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

[00:00] 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 percent 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. [00:30] I think even engineers are like, how do we keep up with ourselves? How to keep up with all our agents. There are 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, ten-year vision even. Now it becomes a vision that's three to six months out and isn't necessarily creating this beautiful depth. It's sometimes just creating a prototype that points people in the right direction. Boris on the podcast recently was saying Cloud Code is now helping him come up with ideas. We'll get better at taste and judgment and design. [01:00] a little bit too much. - Where will 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. [01:18] Thank you. [01:19] Today's guest is Jenny Wen. Jenny was head of design for Claude, is now leading design for Claude Cowork, [01:26] Prior to that she was director of design at Figma, where she led the design teams behind FigJam and Slides. She was also a designer at Dropbox and Square and Shopify. And what I love about this conversation is that Jenny is living in the future of where design as a profession is heading. And she is here to give us a glimpse into what that looks like and how much things are going to be changing for designers.

[01:48] It is pretty wild and extremely interesting. [01:51] A huge thank you to Know11 and Emily Lin Hasham for suggesting topics and questions for this conversation. [01:56] Don't forget to check out Lenny's Product Pass.com for an incredible set of deals available exclusively to Lenny's newsletter subscribers. [02:03] Let's get into it after a short word from our wonderful sponsors. [02:07] This episode is brought to you by Mercury, radically different banking loved by over 300,000 entrepreneurs, including me. I switched to Mercury from Chase over a year ago, and it is such a profoundly better experience. It's like an actual product person built a bank versus a banking person building a product. It is fast, it's elegant, it is super easy to set wires, to track my spending, to set up triggers, to move money around when accounts get low. [02:37] anything else we've tried. It's also really easy to grant people on your team just the right amount of access to help take work off your plate. It's free to get started. No in-person visits, no minimum balances. The product also flexes to all sizes of company, from startups to large enterprises. Just visit mercury.com to learn more and apply online in minutes. Mercury is a fintech company, not an FDIC-insured bank. Banking services provided through Choice Financial Group and Column NA members FDIC. [03:03] This episode is brought to you by Orcus, the company behind Open Source Conductor, the orchestration platform powering modern enterprise applications. Modern systems are built on microservices, APIs, and event-driven architectures, but legacy automation tools can't keep up. Siloed, low-code platforms, outdated process management, and disconnected API tooling break down under real-world scale and constant change.

[03:33] APIs, data pipelines, human tasks, and agentic workflows with deterministic control flow, retries, observability, and governance. Built for enterprise scale, Orkiz 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 [04:03] systems, agents, and humans together to deliver smarter outcomes faster. Learn more at orkis.io slash Lenny. That's O-R-K-E-S dot I-O slash Lenny. [04:17] - 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, the role of product management, how much that role is changing. [04:35] I haven't spent a lot of time on how design is changing. [04:38] Clearly, it is also changing in a really big way. [04:42] And [04:43] You have such a front row seat to where things are heading. [04:46] I also know you have a lot of very strong opinions about where things are heading. So there's a lot of stuff I want to talk about. I want to just start with this just this broad question. [04:54] How is the design process changing with the rise of AI? It's changing a lot. [05:02] I think it's still also got a lot

[05:04] a long way to go in terms of the way it's changing. Like, I think we've actually seen... [05:09] engineering changed a lot more in the past little while than design actually has. But I think the result of engineering changing a bunch is that [05:18] design is forced to change. I think some context around this is, I did a talk at a conference in Berlin a few months ago in September, and I called it "Don't trust the design process, [05:30] where I basically just said like, Hey, you know, this design process that [05:34] 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 tried so hard to preserve and we were like, trust the process. [05:50] that is that's basically dead. I think it was sort of dying before the age of AI. But given now that [05:57] you know, engineers can go off and spin off their like seven clods. I think as designers, we really [06:04] have to [06:05] let go of that process. I think that's the big thing that's changing. [06:08] But I think even in the past three to four months since I did that talk, that talk actually starts to feel [06:14] pretty it kind of feels outdated to me which is a little embarrassing [06:17] But especially with the big shift of like Opus 4-6 and a bunch of folks just like really discovering and using cloud code over the holiday break... [06:26] I think we're seeing... [06:28] this like force to change our process happen even more. The way I sort of see it now is like,

[06:34] there are basically two types of design work and design work is kind of like becoming really stratified in this new work in this new world um so there's like the first one which is really just like [06:45] supporting the implementation and execution, [06:48] So this is the one where, you know, engineers are using their seven clods 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 [07:09] do not have the time to make these beautiful mocks anymore or to like kind of lead in this way. [07:16] And then I think there's the second kind of work that feels [07:19] also really important, which is like creating the sort of vision or direction for things. This one feels like the hardest to [07:26] 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 because i think we used to go off and say you know we're going to do this design vision we're going to go off and make this like [07:37] two year, five year, whatever, ten year vision even, and we're going to like point us towards something. [07:43] But the way that the technology is changing now, like we actually don't [07:47] no, we don't know what's going to happen in two years. There's too much changing. And it usually becomes [07:53] a vision that's like three to six months out. [07:55] And isn't necessarily something that is like, [07:58] creating this like beautiful deck that's like beautifully story told it's sometimes just like [08:03] creating a prototype that points people in the right direction

[08:06] 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 seven clods, make whatever features they want in any direct at any. [08:15] kind of like direction or... [08:17] 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 [08:26] done in a way where it's like efficient, right? Like if we're all working towards something [08:30] but has one greater cause, it's like much more efficient to do that than than just random things. 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. So what you're saying here is it's not like. [08:46] you or the design field is like, we need to change. It's engineering and the fact that you can build [08:52] so quickly just forces the role of a designer to change because, as you said, engineers can just ship, ship, ship, ship, ship. And what you're finding here is like you're better off not blocking that, letting them [09:05] cook, as they say. And then there's kind of this mode of helping them along as they ship [09:11] bring it together, make sure it all kind of connects, guide them a little bit. [09:15] Yeah, I think so. Yeah, I don't think there is like one unifying voice that's like, [09:19] designers we need to change right now but [09:21] there is sort of like the follow on effects of [09:25] engineering tooling really changing. I think we'll probably see design tooling change 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, I'm doing a lot of last mile stuff where I'm implementing all the polish and like, and sort of like working with engineers really closely to

[09:54] get the feature across the line and also prototype stuff in actual code as opposed to relying on engineers to do that again. [10:02] How true do you think this is at all companies at all? [10:06] say AI companies, non-AI companies, someone may be hearing this, okay, Anthropa, Claude, 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, this is not going to happen at Salesforce. This is not going to happen at [10:20] I don't know, ServiceNow or whatever. So I guess, do you feel like this is where all teams are heading? Is it mostly AI? [10:27] bleeding edge companies how widespread do you think the design process shift is going to be [10:32] So the talk that I did last year... [10:35] has really been like the most resonant talk that I've done. And [10:40] 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 Cloud Code and B0 and whatnot to start to spin up prototypes and PMs are trying to spin up prototypes and stuff like that as well. So I think there's something there emerging. [10:59] But the other interesting observation with that talk, too, was there was actually also... [11:03] a decent amount of like backlash like people were people clearly have invested their entire careers [11:10] in learning, teaching, using this like really stable design process. And they were I think there was a lot of like discrediting like, oh, yeah, like we can't do without discovery, we can't do without these pieces of process. So I think there is still a piece of the industry that is not quite there yet.

[11:26] 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, the question is what leads to the best, most successful products and companies? And you could argue it's spending time doing discovery, user research, mocks, iterating, beta testing, [11:41] Or it could be [11:42] Just engineer ship stuff. That's okay. Not amazing. [11:46] Good enough. We learn, iterate, build, iterate, [11:49] Is your sense that that [11:50] Second path is not only is that just like what everyone's doing, but that actually leads to the better product at this point. [11:56] I think you sort of have to choose and use your discretion as to like when to actually ship something. [12:00] But I think the the ability to [12:03] execute, try something out and try it with real data and a real user's [12:11] kind of mindset in the product. I think that does lead to a better product, especially as we're all working with these like [12:16] new developing AI models that are non deterministic, 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 like a clickable prototype with it, you sort of have to use the actual models underneath and you have to sort of see people tried out with their use cases because [12:35] with these models, like you discover you can design them for [12:38] different use cases, but you have to discover use cases as you see people using them. 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 at certain things, the non-deterministic piece of it. So you can create these amazing mocks of what it might be, and then people use it in a completely different way.

[12:57] which is where Cowork came from and probably even Cloud Code at the beginning. And so [13:02] So what's it just like to be a designer at Anthropic? Just like give us a day in the life of working at Anthropic at the center of the storm. [13:10] a good amount of time [13:13] at Anthropic is [13:15] actually just like catching up on what people what's happening at the company. I think this is the company where [13:22] I've worked at a few other companies around this size where I think there's just a lot of 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. [13:44] code names and stuff like that. And a lot of time I'm just like trying to navigate and figure out what those projects are. Because I think I'm just trying to spot and see like, hey, what's coming up ahead for me? Because there's stuff from both the research team, but also some of our like labs teams that are closer to research and trying out and prototyping stuff. [14:03] 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 [14:11] I am just curious and I want to try those things out. And then I think there's also a lot of folks who internally have a lot of insights and opinions on where the industry is going. And some of those are just like really interesting to read, because a lot of these are like philosophical debates or directions of the company and stuff like that. And yeah, I feel like I just want to keep up with these things. Whereas I think at a normal company, I'm like,

[14:36] It's fine. This is stuff that's happening outside of my reach. I don't really care as much. Where here I think it's both the volume and the kinds of things that are happening that I'm really interested in keeping up with. And then aside from that sort of keep up, 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. A big part of the design role now is helping engineers and teams execute, not just telling them, here's the mock, here's the design. [15:06] experience as it's happening. [15:07] So that makes sense. Yeah. Yeah. Yeah. And I think part of it is just curiosity. You know, like it feels like I have this front row seat to so much 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 read through the things that people are working on. 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 feeds to watch. Yeah, yeah. I think that is the best AI news is probably internally if you're ever at one of these companies in the Slack. [15:40] Damn, yeah. [15:42] It just problem keeps getting harder. I'm just keeping keeping track what's going on. Okay, so okay, so that's part of the job. Well, there is still some of like the traditional like, let me think about what's [15:52] 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, Oh, cool, like we have been [16:00] 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

[16:07] three months? So it's like, and where does that actually, where could that actually go given where [16:12] the markets 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. [16:21] And then I also spend a bunch of my day [16:24] Just. [16:25] jamming on stuff with engineers, like a lot of it is just a conversation or like whiteboarding. [16:30] 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] Then I spend a part of my day [16:41] in code, like polishing, implementing stuff. Sometimes what happens is an engineer and I have [16:47] we're through something and they've implemented a first version of it, and I just go in and polish it with them. [16:53] And that's a really fun part of my job that I think [16:56] didn't exist. [16:57] as much a few months ago. [16:59] are you still doing elements of the traditional design process? Prototyping, user research, panels, I don't know, just like going out and in, you know, like the whole thing you described. [17:09] Yeah, we're still doing I think we're still doing all of that to some extent, like, [17:13] we we have a user researcher on the team who is putting together both like traditional studies as well as surveys. And the whole team is reading that that [17:23] those studies and that feedback, we are... [17:27] still we are still prototyping stuff we are still [17:30] 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.

[17:40] Got it. Okay. So that's a really interesting takeaway. It used to be that was a huge [17:45] I guess, what would be the pie chart of what your life was? [17:48] before where it's like [17:49] traditional [17:50] Thinking, planning, prototyping, mocking, research, and then just like feedback and execution and out today. [17:57] Yeah, I think as a designer a few years ago, [18:01] I would say like maybe [18:03] 60 to 70 percent? [18:05] of it was like, [18:07] mocking and prototyping stuff up. [18:09] and then spending [18:11] you know, the last... [18:12] 20 or some of the last 20 or so [18:16] like doing the sort of like jamming with engineers, consulting with them, and the last like 10% maybe doing... [18:21] you know, coordination meetings, etc. But now I feel like the the mocking up part of it is like 30 to 40%. And then [18:30] there's that other 30 to 40% there that is now, [18:33] 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 like, [18:41] implementation as well. [18:43] 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? What is in my AI stack? Um, well, we're going to throw up. So we're going deep on the cloud stack. Yeah. I am. I'm using obviously like chats. [19:07] Cloud Chat and that but increasingly more and more Cloud Co work. I've basically shifted

[19:13] all of my chat use cases over to co-work because I've been finding that [19:17] Yeah, it sort of is better at these longer running tasks. And most of the things I was asking Cloud for are these these longer running tasks. And then there's Cloud Code, of course, I use it mostly in the [19:29] with VS Code and the IDE because I'm usually tweaking front-end stuff and it helps to just like [19:33] be able to see the code and then talk to Claude as well. [19:37] I've been trying to actually use Claude Code more [19:40] remotely, like through both mobile and through Slack as well. [19:45] It's really fun for somebody to say like, oh yeah, this... [19:48] this one icons off or something and you just mention Claude and Claude does it. And then you pick up the PR and it's done. That's been really, really fun too. [19:57] Yeah, I think that's like, I think we're all fully cloud house here. So yes, that's basically my stock. [20:04] Are you still using Figma as a designer? I am still using Figma, yes. Okay, I was waiting to hear. Okay, so Figma is still part of your life. [20:11] Being a former Figmate, is that what we all were called? Yeah, Figmates, yeah. Yeah, okay. So I know there's this big debate on Twitter just like, [20:20] Is code the future of design? Do we need it? Like many more, do we need a design? [20:24] What's your sense? Figma's still important? I mean, as a former Figma, maybe I'm biased in that way, but I think there is still... [20:33] 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

[20:48] Just think about like eight to ten different ways to do something. [20:52] um i think the best design happens when you're able to just like throw a bunch of ideas at the wall [20:57] and curate and just like [20:59] and push yourself to come up with a bunch of these different directions. Right now, [21:04] coding or right now working with some of these coding tools doesn't lend itself super well to that because it's super linear you get super invested in one direction and you just iterate with a lot. [21:13] on them, for example. [21:15] So Figma has been really great at just like, [21:18] 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 [21:25] sort of visual and interaction details that are also really great 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 [21:40] 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 clearly shifting to [21:56] Command lines, agents, IDs are kind of moving to not be cool anymore. And it makes a lot of sense. You just want to edit some CSS things. [22:05] color stuff and so I could see why not just telling the agent hey just come on change this one hex value [22:10] Just changing it is so much easier. 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? [22:18] That's interesting. I wonder if IDUs now become the...

[22:21] useful for designers and PMs and engineers that have moved on. [22:24] Yeah, maybe, yeah. [22:25] Okay, so a lot of your time you spend working with engineers, giving feedback, kind of nudging them in the right direction. [22:31] There's a sense, I feel, of just like, [22:33] Your advice is let go. Don't feel like you need to be this gatekeeper. [22:39] But there's this piece of, okay, help them [22:41] move in a direction that is cohesive and is [22:44] creating products we're proud of. [22:46] 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. [22:52] What's something you learned about just either how to help your engineers... [22:56] get better at design so that [22:58] it just ends up being better. [23:00] or just kind of 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. [23:11] why I'm thinking a way that I'm thinking. [23:14] to help them like extract principles. [23:16] as opposed to me just being like, no, I don't think this would go here. It's like, no, I think we should have a button here because not everybody realizes you can prompt this. And here's an example where it comes from research and whatnot. So [23:28] I also just like try to point [23:30] engineers to our design system and stuff like that in code, because right now Claude is writing a lot of the code and it's not always picking up stuff in the design system and whatnot. So as much as I can equip them, [23:41] with stuff that they can use [23:43] in the future without me, if that's helpful. [23:46] And then on your points of... [23:49] 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

[23:55] 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] 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. Yeah. Oh, man. How to keep up with all our agents or seven agents who are constantly running. Yeah. [24:18] Okay. So then, [24:20] As a designer, where in this profession, craft and [24:23] great experience and quality and trust. [24:26] are such a core... [24:27] part of the job to help instill [24:29] that in the products because that in theory [24:32] leads to really successful products and companies. [24:35] How do you just think about [24:37] maintaining craft quality trust [24:40] 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 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 [24:51] to handle but um [24:54] I think with this... [24:56] I think about where the features or products are [25:01] where they are sort of in the cycle of [25:04] 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 we caveat that a bunch i think [25:19] 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... [25:27] Similar to our models, you know, this is the worst it's ever going to be. [25:30] But we're going to put it out there because we believe, you know, internally we've tried it a bunch. And there's something really powerful here that some people will benefit from. It might not yet be the easiest to work with. It might not be the highest quality. It might have some issues with it. But we're going to put it out there because we believe the benefits outweigh. [25:48] The cons. [25:49] I think... [25:50] That is okay to do, especially when... [25:53] 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 [26:01] is like, hey, we're going to put out there, but we're going to 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. 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, [26:21] and then nothing ever happens. That is something that degrades a brand. [26:25] But whenever you put something out early, [26:29] it's it's possible to do that and like maintain the brand of your company and i think [26:34] I think that's something that we've been doing pretty well. And I think if there's anything anyone's listening that can anyone's listening can take away from it is like, yeah, we're continuing to do that. And and I think that is actually really fun for me as a designer, because. [26:48] you put something out there and you actually learn [26:51] 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. Yeah, for sure. It's yeah, it's building trust through speed, but also just like

[27:02] 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 [27:13] 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 [27:21] and then shipping, "Hey, we fixed this yesterday, this is happening." [27:24] So there's a clear sense of this is just today and we know this is broken and we will fix it. [27:31] Cloud Code can [27:32] code very quickly. The fixes come very fast. [27:36] 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 another way I've been thinking about it, Lex put it this way recently, is where will human brains [27:48] continue to be valuable as AI gets smarter. [27:51] So we've gone through this progression of [27:54] "Tab completing ELA segments of code" to 100% 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. [28:09] which is like, "Okay, wow, look at that. Look at it go." The whole product workflows, the product development process slowly getting eaten up by AI. [28:17] 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? [28:25] Very, very good at it. [28:27] taste, judgment, design. [28:30] I think it will get better at taste and judgment and design. Yeah, like I think we

[28:35] We might be holding on to that a little bit too much and saying like, oh yeah, like, [28:42] you know, a designer or somebody will always know the [28:45] the best thing to ship or the best version of this. But I do think AI sense of taste will get better. [28:52] I think that if someone has to decide what is actually going to get built... [28:56] 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. [29:04] a lot of the hard parts of building software are actually like not [29:08] building it. If you think about the hardest times that you've had at work, learning is probably things like, oh, you and some other person disagreeing. [29:16] about like what should go into this feature or what shouldn't go into this feature and [29:21] Those things still feel like... [29:23] yes, I can weigh in, but it can't necessarily solve this dispute between you and somebody else. And so there is something about like, [29:30] deciding what actually [29:32] goes into... [29:33] The things we build... [29:35] 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. [29:43] around what to do next. [29:45] Just watching how quickly... [29:46] AI had took over coding, which... [29:49] I think a year ago, definitely two years ago, most people are like, I don't think so. I don't think AI will... [29:55] 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. That's where we got. It just made me reevaluate. [30:04] all these assumptions I've had about

[30:06] "Okay, AI will never be as good as [30:09] really good PMs, designers at [30:11] Judging what is great. [30:12] and deciding what to build. But I'm just starting to think, I think it will get there. Like even an example you shared, 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. [30:27] And I'll go ahead and build it. [30:30] So I think we're just, yeah, to your point, I think we undervalue just how good it'll get at this stuff. [30:36] Okay, so your sense is it'll get better, but your sense is we'll still need awesome designers now. [30:42] to be involved, us MPMs, to help make these decisions, engineers, of course. Yeah, yeah. I think some people still have to decide, like, oh, we want to build this kind of product. [30:51] or given what the AI is presenting us, someone still needs to be accountable for the decision. The same way that [30:58] even though Claude can write all this code for you today. [31:01] it is still an engineer who's accountable for like does that [31:04] code actually work. [31:06] does this actually make sense in the product? So I think there's that decision-making slash judgment layer, which feels like [31:12] Maybe one day we won't have to do that, but it still falls on us. [31:17] 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... [31:24] tell you what is going on. But like the human is mostly useful for signing off on the decision. [31:29] Because someone needs to be liable if they're wrong. [31:31] um, [31:32] Which isn't the best job in the world. [31:35] But that's a different game is health versus code. Yeah, yeah.

[31:39] Okay, another... [31:40] ongoing question in AI and design is just like, it feels like chatbots and terminals are just like, like, I don't think anyone expected this to be the lasting [31:49] user interface to AI. Like chatbots, okay, no, no, this is just like a temporary [31:54] stop along the journey. [31:56] But how it's gone even further than just terminals. [32:00] Do you have thoughts on just, I don't know, where... Do you think there will be a next step of how we interface with AI, or do you think chatbots and terminals are mostly where we end up? There will likely be a combination of... [32:10] both. Like both? [32:12] UIs and interfaces that you are [32:15] interacting with, clicking with, and that feel more tactile, we are already [32:21] seeing this and playing with this. [32:23] within Claude, like the chat. [32:25] bought. So we recently released a bunch of these widgets that let COD 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 [32:39] people still like to see UIs and touch them and click them, and they are much more efficient than, you know, [32:48] typing something to Clyde. But at the same time, when we really leaned into this chatbot paradigm, I think that just gave us this whole world of flexibility that we didn't get with these baked in UIs. So my read here is, I don't think chat is ever going away because this opened up this new wave [33:09] of like infinite ways to work with the model and to sort of like

[33:13] 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. I think that will probably happen here is that a lot of those UIs will be [33:26] generated more and more often. [33:28] by the models as opposed to something that were like, [33:31] hand coding each instance. But I think we... [33:35] Yeah, we're in this space where I don't think chat... [33:37] And maybe even talking to the terminal is going to go away. It's interesting that with OpenClaw, Claude, MoldBot, all the names, one of the big innovations is another way to chat with it through WhatsApp and Telegram and SMS. [33:50] Just like another form of chat pod, but that was a big unlock. Oh, I could just chat with it through WhatsApp. Yeah, and it's like chatting and talking to someone is still... [33:59] 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 interact with a computer, basically. Yeah. So Kevin Wheel, who works at another AI lab, I won't mention, [34:16] He had this great point on the podcast that [34:20] Talking is such a beautiful way to handle every level of intelligence. [34:26] We can talk to people that are very, very smart and not so smart, and it's talking. And it scales so well across the spectrum. We can talk to people at 200 IQ, 300 IQ, it's talking, still works. [34:37] So that's why it's been this beautiful way to... [34:39] deal with the growing intelligence of models as it continues to work. [34:42] Yeah, that totally makes sense. Yeah.

[34:44] 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. [35:14] hits production. 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 ship analytics their customers can trust. That's O-M-N-I dot C-O slash Lenny. [35:33] Okay, I want to come back to this whole idea of management in IC. [35:37] So, [35:39] So you've spent, you've kind of [35:41] 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. [35:48] Yeah, it takes on this. Yeah, so this past year at Anthropic, I joined [35:54] as an IC at first and then I managed a team for a few months in like an org structure that needed it. And now I'm actually back to doing full-time IC work. [36:05] And I joined Ntopic [36:08] As an IC, because I was just really excited about the kind of work that there was to be done as an IC here,

[36:14] but also because I was feeling like [36:18] You know, I sort of want to be close to the work. [36:20] And I think this feels like a really important time to do it before I like [36:25] ascend the corporate ranks, you know, and having these like questions and doubts about like, [36:30] Is middle management like... [36:32] is that safe in the future? Like, is the way that we're working actually [36:38] Is this going to be a job that persists into the future or... [36:43] or should I try something else and get my hands dirty? To be totally fair, I actually love both sides of the coin. I loved managing people, I love setting up teams, [36:54] and being at that level. But I also just really love IC work. Like I was sort of like a reluctant manager when I did it. And I was like, Okay, I'll do it. So I love both sides of these coins, the coin, like pretty equally. [37:05] But I think actually what... [37:07] being an ICO across this past year has taught me is that [37:11] It actually just gave me a lot of skills that I don't think I would have gained if I was just managing throughout this year. Like I mentioned, the design process has changed so, so much in this past year. And I feel like I've just picked up so many hard skills that I wouldn't have necessarily had the time to do if I was just managing a team. [37:29] So that's actually the best thing that's afforded me. And I think at any point, if I'm managing a team again... [37:34] I think it [37:35] 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 a designer and

[37:56] 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 at Figma, right? How big was your team? Like how large was your org? Just to give people a reference. At the max, I probably had [38:16] I think 12, 15 designers or so. And I had a few managers as well. So it was like an org. Cool. And then you went back to IC. Yeah. Okay. So you had the sense that middle management might not last [38:28] 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? I think as long as there is a team of people, it helps to have somebody who is managing a team. I think there is a real value in managers. [38:43] It depends kind of like what the shape of the manager is and what they actually do. But... [38:48] The way I think about [38:50] like what a helpful manager is these days is somebody who is not just like I think [38:54] 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, [39:02] good at work. I think that that is kind of [39:05] Not a thing as much anymore. [39:07] 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, like somebody who can really engage with the team in terms of like the work and giving direction there, as well as like creating the environment for them to do their best work.

[39:26] And do you see yourself going back into management long term? I probably will. I probably will. I think I really just love [39:32] you know, helping a team like build the best product possible. And my motto there is like, whatever it takes, you know, if it's somebody that's, 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. [39:50] So the advice I'm hearing is, [39:51] for people in design that are especially managers is you almost need to move back into IC in order to truly understand what is happening and how much it's changing so that you can be a better manager. 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 [40:14] take a rotation for a few months and pick up a few tasks and really understand how the technology works before they [40:22] become a full-time manager. I think design probably needs to do something similar too, where I think in the past design has been much more like, [40:29] people management oriented. [40:30] What did you find yourself most rusty in when you went back to IC Designer? 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.

[41:00] Yeah. So currently you're leading design 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. [41:15] And he's like, in the end, let's just make it like a... [41:17] terminal basically in the product and just kind of fancy terminal. [41:21] 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. [41:28] With CoWork specifically, we have had a bunch of different prototypes internally of what that could look like. And it's one of those things where we tried a lot of things and then 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. [41:49] It was 10 days, 10 days of building. Yeah, it was it was it was definitely longer than that. Like overall, it was like 10 days to get it from what we had internally to something that we were ready to ship externally. So we'd been building it for a while, but we weren't really sure about like the actual form it was going to take. And so the way it got there is actually there was a lot of different. [42:09] other explorations that we had internally on top of different agent harnesses and whatnot. And we just had prototypes, 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. We tried a bunch of different form factors for the way it works. [42:30] 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

[42:43] 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 it by releasing it. So I think. [42:53] 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 and it blew up the internet when you launched it so it worked out 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 improve? [43:13] Honestly, I think I'm just most proud of us actually just like, [43:16] shipping it, to be honest, and putting it out there and [43:20] - Uh, [43:22] Yeah, I don't know if there's like one specific thing yet. Because I think when, when you work on something and you work at so long, especially as a designer, you're like, [43:30] I don't know if I, you know, all I can do is see flaws in it. But I think there's a lot of stuff that... [43:36] I'm excited about like we have been [43:39] Iterating especially on the homepage... [43:41] and to make that something where it feels more like [43:46] hey, these are tasks you can give Claude and the tasks that Claude are working on. That actually should be rolling out. It might already be rolled out by the time this comes out. I see this little randomizer thing where you click it and it gives you all these different ideas. Yeah. When you actually start to work with Claude on stuff, it feels more like a to-do list. [44:03] like it feels more like these are things Claude's working on. These are things that Claude needs your attention on. And I think there's just a [44:11] 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.

[44:18] And then I'm also excited to think more about... [44:21] What is the actual true form factor of this? [44:24] 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 it wasn't just 10 days to do this thing. There's like these numbers that people throw out there. We build it in 10 days. And your point is like, there was time spent thinking about what direction it should go and prototyping, mocking, trying stuff. And then it's like, okay, now we know what we want it to be. Let's build it and ship it. Yeah, I think for some reason that became like the viral thing that got taken away from all of the [44:53] 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 have worked on different pieces of co-work. [45:04] that's, [45:05] Yeah, it was it was not just 10 days and there's a lot of different people involved. [45:09] it's it's one of those things where it's like the the idea [45:12] kept coming back and it's like never the right moment or there's like different variations of it [45:17] And then all of a sudden is the right moment. And it feels like [45:20] Oh, so obvious all along, but there was a long, long journey to get there. [45:24] And by the way, for people that don't know much about coworker, the way I think about it, it's like clawed with hands. [45:29] Where you do stuff on your computer. 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... [45:41] It's like Claude, but Claude is really good at [45:45] taking all your garbage and then turning it into something nice.

[45:49] Like, I think one of my favorite... [45:51] and like any sort of use case that I really like out of cowork is just like giving it a folder of my [45:57] stuff and it doesn't really matter what's in that folder but I'm able to extract something good out of it. [46:03] I've done that many times. [46:06] Coming back to managing and being a manager and the role of a designer, I'm going to talk about hiring for a little bit. [46:13] So seeing [46:14] how much is changing in the role of a designer, [46:17] What do you look for that's maybe new? What do you now look for when you're hiring designers [46:23] that you think is really important for them to be successful in this new world. [46:26] Well, I do think... [46:27] working specifically in the kind of environment that I do there there's just like a sense of like [46:33] resilience and like roll with it kind of thing. [46:36] 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 [46:48] be stuck in the old processes in the old ways. But then I think about also there's probably three archetypes of folks that are really interesting to me right now. [46:58] And I think these folks were already interesting to me before, but I feel like is... [47:02] in this era feels especially important. [47:05] So the first one I would call is like strong generalists. [47:08] So not just like regular generalists where they're like, [47:11] kind of good at a lot of things, but like [47:14] people that are almost like block-shaped in that T-shaped framework where it's like, [47:18] they're really good at a few core skills, like 80th percentile good.

[47:23] I think this is like pretty... [47:25] rare and hard to hire for, to be honest. [47:28] But I like this because [47:30] the design role we've already seen is kind of like, [47:33] stretching and spanning right like we're all becoming more pm shape or be all becoming engineering shaped um and so if you already have strong skills in a few different buckets it's [47:45] flex around and expand your role. [47:49] That's really exciting to me. It's just somebody who is... [47:52] Really good at a bunch of things. Again, a huge ask. [47:56] And then the other person that's really exciting to me is in that T-shaped framework, like a deep specialist, like someone who's is T-shaped, 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. [48:12] you know, like 10% of the industry and whatnot. Again, super hard to find. And I feel very lucky that like, [48:18] working at some of these places, [48:21] Folks like these. [48:23] you can sort of afford to hire them and actually bring them up on board. [48:27] And then my last one is probably... [48:29] the one that I think we're all overlooking, which is [48:32] what I call the craft new grad. It's just somebody who's like, [48:36] early career and [48:39] feels... [48:40] Kind of like... [48:42] wise and experienced beyond their years, but is also just like very humble and very eager to learn. I think this person is really interesting right now because... [48:52] 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,

[49:05] I think having somebody who almost has a blank slate and is just a really quick learner and is really eager to learn 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. 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. [49:23] This is awesome. [49:25] On the deep T shape... [49:28] What's an example of someone in design that has a skill that they're really good at? Sometimes there's designers who are just like, [49:35] really technical in a way where they could be like 50% of soft. They're basically a software engineer. Like, that's really interesting, especially because right now, like, [49:42] a lot of it is, at least for us, it's like, you know, you're working with directly with the model. So it helps when you have just like deep engineering expertise. But another like deep kind of like [49:52] specialist he is just [49:54] Maybe they're just really good at visual design or just designing icons or something. Where things like that, given that everybody can [50:02] anybody can make anything, you know, having that deep specialist slant [50:07] feels like, oh, yeah, they can really help differentiate the things that we're building. [50:10] Awesome. Okay. And then there's block shape. I had Mark Andreessen on the podcast. We kind of called it the F shape or E shape where there's like multiple T shapes. [50:18] thing sideways F sideways E I guess [50:20] 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. You know, there's so many skills that you spread out. [50:33] Okay, and the correct new grad. So this is just like someone that is...

[50:36] eager, open-minded, [50:39] 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 to break in, trying to [50:49] be successful? What would your advice be to them to help them [50:52] have a shot at Enzo joining Anthropic, for example. [50:56] I would just say just build a bunch of stuff. Try a bunch of stuff out. Build actual things. I think that is... [51:03] That can feel... [51:05] 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 [51:13] like, theoretical and like, here, we're gonna teach you some approaches and whatnot. [51:18] But like the best... The best... [51:20] kind of like crack new grad folks I know are just like people who just like use the technology [51:26] Build actual things. [51:28] don't feel like limited by... [51:30] 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 [51:41] feel like anything is possible. So just building a bunch of stuff and sharing it with people and finding a community of folks that also do that. [51:50] Yeah, I think my one call here too is like, [51:53] I went to a school that started something called Socratico like much about a few years after [51:59] actually 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

[52:09] a really cool movement there of folks who just like [52:12] build things and do things like for example somebody builds this like [52:17] claude robot project this was like a few years ago too where they were uh just assembling robots that were running on claude and then somebody else did something where she just wanted to put googly eyes on a bus in boston or something and there's just like a sense of [52:32] of both 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. [52:40] whatever that looks like, given [52:43] the school that someone's from or graduating from [52:46] Doing that kind of stuff is the stuff that will make people stand out. [52:51] For... [52:52] current designers that are in my career, awesomely senior designers, [52:56] 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. [53:06] to [53:07] Maybe I'll learn how to code... [53:10] so much that that, you know, you're building something from scratch. But I, it does feel like more and more of the designers vocabulary right now is [53:17] implementing some stuff [53:19] I wonder, though, as, you know, the models, both the models and the products get better, if, like... [53:26] We probably will continue to move up the abstraction layers and you won't have to actually know how [53:32] you know, each single line of code will work. [53:35] But I think what I would say is like, [53:37] start to bring that into your toolkit.

[53:39] the coding tools, whether or not it's like you're actually becoming technical [53:42] I think any designer should just be [53:45] 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 learning reactor, etc, etc. How good of a designers is Claude, would you say or Claude Code would have everyone to like, would you hire Claude as a designer is like not there yet? I don't think Claude is there yet. I don't think Claude is there yet in terms of a designer you would hire. I think it is. [54:06] 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 presenting a bunch of different ideas to you, but, uh, nothing there quite feels like, [54:20] Yeah, special and hireable yet. 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. [54:31] pump out amazing, novel, unique creative experiences or is there just [54:35] It's just never going to be that good as a human designer. I mean, it's gotten a lot better in the last year or so. [54:41] even. So, yeah. There's a couple management... [54:45] 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. [54:51] One is that you have this hot take that low leverage time for managers is just not a thing, that there's... [54:57] A lot of benefit you can get out of things that people consider low leverage. [55:01] Can you talk about that? [55:02] Yeah, I remember first becoming a manager. [55:06] And [55:08] I think one of the pieces 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 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 [55:34] you know, like things that are really nitpicky in the weeds or just like literally, yes, probably somebody else could do those tasks. [55:41] But when I think about like leaders and managers that I have [55:45] 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. So one example is whenever you have like senior leaders who just like, [56:04] test the shit out of the product. [56:06] And they're just like so in tune with it. And they dog food it. They repurp the bugs. They spend a bunch of time with like engineers, like sharing the logs and like nitpicking and stuff like that. [56:16] 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 [56:23] it [56:24] creates this like familiarity with the product, which I think is really good. 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. [56:40] I think similarly to what I've seen is like, [56:43] when a senior leader is able to like [56:46] fix a bug now, you know, even like I think I've actually seen like

[56:49] Mike Krieger before like put it put in PRs himself and 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. And I think similar another thing that I love that's a little bit more cultural is when [57:04] 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 because i think it just shows that [57:15] 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 is like, [57:25] choosing the like [57:26] the seemingly low leverage tasks [57:30] that are worth my time. [57:32] Yeah, that is so interesting. What you're saying there is, in a sense, the low leverage stuff is the stuff that often has the most impact. [57:39] because your reports wouldn't expect you to spend time on this thing [57:43] And there's like the low leverage ends up being high leverage. [57:46] Yeah, and I think it's what makes... [57:48] like your style of leadership stand out or feel special to a certain person. [57:52] 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 on the other hand, I hear constantly that the teams that you've built are just the happiest, the highest performing teams. [58:13] Talk about, I guess, this idea of roasting and encouraging that and just what you've learned about building awesome teams. [58:18] 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

[58:24] But when I think about [58:27] 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, [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 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 [58:49] it can be a really good sign when the people on your team [58:54] kind of feel comfortable just like kind of poking fun at each other a little bit um and i think that also can be a good sign when folks also feel the same way about like you as a leader where it's like [59:05] there's just an element of like, 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. [59:13] So an example of this is like, [59:16] with my last team, I feel like [59:18] They would make fun of things that I would say at crits sometimes, like certain phrases I would say. What's an example of that? [59:24] I don't know. Like, oh, I would always be like, [59:27] "Okay, what are next steps?" And like, "How do we follow up on this?" And then they'd be like, "Okay, what are next steps?" And they would sort of channel me in that way. [59:36] Yeah, I just think it shows a level of like, okay, [59:39] these people are like not necessarily afraid of me they know that they trust me they could trust me [59:45] And [59:47] It's it's and then they sort of like know enough about each other and me personally in our personal lives to be able to like know sort of where those boundaries are. But at the same time, I think the.

[59:59] the thing that you sort of err into in that territory is like, are you [1:00:02] 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, [1:00:12] This creates, like, the... You have to create this sort of, like... [1:00:15] baseline of psychological safety and people feel comfortable both with each other and with you, but you also have to make sure that they know that you have really high standards. [1:00:24] I think these two things can feel like they're at tension, but I think they're actually [1:00:29] 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... [1:00:38] actually I think becomes potentially easier because you can do it without fear I think. [1:00:44] And I sort of think about this from the approach of like, [1:00:46] 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 going to be there. [1:00:55] and I'm not just going to 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. [1:01:06] you know, I'm working with them to make the best work possible. And so [1:01:11] 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 roasting you, but at the same time, [1:01:20] They know they have to be doing great work and they will do great work with you. [1:01:24] That is awesome advice. [1:01:25] It's interesting how often this... [1:01:27] just like management style comes back, or management, good management, it comes back, reminds me of

[1:01:34] What is it? Radical candor. Just this combination of caring deeply and challenging directly. [1:01:40] 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. [1:01:47] - Yeah, is that fine? - So interesting. Okay, maybe a final question. [1:01:51] I'm always looking for interesting frameworks and methods and processes that people have [1:01:55] found useful in their work. [1:01:56] 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. [1:02:03] Yeah, this framework, I think... [1:02:06] I saw it on Twitter of maybe last year or something. [1:02:09] And it was Evan Tana, who is a partner at SPC, [1:02:13] He's a BC. So it basically is this like two by two [1:02:17] I don't think it got so much attention, but once I started seeing it, I actually couldn't stop thinking about it. [1:02:23] On the two by two, he basically has like founders, [1:02:26] Founders can be [1:02:28] either illegible or legible. And then ideas can either be [1:02:32] eligible or eligible. [1:02:34] And basically he was saying that like, [1:02:36] okay if if both the founder and idea is like super legible the idea is probably not that novel and somebody's already like [1:02:43] They're already going to implement it or do it. And you're actually not finding something new. [1:02:47] But then where it gets really interesting is where the idea itself is illegible. And by illegible he means like [1:02:54] Oh, it's sort of like really... [1:02:55] 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, [1:03:01] it's not like [1:03:02] being told in the way that makes the most sense to people.

[1:03:06] 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, [1:03:18] at least 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 [1:03:29] and transform it, whether it's through storytelling or whether it's through the actual UX and the form factor. [1:03:35] and put it out there. [1:03:38] 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... [1:03:49] 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 one good example actually that ties to [1:04:01] co-work where there was this internal prototype that we called like cloud studio that [1:04:07] I think somebody built... [1:04:09] like partway through last year. And it essentially was this, this like really interesting, [1:04:14] kind of like dense, powerful interface that was built on top of [1:04:19] some agendic harness. It might have been Claude code at that point in time too. And it had all these displays where it's showing you all this knowledge and all these skills and things Claude was doing and previewing its outputs. [1:04:31] And I think [1:04:32] 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. But then I sort of saw

[1:04:40] the folks in research, the folks building it and just folks internally, there's just a lot of energy around it. And I was like, cool, I think there's like something here, but I just don't understand it yet. I think that really was an example of an ill [1:04:54] illegible idea [1:04:56] And ultimately what came from it was the skills [1:04:59] framework and 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. [1:05:08] That was not something I was directly involved in, and that was more of like, [1:05:12] you know the folks working on this prototype extracted that out of it but when it did come to work on cloud co-work and i was thinking about like [1:05:18] 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 plan and to do's, seeing Claude's like context and the files that it was it was going through. [1:05:33] Like those kinds of things are things that I ended up pulling out of that prototype into quad code work. So, yeah, I think about like. [1:05:40] how can designers almost be more like VCs in this way internally when we're looking at prototypes. [1:05:46] This is super interesting. [1:05:47] I did a research project recently where, with this guy Terrence Rohan and VC, actually, we looked at [1:05:53] what are patterns across [1:05:55] people that have joined companies very early that ended up being massive successes like Palantir and Stripe and [1:06:02] Linear and Notion, all these companies. People that have joined many of these companies early, what were they looking for? And one of the factors was

[1:06:10] the idea is so it's like so crazy that everyone's laughing at this this is [1:06:15] This is impossible. You're never going to do this. This is the craziest thing. Why would you even think like that? [1:06:20] Like OpenAI actually was one of them, just like some research lab doing some stuff. [1:06:24] So it's interesting that, and it's not like every time this will work, and it's not like every crazy idea that makes no sense will be good. [1:06:32] But I think what you're saying is pay attention to stuff that's interesting to you and isn't totally clear. [1:06:38] you can be the person that helps pull it together. [1:06:41] Yeah, yeah, that but also like if there is [1:06:44] some energy around it, but I don't quite under always understand what the energy is. It's like, dive deeper and try to understand what that is. Yeah, yeah. Because I think people who often gravitate towards these early ideas, [1:06:56] they can't always articulate why. [1:06:59] And it's sort of up to you to like dive deeper and understand that. [1:07:02] That's one of those. 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. [1:07:11] And it sounds crazy. That's so interesting. Okay. And then what was the other one? Oh, the founders are just like top 1% was the other one. [1:07:18] piece there, which everyone had anthropic already, so you got that one. [1:07:23] Oh man, Jenny, what a crazy time we're living through. What a world. What a crazy time. How much change. [1:07:28] Okay. [1:07:29] Before we get to our very exciting lightning round, is there anything else that [1:07:33] I should have asked you that you want to leave listeners with, that you want to [1:07:36] double down on. [1:07:37] I think I just want to call out the Anthropic Design team.

[1:07:42] and shout them out 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 [1:07:58] They sort of span this whole spectrum of people who are really technical and prototype-y to all the way to folks that are really high craft and delivering stuff 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 in Turtle and Anthropic, if that sounds more exciting than terrifying. [1:08:21] would love to connect. [1:08:23] What sounds exciting is getting access to these slacks where all the features are being built. Yeah, that's the core benefit. Let's talk to super intelligence right now and tell me where... [1:08:31] I should invest. I'm just joking. And then in terms of hiring, is there anything specific that people should think about to... [1:08:37] If they want to play. Think a little bit about the [1:08:41] the archetypes that I mentioned, especially the strong generalists and the deep specialists, those folks were really excited about. But generally, folks who are... The block and the deep tea. The block and the deep tea. [1:08:53] What could we be talking about? Yeah, folks who feel like they [1:08:59] you know, those archetypes resonate with them, but also folks that are just really excited about the technology, have been building a lot. [1:09:06] and sort of want to be on the frontier. [1:09:10] Amazing. Well, with that, we've reached our very exciting lightning round. We've got five questions for you, Jenny.

[1:09:17] I'm ready. Here we go. What are two or three books that you find yourself recommending most to other people? [1:09:22] The first one is The Power Broker by Robert Caro, which is an incredibly aggressive recommendation, given that it's like 1100 pages. [1:09:34] But I think... [1:09:35] In this era when our [1:09:37] when our attention spans are so short, I think this is actually worth reading end to end. Because I think there are very few [1:09:45] 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 that'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 this like long arc thinking because we're so much we're thinking so much about right now. 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. [1:10:17] Power broker. [1:10:19] 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 was the partner of the scientist Oliver Sox around the time that Oliver Sox died. [1:10:33] And it's just this like really beautiful kind of like ethereal memoir of all of our socks 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, [1:10:45] 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 so that's one of my favorite books.

[1:10:54] My goal here is, you know, I'm trying to create, we're trying to create Renaissance humans. So all of this other stuff is excellent. [1:11:01] Cool. [1:11:02] Interestingly, I saw Julie Zhu, famed design leader, was reading the power broker recently. What's going on over here? Spreading in design land. [1:11:11] Okay. [1:11:12] Do you have a favorite recent movie or TV show that you really enjoyed? [1:11:15] I watched A Sentimental Value recently. I watched it on a plane, which is, you know, how directors want you to watch their films. But it's a Norwegian film by the same director who did The Worst Person in the World. I think just the pacing, the writing, the relationship between the characters is just really subtle and beautiful. [1:11:34] It's basically about this family... [1:11:37] sort of a family drama, but also about this house that they lived in their entire lives. It's beautiful because 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. [1:11:49] And then I would also recommend, obviously, The Pit Season 2. [1:11:52] 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 um so [1:12:00] Yeah. Imagine 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. [1:12:15] And I only recently realized Noah Wiley was in ER as a younger person, and now he's the head of the... [1:12:20] Yeah, yeah. Oh, man. Okay. Favorite product you recently discovered that you really love cannot be co-work.

[1:12:26] Not one that I'd actually discovered recently. Um... [1:12:29] But retro, I've been using it for basically two years now since it came out. [1:12:35] And I think [1:12:36] 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 [1:12:56] like counts, there's no ads, etc. 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 live through. [1:13:11] each week. [1:13:12] of my life basically [1:13:14] Wow. And it's also a beautifully crafted app if you're looking for it. [1:13:18] Building your own taste in design. Yeah. [1:13:20] Designers love retro. I could see I could see that. [1:13:23] Okay, do you have a favorite life motto that you often come back to in work or in life? [1:13:28] Yeah. [1:13:29] Not sure if it's my favorite life motto, but one thing I do catch myself saying a lot is just... [1:13:34] It is what it is. [1:13:36] 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. [1:13:49] you can't control everything. And so sometimes it is what it is, just like brings the levity you need to move forward. [1:13:55] I went to I did a 10-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 answer to it all. It is what it is. Don't cling. Don't try to change. It is what it is. It is what it is. There's so much depth to that. [1:14:11] I was like, okay, smarter than I even thought. [1:14:15] Okay, final question coming back to Co-Work. [1:14:17] Is there... [1:14:19] I don't know, mind-blowing use case, something just like, wow, that's so cool that Co-Work can do that. [1:14:25] 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 I have this [1:14:33] this folder basically of local notes that I have from [1:14:37] that I use IA Writer for. And I basically just write whatever. And over the years, I've collected it with a bunch of different notes. And [1:14:45] 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, etc. [1:14:52] And my favorite... [1:14:54] Like it makes it's cool to me. It's just like, [1:14:57] using co-work to analyze that and have insights out of it, actually create things out of it. So anytime I can learn something new about myself, I love that. But I think a very practical thing I did with it the other day was [1:15:11] along the lines of hiring I was like oh yeah I want to sort of articulate like [1:15:15] 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. 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.

[1:15:30] for evaluating that. So 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. [1:15:40] 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 you all are allowed to use Granola or something like that, like meeting transcripts and ask it. And it's like I was going to ask what prompt you use, but it's just like read all these things I've written and help me. [1:15:59] probably just like understand how I feel about what is design craft. Yeah, basically, I think it was like, [1:16:05] Hey, I have a bunch of interview notes and a bunch of [1:16:07] notes related to design craft in this folder, read it and then help me craft a [1:16:14] like a memo slash rubric for how I assess craft in interviews. [1:16:19] So cool. Yeah. [1:16:22] Jenny, this was awesome. 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? [1:16:31] 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, [1:16:41] That's the best place. And how can folks be helpful to me? [1:16:44] 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. [1:16:55] Yeah, of course. It was great chatting with Lenny. [1:16:57] 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.

[1:17:09] Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. [1:17:16] You can find all past episodes or learn more about the show. [1:17:19] at Lenny's Podcast dot com. [1:17:21] See you in the next episode.