on my monitor, by the way, looking at it. I with co work specifically, we have had a bunch of different prototypes internally of what that could look like. Awesome. And it's one of those things where

41:40 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, we're gonna we're gonna ship it soon. It was like it was ten days. Ten days of building. Yeah, it was uh it was definitely longer than that, like overall. It was like ten 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

42:15 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 tried a bunch of different

42:34 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

42:52 I think Forcing ourselves to release it within that ten 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. And it blew up the internet when you launched it, so it worked out. Yeah. Yeah.

43:06 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 I'm just most proud of us actually just like shipping it, to be honest. Um, and putting it out there and

43:20 Uh Yeah, I I don't know if there's like one specific thing yet. Cause like I 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, but 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 home page.

43:41 And to make that something where It feels more like Hey, th these are like tasks you can give Claude and and the 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 I see like this little randomizer thing where you click it and give you all these different ideas. 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 l working on.

44:07 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?

44:31 I love that you shared that it wasn't just ten days to do this thing. There's like these numbers that people throw out there, we build it in ten 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 where We want it to be let's build it and ship it. 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 ten days, but I think they're

44:57 There have just been so many different explorations. Um, and people that have worked on different pieces of co work. That's Yeah, it was it was not just ten 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

45:12 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 cowork is like the way I think about it, it's like clawed with hands.

45:29 Or you can do stuff on your computer. Is that is what's well, how would you describe it just like in a sentence or two? That's a good description. I actually haven't heard that, but I like that. I might use it more often as clawed with hands. I also think about it as like It's like Claude, but Claude is really good at Taking all your garbage and then turning it into something nice. Like I think one of my favorite

45:51 A like any sort of use case that I I really like out of cowork is just like Giving it a folder of my stuff and it doesn't really matter what's in that folder. But I'm able to extract something good out of it. Mm.

46:04 Mm-hmm. Okay. Coming back to managing and being a manager and the role of a designer, I'm gonna talk about a hiring for a little bit. So seeing How much does change it in the role of a designer?

46:17 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. Uh well I do think Working specifically in the environment the kind of environment that I do there

46:31 There's 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.

46:46 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 these folks were already interesting to me before, but I feel like is In this era feels Especially important.

47:05 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

47:19 They're really good at like a few core skills, like eightieth 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

47:33 It's stretching and spanning, right? Like we're all becoming more PM shaped, we're be 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

47:52 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 shape framework, like a a deep specialist, like someone who's

48:03 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 ten percent in the industry and whatnot. Again, super hard to find.

48:16 And I feel very lucky that like Yeah, working at a at some of these places like Folks like to use. you you could sort of afford to hire them and and and actually bring them up on board. Um and then my last one is probably

48:29 The one that I think we're all overlooking, which is What I called a craft new grad. Um it's just somebody who is like early career and Uh feels Kind of like

48:42 Wise an experience, but it's also just like very humble And and I'm very eager to learn. I think this person is really interesting right now because Mm.

48:53 Uh 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

49:14 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 This is awesome.

49:25 Ah, 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? Sometimes there's designers who are just like really technical in a way where they could be like fifty percent of soft they're they're basically software engineer, like That's really interesting, especially'cause right now, like

49:42 a a lot of it is well at least for us, it's like w 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 he 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.

50:00 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. Awesome. Okay. And then this block shape

50:13 I had Mark Andrew on the podcast. We kind of called it the F F shape or E shape where there's like multiple T Thing, 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. And like basically like I don't know, if you almost had their skill set, it would it would look like a block. There's so many skills that like the tea is spread out. Yeah. Okay, in the correct new grad. So this is just like someone that is

50:36 uh eager and like uh open minded Gritty. Very smart, I imagine, is a big part of it. Yeah. Awesome. Yeah. Yeah.

50:45 If someone's like a new design like a young designer. Trying break in, trying to be successful, what would your advice be to them to help them Have a shot at That ends up joining Anthropic, for example.

50:56 I was supposed to like build a bunch of stuff. Like try a bunch of stuff, I'll 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

51:11 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 bus

51:21 kind of like crack new grad folks I know or just like people who just like use the technology. Build actual things. A don't feel like limited by ha you know, how little experience they might have I think that 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

51:41 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 ab a few years after after a while after I graduated. And basically their whole thing is like

52:03 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 Build this like Claude Robot Project. This was like a few years ago too, where they were uh just assembling robots.

52:23 That we're running on Claude. 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. So

52:40 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. For

52:52 current designers that are in a 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? I think it definitely helps. To

53:08 Maybe I'll 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

53:21 You know, the the models both the models and the products get better. If like Will 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 eight single line of code will work. But I think what I would say is like

53:37 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 a react or or et cetera, et cetera.

53:53 How good of a designer is is Claude, would you say, or Claude Code, would have everyone discussed. Like would you hire Claude as a designer or is like not there yet? I don't think Lotta's there yet. I don't think Lada's 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, yes. Which is good news for designers for now. It sucks at this for now.

54:26 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 there It's just never gonna be that good as a as a human designer. I mean it's gotten a lot better in the last year or so. Even so.

54:42 Yeah. There's a couple of management uh 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 It's just not a thing that there's

54:57 A lot of benefit you can get out of things that people consider low leverage. You talk 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

55:16 uh like to really prioritize your time and categorize your work and there's 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 the 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

55:45 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

56:04 Test the shit out of the product. And they're just like so in tune with it. Um, and they dog foot it, they repro the bugs. I 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 Uh

56:24 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 I think similarly to what I've seen is like when a senior liter is able to like

56:46 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'cause it's like, okay, cool, like we're all in this team together and nothing is like below this person. Um and I think similar 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 nice 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

57:19 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 as like Choosing the like The l the seemingly low leverage tasks. That are like worth my time.

57:32 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.

57:47 Yeah, and I think it's what makes like your style of leadership stand out or feel special to a certain person. Amazing. Another uh I don't know, ritual and kind of way of running teams that I heard about you. Is uh you encourage uh team members roasting each other. Mm.

58:02 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 Or just the happiest, the highest performing teams. Talk about

58:14 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 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 psychology 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

58:36 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 co workers a lot because You it's it's all just about like comfort and s 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

58:55 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 is Just an element.

59:07 of like they don't they don't fear you as much, but they and they feel like there's a s 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 crits sometimes, like s certain phrases I would say. What's an example of that?

59:25 I don't know, 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? 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

59:40 not necessarily afraid of me. They know that they trust me they could they could trust me. Um and It's it's and then I sort of like know enough about each other and me but personally in our personal lives to be able to like know sort of where those boundaries are.

59:56 Um but at the same time I think the The the thing that you sort of air into in that territory is like are you As your man 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 You have to create this sort of like

1:00:15 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

1:00:35 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

1:00:50 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.

1:01:00 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 the balance I think you just write is like, can you create this environment? Of

1:01:15 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. 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

1:01:34 What is it? Candid radical candor. Just this combination of caring deeply and challenging directly. Yeah. And that that's kinda 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. Yeah. Yeah. Interesting. Okay.

1:01:49 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. Mm-hmm. Talk about this, talk about how you use it, why it's so valuable. Yeah, this framework, I think.

1:02:06 I saw it on Twitter of maybe last year or something. And it was Evan Tana, who is a partner at SPC. Uh he's a B C. 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, it he basically has like founders, like

1:02:27 Founders can be. Either illegible or legible. And then ideas can either be Elegible or legible. Um, and basically he was saying that like

1:02:36 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 often 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.

1:02:58 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 s most sense to people. And I think this is obviously a good way for a V C to operate because you're tr try 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 at a at a frontier lab at anthropic is

1:03:22 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

1:03:39 I think there's like when I mention, you know, going through Slock 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.

1:03:57 There's there's one good example actually that like ties to co work uh where there was this internal prototype that we've called like Cloud Studio that I think somebody built like part way through last year. Um, and it essentially was this this like really

1:04:14 kind of like dense powerful interface that was built on top of Some agent harness. I I I it might have been Claude Code at that point in time, too. And it had all these like just displays where 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.

1:04:37 Um but then I sort of saw the 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 ill and it Illegible idea.

1:04:56 And ultimately what came from it was like the skills Framework um and and and 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 work on Claude Co work and I was thinking about like

1:05:19 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 Claude's um plan and to dos, um seeing Claude's like contacts 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 cowork. So yeah, I I think about like How can designers almost be more like VCs in this way internally when we're looking at prototypes? This is super interesting.

1:05:48 I did a research project recently where uh with this guy Terrence Rohan and V C 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

1:06:05 People that have joined many of these companies early, what were they looking for? And one of the factors was The idea's so is like so crazy that everyone's laughing at this. This isn't This is impossible. You're never gonna do this. This is the craest thing. Why would you even think like that? Like all the like Open AI actually was one of them, just like some research lab doing some stuff.

1:06:24 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. We'll 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

1:06:38 You can be the person that 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 so like Dive deeper and try to understand what that is. Yeah. Yeah. Cause I think people who often gravitate towards these early ideas. They can't

1:06:57 Always articulate why. And it's sort of up to you to like dive deeper and understand that. That's one of that was the 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. Mm-hmm. And it's like sounds crazy. That's so interesting. Okay. And then what was the other one?

1:07:15 Oh the founders Or just like top one percent was the other Peace there. Which everyone had anthropic irides. So you got that one. Oh man, Jenny, what a crazy time we're living through. What a world. So much change.

1:07:28 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. Um, I think I just want to call out uh the Anthropic Design Team

1:07:42 um and shout them out. Uh just because it's a team of folks that are just really humble and they're not always a lot of us on social, but they're doing a lot of really great work. And especially through this time our jobs are changing so much. Uh, the team is so resilient. And They're they sort of span this whole spectrum of

1:08:02 people who are really technical and prototypey 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 in Turnanthropic, if that sounds more exciting than terrifying. Um would love to connect. What sounds exciting is getting access to these Slack or all the features being a core benefit. 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 want to play.

1:08:38 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 folks who are the block in the deep tea. The block of the vlog of the deep tea. What could we be talking about?

1:08:56 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 want to be on the frontier. Amazing. Well, with that we've reached our very exciting lightning round. I've got five questions for you, Jenny on I'm ready. Here we go. What are two or three books that you find yourself recommending most to other people?

1:09:23 The first one. is The Power Broker by Robert Carrow, which is an e which is an incredibly aggressive recommendation. Given that it's a hot oh it's like eleven hundred pages. Uh But I think In this era when our

1:09:37 are 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 thro someone's entire life. And you sort of see how somebody changes throughout those decades. Um, and it's also something who's really controversial too. And it's it's nice to sort of like read a really nuanced view of somebody

1:10:00 Robert Moses. And I think we just lose out on some of those this like long arc thinking'cause we're so much we're thinking so much about right now. So Uh 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

1:10:22 A book called Insomniac City, which is written by Bill Hayes. who is was the partner of the scientist All of our socks. Around the time that Oliver Socks died. And it's just this like really beautiful

1:10:35 kind of like Ethereal Memoir of all of our Socks Boss 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 This is 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

1:10:53 That's one of my favorite books. My goal here isn't, you know, I'm trying to create we're trying to create renaissance humans. So all of this other stuff is uh excellent. Cool. Interestingly, I thought Julie Zoo Uh a famed design leader was reading the power broker recently.

1:11:07 I don't know, what's going on over here? Yeah. Spreading in Design Land. Okay. Do you have a favorite recent movie or TV show that you really enjoyed?

1:11:16 Um I watched a Sentimental Value recently. I watch 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 the entire their entire lives. It's beautiful'cause like the house is sort of a character, so

1:11:46 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. I know. 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. Um so Yeah. Mention being an actor on that show, just like how much you have to learn and memorize 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

1:12:11 so much like movement and stuff like that seems really, really hard to be an actor on. And I only recently realized Noah Wiley was in ER as like a younger person and then now he's like the head of the Yeah, yeah. No man. Okay. Favorite product you recently discovered that you really love cannot be co work. Not one that I've actually discovered recently, um

1:12:29 But I retro I've been using it for Basically two years now since it came out. Um and I think I think I discovered new benefits of it recently. So Uh, 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.

1:12:46 Um photos from each week. From a given week as opposed to like all time. Um, and it basically has like none of the social media stuff, like You can't really see co light counts, it's not there's no ads, et cetera. Um, but one really nice thing is now that I've been using it for two years.

1:13:03 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 uh it's also a beautifully crafted app if you're looking for it. Building your own taste.

1:13:19 In the 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 or in life?

1:13:28 Yeah. Um Not sure if my 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

1:13:43 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 ten day meditation retreat a while ago and

1:13:58 I came back from it and it's like Dad, you've been right all along. This is the whole 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. It is what it is. There's so much depth to that. I was like okay, smarter than I even thought. Okay, final question, coming back to co work.

1:14:18 Is there Uh I don't know, mind blowing use case, something just like, wow, that's so cool that Cowork can do that. Either something you use it for, or you've heard somebody using it for. One thing I really like is just like introspection. And so uh I have this

1:14:33 this folder basically of like local notes that I have from That I use like IA writer for and I basically just like write whatever And and 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

1:14:49 kind of like tiny memos, interview notes, et cetera. And my favorite Like it makes it it's it's cool to me. It's just like using cowork to like analyze that and f have insights out of it and actually create things out of it. Um, so like anything I any time I can like learn something new about myself, like I love that. But

1:15:08 I think a very practical thing I did with it the other day was like Al along the lines of hiring I was like, Oh yeah, I wanna sort of articulate like what it is that I look for when I look for in design craft. Cause I think actually a lot of people struggle to articulate that. 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 in the past. And then it made me this rubric. Uh for for evaluating that. So Um, that kind of introspection where it's like, Oh, I don't even

1:15:36 I wouldn't have realized even these things about myself that I'd been putting out there implicitly. That's been really cool for me. 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 or something like that, like Meeting transcript.

1:15:53 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 designcraft. Yeah, basically I think it was like Hey, I have a a bunch of interview notes and a bunch of Notes related to designcraft in this folder.

1:16:10 Um Read it and then help me craft a uh like a a a memo thought rubric for how I assess craft in interviews. So cool. Yeah.

1:16:22 Jenny, this was awesome. What a what a time to be alive. What a time. Two final questions. Where can folks find you online if they want to reach out? And how can listeners be useful to you? Yeah, um I'm on Twitter slash X is what we're calling it these days. Um it's at Jenny underscore one. That's probably the best place. Not really on LinkedIn as much, so that's that's the best place. Um and how can folks be helpful to me? Send us your product feedback, you know, like we're working on co work, uh Or anything cloud related really, just send us our your feedback. We'd love to make it better for you.

1:16:53 Jenny, thank you so much for being here. Yeah, of course. It was great chatting, Lenny. 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.

1:17:10 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 Lenny's podcast dot com. See you in the next episode.

What you see above is a preview of the first minutes. One unlock costs 10 credits and covers this episode forever: full segment and word-level timestamps on this page, plus .txt, .srt, .vtt and word-level JSON downloads, as many times as you like.