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

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.

>> 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 do 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

to change. We used to go off and make this 2 year 5 year 10ear vision even.

Now it becomes a vision that's 3 to 6 months out and isn't necessarily creating this beautiful deck. Sometimes

just creating a prototype that points people in the right direction.

>> Boris on the podcast recently was saying Claude Code is now helping him come up with ideas. We'll get better at taste

with ideas. We'll get better at taste and judgement and design. We might be holding on to 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 three 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 Co-work. Prior

to that, she was director of design at Figma, where she led the design teams behind Fig Jam and Slides. She was also designer at Dropbox and Square and Shopify. And what I love about this

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. It is

pretty wild and extremely interesting. A

huge thank you to no 111 and Emily Lin Hasham for suggesting topics and questions for this conversation. Don't

forget to check out lennisproass.com for an incredible set of deals available exclusively to Lenny's newsletter subscribers. Let's get into it after a

subscribers. Let's get into it after a short word from our wonderful sponsors.

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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

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

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, you know, engineering change a lot more in the in the past little while than design actually has. But I think the result of

actually has. But I think the result of engineering changing a bunch is that design is sort of forced to change. Um,

and so I think some context around this is I I did a talk at a conference in Berlin a few months ago in September and I called it like don't trust the design

process where I basically just said like hey you know this design process that designers have been taught where you go and you go off and you do a bunch of research and discovery and then you like

diverge you converge diverge converge and it's like this process that we sort of treated as gospel and and tried so hard to preserve and we were like trust the process.

that is that's basically dead. Uh I

think it was sort of dying before the age of AI, but given now that you know engineers can go off and spin off their like seven clouds, I think as as

designers, we really have to let go of that process. And I think that's the big

that process. And I think that's the big thing that's changing. But I think even in the past three to four months since I did that talk, that talk actually starts to feel pretty it kind of feels outdated to me, which is a little embarrassing.

But especially with the big shift of like Opus 46 and a bunch of folks just like really discovering and using cloud code over the holiday break, um I think

we're seeing this like force to change our pro process happen even more. the

the way I sort of see it now is like there are basically two types of design work and design work is kind of like becoming really stratified in this new world in this new world. Um so there's

like the first one which is really just like supporting the implementation and execution.

So this is the one where you know engineers are using their seven clouds to to create all these features and anybody can like put an idea out there and you can just like talk about an idea and somebody usually actually an

engineer because they're still better at implementing this stuff than we are.

They will just make a scrappy version of it and you can try it out and you as a designer actually like do not have the time to make these beautiful mocks anymore or to like kind of lead in this

way. And then I think there's like the

way. And then I think there's like the second kind of work that feels also really important which is like creating the sort of vision or direction for things. Um this one feels like the

things. Um this one feels like the hardest to make time for and it's still it's one that like we we still did before but I think the shape of it is 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 2year, 5 year whatever 10 year vision even and we're going to like point us towards something. But the way that the

towards something. But the way that the technology is changing now, like we actually don't know, we don't know what's going to happen in 2 years.

There's too much changing 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 story told. It's sometimes

just like creating a prototype that points people in the right direction.

And I think this kind of work is like still really important in this world because in a world where people can spin off their seven seven claws, make whatever features they want in any

direct in any kind of like direction or or implementation, you need to point them towards something. And in order to make sure that we're all making something that makes sense together and

is also done in a way where it's like efficient, right? like if we're all

efficient, right? like if we're all working towards something that has one greater cause, it's like much more efficient to do that than than just random things. And so that's like the

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 3 months and it might actually change even more. 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 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 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 bats. And I think it's also really

bats. 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 a and and sort of like working with engineers really closely to get the

feature across the line um and also prototype stuff in actual code as opposed to like relying on engineers to do that again. How true do you think

this this is at all companies at say AI companies non AI companies you know someone may be hearing this okay anthropic claude like okay it's like they're at the bleeding edge for one two it's like developer a little bit but I

think people might be feeling like okay I this is not going to happen at Salesforce this is not going to happen at I don't know service now wherever so I guess does do you feel like this is where all teams are heading is it mostly

AI bleeding edge companies how widespread do you think the design process shift is going to 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

anymore. You know we are using tools like claude code and and bzero 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

well. So I think there's something there emerging. But the other interesting

emerging. But the other interesting observation with that talk too was there was actually also a decent amount of like backlash like people were people clearly have invested their entire

careers in learning teaching using this like really stable design process and they were I think there was a lot of like discrediting like oh yeah like we can't do without discovery we can't do without these pieces of process. So I

think there is still a 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 engineer ship is 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,

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 the ability to execute, try something

out and try it with like real data um and and a real user like kind of mindset in the product. I think that does lead to a better product, especially as we're all working with these like new

developing AI models that are non-deterministic. You can't you just

non-deterministic. You can't you just can't you can't mock up all the states, you know, and you can't theorize and you can't even make uh like a clickable prototype with it. 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 don't 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

AI. You don't know how good it'll be at certain things the nondeterministic 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 co-work

came from and probably even cla 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

Anthropic? Just like give us a day in the life of working at Anthropic in at the center of the storm.

>> A good amount of time at Anthropic is actually just like catching up on what people what's happening at the company.

I think this is the company where I I've worked at a few other companies around this size where I think there's just a lot of like information and a lot of things going on, but I feel really

compelled to keep up with it. You know,

like there's there's stuff that is like model developments on the research side and then at any given time there are just so many different teams prototyping and trying different ideas out and

there's a bunch of different like code names and stuff like that. And a lot of time I'm just like trying to navigate and figure out what those what those projects are because I think I'm just trying to spot and see like hey what's coming up ahead for me um because

there's stuff from both the research team but also some of our like labs teams that are that are closer to research and trying out and prototyping stuff. And then there's just like stuff

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 at a normal company I'm like it's

fine. This is stuff that's happening

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 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

earlier. A big part of the design role now is helping engineers and teams execute. Not just telling them here's

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 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 to read through the things that people are working on and they're saying.

>> I never thought about how like there's already so much AI news to keep track of as a regular person and then actually seeing what's actually happening inside a lab is a whole new set of feeds to watch.

>> Yeah. Yeah. It's like I don't I think that is the the best AI news is probably internally if you're ever at one of these companies in the slack.

>> Damn. Yeah.

>> It just problem keeps getting harder of just keeping keeping track what's going on. Okay. So, okay. So, that's part of

on. Okay. So, okay. So, that's part of the job. What else?

the job. What else?

>> There is still some of like the traditional like let me think about what's happening in the in the future and let me like make some designs for that. That's something that for example

that. That's something that for example this week I've allotted some time to where I'm like okay cool. like we have been in a lot of like execution mode for co-work and now I want to set aside some

time to think about hey what do the next like 3 months look like and and where does that act where could that actually go given where the market's at where the models are at and what could that be

because I think it's still really helps to visualize that and show that to the team and point everyone in the same direction um and then I also spend a bunch of my day just jamming on stuff

with engineers like a lot of it is just a conversation or like whiteboarding or going through something that they built and giving them feedback on it and being a designer in that kind of way where

we're like consulting. Um, and then I spend a part of my day in code, you know, like polishing, implementing stuff. Sometimes what happens is an

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 do I think we're still doing all of that to some extent. like

we we have a user researcher on the team who is putting together uh both like traditional studies as well as surveys and the whole team is reading that that

the those studies and that feedback. We

are still we are still prototyping stuff. We are still I'm still mocking

stuff. We are still I'm still mocking stuff up. I think it's just I have a

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

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 etc. 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. I want to talk about how you

manager. I want to talk about how you actually are I see also what's in your AI stack. What tools are you using in

AI stack. What tools are you using in your role?

>> What is in my AI stack? Um well, we we're working on topics. So, it's we're going deep on the cloud stack. Yeah.

>> Um I am I'm using obviously like chat uh cloud chat and then but increasingly more and more cloud co-work. I've

basically shifted all of my chat use cases over to co-work um because I've been finding that yeah it sort of is better at these longer running tasks and most of the things I was asking claude

for are these these longer running tasks and then there's cloud code of course I use it mostly in the with 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 to claude as well. I've been trying to actually use cloud code more uh remotely like through both mobile and through

Slack as well. Um it's really fun for somebody to say like oh yeah this this one icons off or something and you just at mention Claude and Claude does it and then you pick up the PR and it's done.

That's been really really fun too. And

yeah I think that's just like I think we're a fully Claude house here. So yes

that's basically my stack.

>> 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 you were called?

>> Yeah. Yeah. Figates. 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 like Figma anymore? Do we need to design?

Figma anymore? Do we need to design?

What's your what's your sense? Figma is

still important. I mean, as a as a former Figmate, I I'm maybe even 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

different options. I think that's a really important part of the design process to be able to just think about like eight to 10 different ways to do something. Um, I think the best design

something. Um, I think the best design happens when you're able to just like throw a bunch of ideas at the wall and curate and just like and and push yourself to to come up with a bunch of

these different directions. Right now,

coding or or right now working with some of these coding tools doesn't lend itself super well to that because it's super linear. You super invest in one

super linear. You super invest in one direction and you just iterate with cloud on them for example. Um, so I Figma has been really great at just like exploring all these different options and I think it's still going to exist

that way to some extent. And then I think there's like really fine sort of visual and interaction details that are also really great to to to be able to just try out in Figma. Again, it's a lot

of different directions, but it's micro directions. It's being able to think

directions. It's being able to think about like different typography or styles. Having those in a canvas where

styles. Having those in a canvas where you can just explore that specifically is still so so helpful and is not something that I always want to like go directly to code in.

>> It's interesting you still use an IDE because in engineering it's clearly shifting to uh command lines, agents, ids are kind of moving moving to not be cool anymore. So it's and it makes a lot

cool anymore. So it's and it makes a lot of sense. you just want to edit some CSS

of sense. you just want to edit some CSS things, some like >> color stuff. And so I could see why not just telling the agent, hey, just come on, change this one hex value, just changing it is so much easier.

>> 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 IDs now become the 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

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

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 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 the 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 and code because right now Claude is like writing a lot of the code and it's like not always it's not always like picking up stuff in the design system and whatnot. So, as much as I can sort

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

helpful. And then on your point of trying not to go crazy, I think it's hard, you know. I think it's really hard right now. And I I see this a lot from

right now. And I I see this a lot from actually like both engineers and designers where it's like now that we're sort of capable of doing so much, we want to do more. Uh and and so I think

it's not just designers who are feeling like, oh yeah, we have to keep up with engineers. I think even engineers are

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.

>> That's so true. Oh man, how to keep up with all our agents. Our seven agents we're constantly running.

>> Yeah.

>> Okay. So then as a designer where in this profession, craft and great experience and quality and trust are such a core part of the job to help instill that in the products because

that in theory leads to really successful products and companies. How

do you just think about maintaining craft quality, trust as your products are just shipping a thousand times a day and you're not able to stay on top of them and there's no designer involved?

>> It's not that there's no designer involved. It's more just like there's

involved. It's more just like there's it's almost that there's too much for one designer uh to handle. But um I

think with this I think about where the features or products are that like where they are sort of in the cycle of adoption versus like kind of early

preview. So for example like we

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 going to have a bunch of these flaws and and we caveat that a bunch. I think Quad Co-work is actually

bunch. I think Quad Co-work is actually a good example of this where we labeled it a research preview and we put it out there knowing that hey this is like similar to our models. You know, this is the worst it's ever going to be, 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 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 going to

put it 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

better. And you have to sort of commit that. You have to show that to the

that. You have to show that to the world. You have to respond to people's

world. You have to respond to people's feedback and you have to show that you are continuously shipping and improving it because I think the way that you really lose trust around quality and releasing something early is if you

release it early and then nothing ever happens. That that is what something

happens. That that is what something that degrades a brand but whenever you put something out early like it's it's possible to do that and like maintain the brand of of your company. And I

think I think that's something that we've been doing pretty well and and I think if there's anything anyone's listening that can if anyone's listening can take away from it is like yeah we're continuing to do that and and I think

that is actually really fun for me as a designer because you put something out there and you actually learn and you get feedback about it immediately and you know what to do next.

>> 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 you all are very good at this. Everyone on the team is

at this. Everyone on the team is tweeting and just like responding to tweets and comments and and then shipping, hey, we fixed this yesterday and this is happening. So there's a clear sense of this is just today and we

know this is broken and we will fix it and and then because cloud code can code very quickly. Uh the fixes come very

very quickly. Uh the fixes come very fast.

Okay. So another big question that people are asking that I ask a lot on this podcast is around just like what skills become valuable and like another way I've been thinking about it Lex put it this way recently is where will human

brains continue to be valuable as AI gets smarter. So we've gone through this

gets smarter. So we've gone through this progression of uh 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 cloud code is now helping him come up with ideas and decide what to build which is like okay wow look at that look at it go the whole product workflows the product development process slowly get eaten up

by AI. So the question is just like

by AI. So the question is just like where will human brains still be useful at least until we have super intelligence? Do you think like a do you

intelligence? Do you think like a 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. Like I I think we we might be holding on to that a little bit too much and saying like oh yeah

like you know a 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 that like AI sense of taste will get better at the end of the

day. Someone has to decide like what is

day. Someone has to decide like what is actually going to get built and and what actually matters. And and when I think

actually matters. And and when I think about people saying like, oh, you know, like AI is just going to build this software for us, a lot of the hard parts of building software are actually like

not building it. You know, if you think about the hardest times that you've had at work, honey, is probably things like, oh, you and some other person like disagreeing about like what should go into this feature or what shouldn't go

into this feature. And those things still feel like yes, AI can weigh in, but it can't necessarily solve this dispute between you and somebody else.

And so there is something about like deciding what actually goes into the things we build which I guess is taste in some way but maybe not taste in like the way we think about like aesthetic

taste or or whatnot. There's some sort of like it's like judgment around what to do next.

>> Just watching how quickly AI had took over coding which I think a year ago definitely two years ago most people are like I don't think so. I don't think AI

will get this good and that the best engineers in the world trust it so much they're not even looking at the code anymore. Like that's where we kind it

anymore. Like that's where we kind it just made me re-evaluate 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

get there. Like even in the example you shared like it could give these two people trying to make a decision. Here's

all of the data you need to make a decision and here's why this is the right answer and just press yes. Press

one and I'll go ahead and build it.

>> 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. Yeah, I think someone will still have to decide like oh we want to 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 cloud can write all this code for you today it is still an engineer who's accountable for like does that code actually work does this actually make sense in the product so I think there's that like

decision-making/judgment layer which feels like maybe one day we won't have to do that but it's uh 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 like 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 is health versus code.

>> Yeah.

>> Okay. Another ongoing question in AIing design is just like it feels like chat bots and terminals are just like like I don't think anyone expected this to be the lasting uh user interface to AI like

chat bots. Okay. No no no this is just

chat bots. Okay. No no no this is just like a temporary stop along the journey but now it's like got even further and just terminals.

Um do you have thoughts on just I don't know where like do you think there will be a next step of how we interface with AI or do you think chat bots and terminals are are mostly where we end up? There will likely be a combination

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

tactile. We are already seeing this and playing with this within Claude, like the chat bot. Um, so we recently released a bunch of these widgets that let Claude sort of elicit and ask you

questions and also show you, you know, things like the weather and stocks and whatnot in interactive ways. And I think those have had a really good reception

because people still like to see UIs and touch them and and click them and they are much more efficient than you know typing something to to Claude. But at

the same time when we really leaned into this like chatbot paradigm like I think that just gave us this whole world of flexibility that we didn't get with these sort of like baked in UIs. Um, so

my read here is like I don't think Tad is ever going away because this opened up this like new way of like infinite ways to to work with the model and to

sort of like talk to the computer that we just didn't have before. But I think that it will still be most direct for very specific things to exist in this UI. And I think that what will probably

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 going to go away. It's

interesting that like with openclaw claude mbot 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 Wheel 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

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 and it continues to work.

>> Yeah, that totally makes sense. Yeah.

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>> Okay. I want to come back to this whole idea of management and IC. So, so you've spent you've kind of put yourself back into the IC role in a lot of ways. Talk

about that and if you think that's just like a thing design managers need to be doing.

>> Yeah, I have takes on this. Um, yeah.

So, this past year at Anthropic, I joined as an IC at first. Um, and then I managed a team for a few months in in like an orch structure that sort of

needed it. And now I'm actually back to

needed it. And now I'm actually back to doing full-time IC work. And I joined Endopic as an IC cuz I was just really excited about the kind of work that

there was to be done as an IC here, but also because I was feeling like, you know, I I I sort of want to be close to the work and I I think this feels like a

really important time to do it before I like ascend the corporate ranks, you know, and and I was having these like questions and doubts about like is is middle management like is that safe in

the future? like are is is is the way

the future? like are is is is the way that we're working actually is this going to be a job that persists into the future or or should I you know try something else

and like get my hands dirty kind of thing. Um and and to be totally fair

thing. Um and and to be totally fair like I actually love both sides of the coin like I loved I love managing people. I love like setting up teams um

people. I love like setting up teams um and being at that level but I also just really loved IC work. Like I was sort of like a reluctant manager when I did it and I was like okay I'll do it. Um, so I love both sides of these co the coin

like pretty equally. But I think actually what being an ICO across this past year has taught me is that it actually just like gave me a lot of skills that I I don't think I would have

gained if I was just managing throughout this year. Um, like the design, like I

this year. Um, like the design, like I mentioned, the design process has changed so so much in this past year and I feel like I've just picked up so many hard skills that I wouldn't have necessarily had the time to do if I was

just managing a team. Um, so that's actually the best thing it's afforded me. And I think at any point if I'm like

me. And I think at any point if I'm like managing a team again, I think it will give me the empathy and understanding of how the design process has changed. And

I think that's actually a really important thing right now because yeah, the teams are working so differently. I

think it's actually pretty hard to empathize if you are not working in that way or you're like not always like testing all the tools and trying stuff.

But yeah, like it's it's an interesting time to be a designer and if I had not worked in this environment, I don't know if I would have totally understood it or like knew what to do or how to guide my teams. So that that's sort of what this

year really gave me.

>> And so you were previously a director of design at Figma, right? How big was your team? Like how large was your or just to

team? Like how large was your or just to give people reference?

>> At the max I probably had, I think 12, 15 designers or so and and I had a few managers as well. So

>> cool. And then

>> yeah okay so you had this sense that middle management might not last what's your current feeling do you think manage design management is a thing that persists long term or do you think everyone turns into IC

>> I think as long as there is a team of people it it helps to have somebody who is managing a team like I think there is there's like real value in managers it depends kind of like what the shape of

the manager is and what they actually do but the way I think about like what a helpful manager is these days is somebody who is not just like I think pure people management like oh like just

somebody to sort of set you up help you in your career have one-on- ones make sure you're feeling like good at work I think that that is kind of not a thing as much anymore but I think somebody who

can really function as like giving the team direction as well as doing some of the people management stuff like that tied together I think is the future of what managing looks like at least for now um like somebody who can really

engage with the team in terms of like the work and giving direction there. Um,

as well as like creating the environment for them to do their best work.

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

>> I probably will. I probably will. Like I

I think I I really just love, you know, helping a team like build the best product possible. And my my motto there

product possible. And my my motto there is like whatever it takes. You know, if it's somebody that if if if the team needs somebody to give the team direction and like set up the team and whatnot, that could be me. If the team

just like needs somebody to execute on it, that could be me as well. 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 EM or even sometimes like directors there they actually make the

EM like take a rotation for a few months and and pick up a few tasks and really understand how the technology works before they become a full-time manager.

And I think design probably needs to do something similar too where I think in the past design has been much more like people management oriented. What did you find yourself most rusty in when you

went back to IC designer?

>> Actually like doing crits, you know, um and just getting criticized. Yeah.

Getting criticized. You're like, "Oh, yeah." Like it is hard to get uh it is

yeah." Like it is hard to get uh it is hard to get critical feedback and to hear it and to hear on such a regular basis because that's the thing you have to do as a designer is like it's a

pretty vulnerable exercise to share work and present it with your team and then also just get a lot of critical feedback and and take that all the time.

>> Yeah.

>> So currently you're you're leading design uh slic designing on co-work is that right?

>> Yeah.

>> Awesome. So Boris, he was on the pod recently talked about how there's like a lot of debate about what co-work should be and there's all these big ideas and he's like in the end let's just make it like a terminal basically in the product

and just kind of a fancy terminal. Is

there anything you could share about just the process of landing on where you landed for that experience of co-work? I

have it here on my monitor by the way looking at it.

>> With co-work specifically we have had a bunch of different prototypes internally of what that could look like. Um, and

it's one of those things where we tried a lot of things and then we I think we weren't really sure like when it was actually going to be ready to ship and then it was sort of like everything all at once. Like we were like, "Okay, we're

at once. Like we were like, "Okay, we're going to we're going to ship it soon."

>> It was 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. Um, and so the way it got there is actually there was a lot of different other explorations that we had internally on top of different agent

harnesses and whatnot. And we just had prototyped little parts of the different interactions that ended up in co-work.

So things like um when Claude gives you a to-do list, we tried a bunch of different form factors for that. We

tried a bunch of different form factors for the way it uh presents you different like multiple choice questions. We tried

a bunch of different um ways to teach people what the use cases are and whatnot. And I don't know if we like

whatnot. And I don't know if we like landed on the best form factor ever, but uh essentially it was like stuff that was sort of already working internally that people liked that we just thought

we were going to get some more signal on by by releasing it. So I think forcing ourselves to release it within that 10 days that we did, it was just sort of like whatever we had, 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

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

>> Yeah.

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

>> Honestly, I think we're I I'm just most proud of us actually just like shipping it to be honest. Um and putting it out there. And uh

there. And uh yeah, I don't know if there's like one specific thing yet cuz like I think when when you work on something and you work on it so long, especially as a designer,

you're like I don't know if I like, you know, I all I can do is see flaws in it.

But I think there's a lot of stuff that I'm excited about. Like we have been uh iterating especially on the homepage and to make that something where it feels

more like hey these are like tasks you can give Claude and and that tasks that Claude are working on. Um and so that actually should be rolling out. It might

already be rolled out by the time this this >> All right. So I see like this little randomizer thing where you click it and gives you all these different ideas.

>> 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 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

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 build it in 10 days. And your

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

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 the sort of co-work announcements is that it only took 10 days. But I think there there have just been so many different

explorations uh and people that have worked on different pieces of co-work yeah it was it was not just 10 days and there was a lot of different people

involved. It's it's one of those things

involved. It's it's one of those things where it's like the the idea kept coming back and it's like never the right moment or there's like different variations of it and then all of a sudden it's the right moment and it

feels like it was 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 co work is like the way I think about it it's like clawed with hands where you could do stuff on your computer.

>> Is that is what's how would you describe it just like in a sentence or two?

>> That's a good 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

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 I really like out of co-work 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.

>> I've done that many times. Okay, coming

back to managing and being a manager and the role of a designer. I want 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?

Well, I do think working specifically in the envir kind of environment that I do there there's just like a sense of like resilience and like roll with it kind of thing. Um that I think is really

thing. Um that I think is really important because yeah so much is changing around us and you have to be really willing to adapt to try out new methods to try out new tools and learn

stuff as opposed to just like be stuck in the old processes and the old ways.

Um, but then I think about also there's probably three archetypes of folks that are really interesting to me right now.

Um, and I think these folks were already interesting to me before, but I feel like is in this era feels especially important. Um, so the first one I would

important. Um, so the first one I would call is like strong generalists. Um, so

not just like regular generalists where they're like kind of good at a lot of things, but like people that are like almost like block shaped, you know, in that T-shaped framework where it's like

they're really good at like a few core skills, like 80th percentile good. I

think this is like pretty rare and hard to hire for to be honest. But I like this because the design role we've already seen is kind of like is stretching and spanning, right? Like

we're all becoming more PM shape. we're

be all becoming engineering shaped. Um,

and so if you already have strong skills in a few different buckets, it's really easy for you to sort of like flex around and expand your 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. Um, and

of things. Again, a huge ask. Um, and

then the other person that's really exciting to me is in that T-shaped framework, like a a deep specialist, like someone who's is T-shaped, but like the the the tip of the tea probably is

like goes down farther than most other people. So, folks that are maybe like

people. So, folks that are maybe like the top, you know, like 10% in the industry and whatnot. again, super hard to find. And I feel very lucky that

to find. And I feel very lucky that like, you know, working at at some of these places, like folks like these, you you can sort of afford to hire them and

and and actually bring them on board.

Um, and then my last one is probably the one that I think we're all overlooking, which is what I call the craft newrad.

Um, it's just somebody who is like early career and uh feels kind of like wise and experienced beyond their years, but

is also just like very humble and and and very eager to learn. I think this person is really interesting right now because I think most companies are just hiring

like senior talent, like folks that have done things before, are super experienced, but given how much the roles are changing and what we're expected to do is changing, I think having somebody who almost has like a

blank slate and is just like a really quick learner and is really eager to learn um new tactics and stuff like that and doesn't have like all these baked in processes and rituals in their mind,

that's super valuable. Um, so I think those are the folks that I think a lot of us are just like overlooking, but I'm like really excited about.

>> This is awesome. Uh, on the deep tea shape, what's an example of someone in design that has a like what's what's a skill that they're really good at?

>> Sometimes there's designers who are just like really technical in a way where they could be like 50% of soft they're they're basically a software engineer.

That's really interesting especially because right now like a lot of it is at least for us it's like you know you're working with directly with the model so it can it helps when you have just like deep engineering expertise. Um, but

another like deep kind of like specialist T is just, you know, maybe they're just really good at like visual design or or just like designing icons or something where things like that

given that everybody can anybody can make anything, you know, having that deep specialist slant feels like, oh yeah, they can really help differentiate the things that we're building.

>> Awesome. Okay. And then this block shape, we had Mark Andrees on the podcast. We kind of called it the F

podcast. We kind of called it the F Fshape or E shape where there's like multiple T thing. Sideways F, sideways E, I guess. Is that what you're describing where there's like many things you're really really good at?

>> Yeah. Yeah. And like basically like I don't know if you almost had their skill set, it would it would look like a block, you know, like >> there's so many skills that like the tea is spread out. Okay.

>> Okay. And the correct new grad. So this

is just like someone that is uh eager 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 at ends up joining Anthropic, for example?

>> I would just say just like build a bunch of stuff like try a bunch of stuff out, build build actual things. I I think that is that can feel I don't really know what the state of like design

education or education is these days but at least from like back when I was in school like everything was very like theoretical and like here we're going to teach you some approaches and whatnot

but like the best the best kind of like crack new grad folks I know are just like people who just like use the technology build actual things don't

feel like limited by you know how little experience they might have. I think that sometimes they're actually unburdened by that cuz like we have expectations of ourselves after being in industry for so

long, but they actually don't and they sort of feel like anything is possible.

And so just like building a bunch of stuff and and sharing it with people and finding a community of folks that uh that also do that. Um yeah, I think my my one call here too is like I went to a

school that started something called Socratica like much a few years after actually a while after I graduated and basically their whole thing is like building stuff and showcasing it almost

like a science project and I think there's just been a really cool movement there of folks who just like build things and do things. Like for example,

somebody built this like claude robot project. This was like a few years ago

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 of both like agency in terms of like yeah we can just do stuff but then also this community where people were just trying and building things and sharing things with each

other. So whatever that looks like given

other. So whatever that looks like given that, 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 make 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

other stuff? I think it definitely helps to maybe not like learn how to code so much that that uh you know you're building something from scratch but I it does feel like more and more of the

designer vocabulary right now is implementing some stuff. I wonder though as you know the the models both the models and the products get better if like

we I mean we probably will continue to like move up the abstraction layer and layers and you won't have to actually know how you know each 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

and as opposed to maybe like learning and like going off and you know learning react or or etc etc. >> How good of a designer is Claude would you say or Claude code what however you want to like would you hire Claude as a

designer or 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 crack new.

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 hirable 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

at this. That's like such a big open question is >> can it pump out amazing novel unique creative experiences or is this just never going to be that good as a as a

human designer? I mean, it's gotten 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 a manager is 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. Um yeah, I remember like first becoming a manager and I think one of the pieces like of advice that I either got from a course or a book or something

is like yeah now that you're a manager you have to uh like really prioritize your time and categorize your work and there was like this 2 by two of like I I don't remember what it was in it but you essentially say like oh these are the

things that only I can do these are the things anybody else can do and everything else you know like it's low leverage and you shouldn't do that anymore and a lot of the lowle 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

tasks. But when I think about like leaders and managers that I have respect the most, um I actually think some of the their best traits is that they

choose like lowlever tasks that they take on themselves and that actually ends up being actually a very high lever thing because it's them who's doing it.

Um, so one example is, uh, whenever you have like senior leaders who just like test the out of the product and they're just like so in tune with it.

Um, and they dog food it, they repro the bugs, they spend a bunch of time with like engineers like sharing the logs and like nitpicking and stuff like that. Um,

and I think that ends up being like super actually high leverage even though it's a lot of time of like nitty-gritty time because it creates this like familiarity with the product which I

think is really good. Uh it also creates this vibe where it's like, oh yeah, the this senior leader really cares deeply and they actually know the ins and out of the product and they're rolling up their sleeves and they're giving this

feedback and working with the team on it. Um and I think similarly too what

it. Um and I think similarly too 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 Kger before like put put in PRs himself. Um, and it's it's it's

PRs himself. Um, and it's it's it's really nice cuz it's like, okay, cool.

Like, we're all on this team together and nothing is like below this person.

Um, and I think simil another thing that I love that's a little bit more cultural is when somebody like goes out of the way to like make somebody's like anniversary card or something. um and

like vibe code them super 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 later is just somebody who cares so

much about their team that they put in the effort. So that's something I try to

the effort. So that's something I try to embody is like choosing the like the the seemingly lowlever tasks that are like worth my time.

>> Yeah, that is so interesting. Like what

you're saying there is in a sense like the low leverage stuff is the one is the stuff that often has the most impact because your reports wouldn't expect you to spend time on this thing and there's a 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 uh I don't know ritual and kind of way of running teams that I heard about you is uh you encourage uh team members roasting each other which on the surface doesn't sound like a

wonderful environment but uh on the other hand I hear constantly that the teams that you've built are just the happiest the highest performing teams. Talk about I guess this idea of roasting and encouraging that and just what

you've learned about building awesome teams. Yeah, I think it's not that I'm like, "Yo, you should roast each other," you know, like I'm not like forcing it in that way or anything. Um, but when I

think about the sort of psychological safety and teams and like people that just get along with each other, like when you think about your friends, you know, you're you're always sort of willing to like push the boundaries a little bit and like roast them. Like

you're roasting your friends a lot, but you actually might not be roasting your co-workers a lot because you it's it's all just about like comfort and and safety, right? So, it's not that I'm

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

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

little bit. Um, and I think that also can be a good sign when folks also feel the same way about like you as a leader where it's like there's just an element of like they don't they don't fear you

as much, but they and they feel like there's a sense of safety where if they say something, they're not going to get fired. Um, so an example of this is like

fired. Um, so an example of this is like with my last team, I feel like they would make fun of things that I would say at crits sometimes, like certain phrases I would say.

>> What's an example of that?

>> I don't like I Oh, I would always be like, "Okay, like what are next steps?"

And like, "How do we follow up on this?"

And then they'd be like, "Okay, like what are next steps?" Um, and 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 can they can trust

me. Um, and it's it's and then they sort

me. Um, and it's it's and then they sort of like know enough about each other and me like personally in our personal lives to be able to like know sort of where those boundaries are. Um, but at the

same time, I think the the the thing that you sort of air into in that territory is like are you as your as a manager, are you friends with your reports, which is I think the thing people tell you like not to do. And so

the way I think about balancing this out is like this creates like the you have to create this sort of like uh baseline of psychological safety and people feel comfortable both with each other and

with you, but you also have to make sure that you they know that you have really high standards. Um, and I think these

high standards. Um, and I think these two things can feel like they're at tension, but I think they're actually they work really well together because it's like once you have that psychological safety, you have people

trusting each other and you applying the high standards actually I think becomes potentially easier because you can do it without fear. I think um and I sort of

without fear. I think um and I sort of think about this from the approach of like kind of like being a tough parent a little bit, you know? It's like, oh yeah, like they my team, I work with

them in a way where they know I'm always going to be there. Um, and I'm not just going to fire them on a whim or something, but at the same time, they also know that I want the best for them,

you know, and that I have high standards and that, you know, I I'm working with them to to make the best work possible.

And so yeah, that's the balance I need to 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 and they will

do great work with you.

>> That is awesome advice. It's interesting

how often this this uh just like management style comes back or management uh good management it comes back reminds me of what was it candid radical cander 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.

>> So interesting. Okay. Maybe a final question. I'm always looking for

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 maybe last year or something and it was Evan Tana who is a partner at SPC uh he's a BC so it it basically is this

like 2 by 2 I don't think it like got so much attention but I once I started seeing it I like actually couldn't stop thinking about it so um on the 2 by 2 PBS has like founders like founders can

be either illeible or legible and then ideas can either be illegible or legible. Um, and basically he was saying

legible. Um, and basically he was saying that like, okay, if if both the founder and idea is like super legible, the idea is probably not that novel and somebody's already like they're already going to implement it or or or do it and

you're actually not finding something new. Um, but then where it gets really

new. Um, but then where it gets really interesting is where like the idea itself is illegible. And by illegible he means like oh it's sort of like really you know on the frontier people might

not get it yet or like the way it's being told it just doesn't it's not like being told in the in the in the way that makes 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 um at

least at at a at a frontier lab at anthrop topic is kind of spotting the ideas that are illeible and trying to understand what's there and how to take that and like transform it whether it's

through storytelling or whether it's through like the actual UX and the form factor and and and and put it out there.

Um and I think there's like like when I mentioned you know going through Slack and like looking at all the stuff that people are making like that's kind of what I'm doing. I'm trying to see like, oh yeah, what are the ideas that are

really that like there's like some energy there around but like might not make sense yet that that are worth me like thinking about more in my work.

There's there's one good example actually that like ties to co-work uh where there was this internal prototype that we've called like cloud studio that

I think somebody built like partway through last year. Um, and

it essentially was just this like really kind of like dense powerful interface that was built on top of some agentic harness. I I it might have been Claude

harness. I I it might have been Claude code at that point in time too. And it

had all these like displays where showing you like all this knowledge and all these skills and and things Claude was doing and like previewing it outputs. Um, and I think to a designer I

outputs. Um, and I think to a designer I looked at it and I was like this is like I don't know what's going on. I don't

really get it. Um, but then I sort of saw the folks in research, the folks building it and and just folks internally, there's just a lot of energy around it and I was like, cool. Like I

think there's like something here, but I just don't understand it yet. And I

think that really was an example of an anil illeible idea. And ultimately what came from it was like the skills framework um and and and uh like the

sort of like markdown files that sort of that instruct Claude on how to do something. So that came out of that

something. So that came out of that specific prototype that was not something I was directly involved in and that was more of like you know the folks working on this prototype extracted that out of it. But when it did come to

working on Claude co-work and I was thinking about like oh yeah what is the form factor for those things seeing that prototype and seeing the kinds of information that people found really

helpful like seeing Claude's um plan and to-dos um seeing Claude's like context and the files that it was it was going through like those kinds of things are things that I ended up pulling out of

that prototype into cloud co-work so yeah I think about like how can designers almost be more like VCs in this way internally only when we're looking at prototypes.

>> This is super interesting. I did a research project recently where uh with this guy Terrence Rohan VC actually we looked at what are patterns across people that have joined companies very

early that ended up being massive successes like Palanteer 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 so is 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 pal like all the like openi actually was one of them just like some research lab doing some stuff. So so it's interesting that and

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

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 to like dive deeper and try to understand what that is. Yeah. Yeah. Cuz

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 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.

>> Mh. 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 had anthropic radius. So, you got that one.

anthropic radius. So, you got that one.

>> Oh, man. Jenny, what a crazy time we're living through. What a so much change.

living through. What a 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? Um, I think I

just want to call out uh the Anthropic Design team um and shout them out uh just because it's a team of folks that are just really humble and they're not always allowed us on social but they're

doing a lot of really great work and especially through this time where our jobs are changing so much. Uh the team is so resilient and they're they sort of

span this whole spectrum of people who are really technical and prototypy to all the all the way to folks that are really high craft and and and delivering stuff that's that's going out the door

and is fabulous. Um and we are hiring throughout the year. So I just wanted to call that out if I didn't scare you with the way that we work internally anthropic. If that sounds more exciting

anthropic. If that sounds more exciting than terrifying um would love to connect. What sounds exciting is getting

connect. What sounds exciting is getting access to these slacks or all the features being built?

>> Yeah, that's the core benefit.

>> Let's talk to super intelligence right now and tell me where I should invest.

I'm just joking. And then in terms of hiring, is there anything specific that people should think about to if they want to apply?

>> Think a little bit about the the archetypes that I mentioned, especially the strong generalist and the deep specialist. Those folks were really

specialist. Those folks were really excited about uh but generally folks who are >> the block and the deep tea. the block

the block of the deep tea.

What could we be talking about? Uh yeah,

folks who feel like they, you know, they those archetypes resonate with them, but also folks that are just really excited about the technology have been building a lot um and and sort of

want to be on the frontier.

>> Amazing. Well, with that, we've reached our very exciting lightning round and we got five questions for you. Jenny, are

you ready?

>> All right, I'm ready.

>> Here we go. What are two or three books that you find yourself recommending most to other people?

>> The first one is The Power Broker by Robert Caro, which is an which is an incredibly aggressive recommendation given that it's a it's like 1100 pages.

Uh but I think in this era when our our when our attention spans are so short, I think this is actually worth reading end to end. Um because there I think there

to end. Um because there I think there are very few like collections or memoirs where it spans through someone's entire life and you sort of see how somebody

changes throughout those decades. Um and

it's also somebody who's really controversial too and it's it's nice to sort of like read a really nuanced view of somebody Robert Moses and I think we just lose out on some of this like long

arc thinking because we're so much we're thinking so much about right now. So,

uh, it's just an important reminder that careers are long and is also really good for kind of understanding how somebody just gets things done really well. So,

Power Broker. Um, the second one that I recommend to a lot of people is uh, a book called Insomniac City, which is written by Bill Hayes, who is was the

partner of the scientist Oliver Socks around the time that Oliver Sox died.

and it's just this like really beautiful kind of like ethereal memoir of all of her socks lost days and their sort of love story. Um, I think this has like

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

Renaissance humans. So, all of this other stuff is excellent.

>> Cool. Interestingly, I saw Julie Zoo, uh, famed design leader, was reading The Power Broker recently. I don't know what's going on over here, spreading in design.

>> 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

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

World. I think just the the pacing, the writing, the relationship between the characters is just really subtle and beautiful. Um, it's basically about this

beautiful. Um, it's basically about this family, sort of a family drama, but also about this house that they lived in the entire their entire lives. It's

beautiful cuz like the house is sort of a character. So, I don't know what else

a character. So, I don't know what else to say about that, but that was a really good movie. Um, and then I would also

good movie. Um, and then I would also recommend obviously The Pit season 2.

You know, we're on that. We're on that.

I think everybody just likes to watch people who are really competent at their jobs do something. Um, so yeah, >> 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

>> Yeah. Yeah. It just also seems really fast-paced, too. Like they do so much

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

that. Seems really really hard to be an aon.

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

>> Yeah. Yeah.

>> Oh man. Okay. favorite product you've recently discovered that you really love cannot be co-work.

>> Not one that I actually discovered recently. Um but I retro I've been using

recently. Um but I retro I've been using it for basically two years now since it came out. Um and I think I think I

came out. Um and I think I think I discovered new benefits of it recently.

So uh for folks who don't know about Retro, it's sort of like this small community photo sharing app in which you can only share um photos from each week from a given week as opposed to like all

time. Um, and it basically has like none

time. Um, and it basically has like none of the social media stuff. Like you

can't really see like counts. It's not

there's no ads, etc. 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 two years ago I was doing this and

it's become this really special way to like live through each week of my life basically.

>> Wow. And uh it's also a beautifully 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

>> Yeah.

>> Yeah.

>> It sounds super defeist, but I promise it's not. I think just given how much

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 10day 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

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.

>> It's there's so much depth to that. I

was like, "Okay, smarter than I even thought."

thought." >> Okay, final question. Coming back to co-work, is there a I don't know, mind-blowing use case, something just like, "Wow, that's so cool that Co-work

can do that either something you use it for or you've heard somebody using it for."

for." >> One thing I really like is just like introspection. And so, uh, I have this

introspection. And so, uh, I have this this folder basically of like local notes that I have from that I use like IIA writer for and I basically just like write whatever and and over the years

have collected it with a bunch of different notes and they span like all different things like one-on-one notes like random thoughts like kind of like

tiny memos, interview notes, etc. And my favorite like it makes it's it's cool to me is just like using co-work to like analyze that and have insights out of it

and actually create things out of it. Um

so like anything I anytime I can like learn something new about myself like I love that. But I think a very practical

love that. But I think a very practical thing I did with it the other day was like along the lines of hiring, I was like, "Oh yeah, I want to sort of articulate like what it is that I look for, what I look for in 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 uh for for evaluating that. So, um, that kind of introspection where it's like, "Oh, I don't even I wouldn't have realized even these things about myself that I've been putting out there

implicitly, that's been really cool for me."

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, 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.

>> 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 a memo 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.

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

>> Yeah. Um I'm on Twitterx is what we're calling it these days. Um it's

jenny_wen. That's probably the best place. Not really on LinkedIn as much.

place. Not really on LinkedIn as much.

So that's that's the best place. Um and

how can folks be helpful to me? Send us

your product feedback. You know, like we're working on co-work uh or anything cloudreated really. Just send us our

cloudreated really. Just send us our your feedback. We'd love to make it

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 with Lenny.

>> It was wonderful. Jenny, thank you. Bye,

everyone.

>> Thank you so much for listening. If you

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See you in the next episode.