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

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%.

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 7 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 2-year, 5-year, 10-year vision even. Now it becomes a vision that's 3 to 6 months out and isn't necessarily creating this beautiful deck. It's 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.

It will get better at taste and judgment and design. We might be holding onto that 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 3 archetypes of folks that are really interesting to me right now.

Today's guest is Jenny Wen. Jenny was head of design for Claude, is now leading design for Claude Cowork. Prior to that, she was director of design at Figma, where she led the design teams behind FigJam and Slides. She was also a designer at Dropbox and Square and Shopify. And what I love about this conversation is that Jenny is living in the future of where design as a profession is heading, and she's here to give us a glimpse into what that looks like and how much things are going to be changing for designers. It is pretty wild and extremely interesting. A huge thank you to Noah Levin and Emily Lynn Hasham for suggesting topics and questions for this conversation. Don't forget to check out lennysproductpass.com. For an incredible set of deals available exclusively to Lenny's newsletter subscribers. Let's get into it after a short word from our wonderful sponsors. This episode is brought to you by Mercury, radically different banking loved by over 300,000 entrepreneurs, including me. I switched to Mercury from Chase over a year ago, and it is such a profoundly better experience. It's like an actual product person built a bank versus a banking person building a product. It is fast, it's elegant, it is Super easy to set wires, to track my spending, to set up triggers to move money around when accounts get low. We moved all of our invoicing to Mercury and it is such a smoother experience than anything else we've tried. It's also really easy to grant people on your team just the right amount of access to help take work off your plate. It's free to get started. No in-person visits, no minimum balances. The product also flexes to all sizes of company, from startups to large enterprises. Just visit mercury.com to learn more and apply online in minutes. Mercury is a fintech company, not an FDIC-insured bank. Banking services provided through Choice Financial Group and Columna members FDIC. This episode is brought to you by Orkus, 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. Orkus 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, Orkus supports visual and code-first development with built-in compliance and reliability. Through a built-in MCP gateway, AI agents handle reasoning and decision-making while safely accessing existing APIs and internal systems as MCP tools. This enables agents to operate across enterprise environments and scale from demos to production, orchestrating systems, agents, and humans together to deliver smarter outcomes faster. Learn more at orkes.io/lenny. That's orkes.io/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, uh, the role of product management, how much that role is changing. I haven't spent a lot of time on how design is changing. Clearly it is also changing in a really big way. And you have such a front row seat to where things are heading. Uh, I also know you have a lot of very strong opinions about where things are heading. So, uh, there's a lot of stuff I want to talk about. I want to just start with this, just this broad question. How is the design process 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 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 design is sort of forced to change. And so 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 like, Don't Trust the Design Process, where I basically just said like, hey, you know this design process that designers have been taught where you go and you go off and you do a bunch of research and discovery, and then you like diverge, you converge, diverge, converge. And it's like this process that we sort of treated as gospel and tried so hard to preserve. And we were like, trust the process. That is, that's basically dead. 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 7 clods. I think as, as designers, we really have to let go of that process. And I think that's the big thing that's changing. But I think even in the past 3 to 4 months since I did that talk, that talk actually starts to feel pretty, it, it kind of feels outdated to me, which is a little embarrassing. But especially with the big shift of like Opus 4.6 and a bunch of folks just like really discovering and using Claude Code over the holiday break, um, I think we're seeing this like force to change our process happen even more. The way I sort of see it now is like there are basically 2 types of design work and design work is kind of like becoming really stratified in this new world. So there's like the first one, which is really just like supporting the implementation and execution. So this is the one where, you know, engineers are using their 7 clods to create all these features and anybody can like put an idea out there. And you can just 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 do not have the time to make these beautiful mocks anymore or to kind of lead in this way. And then I think there's the second kind of work that feels also really important, which is creating the sort of vision or direction for things. This one feels like the hardest to make time for, and it's one that 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, we're going to do this design vision. We're going to go off and make this 2-year, 5-year, whatever, 10-year vision even, and we're going to point us towards something. But the way that the technology is changing now, we actually don't know. We don't know what's going to happen in 2 years. There's too much changing.

Yeah.

And it usually becomes a vision that's like 3 to 6 months out and isn't necessarily something that is like creating this like beautiful deck that's like beautifully storytold. 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 7 quads, make whatever features they want in any kind of like direction or or in implementation, you need to point them towards something. And in order to make sure that we're all making something that makes sense together and is also done in a way where it's efficient, right? If we're all working towards something that has one greater cause, it's much more efficient to do that than just random things. So that's the big shift that I'm seeing. And I think I have opinions about it now, but ask me in 3 months and it might actually change.

So what you're saying here is it's not like, uh, you or the design field is like, we need to change. It's engineering and the fact that you can build so quickly just forces, uh, the role of a designer to change. Because as you said, engineers can just ship, ship, ship, ship, ship. And what you're finding here is like, you're better off not blocking that, letting them cook, as they say. And, uh, and then there's kind of this mode of helping them along as they ship.

Yeah.

Bring it together, make sure it all kind of connects, 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 follow-on effects of engineering tooling really changing. I think we'll probably see design tooling change in this next year or so as well. But 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 doing a lot of last mile stuff where I'm implementing all the polish and sort of like working with engineers really closely to get the feature across the line and also prototype stuff in actual code as opposed to relying on engineers to do that again.

How true do you think this is at All companies at, say, AI companies, non-AI companies, you know, someone may be hearing this, okay, Anthropic, Claude, like, okay, it's like, they're at the bleeding edge for one, two, it's like developer-y a little bit, but I think people might be feeling like, okay, this is not going to happen at Salesforce. This is not going to happen at, I don't know, ServiceNow, wherever. So I guess, 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 going to be?

So the talk that I did last year has weirdly been like the most resonant talk that I've done. And I, so I think it's something that people are starting to feel across the industry where they're like, oh yeah, we can't do the old design process anymore. You know, we are using tools like Claude Code and, and v0 and whatnot to, to start to spin up prototypes and PMs are starting to spin up prototypes and stuff like that as well. So I think there's something there emerging. But the other interesting observation with that talk too was there was actually also a decent amount of backlash. People clearly have invested their entire careers in learning, teaching, using this really stable design process. And I think there was a lot of discrediting, like, oh yeah, 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 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, or it could be just engineers ship stuff that's okay, not amazing, good enough. We learn, iterate, build, iterate. Is your sense that that second path is, not only is that just like what everyone's doing, but that actually leads to the better product at this point?

I think you sort of have to choose and use your discretion as to like when to actually ship something. But I think the ability to execute, try something out and try it with like real data and a real user's like kind of mindset in the product, I think that does lead to a better product, especially as we're all working with these like new developing AI models that are non-deterministic, you just can't, you 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 try it out with their use cases because with these models, like you discover, you can design them for different use cases, but you actually 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, which is where Cowork came from and probably even Claude Code at the beginning. And so, so what's it, what's it just like to be a designer at Anthropic? Just like give us a day in the life of working at Anthropic in the, at the center of the storm.

A good amount of time at Anthropic is actually just catching up on what people, what's happening at the company. I think this is the company where 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. There's stuff that is 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 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. And then there's just like stuff I want to try out. You know, like we have a bunch of like, we have a bunch of prototypes and products internally that we can use. And I am just curious and I 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 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 it's both the volume and the kinds of things that are happening that I'm like really interested in keeping up with. Um, and then aside from that sort of keep up, 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 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 feels like I have this front row seat to so much that's happening in the industry. And so a lot of it is like, yeah, our Slack is a goldmine, you know, like I'm just excited to read through the things that people are working on and they're saying.

I never thought about how 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, I think that is the best AI news is probably internally if you're ever at one of these companies in the Slack.

Damn. Yeah. It's just the problem keeps getting harder of just keeping track of what's going on. Okay, so that's part of the job. What else?

There is still some of the traditional, let me think about what's happening in the future and let me 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. We have been in a lot of execution mode for Cowork and now I want to set aside some time to think about, hey, what do the next 3 months look like and where could that actually go given where the market's at, where the models are at? And what could that be? Because I think it still really helps to visualize that and show that to the team and point everyone in the same direction. And then I also spend a bunch of my day just jamming on stuff with engineers. Like a lot of it is just a conversation or like whiteboarding or going through something that they built and giving them feedback on it and being a designer in that kind of way where we're like consulting. And then I spend a part of my day in code, you know, like polishing, implementing stuff. Sometimes what happens is an engineer and I have worked through something and they've implemented a first version of it, and I, I just go in and polish it with them. 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.

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

Yeah, we're still doing— I think we're still doing all of that to some extent. Like, we, we have a user researcher on the team who is putting together, uh, both like traditional studies as well as surveys, and the whole team is reading that, that the, those studies and that feedback. We are still, we are still prototyping stuff. We are still— I'm still mocking stuff up. I think it's just I have a wider set of tools now and I think the proportion of time I spend doing each thing just has changed.

Got it. Okay. So that's a really interesting takeaway. It used to be, that was a huge, like, I guess what would be the pie chart of what your life was before where it's like traditional thinking, planning, prototyping, mocking, research, and then just like feedback and execution and now today?

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

Like actually building and shipping.

Yeah.

Amazing. So kind of following that thread, what's in your AI stack? What do you as a designer, I know you're a manager and I want to talk about how you actually are IC also. What's in your AI stack? What tools are you using in your role?

What is in my AI stack? Well, we work at Anthropic, so it's—

Of course.

We're going deep on the Claude stack. I'm using obviously like chats, Claude Chat, but increasingly more and more Claude Cowork. I've basically shifted all of my chat use cases over to Cowork, 'cause I've been finding that, yeah, it sort of is better at these longer running tasks. And most of the things I was asking Claude for, are these longer running tasks. And then there's Claude Code, of course. I use it mostly in the, with VS Code in the IDE because I'm usually tweaking frontend stuff and it helps to just like be able to see the code and then talk to Claude as well. I've been trying to actually use Claude Code more remotely, like through both mobile and through Slack as well. It's really fun for somebody to say like, oh yeah, this, This one icon's off or something, and you just @mention Claude and Claude does it, and then you pick up the PR and it's done. That's been really, really fun too. And yeah, I think that's just like, I think we're a fully Claude house here. So yes, that's basically my stack.

Are you still using Figma as a designer?

I am still using Figma.

Yes.

Yes.

Okay. I was waiting to hear. Okay. So Figma is still part of your, your life, uh, being a former Figmate. Is that, is that what y'all were called?

Yeah. Yeah. Figmates. Yeah.

Yeah. Okay. So I know there's this big debate on Twitter, just like, is code the future of design? Do we need to think many more? Do we need to design? What's your, what's your sense? Figma's still important?

I mean, as a, as a former Figmate, I, I maybe I'm biased in that way, but I, I, I think there is still, like, when I use Figma, I'm like, yes, this is what I should be using. And it still fills a very good gap for me. Um, I think a lot of that is actually just like, one is Exploring a lot of different options. I think that's a really important part of the design process to be able to just think about like eight to ten different ways to do something. 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 push yourself to come up with a bunch of these different directions. Right now, 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 Claude. On them, for example. Um, so I, Figma has been really great at just like exploring all these different options, and I think it's still gonna exist that way to some extent. And then I think there's like really fine sort of visual and interaction details that are also really great to, to, to be able to just try out in Figma. Again, it's a lot of different directions, but it's micro directions. It's being able to think about like different typography or styles. Having those in a canvas where you can just explore that specifically is still so, so helpful and is not something that I always wanna like go directly to code in.

It's interesting you still use an IDE because in engineering it's clearly shifting to, uh, command lines, agents, IDEs are kind of moving, moving, uh, to not be cool anymore. So it's, and it makes a lot of sense. You just wanna edit some CSS things. Yeah. 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.

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 IDEs now become useful for designers and PMs and engineers have moved on.

Yeah, maybe. Yeah.

Okay. So a lot of your time you spend working with engineers, giving them feedback, kind of nudging them in the right direction. There's a sense I feel of just like, like your advice is like, let go. Don't feel like you need to be this gatekeeper, but there's this piece of, okay, help them move in a direction that is cohesive and is creating products we're proud of. A lot of designers I think are in this boat right now of just like, oh my God, I can't keep up with all these engineers shipping stuff all day. What's something you learned about just either how to help your engineers get better at design so that It just ends up being better, or just kind of keeping on top of this and not going crazy.

Whenever I do work with engineers on projects and it's more on like a consulting basis, I do just try to explain, you know, why I'm thinking a way that I'm thinking to help them like extract principles as opposed to me just being like, no, I don't think this should go here. It's like, no, I think we should have a button here because not everybody realizes you can prompt this. Um, and, and here's an example where it comes from research and whatnot. So I also just like try to point engineers to our design system and stuff like that in code, because right now Claude is like writing a lot of the code and it's like not always, it's not always like picking up stuff in the design system and whatnot. So as much as I can sort of equip them with stuff that they can use in the future without me, that's helpful. And then on your point of Trying not to go crazy. I think it's hard, you know, I think it's really hard right now. And I see this a lot from actually both engineers and designers where it's like, now that we're sort of capable of doing so much, we want to do more. 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 7 agents we're constantly running.

Yeah.

Okay. So then as a designer, where in this profession, craft and great experience and quality and trust are such a core part of the job to help instill that in the products, because that in theory leads to really successful products and companies. How do you just think about maintaining craft, quality, trust as your products are just shipping 1,000 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 that there's too much for one designer to handle. But I think with this, I think about where the features or products are that, like where they are sort of in the cycle of adoption versus like kind of early preview. So for example, like we sometimes will launch things and we will say, hey, this is a research preview. It's It's early, it's gonna have a bunch of these flaws, and, and we caveat that a bunch. I think Claude Cowork is actually a good example of this, where we labeled it a research preview and we put it out there knowing that, hey, this is like similar to our models, you know, this is the worst it's ever gonna be, but we're gonna put it out there because we believe, you know, internally we've tried it a bunch and there's something really powerful here that some people will benefit from. It might not yet be the easiest to work with. It might not be the highest quality. It might have some issues with it, but we're gonna put it out there because we believe the benefits outweigh the cons. I think that is like okay to do, especially when there is something really valuable with the product already and it's worth putting it out there. But I think the promise you sort of have to make your users is, is like, hey, we're, we're gonna put it out there, but we're gonna, we're gonna iterate. We're gonna take your feedback and we're gonna iterate and we're gonna make it better. And you have to sort of commit that. You have to show that to the world. You have to respond to people's feedback and you have to show that you are continuously shipping and improving it. Because I think the way that you really lose trust around quality and releasing something early is if you release it early and then nothing ever happens. That is what something that degrades a brand. But whenever you put something out early, like it's possible to do that and like maintain the brand of your company. And I think I think that's something that we've been doing pretty well. And I think if there's anything anyone's listening that can, if anyone's listening can take away from it is like, yeah, well, we're continuing to do that. And I think that is actually really fun for me as a designer because you put something out there and you actually learn and you get feedback about it immediately and you know what to do next.

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 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, everyone on the team is tweeting and just like responding to tweets and comments and, and then shipping, hey, we fixed this yesterday and this is happening. So there's a clear sense of this is just today, and we know this is broken and we will fix it. And then because Claude Code can code very quickly, the fixes come very fast. Okay, so another big question that people are asking that I ask a lot on this podcast is around just like what skills become valuable. And like another way I've been thinking about it, Lex put it this way recently, is where will human brains continue to be valuable as AI gets smarter? So we've gone through this progression of Tab completing segments of code to 100% of code is written by AI now. Like, it's crazy. To now AI is reviewing its own code. Boris on the podcast recently was saying Claude Code is now helping him come up with ideas and decide what to build, which is like, okay, wow, look at that. Look at it go. The whole product workflows, the product development process slowly getting eaten up by AI. So the question is just like, where will human brains still be useful, at least until we have superintelligence. Do you think AI is going to get very, very good at taste, judgment, design?

I think it will get better at taste and judgment and design. Yeah. I think we might be holding onto that a little bit too much and saying like, oh yeah, a designer or somebody will always know the the best thing to ship or the best version of this. And I, but 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 what actually matters. And when I think about people saying like, oh, you know, like AI is just gonna build this software for us, a lot of the hard parts of building software are actually like not building it. You know, if you think about the hardest times that you've had at work, Lenny, it's probably things like, Oh, you and some other person disagreeing about 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 deciding what actually goes into the things we build, which I guess is taste in some way, but maybe not taste in the way we think about aesthetic taste or— Or whatnot. There's some sort of like, it's like judgment around what to do next.

Just watching how quickly AI had took over coding, which I think a year ago, definitely 2 years ago, most people are like, I don't think so. I don't think AI will get this good. And that the best engineers in the world trust it so much. They're not even looking at the code anymore. Like that's where we've gone. It just made me reevaluate all these assumptions I've had about Okay, AI will never be as good as really good PMs, designers at judging what is great and deciding what to build. But I'm just like starting to think, I think it will get there. Like even in the example you shared, like it could give these 2 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 1 and I'll go ahead and build it.

Yeah.

So I think we're just, yeah, to your point, I think We undervalue just how good it'll get at this stuff. Okay, so your sense is it'll get better, but your sense is we'll still need awesome designers to be involved, awesome PMs to help make these decisions, engineers, of course.

Yeah, yeah. I think someone will still have to decide like, oh, we wanna build this kind of product. Or like, given what the AI is presenting us, like someone still needs to be accountable for the decision. You know, the same way that like, even though Claude can write all this code for you today, It is still an engineer who's accountable for, does that code actually work? Does this actually make sense in the product? So I think there's that decision-making/judgment layer, which feels like maybe one day we won't have to do that, but it still falls on us. Yeah.

It doesn't make sense. It makes me think about the radiology example where there's always the sense that AI is going to take over that field of radiology and tell you what is going on, but the human is mostly useful for signing off on the decision. Because someone needs to be liable if they're wrong. Um, which isn't the best job in the world, 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 chatbots and terminals are just like, like, I don't think anyone expected this to be the lasting, uh, user interface to AI, like chatbots. Okay. No, no, this is just like a temporary stop along the journey. But now it's like gone even further and just terminals. Um, do you have 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 both, like both UIs and interfaces that you are interacting with, clicking with, and, and, and that feel like more tactile. We are already Seeing this and playing with this within Claude, like the chatbot. So we recently released a bunch of these widgets that let Claude sort of elicit and ask you questions and also show you, you know, things like the weather and stocks and whatnot in interactive ways. And I think those have had a really good reception because people still like to see UIs and touch them and click them, and they are much more efficient than, you know, Typing something to Claude. 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 sort of baked-in UIs. So my read here is, I don't think chat is ever going away because this opened up this new way of infinite ways to work with the model and to sort of talk to the computer. that we just didn't have before. But I think that it will still be most direct for very specific things to exist in this UI. And I think that what will probably happen here is that a lot of those UIs will be generated more and more often by the models, as opposed to something that we're like hand coding each instance. But I think we, yeah, we're in this space where I don't, I don't think chat and, and, and, and maybe even like talking to the terminal is, is gonna go away. Yeah.

It's interesting that like with OpenCLAW, Claude, Mollbot, all the names, the innovation, one of the big innovations is like another way to chat with it through WhatsApp and Telegram and SMS, just like another form of chatbot. But that just like, that was a big 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. And so, and it's a way for us to interact in a really rich way. And now we just have this other medium to like interact with a computer basically.

Yeah. Um, so Kevin Weil, uh, who works at another AI lab I won't mention, he had this great point on the podcast that talking is such a beautiful way to handle every level of intelligence. We can talk to people that are very, very smart and not so smart, and it's talking. And it scales so well across the spectrum. We can talk to people at 200 IQ, 300, 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 you continue to work.

Yeah, that totally makes sense. Yeah.

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Yeah, I have takes on this. Um, yeah, so this past year at Anthropic, I joined As an IC at first, and then I managed a team for a few months in an org structure that sort of needed it. And now I'm actually back to doing full-time IC work. And I joined Anthropic as an IC because I was just really excited about the kind of work that there was to be done as an IC here, but also because I was feeling like I sort of want to be closer to the work. And I think this feels like a really important time to do it before I like ascend the corporate ranks, you know? And I was having these like questions and doubts about like, is middle management, like, is that safe in the future? Like, is the way that we're working actually, is this going to be a job that persists into the future or should I, you know, try something else and like get my hands dirty kind of thing? And to be totally fair, I actually love both sides of the coin. I love managing people. I love setting up teams and being at that level, but I also just really loved IC work. 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 the coin pretty equally. But I think actually what being an IC across this past year has taught me is that it actually just gave me a lot of skills that that I don't think I would've gained if I was just managing throughout this year. Like I mentioned, the design process has changed so, so much in this past year, and I feel like I've just picked up so many hard skills that I wouldn't have necessarily had the time to do if I was just managing a team. So that's actually the best thing it's afforded me. And I think at any point, if I'm managing a team again, I think it will give me the empathy and understanding of how the design process has changed. And I think that's actually a really important thing right now because, yeah, the teams are working so differently. And I think it's actually pretty hard to empathize if you are not working in that way or you're like not always like testing all the tools and trying stuff. But yeah, like it's, it's an interesting time to be a designer. And if I had not worked in this environment, I don't know if I would've 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.

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, I think, 12, 15 designers or so. And I had a few managers as well.

So it was like an org. Yeah. Okay. So you had the sense that middle management might not last. What's your current feeling? Do you think design management is a thing that persists long-term or do you think everyone turns into IC?

I think as long as there is a team of people, it helps to have somebody who is managing a team.

Okay.

I think there's real value in managers. It depends kind of what the shape of the manager is and what they actually do. But the way I think about what a helpful manager is these days is somebody who is not just, I think, pure people management, like, oh, just somebody to sort of set you up, help you in your career, have one-on-ones, make sure you're feeling like good at work. I think that that is kind of not a thing as much anymore, but I think somebody who can really function as like giving the team direction as well as doing some of the people management stuff, like that tied together, I think is the future of what managing looks like, at least for now. 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.

And do you see yourself going back into management long-term?

I probably will. I probably will. Like, I think I really just love, 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, if the team needs somebody to give the team direction and like set up the team and whatnot, that can 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 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, 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 pick up a few tasks. And really understand how the technology works before they become a full-time manager. And I think design probably needs to do something similar too, where I think in the past design has been much more like people management oriented.

What did you find yourself most rusty in when you went back to IC designer?

Actually like doing crits, you know, um, and just being—

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 it on such a regular basis because that's the thing you have to do as a designer is like, it's a pretty vulnerable exercise to share work and present it with your team and then also just get a lot of critical feedback and take that all the time. Yeah.

So currently you're, you're leading design, uh, slash IC designing on Cowork. 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 terminal basically in the product and just kind of a fancy terminal. Is there anything you could share about just the process of landing on where you landed for that experience of Cowork? I have it here on my monitor, by the way, looking at it.

Uh, with Cowork specifically, we have had a bunch of different prototypes internally of what that could look like. Um, and it's one of those things where we tried a lot of things and then we, I think we weren't really sure like when it was actually going to be ready to ship. And then it was sort of like everything all at once. Like we were like, okay, we're gonna, we're gonna ship it soon.

It was like, it was 10 days, 10 days of building.

Yeah, it was, uh, 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 gonna take. And so the way it got there is actually there was a lot of different other explorations that we had internally on top of different agent harnesses and whatnot. And we just had prototyped little parts of the different interactions that ended up in Cowork. So things like when Claude gives you a to-do list, we tried a bunch of different form factors for that. We tried a bunch of different form factors for the way it presents you different, like, multiple choice questions. We tried a bunch of different ways to teach people what the use cases are and whatnot. And I don't know if we like landed on the best form factor ever, but essentially it was like stuff that was sort of already working internally that people liked that we just thought we were gonna get some more signal on by releasing it. So I think forcing ourselves to release it within that 10 days that we did, it was just sort of like whatever we had, let's put it out there and then let's go out there and iterate from there, which is what we're doing.

And it blew up the internet when you launched it, so it worked out.

Yeah.

Is there a feature of Cowork today that you're either most proud of or just like can't wait to fix and improve?

Honestly, I think we're— I'm just most proud of us actually just like shipping it, to be honest, and putting it out there. And yeah, I don't know if there's like one specific thing yet, 'cause like I think when you work on something and you work on it So long, especially as a designer, you're like, I don't know if I, all I can do is see flaws in it. But I think there's a lot of stuff that I'm excited about. We have been iterating, especially on the homepage, and to make that something where it feels more like, hey, these are tasks you can give Claude and the tasks that Claude are working on. 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 gives you all these different ideas.

Mm-hmm. Yeah, yeah, yeah. And then so when you actually start to work with Claude on stuff, it feels more like a to-do list. Like it feels more like these are things Claude's working on. Um, these are things that Claude needs your attention on. And I think there's a, just a, there's an opportunity here to make it feel much more like this, like shared to-do list between you and Claude. So excited to iterate on that. And then I'm also excited to think more about Uh, yeah, like what is the actual true form factor of this? Like, is it stuck in the screen always, or how does this sort of like reach out to the different surfaces that it's working with?

I love that you shared that it wasn't just 10 days to do this thing. There's like these numbers that people throw out there, we built 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 sort of Cowork 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 Cowork that, yeah, it was not just 10 days and there was a lot of different people involved. It's one of those things where it's like the idea kept coming back and it's never the right moment or there's 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 Copilot, the way I think about it, it's like Claude with hands where you can do stuff on your computer. How would you describe it just 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 Claude 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, like any sort of use case that 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.

Hmm. I've done that many times. Okay. Coming back to managing and being a manager and the role of a designer, I wanna talk about hiring for a little bit. So seeing how much is changing in the role of a designer, what do you look for that's maybe new? 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. There's just a sense of resilience and roll with it kind of thing that I think is really important because, yeah, so much is changing around us and you have to be really willing to adapt, to try out new methods, to try out new tools and learn stuff as opposed to just be stuck in the old processes and the old ways. But then I think about also there's probably 3 archetypes of folks that are really interesting to me right now. And I think these folks were already interesting to me before, but I feel like in this era feels especially important. So the first one I would call is strong generalists. So not just regular generalists where they're kind of good at a lot of things, but people that are almost block-shaped in that T-shaped framework where it's like they're really good at a few core skills, like 80th percentile good. I think this is like pretty rare and hard to hire for, to be honest. But I like this because the design role we've already seen is kind of like stretching and spanning, right? Like we're all becoming more PM-shaped, we're all becoming engineering-shaped. And so if you already have strong skills in a few different buckets, it's really easy for you to sort of like flex around and expand your role. So That's really exciting to me. It's just somebody who is really good at a bunch of things. Again, a huge ask. And then the other person that's really exciting to me is in that T-shaped framework, like a deep specialist, like someone who is T-shaped, but like the tip of the T probably goes down farther than most other people. So folks that are maybe like the top 10% in the industry and whatnot. Again, super hard to find. And I feel very lucky that working at some of these places, folks like these, you can sort of afford to hire them and actually bring them on board. And then my last one is probably the one that I think we're all overlooking, which is what I call the craft new grad. It's just somebody who's early career and feels kind of like, wise and experienced beyond their years, but is also just like very humble and, and, and very eager to learn. I think this person is really interesting right now because I think most companies are just hiring like senior talent, like folks that have done things before, are super experienced. But given how much the roles are changing and what we're expected to do is changing, I think having somebody who almost has like a blank slate and is just a really quick learner and is really eager to learn new tactics and stuff like that and doesn't have all these baked-in 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 overlooking, but I'm really excited about.

This is awesome. On the deep T shape, what's an example of someone in design that has a— what's a skill that they're really good at?

Sometimes there's designers who are just really technical in a way where they could be 50% of soft— they're basically a software engineer. That's really interesting, especially 'cause right now a lot of it is, at least for us, it's like you're working directly with the model, so it helps when you have just deep engineering expertise. But another deep kind of specialty is just maybe they're just really good at visual design or just designing icons or something where Things like that, given that everybody can, anybody can make anything, 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, I had Marc Andreessen on the podcast, we kind of called it the F shape or E shape where there's multiple T things, sideways F, sideways E, I guess. Is that what you're describing where there's many things you're really, really good at? Yeah. Yeah.

And basically, I don't know, if you almost had their skill set, it would, it would look like a block, you know, like it would—

Because there's so many skills that like the T is spread out. Yeah. Okay. And the crack new grad. So this is just like someone that is, uh, eager and like, uh, open-minded, gritty, very smart, I imagine is a big part of it. Yeah. Awesome.

Yeah. Yeah.

If someone's like a new design, like a young designer trying to break in, trying to be successful, what would your advice be to them to help them? have a shot at joining Anthropic, for example?

I would just say just build a bunch of stuff. Try a bunch of stuff out. Build actual things. I think that can feel— I don't really know what the state of design education or education is these days, but at least from back when I was in school, everything was very theoretical and here, we're going to teach you some approaches and whatnot. But the best kind of cracked new grad folks I know are just people who just use the technology, build actual things, don't feel limited by how little experience they might have. I think that sometimes they're actually unburdened by that because we have expectations of ourselves after being in industry for so long, but they actually don't and they sort of feel like anything is possible. And so Just building a bunch of stuff and sharing it with people and finding a community of folks that also do that. Yeah, I think my one call here too is I went to a school that started something called Socratica a few years after, actually a while after I graduated. And basically their whole thing is 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 build things and do things. Like, for example, somebody built this Claude robot project. This was a few years ago too, where they were 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 a sense of both agency in terms of, yeah, we can just do stuff, but then also this community where people were just trying and building things and sharing things with each other. So Whatever that looks like, given the, you know, the school that someone's from or graduating from. Yeah, doing that kind of stuff is, is, is the stuff that will make people stand out.

For current designers that are in a mid-career, awesomely senior, do you think you need to get technical and learn to code, at least build, or do you think you could be really successful and just not lean into that and get better at other stuff?

I think it definitely helps. to maybe not learn how to code so much that you're building something from scratch, but it does feel like more and more of the designer's vocabulary right now is implementing some stuff. I wonder though, as both the models and the products get better, if we'll— I mean, we probably will continue to move up the abstraction layers and you won't have to actually know how you know, each single line of code will work. But I think what I would say is like, start to bring that into your like toolkit, the coding tools, whether or not it's like you're actually becoming technical. I think any designer should just be really aware and like know how to use the tools that are at hand as opposed to maybe like learning and like going off and, you know, learning React or, or et cetera, et cetera.

How good of a designer is Claude, would you say? Or Claude Code, would everyone describe? 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, it is not yet the strong generalist or the deep specialist or the cracked new grad. I think it's, it's pretty good at a first pass and at presenting a bunch of different ideas to you, but, uh, nothing there quite feels like, yeah, special and hireable yet.

Which is good news for designers for now, that it sucks at this for now. And I'm so curious to see how good it could get at this. That's like such a big open question is, Can it pump out amazing, novel, unique creative experiences, or is this— it's just never going to be that good as a human designer?

I mean, it's gotten a lot better in the last year or so, even. So, yeah.

There's a couple management, uh, I don't know, rituals or takes you have that I've heard from folks that you work with that I want to touch on. One is that you have this hot take that low leverage time for managers is just not a thing, that there's A lot of benefit you can get out of things that people consider low leverage. Can you talk about that?

Yeah. 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 like really prioritize your time and categorize your work. And there was like this 2 by 2 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 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 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 test the shit out of the product and they're just like so in tune with it and they dogfood it, they report the bugs, they spend a bunch of time with like engineers, like sharing the logs and like nitpicking and stuff like that. And I think that ends up being like super actually high leverage, even though it's a lot of time of like nitty gritty time. Because it creates this like familiarity with the product, which I think is really good. It also creates this vibe where it's like, oh yeah, this senior leader really cares deeply and they actually know the ins and outs of the product and they're rolling up their sleeves and they're giving this feedback and working with the team on it. And I think similarly to what I've seen is like when a senior leader is able to like fix a bug now, you know, even like I think I've actually seen like Mike Krieger before, like, put 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 another thing that I love that's a little bit more cultural is when somebody like goes out of the way to like make somebody's like anniversary card or something and like vibe code them super nice, something super nice, or make them something, a super nice card. Because I think it just shows that. Yeah, it's like an EA or somebody can put together the card, but this leader is just somebody who cares so much about their team that they put in the effort. So that's something I try to embody is choosing the seemingly low-leverage tasks that are worth my time.

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 because your reports, wouldn't expect you to spend time on this thing. And there's a lot, like the low leverage ends up being high leverage.

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

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. Talk about, I guess, this idea of roasting and encouraging that and just what you've learned about building awesome teams.

Yeah, I think it's not that I'm like, yo, you should roast each other. I'm not forcing it in that way or anything. But when I think about the sort of psychological safety and teams and people that just get along with each other, when you think about your friends, you're always sort of willing to push the boundaries a little bit and like roast them. Like, you're roasting your friends a lot, but you actually might not be roasting your coworkers a lot because you, it's, it's all just about like comfort and, and safety, right? So it's not that I'm like, oh, I want my teams to roast each other, but I think it can be a really good sign when, uh, the people on your team kind of feel comfortable just like kind of poking fun at each other a little bit. Um, and I think that also can be a good sign when folks also feel the same way about like you as a leader where it's like there's just an element of like they don't fear you as much, but they, and they feel like there's a sense of safety where if they say something, they're not gonna get fired. So an example of this is like with my last team, I feel like they would make fun of things that I would say at crits sometimes, like certain phrases I would say.

What's an example of that?

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? And they would sort of channel me in that way. Yeah, I just think it shows a level of like, okay, these people are like not necessarily afraid of me. They know that they trust me, they could trust me. And it's, and then they sort of like know enough about each other and me, like personally in our personal lives to be able to like know sort of where those boundaries are.

Yeah.

But at the same time, I think the thing that you sort of err into in that territory is like, are you, as a manager, are you friends with your reports? Which is, I think, the thing people tell you not to do. And so the way I think about balancing this out is like, this creates the— you have to create this sort of 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. And I think these 2 things can feel like they're at tension, but I think they're actually, they work really well together. Because it's like, once you have that psychological safety, you have people trusting each other and you, applying the high standards actually, I think, becomes potentially easier because you can do it without fear, I think. And I sort of think about this from the approach of kind of being a tough parent a little bit. Oh yeah, like they, my team, I work with them in a way where they know I'm always gonna be there and I'm not just gonna fire them on a whim or something. But at the same time, they also know that I want the best for them, you know, and that I have high standards and that, you know, I'm working with them to make the best work possible. And so, yeah, that's the balance I think you just strike is like, can you create this environment of one where your team feels comfortable roasting you, but at the same time, like, they know they have to be doing great work and they will do great work with you.

That is awesome advice. It's interesting how often this, this just like management style comes back or management, good management. It comes back, reminds me of what was it, Candid, Radical Candor, just this combination of caring deeply and challenging directly.

Yeah.

And that's kind of what I hear here is just make sure people know that you care deeply about them, but also be very direct and have high standards.

Yeah, yeah, exactly.

So interesting. Okay, maybe a final question. I'm always looking for interesting frameworks and methods and processes that people have found useful in their work, and I hear you're a big fan of something called the Legibility Framework. Talk about this, talk about how you use it, why it's so valuable.

Yeah, this framework, I think I saw it on Twitter of maybe last year or something, and it was Evan Tonna, who is a partner at SPC. He's a VC. So it basically is this 2x2. I don't think it got so much attention, but once I started seeing it, I actually couldn't stop thinking about it. So on the 2x2, he basically has founders. Founders can be either illegible or legible, and then ideas can either be illegible or legible. And basically he was saying that, okay, if both the founder and the idea is super legible, the idea is probably not that novel and somebody's already like, they're already going to implement it or do it and you're actually not finding something new. But then where it gets really interesting is where like the idea itself is illegible. And by illegible, he means like, oh, it's sort of like really, you know, on the frontier, people might not get it yet. Or like the way it's being told, it just doesn't, it's not like being told in the way that makes the most sense to people. And I think this is obviously a good way for a VC to operate because you're 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, at least at a frontier lab at Anthropic, is kind of spotting the ideas that are illegible and trying to understand what's there and how to take that and like transform it, whether it's through storytelling or whether it's through like the actual UX and the form factor. and put it out there. And I think there's like, when I mentioned going through Slack and looking at all the stuff that people are making, that's kind of what I'm doing. I'm trying to see like, oh yeah, what are the ideas that are really, that there's some energy there around, but might not make sense yet that are worth me thinking about more in my work? There's one good example actually that ties to Cowork, where there was this internal prototype that we've called like Claude Studio that I think somebody built like partway through last year. And essentially it was just this like really kind of like dense, powerful interface that was built on top of some agent like Harness. It might've been Claude Code at that point in time too. And it had all these like displays where it's showing you like all this knowledge and all these skills. and things Claude was doing and previewing its outputs. 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. But then I sort of saw 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 something here, but I just don't understand it yet. And I think that really was an example of an an illegible idea. And ultimately what came from it was like the skills 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. 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 Cowork and I was thinking about like, oh yeah, what is the form factor for those things? Seeing that prototype, And seeing the kinds of information that people found really helpful, like seeing Claude's plan and to-dos, seeing Claude's like context and the files that it was, it was going through. Like those kinds of things are things that I ended up pulling out of that prototype into Claude Copilot. So yeah, 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. I did a research project recently where, uh, with this guy, Terence Rohan, a VC actually, we looked at what are patterns across people that have joined companies very early that ended up being massive successes like Palantir and Stripe and, um, Linear and Notion, all these companies, like people that have joined many of these companies early, what were they looking for? And one of the factors was the idea is so, it's like so crazy that everyone's laughing at this. This is This is impossible. You're never going to do this. This is the craziest thing. Why would you even think like that? Like all the, like OpenAI actually was one of them, just like some research lab doing some stuff. So, so it's interesting that, and it's not like every time this will work and it's not like every crazy idea that sounds, makes no sense will be good. But I think what you're saying is pay attention to stuff that's like interesting to you and isn't totally clear. Maybe you can be the person that helps pull it together.

Yeah, yeah, that, but also like if there is some energy around it, but I don't quite always understand what the energy is, it's to like dive deeper and try to understand what that is. Yeah, yeah. Because I think people who often gravitate towards these early ideas, they can't always articulate why, and it's sort of up to you to like dive deeper and understand that.

That's one of— that was— so there's 3 patterns we found. One of the other ones was there's just Pay attention to people getting very excited about this thing, even if you don't get it. And it's like, sounds crazy. That's so interesting. Okay. And then what was the other one? Oh, the founders are just like top 1% was the other piece there, which everyone at Anthropic already is. So you got that one. Oh man, Jenny, what a crazy time we're living through. What a world.

What a crazy time.

So much change. Okay. Before we get to our very exciting lightning round, is there anything else that I should have asked you that you want to leave listeners with, that you want to double down on?

I think I just want to call out the Anthropic design team and shout them out, just because it's a team of folks that are just really humble, and they're not always the loudest on social, but they're doing a lot of really great work. And especially through this time where our jobs are changing so much, the team is so resilient. They sort of span this whole spectrum of people who are really technical and prototype-y, 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 internally at Anthropic, if that sounds more exciting than terrifying, would love to connect.

What sounds exciting is getting access to these Slacks where you have all the features being built.

Yeah, yeah, that's the core benefit.

Let's talk to superintelligence right now Tell me where I should invest. I'm just joking. And then in terms of hiring, is there anything specific that people should think about if they want to apply?

Think a little bit about the archetypes that I mentioned, especially the strong generalist and the deep specialist. Those folks we're really excited about. But generally folks who are—

The block and the deep tea.

The block and the deep tea. What could we be talking about? 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, and sort of want to be on the frontier.

Amazing. Well, with that, we've reached our very exciting lightning round. I've got 5 questions for you, Jenny.

Are you ready? All right, I'm ready.

Here we go. What are 2 or 3 books that you find yourself recommending most to other people?

The first one is The Power Broker by Robert Caro, which is an incredibly aggressive recommendation given that it's like 1,100 pages. But I think in this era when our attention spans are so short, I think this is actually worth reading end to end because I think there are very few collections or memoirs where it spans through someone's entire life. And you sort of see how somebody changes throughout those decades. And it's also somebody who's really controversial too. And it's nice to sort of like read a really nuanced view of somebody, Robert Moses. And I think we just lose out on some of this like long arc thinking because we're thinking so much about right now. So it's just an important reminder that careers are long and is also really good for kind of understanding how somebody just gets things done really well. So, Power Broker. The second one that I recommend to a lot of people is a book called Insomniac City, which is written by Bill Hayes, who was the partner of the scientist Oliver Sacks around the time that Oliver Sacks died. And it's just this really beautiful kind of ethereal memoir of Oliver Sacks' last days and their sort of love story. Um, I think this has like very little to do with the stuff on your podcast, Lenny, but it's just like, it's just a book that I really love. Um, and just like makes you think about mortality, but also like love and life and stuff like that. So that's one of my favorite books.

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 excellent.

Cool.

Interestingly, I saw Julie Zhu, uh, famed design leader, was reading The Power Broker recently. I don't know what's going on over here. Spreading in design land. Okay. Do you have a favorite recent movie or TV show that you really enjoyed?

Um, I watched A Sentimental Value recently. I watched it on a plane, which is, you know, how, how directors want you to watch their films. Um, but it's a, it's a Norwegian film by the same director who did The Worst Person in the World. I think just the, the pacing, the writing, and the relationship between the characters is just really subtle and beautiful. It's basically about this family, sort of a family drama, but also about this house that they lived in their entire lives. It's beautiful because the house is sort of a character. So I don't know what else to say about that, but that was a really good movie. And then I would also recommend obviously The Pit Season 2. 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. So. 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 so much like movement and stuff like that. Seems really, really hard to be an actor on.

And I only recently realized Noah Wyle was in ER as like a younger person and then now he's like the head of this thing.

Yeah.

Yeah. Oh man. Okay. Favorite product you recently discovered that you really love cannot be cowork.

Not one that I've actually discovered recently, but Retro, I've been using it for basically 2 years now since it came out. And I think I discovered new benefits of it recently. So for folks who don't know about Retro, it's sort of like this small community photo sharing app in which you can only share photos from each week, from a given week, as opposed to like all time. And it basically has like none of the social media stuff, like You can't really see like counts. It's not, there's no ads, et cetera. Um, but one really nice thing is now that I've been using it for 2 years, I can now look back at each year and see like, oh yeah, this week 2 years ago I was doing this. And it's become this really special way to like live through each week of my life, basically.

Wow. And, uh, it's also a beautifully crafted app if you're looking for building your own taste in design.

Yeah. 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?

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.

I love it.

Yeah.

Yeah. It sounds super defeatist, but I promise it's not. I think just given how much stuff is going on in the world right now, and especially with the industry and whatnot, Uh, you can't control everything. And so sometimes it is what it is just like brings the levity you need to move forward.

I went to, I did a 10-day meditation retreat a while ago and I came back from it and it's like, Dad, you've been right all along. This is the whole, 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 thoughts. Okay, final question, coming back to Cowork. 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, 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 over the years have collected it with a bunch of different notes and they span like all different things, like one-on-one notes, like random thoughts, like kind of like tiny memos, interview notes, et cetera. And my favorite, like it makes, it's cool to me, is just like using Cowork to like analyze that and have insights out of it and actually create things out of it. So like anything I, anytime I can like learn something new about myself, like I love that, but I think a very practical thing I did with it the other day was along the lines of hiring. I was like, oh yeah, I want to articulate 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 interview notes and other things that I cared about and memos and stuff like that I've written in the past. And then it made me this rubric for evaluating that. So that kind of introspection where it's like, oh, I don't even I wouldn't have realized even these things about myself that I'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, something like that, like meeting transcripts and ask it. And it's like, I was gonna ask what prompt you use, but it's just like, read all these things I've written and help me probably just like understand how I feel about what is Design craft.

Yeah, basically I think it was like, hey, I have a bunch of interview notes and a bunch of notes related to design craft in this folder. Um, read it and then help me craft a, uh, like a memo slash rubric for how I assess craft in interviews.

So cool.

Yeah.

Jenny, this was awesome. What a, what a time to be alive.

What a time.

2 final questions. Where can folks find you online if they want to reach out and how can listeners be useful to you?

Yeah, I'm on Twitter/X is what we're calling it these days. It's @jenny_wen. That's probably the best place. Not really on LinkedIn as much, so that's, that's the best place. And how can folks be helpful to me? Send us your product feedback. You know, like we're working on Cowork or anything cloud related, really. Just send us your feedback. We'd love to make it better for you.

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. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.