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

Summary

Jenny Wen, head of design at Claude (Anthropic), argues that the traditional design process—centered on extensive research, mockups, and prototyping—is effectively dead. The rapid acceleration of engineering capabilities, driven by AI tools like Claude Code, forces designers to adapt. Instead of creating polished mockups, designers now spend more time collaborating directly with engineers, providing real-time feedback, and even implementing front-end polish themselves. The role has shifted from gatekeeper to facilitator and co-builder.

Wen breaks design work into two key modes in the AI era: supporting implementation/execution and creating vision/direction. With engineers able to spin up features quickly using AI agents, designers can’t afford to block progress with lengthy mockup phases. Instead, they focus on guiding teams toward cohesive experiences through lightweight prototypes and directional thinking. Vision work now looks 3-6 months ahead rather than years, and often takes the form of functional prototypes rather than polished decks.

At Anthropic, Wen’s daily work involves staying current with rapid internal developments, pairing with engineers, and using Claude tools extensively. She estimates that mocking/prototyping now occupies only 30-40% of her time, down from 60-70% a few years ago, with the remainder spent on collaboration and implementation. She emphasizes that maintaining quality and trust requires shipping early as “research previews” and iterating rapidly based on user feedback—building trust through speed.

Regarding hiring, Wen identifies three valuable designer archetypes in this new landscape: strong generalists (“block-shaped” individuals excelling in multiple areas), deep specialists (top 10% in specific domains), and “craft new grads” (early-career designers with fresh perspectives and learning agility). She advises designers to build actual products using available tools rather than relying solely on theoretical training.

Wen believes AI will improve at taste and judgment but that humans will remain essential for decision-making and accountability. She sees chatbots and terminals coexisting with more tactile interfaces, and encourages designers to embrace coding tools while maintaining Figma for exploration. Her management philosophy combines psychological safety with high standards, and she uses the “legibility framework” to identify promising but unclear ideas within Anthropic’s innovation pipeline.

Recommendations

Books

The Power Broker by Robert Caro — Jenny recommends this 1,100-page biography for its long-arc perspective on careers and how people get things done, contrasting with today’s short attention spans.
Insomniac City by Bill Hayes — A memoir about the author’s relationship with Oliver Sacks during Sacks’ final days, described as a beautiful reflection on love, life, and mortality.

Frameworks

Legibility framework (Evan Tana) — A 2x2 matrix evaluating founders and ideas as ‘legible’ or ‘illegible.’ Illegible ideas (frontier, unclear) paired with legible founders can signal novel opportunities. Jenny uses this to spot promising internal prototypes at Anthropic.

Movies

A Sentimental Value — A Norwegian film by the director of ‘The Worst Person in the World’ praised for its subtle pacing, writing, and character relationships, centering on a family drama involving a house that becomes a character.
The Bear season two — Recommended for its portrayal of highly competent professionals doing their jobs with intensity and precision.

Products

Retro — A photo-sharing app where users can only share photos from the current week (not all-time). Jenny appreciates its lack of social media features (counts, ads) and how after two years it provides a meaningful timeline of her life week-by-week.

Topic Timeline

00:04:54 — How AI is forcing design process changes — Jenny explains that engineering’s acceleration with AI tools is forcing design to change. The traditional design process—research, divergence/convergence cycles—is ‘basically dead.’ Designers no longer have time for beautiful mockups; instead, they must support engineers in execution and provide directional vision through prototypes.
00:09:49 — Two types of design work in the AI era — Wen stratifies design work into two categories: supporting implementation/execution (helping engineers ship quickly) and creating vision/direction (setting 3-6 month goals through prototypes rather than long-term decks). She emphasizes that in a world where anyone can spin up features, designers must provide cohesion and ensure teams work efficiently toward shared objectives.
00:17:40 — Shift in time allocation for designers — Jenny quantifies how her work distribution has changed: previously 60-70% mocking/prototyping, now only 30-40%. The remaining time shifts to jamming with engineers (30-40%) and implementation work. She uses Claude Chat, Claude Co-Work, and Claude Code extensively, often polishing front-end code directly in VS Code or via Slack.
00:28:48 — Where human judgment remains valuable — While AI will improve at taste and design judgment, Wen argues humans are still needed to decide what gets built and what matters. She compares it to radiology: AI can analyze, but someone must be accountable for decisions. The hardest parts of software aren’t building but resolving disagreements about what should be included.
00:35:52 — Returning to IC work as a manager — Wen discusses why she moved back to individual contributor work at Anthropic after being a director at Figma. She wanted hands-on experience with changing tools and processes before potentially returning to management. This gives her empathy for how design work is evolving—a shift she believes design managers need to understand firsthand.
00:46:57 — Three designer archetypes for the AI era — Jenny outlines three valuable designer profiles: strong generalists (block-shaped, excellent in multiple areas), deep specialists (top 10% in specific domains like visual design or technical implementation), and ‘craft new grads’ (early-career designers unburdened by old processes, eager to learn). She advises aspiring designers to build actual products using available tools.
00:56:52 — Management philosophy: psychological safety with high standards — Wen shares her approach to building teams where members feel comfortable ‘roasting’ each other—a sign of psychological safety. She balances this with clear high standards, similar to ‘radical candor.’ She also advocates for managers taking on ‘low-leverage’ tasks like testing products or writing anniversary cards, which demonstrate care and create disproportionate impact.
01:02:00 — Using the legibility framework to spot innovation — Jenny describes Evan Tana’s ‘legibility framework’ (founders/ideas as legible or illegible) as a tool for identifying promising but unclear ideas at Anthropic. She cites Claude Co-Work’s evolution from an illegible internal prototype called ‘Claude Studio’—which seemed confusing but had energy—to a shipped product. Designers can act like VCs by spotting and shaping illegible ideas.

Episode Info

Podcast: Lenny’s Podcast: Product | Career | Growth
Author: Lenny Rachitsky
Category: Technology Business Entrepreneurship
Published: 2026-03-01T13:31:18Z
Duration: 01:17:25

References

URL PocketCasts: https://pocketcasts.com/podcast/aff3edd0-c8a4-013a-d954-0acc26574db2/episode/a7375fcf-1405-4fac-8384-b50aa3107c71/
Episode UUID: a7375fcf-1405-4fac-8384-b50aa3107c71

Podcast Info

Name: Lenny’s Podcast: Product | Career | Growth
Type: episodic
Site: https://www.lennysnewsletter.com/podcast
UUID: aff3edd0-c8a4-013a-d954-0acc26574db2

Transcript

[00:00:00] This design process that designers have been taught, we sort of treat it as gospel.

[00:00:04] That’s basically dead.

[00:00:05] You as a designer actually like do not have the time to make these beautiful mocks anymore.

[00:00:09] A big part of the design role now is helping engineers and teams execute,

[00:00:13] not just telling them here’s the design.

[00:00:15] A few years ago, 60 to 70% of it was mocking and prototyping.

[00:00:20] But now I feel the mocking up part of it is 30 to 40%.

[00:00:23] You’re better off not blocking that, letting them cook.

[00:00:26] It’s not just designers who are feeling like, oh yeah, we have to keep up with engineers.

[00:00:29] I think even engineers are like, how do we keep up with ourselves?

[00:00:32] How to keep up with all our agents.

[00:00:33] There are seven agents who are constantly running.

[00:00:35] The result of engineering changing a bunch is that design is sort of forced to change.

[00:00:38] We used to go off and make this two-year, five-year, ten-year vision even.

[00:00:42] Now it becomes a vision that’s three to six months out

[00:00:45] and isn’t necessarily creating this beautiful deck.

[00:00:49] It’s sometimes just creating a prototype that points people in the right direction.

[00:00:52] Boris on the podcast recently was saying Cloud Code is now helping him come up with ideas.

[00:00:55] We’ll get better at taste and judgment and design.

[00:00:58] We might be holding on to that.

[00:00:59] We might be holding on to that a little bit too much.

[00:01:01] Where will human brains continue to be valuable?

[00:01:03] At the end of the day, someone has to decide what is actually going to get built

[00:01:06] and what actually matters.

[00:01:08] Someone still needs to be accountable for the decision.

[00:01:10] What do you now look for when you’re hiring designers?

[00:01:13] There’s probably three archetypes of folks that are really interesting to me right now.

[00:01:20] Today’s guest is Jenny Nguyen.

[00:01:22] Jenny was head of design for Claude, is now leading design for Claude Cowork.

[00:01:26] Prior to that, she was director of design at Figma,

[00:01:28] where she led the design teams behind FigJam and Slides.

[00:01:32] She was also a designer at Dropbox and Square and Shopify.

[00:01:35] And what I love about this conversation is that Jenny is living in the future

[00:01:39] of where design as a profession is heading.

[00:01:41] And she is here to give us a glimpse into what that looks like

[00:01:45] and how much things are going to be changing for designers.

[00:01:48] It is pretty wild and extremely interesting.

[00:01:51] A huge thank you to Noah Levin and Emily Lynn Hasham

[00:01:53] for suggesting topics and questions for this conversation.

[00:01:56] Don’t forget to check out lenny’sproductpass.com.

[00:01:58] for an incredible set of deals available exclusively to Lenny’s Newsletter subscribers.

[00:02:03] Let’s get into it after a short word from our wonderful sponsors.

[00:02:08] This episode is brought to you by Mercury.

[00:02:10] Radically different banking loved by over 300,000 entrepreneurs, including me.

[00:02:14] I switched to Mercury from Chase over a year ago, and it is such a profoundly better experience.

[00:02:20] It’s like an actual product person built a bank versus a banking person building a product.

[00:02:25] It is fast.

[00:02:26] It’s elegant.

[00:02:27] It is super easy to set up.

[00:02:28] It is fast. It’s elegant. It is super easy to set up.

[00:02:28] It’s easy to set up wires, to track my spending, to set up triggers, to move money around when accounts get low.

[00:02:33] We moved all of our invoicing to Mercury, and it is such a smoother experience than anything else we’ve tried.

[00:02:39] It’s also really easy to grant people on your team just the right amount of access to help take work off your plate.

[00:02:43] It’s free to get started.

[00:02:45] No in-person visits.

[00:02:46] No minimum balances.

[00:02:47] The product also flexes to all sizes of company, from startups to large enterprises.

[00:02:52] Just visit mercury.com to learn more and apply online in minutes.

[00:02:55] Mercury is a fintech company, not an FDIC-insured bank.

[00:02:58] You can get specific banking services provided through Choice Financial Group and Column N.A. members FDIC.

[00:03:02] This episode is brought to you by Orcus, the company behind Open Source Conductor,

[00:03:07] the orchestration platform powering modern enterprise applications.

[00:03:11] Modern systems are built on microservices, APIs, and event-driven architectures.

[00:03:16] But legacy automation tools can’t keep up.

[00:03:19] Siloed low-code platforms, outdated process management, and disconnected API tooling

[00:03:23] break down under real-world scale in constant change.

[00:03:27] Orcus Conductor provides

[00:03:28] a production-grade orchestration layer

[00:03:30] for coordinating microservices, APIs, data pipelines, human tasks, and agentic workflows

[00:03:36] with deterministic control flow, retries, observability, and governance.

[00:03:41] Built for enterprise scale,

[00:03:43] Orcus supports visual and code-first development with built-in compliance and reliability.

[00:03:48] Through a built-in MCP gateway,

[00:03:50] AI agents handle reasoning and decision-making

[00:03:52] while safely accessing existing APIs and internal systems as MCP tools.

[00:03:57] This enables agents,

[00:03:58] to operate across enterprise environments and scale from demos to production, orchestrating

[00:04:03] systems, agents, and humans together to deliver smarter outcomes faster. Learn more at orkes.io

[00:04:09] slash Lenny. That’s O-R-K-E-S dot I-O slash Lenny.

[00:04:17] Jenny, thank you so much for being here and welcome to the podcast.

[00:04:21] Yeah, excited to be here.

[00:04:22] I’ve been looking forward to this conversation because I spent a lot of time on this podcast

[00:04:26] talking about the future of software engineering, how much that role is changing,

[00:04:31] the role of product management, how much that role is changing.

[00:04:35] I haven’t spent a lot of time on how design is changing.

[00:04:38] Clearly, it is also changing in a really big way.

[00:04:42] And you have such a front row seat to where things are heading.

[00:04:46] I also know you have a lot of very strong opinions about where things are heading.

[00:04:49] So there’s a lot of stuff I want to talk about.

[00:04:52] I want to just start with this, just this broad question.

[00:04:54] How is the design process?

[00:04:56] How is the design process changing with the rise of AI?

[00:04:59] It’s changing a lot.

[00:05:01] I think it’s still also got a lot, a long way to go in terms of the way it’s changing.

[00:05:07] Like, I think we’ve actually seen, you know, engineering change a lot more in the past

[00:05:13] little while than design actually has.

[00:05:15] But I think the result of engineering changing a bunch is that design is sort of forced to

[00:05:19] change.

[00:05:20] And so I think some context around this is I did a talk at a conference in Berlin.

[00:05:26] A few months ago in September, and I called it like, don’t trust the design process, where

[00:05:31] I basically just said like, hey, you know, this design process that designers have been

[00:05:35] taught where you go and you go off and you do a bunch of research and discovery, and

[00:05:39] then you like diverge, you converge, diverge, converge.

[00:05:43] And it’s like this process that we sort of treat it as gospel and, and tried so hard

[00:05:47] to preserve.

[00:05:48] And we were like, trust the process.

[00:05:49] That is, that’s basically dead.

[00:05:51] I think it was sort of dying before the age of AI.

[00:05:54] But given now that…

[00:05:56] You know, engineers can go off and spin off their like seven clods, I think as designers,

[00:06:03] we really have to let go of that process.

[00:06:06] And I think that’s the big thing that’s changing.

[00:06:08] But I think even in the past three to four months since I did that talk, that talk actually

[00:06:13] starts to feel pretty, it kind of feels outdated to me, which is a little embarrassing, but

[00:06:18] especially with the big shift of like Opus 4.6 and a bunch of folks just like really

[00:06:22] discovering and using clod code over the holiday break.

[00:06:25] I think we’re seeing this like force to change our process happen even more.

[00:06:32] The way I sort of see it now is like, there are basically two types of design work and design

[00:06:38] work is kind of like becoming really stratified in this new world, in this new world.

[00:06:42] So there’s like the first one, which is really just like supporting the implementation and

[00:06:46] execution.

[00:06:48] So this is the one where, you know, engineers are using their seven clods to create all these

[00:06:53] features.

[00:06:54] And anybody can like put an app on it.

[00:06:55] Yeah.

[00:06:55] You can put an idea out there and you can just like talk about an idea and somebody

[00:06:59] usually actually an engineer, because they’re still better at implementing this stuff than

[00:07:02] we are.

[00:07:03] They will just make a scrappy version of it and you can try it out.

[00:07:07] And you as a designer actually like do not have the time to make these beautiful mocks

[00:07:11] anymore or to like kind of lead in this way.

[00:07:15] And then I think there’s the second kind of work that feels also really important, which

[00:07:20] is like creating the sort of vision or direction for things.

[00:07:23] This one feels like the hardest to.

[00:07:25] Make time for, and it’s still, it’s one that like we, we still did before, but I think

[00:07:31] the shape of it’s very much changing.

[00:07:32] Cause I think we used to go off and say, you know, we’re going to do this design vision.

[00:07:35] We’re going to go off and make this like two year, five year, whatever, 10 year vision

[00:07:40] even.

[00:07:40] And we’re going to like point us towards something, but the way that the technology is changing

[00:07:45] now, like we actually don’t know, we don’t know what’s going to happen in two years.

[00:07:49] There’s too much changing and it’s usually becomes a vision that’s like three to six

[00:07:54] months out.

[00:07:55] And isn’t necessarily something that is like creating this like beautiful deck.

[00:08:00] That’s like beautifully story told.

[00:08:02] It’s sometimes just like creating a prototype that points people in the right direction.

[00:08:06] And I think this kind of work is like still really important in this world because in

[00:08:10] a world where people can spin off their second seven clods, make whatever features they want

[00:08:14] in any direct, in any kind of like direction or, or in implementation, you need to point

[00:08:20] them towards something.

[00:08:21] And in order to make sure that we’re all making something that makes sense together.

[00:08:25] And it’s also done in a way where it’s like efficient, right?

[00:08:28] Like if we’re all working towards something that has one greater cause, it’s like much

[00:08:32] more efficient to do that than, than just random things.

[00:08:36] And so that’s like the big shift that I’m seeing.

[00:08:38] And I think I have opinions about it now, but ask me in like three months and it might

[00:08:42] actually change even more.

[00:08:44] So what you’re saying here is it’s not like you or the design field is like, we need to

[00:08:49] change.

[00:08:50] It’s engineering.

[00:08:51] And the fact that you can build so quickly just forces.

[00:08:54] Uh,

[00:08:55] the role of a designer to change, because as you said, engineers can just ship, ship,

[00:08:59] ship, ship, ship.

[00:09:00] And what you’re finding here is like, you’re better off not blocking that, letting them

[00:09:05] cook as they say.

[00:09:06] And, uh, and then there’s kind of this mode of helping them along as they ship, bring

[00:09:11] it together, make sure it all kind of connects, guide them a little bit.

[00:09:15] Yeah, I think so.

[00:09:16] Yeah.

[00:09:16] I don’t think there is like one unifying voice.

[00:09:18] It’s like designers, we need to change right now, but there, yeah, there is sort of like

[00:09:22] the, the follow-on effects of engineering.

[00:09:25] I think we’ll probably see design tooling change in this next year or so as well, but

[00:09:31] a lot of it right now is trailing bats.

[00:09:34] And I think it’s also really empowering for us too, because as designers, we also now

[00:09:38] have access to a lot of these coding tools and we can be a part of the process in a way

[00:09:43] where we’re implementing stuff.

[00:09:45] Like it’s like, I’m, I’m, I’m doing a lot of last mile stuff where I’m implementing

[00:09:49] all the polish and like, and, and sort of like working with engineers really closely

[00:09:53] to get the feature across the line.

[00:09:55] Um, and also prototype stuff in actual code, as opposed to like relying on engineers to

[00:10:01] do that again.

[00:10:02] How true do you think this, this is at all companies at say AI companies, non-AI companies,

[00:10:08] you know, someone may be hearing this.

[00:10:09] Okay.

[00:10:10] Anthropic, Claude, like, okay.

[00:10:11] It’s like, they’re at the bleeding edge for one, two, it’s like developer-y a little bit,

[00:10:15] but I think people might be feeling like, okay, this is not going to happen at Salesforce.

[00:10:19] This is not going to happen at, I don’t know, ServiceNow or wherever.

[00:10:22] So I guess, do you feel like this is where all teams are?

[00:10:25] Is it mostly AI, bleeding edge companies?

[00:10:29] How widespread do you think the design process shift is going to be?

[00:10:32] So the talk that I did last year has weirdly been like the most resonant talk that I’ve

[00:10:38] done.

[00:10:39] And I, so I think it’s something that people are starting to feel across the industry where

[00:10:44] they’re like, oh yeah, we can’t do the old design process anymore.

[00:10:47] You know, we are using tools like CloudCode and, and B0 and whatnot to, to start to spin

[00:10:53] up prototypes.

[00:10:54] And PMs are starting to spin.

[00:10:55] They’re starting to spin up prototypes and stuff like that as well.

[00:10:57] So I think there’s something there emerging, but the other interesting observation with

[00:11:01] that talk too, was there was actually also a decent amount of like backlash.

[00:11:05] Like people were, people clearly have invested their entire careers in learning, teaching,

[00:11:12] using this like really stable design process.

[00:11:14] And they were, I think there was a lot of like discrediting, like, oh yeah, like we

[00:11:17] can’t do without discovery.

[00:11:18] We can’t do without these pieces of process.

[00:11:20] So I think there is still a piece of the industry that is not quite there yet.

[00:11:25] In terms of this way of working, if that makes sense.

[00:11:28] Yeah.

[00:11:29] Yeah.

[00:11:29] And a big part of this is like, you could argue, like the question is what leads to

[00:11:33] the best, most successful products and companies.

[00:11:35] And you could argue it’s spending time doing discovery, user research, mocks, iterating,

[00:11:40] beta testing, or it could be just engineer ship of stuff.

[00:11:44] That’s okay.

[00:11:45] Not amazing.

[00:11:46] Good enough.

[00:11:46] We learn, iterate, build, iterate.

[00:11:49] Is your sense that that second path is not only is that just like what everyone’s doing,

[00:11:53] but that actually leads to the better product?

[00:11:55] I think you sort of have to choose and use your discretion as to like when to actually

[00:11:59] ship something.

[00:12:00] But I think the, the ability to execute, try something out and try it with like real data

[00:12:07] and a real user’s like kind of mindset in the product, I think that does lead to a better

[00:12:13] product, especially as we’re all working with these like new developing AI models that are

[00:12:18] non-deterministic.

[00:12:19] You can’t, you just can’t, you can’t mock up all the states, you know, and you can’t

[00:12:23] theorize and you can’t even, you know, you can’t, you can’t, you can’t, you can’t, you

[00:12:25] can’t, you can’t, you can’t, you can’t, you can’t, you can’t, you can’t, you can’t, you

[00:12:25] can’t make like a clickable prototype with it.

[00:12:27] You sort of have to use the actual models underneath and you have to sort of see people

[00:12:31] try it out with their use cases because with these models, like you discover, you can design

[00:12:37] them for different use cases, but you don’t, you have to discover use cases as you see

[00:12:41] people using them.

[00:12:42] So, yes.

[00:12:43] The other thing I always hear and building on what you just said is just, you don’t know

[00:12:46] what people will do with AI.

[00:12:48] You don’t know how good it’ll be at certain things, the non-deterministic piece of it.

[00:12:52] So you can create these amazing mocks of what it might be.

[00:12:55] And then people use it in a completely different way, which is where cohort came from and probably

[00:13:00] even cloud code at the beginning.

[00:13:01] And so, so what’s it, what’s it just like to be a designer at Anthropic?

[00:13:06] Just like give us a day in the life of working at Anthropic at the center of the storm.

[00:13:11] A good amount of time at Anthropic is actually just like catching up on what people, what’s

[00:13:18] happening at the company.

[00:13:19] I think this is the company where I’ve worked at a few other companies around this size,

[00:13:24] where I think there’s just a lot of like information and a lot of things going on, but I feel

[00:13:30] really compelled to keep up with it.

[00:13:31] You know, like there’s, there’s stuff that is like model developments on the research

[00:13:35] side.

[00:13:36] And then at any given time, there are just so many different teams prototyping and trying

[00:13:42] different ideas out.

[00:13:43] And there’s a bunch of different like code names and stuff like that.

[00:13:46] And a lot of time I’m just like trying to navigate and figure out what those, what those

[00:13:49] projects are, because I think I’m just trying to spot and see like, Hey, what’s coming up

[00:13:53] ahead for me?

[00:13:54] Um, because.

[00:13:54] Because there’s stuff from both the research team, but also some of our like labs teams

[00:13:59] that are, that are closer to research and trying out and prototyping stuff.

[00:14:03] And then there’s just like stuff I want to try out.

[00:14:05] You know, like we have a bunch of like, we have a bunch of prototypes and products internally

[00:14:09] that we can use.

[00:14:11] And I am just curious and I want to try those things out.

[00:14:15] And then I think there’s also a lot of folks who internally have a lot of insights and

[00:14:20] opinions on where the industry is going.

[00:14:23] And some of those are just like really interesting.

[00:14:24] It’s interesting to read because a lot of these are like philosophical debates or directions

[00:14:29] of the company and stuff like that.

[00:14:31] And yeah, I feel like I just want to keep up with these things.

[00:14:34] Whereas I think at a normal company, I’m like, it’s fine.

[00:14:36] This is stuff that’s happening outside of my reach.

[00:14:38] I don’t, I don’t really care as much where here, I think that it’s both the volume and

[00:14:43] the kinds of things that are happening that I’m really interested in keeping up with.

[00:14:47] Um, and then aside from that sort of keep up, but that’s not a huge part of my job, but

[00:14:51] I do think it’s a really interesting part of it.

[00:14:53] Well, it connects to the point you made.

[00:14:54] Earlier, a big part of the design role now is helping engineers and teams execute, not

[00:15:00] just telling them here’s the mock, here’s the design.

[00:15:02] It’s helping them stay on track, helping them connect ideas, create a cohesive experience

[00:15:06] as it’s happening.

[00:15:07] So that makes sense.

[00:15:08] Yeah.

[00:15:09] Yeah.

[00:15:10] Yeah.

[00:15:11] And I think part of it is just curiosity.

[00:15:12] You know, like it feels like I have this front row seat to so much happening in the industry.

[00:15:15] And so a lot of it is like, yeah, our Slack is a goldmine, you know, like I’m just excited

[00:15:19] to re to read through the things that people are working on and they’re saying.

[00:15:22] I never thought about how, like.

[00:15:24] There’s already so much AI news to keep track of as a regular person.

[00:15:27] And then actually seeing what’s actually happening inside a lab is a whole new set of feeds to

[00:15:32] watch.

[00:15:33] Yeah.

[00:15:34] Yeah.

[00:15:35] It’s like, I think that is the best AI news is probably internally.

[00:15:39] If you’re ever at one of these companies in the Slack.

[00:15:41] Damn.

[00:15:42] Yeah.

[00:15:43] Yeah.

[00:15:44] Just problem keeps getting harder.

[00:15:45] I’m just keeping keeping track.

[00:15:46] What’s going on?

[00:15:47] Okay.

[00:15:48] So, okay.

[00:15:49] So that’s part of the job.

[00:15:50] What else?

[00:15:51] There is still some of like the traditional, like, let me think about what’s happening

[00:15:52] in the, in the future.

[00:15:53] And let me like.

[00:15:54] I think the, there’s still a lot of benefit there.

[00:15:56] But, I feel like there’s still a lot of flexibility.

[00:15:57] I still have to work with a lot of people.

[00:15:58] And even though I am, I don’t think that’s something that I have to work on.

[00:15:59] But.

[00:16:00] I’m getting more part of it.

[00:16:01] And I just think it’s, I think the way I can schedule things, I’m about to get more

[00:16:02] into, like, you know, going to like business

[00:16:19] things and, and getting into like like, you know, like, like the digital stuff and, and,

[00:16:20] you know, kind of, like the, the established business.

[00:16:21] You know, I, I just think it’s, it’s quite a good way to do that.

[00:16:22] Right.

[00:16:23] day just jamming on stuff with engineers. Like a lot of it is just a conversation or like

[00:16:28] whiteboarding or going through something that they built and giving them feedback on it and

[00:16:34] being a designer in that kind of way where we’re like consulting. And then I spend a part of my day

[00:16:40] in code, you know, like polishing, implementing stuff. Sometimes what happens is an engineer and

[00:16:46] I have worked through something and they’ve implemented a first version of it and I just

[00:16:51] go in and polish it with them. And that’s a really fun part of my job that I think

[00:16:56] didn’t exist as much a few months ago. Are you still doing elements of the traditional

[00:17:01] design process? Prototyping, user research, panels, I don’t know, just like going out and

[00:17:07] you know, like the whole thing you described. Yeah, we’re still doing, I think we’re still

[00:17:11] doing all of that to some extent. Like we have a user researcher on the team who is putting

[00:17:17] together both like traditional studies as well as surveys. And

[00:17:21] the whole team is reading that, those studies and that feedback. We are still, we are still

[00:17:28] prototyping stuff. We are still, I’m still mocking stuff up. I think it’s just, I have a wider set of

[00:17:35] tools now. And I think the proportion of time I spend doing each thing just has changed.

[00:17:40] Got it. Okay. So that’s a really interesting takeaway. It used to be, that was a huge,

[00:17:45] like, I guess what would be the pie chart of what your life was before where it’s like traditional

[00:17:51] thinking, planning, prototyping, mocking, research, and then just like feedback and

[00:17:56] execution and now today? Yeah, I think as a designer a few years ago, I would say like maybe

[00:18:03] 60 to 70% of it was like mocking and prototyping stuff up. And then spending, you know, the last

[00:18:12] 20 or so, some of the last 20 or so, like doing the sort of like jamming with engineers,

[00:18:18] consulting with them, and the last like 10%, maybe.

[00:18:21] You know, coordination meetings, et cetera. But now I feel like the mocking up part of it is like

[00:18:27] 30 to 40%. And then there’s that other 30 to 40% there that is now jamming and pairing directly

[00:18:35] with engineers. And then there’s like a slice, I don’t know how much I have left, but like there’s

[00:18:39] a slice of it that is now like implementation as well. Yeah. Like actually building and shipping.

[00:18:45] Yeah. Amazing. So kind of following that thread, what’s in your AI stack? What do you,

[00:18:50] as a designer?

[00:18:51] I know you’re a manager and I want to talk about how you actually are IC also. What’s in your AI

[00:18:55] stack? What tools are you using in your role? What is in my AI stack? Well, we’re philanthropic,

[00:19:00] so we’re going deep on the cloud stack. I’m using obviously like chat, cloud chat,

[00:19:08] but increasingly more and more cloud co-work. I’ve basically shifted all of my chat use cases over to

[00:19:15] co-work because I’ve been finding that, yeah, it sort of is better at these longer running tasks.

[00:19:20] And most of the things that I do are like, I’m going to do this, I’m going to do that.

[00:19:21] I was asking cloud for, are these, these longer running tasks? And then there’s cloud code. Of

[00:19:26] course, I use it mostly in the, with, with VS code and the IDE, because I’m usually tweaking front

[00:19:32] end stuff and it helps to just like be able to see the code and then talk to, to cloud as well.

[00:19:37] I’ve been trying to actually use cloud code more remotely, like through both mobile and through

[00:19:43] Slack as well. It’s really fun for somebody to say like, oh yeah, this, this one icon’s off or

[00:19:50] something. And you just add my code and it’s like, oh yeah, this, this one icon’s off or something.

[00:19:50] And you just add my code and it’s like, oh yeah, this, this one icon’s off or something. And you just

[00:19:50] add my code and it’s like, oh yeah, this, this one icon’s off or something. And you just add my

[00:19:51] code and it’s like, oh yeah, this, this one icon’s off or something. And you just add my code and

[00:19:51] cloud does it. And then you pick up the PR and it’s done. That’s been really, really fun too.

[00:19:57] And yeah, I think that’s just like, I think we’re a fully cloud house here. So

[00:20:00] yes, that’s basically my stack.

[00:20:03] Are you still using Figma as a designer?

[00:20:05] I am still using Figma. Yes. Yes.

[00:20:07] Okay. I was waiting to hear. Okay. So Figma is still part of your, your life.

[00:20:12] Being a former Figma mate, is that, is that what you all were called?

[00:20:15] Yeah. Yeah. Figma mates. Yeah.

[00:20:15] Yeah. Okay. So I know there’s this big debate on Twitter, just like,

[00:20:19] is code the future of design? Do we need a Figma anymore? Do we need a design?

[00:20:24] What’s your, what’s your sense? Figma is still important.

[00:20:27] I mean, as a, as a former Figma mate, I maybe I’m biased in that way, but I, I think there is still

[00:20:32] like when I use Figma, I’m like, yes, this is what I should be using. And it still fills a very good

[00:20:38] gap for me. I think a lot of that is actually just like, one is exploring a lot of different

[00:20:44] options. I think that’s a really important part of the design process to be able to just think

[00:20:49] about like,

[00:20:49] eight to 10 different ways to do something. I think the best design happens when you’re able

[00:20:54] to just like throw a bunch of ideas at the wall and curate and just like, and, and push yourself

[00:21:00] to, to come up with a bunch of these different directions. Right now coding or, or right now

[00:21:05] working with some of these coding tools doesn’t lend itself super well to that because it’s super

[00:21:09] linear. You could super invest in one direction and you just iterate with a lot on them, for

[00:21:14] example. So I, Figma has been really great at just like exploring all these different options.

[00:21:19] And I think it’s still going to exist that way to some extent. And then I think there’s like really

[00:21:24] fine sort of visual and interaction details that are also really great to, to, to be able to just

[00:21:31] try out in Figma. Again, it’s a lot of different directions, but it’s micro directions. It’s being

[00:21:36] able to think about like different typography or styles, having those in a canvas where you can

[00:21:43] just explore that specifically is still so, so helpful and is not something that I always want

[00:21:49] to go directly to code in.

[00:21:51] It’s interesting you still use an IDE because in engineering it’s clearly shifting to command lines,

[00:21:57] agents, IDs are kind of moving, moving to not be cool anymore. So it’s, and it makes a lot of sense.

[00:22:02] You just want to edit some CSS things, some like color stuff. And so I could see why not just telling

[00:22:08] the agent, Hey, just come on, change those one hex value. Just changing it is so much easier.

[00:22:12] Yeah. It’s really annoying to be like, can you change this to this class when you can just

[00:22:16] go in and change it to a different class?

[00:22:18] So that’s interesting. I wonder,

[00:22:19] if IDEs now become the useful for designers and PMs and engineers have moved on.

[00:22:23] Yeah, maybe. Yeah.

[00:22:25] Okay. So a lot of your time you spend working with engineers, giving them feedback,

[00:22:29] kind of nudging them in the right direction. There’s a sense I feel of just like, like your

[00:22:34] advice is like, let go. Don’t feel like you need to be this gatekeeper, but there’s this piece of,

[00:22:40] okay, help them move in a direction that is cohesive and is creating products we’re proud of.

[00:22:46] A lot of designers I think are in this boat right now. I’m just like, Oh my God,

[00:22:49] I can’t get out of this.

[00:22:49] I can’t keep up with all these engineers shipping stuff all day. What’s something you learned about

[00:22:53] just either how to help your engineers get better at design so that it just ends up being better

[00:23:00] or just kind of keeping on top of this and not going crazy.

[00:23:03] Whenever I do work with engineers on projects and it’s more on like a consulting basis,

[00:23:09] I do just try to explain, you know, why I’m thinking a way that I’m thinking to help them

[00:23:14] like extract principles as opposed to me just being like, no, I don’t think this would go here.

[00:23:19] It’s like, no,

[00:23:19] I think we should have a button here because not everybody realizes you can prompt this.

[00:23:24] And here’s an example where it comes from research and whatnot.

[00:23:27] So I also just like try to point engineers to our design system and stuff like that in code because

[00:23:33] right now Claude is like writing a lot of the code and it’s like not always, it’s not always like

[00:23:37] picking up stuff in the design system and whatnot. So as much as I can sort of equip them with stuff

[00:23:41] that they can use in the future without me, that’s helpful. And then on your point of,

[00:23:49] trying not to go crazy, I think it’s hard. You know, I think it’s really hard right now.

[00:23:53] And I see this a lot from actually both engineers and designers where it’s like,

[00:23:58] now that we’re sort of capable of doing so much, we want to do more. And so I think it’s not just

[00:24:04] designers who are feeling like, oh yeah, we have to keep up with engineers. I think even engineers

[00:24:08] are like, how do we, how do we keep up with ourselves right now? So that’s something I’m

[00:24:12] hearing a lot.

[00:24:12] That’s so true. Oh man. How to keep up with all our agents, our seven agents we’re constantly

[00:24:17] running.

[00:24:17] Yeah.

[00:24:18] Yeah.

[00:24:18] Okay. So then,

[00:24:20] as a designer where in this profession, craft and great experience and quality and trust are

[00:24:26] such a core part of the job to help instill that in the products, because that in theory

[00:24:32] leads to really successful products and companies. How do you just think about

[00:24:37] maintaining craft quality trust as your products are just shipping a thousand times a day and

[00:24:43] you’re not able to stay on top of them and there’s no designer involved?

[00:24:45] It’s not that there’s no designer involved. It’s more just like there’s,

[00:24:49] it’s almost like there’s too much for one designer to handle. But I think with this,

[00:24:56] I think about where the features or products are that like where they are sort of in the cycle

[00:25:03] of adoption versus like kind of early preview. So for example, like we sometimes will launch things

[00:25:11] and we will say, Hey, this is a research preview. It’s, it’s early. It’s going to have a bunch of

[00:25:16] these flaws. And, and we caveat that a bunch. I think.

[00:25:19] Quad cowork is actually a good example of this, where we labeled it a research preview

[00:25:23] and we put it out there knowing that, Hey, this is like similar to our models. You know,

[00:25:28] this is the worst it’s ever going to be, but we’re going to put it out there because we believe,

[00:25:32] you know, internally, we’ve tried it a bunch and there’s something really powerful here that

[00:25:36] some people will benefit from. It might not yet be the easiest to work with. It might

[00:25:41] not be the highest quality. It might have some issues with it, but we’re going to put it out

[00:25:45] there because we believe the benefits outweigh the cons.

[00:25:49] I think that is like, okay to do, especially when there is something really valuable with

[00:25:55] the product already and it’s worth putting out there. But I think the promise you sort of have

[00:25:59] to make your users is, is like, Hey, we’re going to put it out there, but we’re going to, we’re

[00:26:04] going to iterate. We’re going to take your feedback and we’re going to iterate and we’re

[00:26:06] going to make it better. And you have to sort of commit that you have to show that to the world.

[00:26:10] You have to respond to people’s feedback and you have to show that you are continuously shipping

[00:26:14] and improving it. Because I think the way that you really lose trust around quality,

[00:26:18] and releasing something early is if you release it early and then nothing ever happens.

[00:26:23] That is something that degrades a brand. But whenever you put something out early,

[00:26:28] like it’s possible to do that and like maintain the brand of your company. And I think,

[00:26:34] I think that’s something that we’ve been doing pretty well. And I think if there’s anything

[00:26:38] anyone’s listening to that can, if anyone’s listening can take away from it is like, yeah,

[00:26:43] we’re continuing to do that. And, and I think that is actually really fun for me as a designer because

[00:26:48] you put something out there and you actually learn and you get feedback about it immediately.

[00:26:53] And you know what to do next.

[00:26:55] The way I’ve heard you describe this as building trust through speed.

[00:26:58] Yeah, for sure. It’s yeah, it’s building trust through speed, but also just like making

[00:27:02] people feel like they’ve been heard and that we’re fixing things based on what they’re

[00:27:06] trying to use it for. And their feedback is actually appreciated and used.

[00:27:11] Yeah. It’s clear when, when the labs launch stuff and y’all are very good at this, everyone on the

[00:27:17] team is tweeting and they’re like, oh, we’re going to do this. We’re going to do this. We’re going to

[00:27:18] do this. And just like responding to tweets and comments and, and then shipping, hey, we fixed

[00:27:22] this yesterday and this is happening. So there’s a clear sense of this is just today and we know

[00:27:28] this is broken and we will fix it. And, and then because cloud code can code very quickly,

[00:27:33] uh, the fixes come very fast. Okay. So another big question that people are asking that I ask

[00:27:40] a lot on this podcast is around just like what skills become valuable. And like another way

[00:27:45] I’ve been thinking about it, Lex put it this way recently is where will human brains,

[00:27:48] and human language skills continue to be valuable as AI gets smarter.

[00:27:51] So we’ve gone through this progression of. Uh, tab completing Ella segments of code

[00:27:57] to a hundred percent of code is written by AI now. Like it’s crazy to now AI is reviewing its

[00:28:03] own code. Boris on the podcast recently was saying cloud code is now helping them come up with ideas

[00:28:08] and decide what to build, which is like, okay, wow. Look at that league to go the whole

[00:28:12] product workflows, the product development process slowly getting eaten up by AI.

[00:28:17] So the question,

[00:28:18] is just like where will human brains still be useful at least until we have super intelligence

[00:28:23] do you think like do you think ai is going to get very very good at taste judgment design

[00:28:29] i think it will get better at taste and judgment and design yeah like i i think we

[00:28:34] we might be holding on to that a little bit too much and saying like oh yeah like

[00:28:41] you know a designer or somebody will always know the the best thing to ship or the best version

[00:28:47] of this and i but i do think ai that like ai sense of taste will get better at the end of the day

[00:28:53] someone has to decide like what is actually going to get built and and what actually matters and and

[00:28:59] when i think about people saying like oh you know like ai is just going to build this software for

[00:29:03] us a lot of the hard parts of building software are actually like not building it you know if

[00:29:10] you think about the hardest times that you’ve had at work letting is probably things like

[00:29:13] oh you and some other person like disagreeing about like what should go in

[00:29:17] this feature or what shouldn’t go into this feature and those things still feel like yes

[00:29:23] ai can weigh in but it can’t necessarily solve this dispute between you and somebody else and

[00:29:28] so there is something about like deciding what actually goes into the things we build which i

[00:29:35] guess is taste in some way but maybe not taste in like the way we think about like aesthetic taste

[00:29:39] or or whatnot there’s some sort of like it’s like judgment around what to do next just watching how

[00:29:46] quickly ai had took over coding which i think a year ago definitely two years ago most people are

[00:29:52] like i don’t think so i don’t think ai will get this good and that the best engineers in the world

[00:29:59] trust it so much they’re not even looking at the code anymore like that’s where we’ve gone it just

[00:30:03] made me reevaluate all these assumptions i’ve had about okay ai will never be as good as really good

[00:30:10] pms designers at judging what is great and deciding what to build but i’m just like starting to think

[00:30:15] i think

[00:30:16] it will get there like even an example you shared like it could give these two people trying to make

[00:30:20] a decision here’s all of the data you need to make a decision and here’s why this is the right

[00:30:25] answer and just press yes press one and i’ll go ahead and build it so i think we’re just yeah to

[00:30:32] your point i think we undervalue just how good it’ll get at this stuff okay so your sense is

[00:30:37] it’ll get better but your senses will still need awesome designers to be involved awesome pms to

[00:30:44] help make these decisions engineers

[00:30:46] you

[00:30:46] yeah yeah i think someone will still have to decide like oh we want to build this kind of

[00:30:50] product or like given what the ai is presenting us like someone still needs to be accountable for

[00:30:55] the decision you know the same way that like even though claude can write all this code for you

[00:31:00] today it is still an engineer who’s accountable for like does that code actually work does this

[00:31:06] actually make sense in the product so i think there’s that like decision making such judgment

[00:31:10] layer which feels like maybe one day we won’t have to do that but it’s uh

[00:31:16] it still falls on us yeah it doesn’t make sense it makes me think about the radiology

[00:31:20] example where there’s always the sense that ai is going to take over that field of radiology and

[00:31:24] tell you what is going on but like the human is mostly useful for signing off on the decision

[00:31:29] because someone needs to be liable if they’re wrong um which isn’t the best job in the world

[00:31:34] but uh but that’s a different game as hell versus code yeah okay another ongoing question in ai and

[00:31:43] design is just like it feels like chatbots and terminals are just like the same thing but they’re

[00:31:46] like like i don’t think anyone expected this to be the lasting uh user interface to ai like chatbots

[00:31:52] okay no no this is just like a temporary stop along the journey but now it’s like not even

[00:31:57] further and just terminals um do you have thoughts on just i don’t know where like do you think there

[00:32:02] will be a next step of how we interface with ai or do you think chatbots and terminals are

[00:32:07] are mostly where we end up there will likely be a combination of both like both uis and interfaces

[00:32:13] that you are interacting with and you’re interacting with and you’re interacting with

[00:32:16] with clicking with and and that feel like more tactile we are already seeing this and playing

[00:32:22] with this within claude like the chat but um so we recently released a bunch of these widgets that

[00:32:29] let claude sort of elicit and ask you questions and also show you you know things like the weather

[00:32:34] and stocks and whatnot in interactive ways and i think those have had a really good reception

[00:32:38] because people still like to see uis and touch them and and click them and they

[00:32:45] are much more interactive and they’re more interactive and they’re more interactive and

[00:32:46] more efficient than you know typing something to to claude but at the same time when we

[00:32:51] really leaned into this like chatbot paradigm like i think that just gave us this whole world

[00:32:57] of flexibility that we didn’t get with these sort of like baked in uis um so my read here is like

[00:33:03] i don’t think chat is ever going away because this opened up this like new way of like infinite

[00:33:10] ways to to work with the model and to sort of like talk to the computer that we just didn’t

[00:33:16] have before but i think that it will still be most direct for very specific things to exist in

[00:33:22] this ui and i think that will probably happen here is that a lot of those uis will be generated more

[00:33:27] and more often by the models as opposed to something that we’re like hand coding each

[00:33:32] instance but i think we yeah we’re in this space where i don’t i don’t think chat and and and maybe

[00:33:39] even like talking to the terminal is going to go away it’s interesting that like with open claw

[00:33:43] claude mold plot all the names the innovation one of the big innovations is that we’re going to be

[00:33:46] like another way to chat with it through whatsapp and telegram and sms just like another form of

[00:33:51] chatbot but that just like that was a big unlock oh i could just chat with it through whatsapp yeah

[00:33:55] and it’s like you like chatting and talking to someone is still like you know we as humans are

[00:34:01] doing it and so and it’s a way for us to interact in a really rich way and now we just have this

[00:34:07] other medium to like interact with a computer basically yeah um so kevin wheel uh who works

[00:34:14] at another ai lab i won’t mention

[00:34:16] he had this great point on the podcast that talking is such a beautiful way to handle

[00:34:23] every level of intelligence we can talk to people that are very very smart and not so smart and it’s

[00:34:30] talking and it scales so well across the spectrum we can talk to people at 200 iq 300 like it’s

[00:34:35] talking still works so that’s why it’s been this beautiful way to deal with the growing intelligence

[00:34:41] of models and it continues to work yeah that totally makes sense yeah this episode is brought

[00:34:45] to you by

[00:34:46] omni many product teams today are in the process of debating how to ship ai analytics the hard part

[00:34:52] is obvious having an llm gas at sql in production is a huge mess and just a bad idea omni takes a

[00:34:59] different approach they have a semantic layer built in so that when you embed their analytics

[00:35:05] the ai actually knows your business definitions not just your raw tables you can test queries

[00:35:10] validate the reasoning and lock down permissions before anything hits production

[00:35:14] if you want ai to be able to do that you can test queries validate the reasoning and lock down

[00:35:16] permissions before anything hits production if you want ai to be able to do that you can test queries

[00:35:16] validate the reasoning and lock down permissions before anything hits production if you want ai

[00:35:16] analytics in your product without building the whole stack from scratch check out omni.co

[00:35:21] omni.co lenny for a free three-week trial companies like perplexity dbt and bus fee

[00:35:26] use omni to ship analytics their customers can trust that’s o-m-n-i dot co lenny

[00:35:33] okay i’m going to come back to this whole idea of management and ic so so you’ve spent you’ve

[00:35:40] kind of put yourself back into the ic role in a lot of ways talk about that and if you think that’s

[00:35:46] thing design managers need to be doing yeah it takes on this um yeah so this past year at

[00:35:52] Anthropic I joined as an IC at first um and then I managed a team for a few months in in like an

[00:36:00] architecture that sort of needed it and now I’m actually back to doing full-time IC work and I

[00:36:06] joined Anthropic as an IC because I was just really excited about the kind of work that there was to

[00:36:12] be done as an IC here but also because I was feeling like you know I I sort of want to be

[00:36:19] close to the work and I I think this feels like a really important time to do it before I like

[00:36:25] ascend the corporate ranks you know and I was having these like questions and doubts about like

[00:36:29] is is middle management like is that safe in the future like it’s our is is is the way that we’re

[00:36:36] working actually is this going to be a job that persists into the future or

[00:36:42] or should I you know try something else and like get my hands dirty kind of thing

[00:36:47] um and and to be totally fair like I actually love both sides of the coin like I loved

[00:36:51] I love managing people I love like setting up teams um and being at that level but I also

[00:36:56] just really loved IC work like I was sort of like a reluctant manager when I did it and I was like

[00:37:00] okay I’ll do it um so I love both sides of these coin the coin like pretty equally but I think

[00:37:06] actually what being an IC across this past year has taught me is that it actually just like gave

[00:37:12] me a lot of support and I think it’s really important to be able to be able to be able to

[00:37:12] be able to be able to be able to be able to be able to be able to be able to be able to be able to be able to

[00:37:12] have the skills that I don’t think I would have gained if I was just managing throughout this

[00:37:16] year um like the design like I mentioned the design process has changed so so much in this

[00:37:21] past year and I feel like I’ve just picked up so many hard skills that I wouldn’t have

[00:37:25] necessarily had the time to do if I was just managing a team um so that’s actually the best

[00:37:30] thing that’s afforded me and I think at any point if I’m like managing a team again I think it

[00:37:34] will give me the empathy and understanding of how the design process has changed

[00:37:39] and I think that’s actually a really important thing right now because

[00:37:42] yeah the teams are working so differently I think it’s actually pretty hard to empathize if you

[00:37:48] are not working in that way or you’re like not always like testing all the tools and trying stuff

[00:37:52] but yeah like it’s it’s an interesting time to be designer and if I had not worked in this

[00:37:57] environment I don’t know if I would have totally understood it or like knew what to do or how to

[00:38:01] guide my teams so that that’s sort of what this year really gave me and so you were previously

[00:38:06] a director of design at Figma right how big was your team like how large was your work just to

[00:38:12] get started and how big was your team like how big was your team like how big was your

[00:38:12] people reference at the max I probably had I think 12 15 designers or so and and I had a few

[00:38:20] managers as well so and then it was like yeah okay so you’ve had the sense that middle management

[00:38:26] might not last what’s your current feeling do you think management design management is a thing that

[00:38:31] persists long term or do you think everyone turns into IC I think as long as there is a team of

[00:38:37] people it helps to have somebody who is managing a team like I think there is there’s like real

[00:38:42] value in managers it depends kind of like what the shape of the manager is and what they actually

[00:38:46] do but the way I think about like what a helpful manager is these days is somebody who is not just

[00:38:54] like I think pure people management like oh like just somebody to sort of set you up help you in

[00:38:58] your career have one-on-ones make sure you’re feeling like good at work I think that that is

[00:39:04] kind of not a thing as much anymore but I think somebody who can really function as like giving

[00:39:09] the team direction as well as doing some of the people management work so I think that’s kind of

[00:39:12] stuff like that tied together I think is the future of what managing looks like at least for

[00:39:17] now like somebody who can really engage with the team in terms of like the work and giving direction

[00:39:22] there as well as like creating the environment for them to do their best work and do you see

[00:39:26] yourself going back into management long term I probably will I probably will like I think I

[00:39:31] I really just love you know helping a team like build the best product possible and my my motto

[00:39:37] there is like whatever it takes you know if it’s somebody that’s if you if if

[00:39:42] the team needs somebody to give the team direction and like set up the team and whatnot

[00:39:45] that could be me if the team just like needs somebody to execute on it that could be me as

[00:39:49] well so the advice I’m hearing for people in design that are especially managers is

[00:39:54] you almost need to move back into IC in order to truly understand what is happening and how

[00:40:00] much it’s changing so that you can be a better manager I think so and I think traditionally

[00:40:04] at least what I’ve seen a lot of like the engineering disciplines like when they hire

[00:40:12] they actually make the EMs like take a rotation for a few months and pick up a few tasks

[00:40:17] and really understand how the technology works before they become a full-time manager and I

[00:40:23] think design probably needs to do something similar to where I think in the past design

[00:40:27] has been much more like people management oriented what did you find yourself most rusty

[00:40:32] in when you went back to IC designer actually doing crits you know and just getting criticized

[00:40:39] yeah getting criticized you’re like I’m not going to be doing this anymore I’m going to be doing this

[00:40:42] oh yeah like it is hard to get uh it is hard to get critical feedback and to hear it and to hear

[00:40:47] on such a regular basis because that’s the thing you have to do as a designer is like it’s a pretty

[00:40:52] vulnerable exercise to share work and present it with your team and then also just get a lot

[00:40:58] of critical feedback and take that all the time yeah so currently you’re you’re leading design

[00:41:04] slash i see designing on co-work is that right yeah awesome so boris he was on the pod recently

[00:41:10] talked about how there’s like a lot of debate about what co-work should be and there’s all

[00:41:14] these big ideas and he’s like in the end let’s just make it like a terminal basically in the

[00:41:19] product and just kind of a fancy terminal is there anything you could share about just the

[00:41:23] process of landing on where you landed for that experience of co-work i have it here on my monitor

[00:41:27] by the way looking at it with co-work specifically we have had a bunch of different prototypes

[00:41:34] internally of what that could look like and it’s one of those things where we tried a lot

[00:41:40] of things and then we i think we weren’t really sure like when it was actually going to be ready

[00:41:45] to ship and then it’s sort of like everything all at once like we were like okay we’re gonna we’re

[00:41:48] gonna ship it soon it was 10 days 10 days of building yeah it was it was definitely longer

[00:41:53] than that like overall it was like 10 days to get it from what we had internally to something that

[00:41:59] we were ready to ship externally so we’d been building it for a while but we weren’t really

[00:42:03] sure about like the actual form it was going to take um and so the way it got there is actually

[00:42:08] there was a lot of different other explorations that we had internally on top of different agent

[00:42:12] harnesses and whatnot and we just had prototyped little parts of the different interactions that

[00:42:19] ended up in co-work so things like um when claude gives you a to-do list we tried a bunch of

[00:42:24] different form factors for that we tried a bunch of different form factors for the way it uh presents

[00:42:30] you different like multiple choice questions we tried a bunch of different um ways to teach people

[00:42:36] what the use cases are and whatnot

[00:42:38] and i don’t know if we like landed on the best form factor ever but uh essentially it was like

[00:42:44] stuff that was sort of already working internally that people liked that we just thought we were

[00:42:49] gonna get some more signal on by by releasing it so i think forcing ourselves to release it within

[00:42:55] that 10 days that we did it was just sort of like whatever we had let’s put it out there and then

[00:42:59] let’s go out there and iterate from there which is what we’re doing and it blew up the internet

[00:43:03] when you launched it so it worked out yeah is there a feature of

[00:43:07] co-working that you’re not used to?

[00:43:08] is there a part of the work today that you’re either most proud of or just like

[00:43:10] can’t wait to fix and and improve honestly i think we’re i’m just most proud of us actually

[00:43:15] just like shipping it to be honest um and putting it out there and uh yeah i don’t know if there’s

[00:43:23] like one specific thing yet because like i think when when you work on something and you work on

[00:43:27] 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

[00:43:32] see flaws in it but i think there’s a lot of stuff that i’m excited about like we have a lot of stuff

[00:43:38] that we’ve been uh iterating especially on the home page and to make that something where it feels

[00:43:44] more like hey these are like tasks you can give claude and the tasks that claude are working on

[00:43:50] um and so that actually should be rolling out it might already be rolled out by the time this

[00:43:53] this i see like this little randomizer thing where you click it and gives you all these different

[00:43:57] ideas yeah yeah and then so when you actually start to work with claude on stuff it feels more

[00:44:02] like a to-do list like it feels more like these are things claude’s working on um these are things

[00:44:07] that are going to be working on so i think it’s a good idea to do that so i think it’s a good idea

[00:44:08] claude needs your attention on and i think there’s just a there’s an opportunity here to

[00:44:12] make it feel much more like this like shared to-do list between you and claude so excited to iterate

[00:44:16] on that and then i’m also excited to think more about uh yeah like what is the actual true form

[00:44:23] factor of this like is it stuck in the screen always or how does this sort of like reach out

[00:44:29] to the different surfaces that it’s working with i love that you shared that it wasn’t just 10 days

[00:44:33] to do this thing there’s like these numbers that people throw out there we build it in 10 days

[00:44:37] and you’re probably like oh my god i’m like oh my god i’m like oh my god i’m like oh my god i’m

[00:44:38] like there was time spent thinking about what direction it should go and prototyping mocking

[00:44:43] trying stuff and then it’s like okay now we know what we want it to be let’s build it and ship it

[00:44:48] yeah i think for some reason that became like the viral thing that got taken away from all of the

[00:44:53] the sort of co-work announcements is that it only took 10 days but i think there

[00:44:57] there have just been so many different explorations uh and people that have worked

[00:45:01] on different pieces of co-work that yeah it was it was not just 10 days and there’s a lot

[00:45:07] of different people that have worked on different pieces of co-work that yeah it was it was not just

[00:45:07] people involved it’s it’s one of those things where it’s like the the idea kept coming back

[00:45:14] and it’s like never the right moment or there’s like different variations of it and then all of

[00:45:18] a sudden it’s the right moment and it feels like oh so obvious all along but there’s a long long

[00:45:23] journey to get there and by the way for people that don’t know much about co-work is like the

[00:45:26] way i think about it’s like clawed with hands where you do stuff on your computer is that is

[00:45:31] what’s how would you describe it just like in a sentence or two that’s a good description i

[00:45:34] actually haven’t heard that but i like that i might use it more often it’s clawed with

[00:45:37] hands i also think about it as like it’s like clawed but clawed is really good at taking all

[00:45:46] your garbage and then turning it into something nice like i think one of my favorite and like

[00:45:52] any sort of use case that i i really like out of co-work is just like giving it a folder of my

[00:45:57] stuff and it doesn’t really matter what’s in that folder but i’m able to extract something

[00:46:02] good out of it i’ve done that many times okay coming back to

[00:46:07] managing and being a manager and the role of a designer i’m talking about hiring for a little

[00:46:12] bit so seeing how much is changing in the role of a designer what do you look for that’s maybe new

[00:46:19] like what do you now look for when you’re hiring designers that you think is really important for

[00:46:24] them to be successful in this new world well i do think working specifically in the kind of

[00:46:30] environment that i do there there’s just like a sense of like resilience and like roll with it

[00:46:35] kind of thing um that and i think it’s really important to be successful in the role of a

[00:46:37] designer i think it’s really important because yeah so much is changing around us and you have

[00:46:42] to be really willing to adapt to try out new methods to try out new tools and learn stuff

[00:46:47] as opposed to just like be stuck in the old processes in the old ways um but then i think

[00:46:52] about also there’s probably three archetypes of folks that are really interesting to me right now

[00:46:57] um i think these folks were already interesting to me before but i feel like is

[00:47:01] in this era feels especially important um so the first one i would call is like strong

[00:47:07] generalists um so not just like regular generalists where they’re like kind of good at a lot of things

[00:47:13] but like people that are like almost like block shaped you know in that t-shaped framework where

[00:47:18] it’s like they’re really good at like a few core skills like 80th percentile good i think this is

[00:47:24] like pretty rare and hard to hire for to be honest but i like this because the design role we’ve

[00:47:32] already seen is kind of like stretching and spanning right like we’re all becoming more pm

[00:47:37] all becoming engineering shaped um and so if you already have strong skills and a few different

[00:47:42] buckets it’s really easy for you to sort of like flex around and expand your and expand your role

[00:47:48] so that’s really exciting to me it’s just somebody who is really good at a bunch of things again a

[00:47:54] huge ask um and then the other person that’s really exciting to me is in that t-shaped framework like

[00:48:00] a deep specialist like someone who’s is t-shaped but like the the tip of the t probably is like

[00:48:07] you know a little bit smaller than most other people so folks that are maybe like the top

[00:48:11] you know like 10 percent of the industry and whatnot again super hard to find and i feel

[00:48:16] very lucky that like you know working at some of these places like folks like these you you can

[00:48:23] sort of afford to hire them and and actually bring them up on board um and then my last one

[00:48:28] is probably the one that i think we’re all overlooking which is what i call the craft new

[00:48:33] grad um it’s just somebody who’s like early career

[00:48:37] and uh feels kind of like wise and experienced beyond their years but is also just like

[00:48:45] very humble and and and very eager to learn i think this person is really interesting right

[00:48:51] now because i think most companies are just hiring like senior talent like folks that have

[00:48:57] done things before are super experienced but given how much the roles are changing and what

[00:49:03] we’re expected to do is changing i think having somebody who almost has like a blank slate and

[00:49:07] just like a really quick learner and is really eager to learn um new tactics and stuff like that

[00:49:12] and doesn’t have like all these baked in processes and rituals in their mind that’s super valuable

[00:49:17] um so i think those are the folks that i think a lot of us are just like overlooking but i’m like

[00:49:22] really excited about this is awesome uh on the deep t shape what’s an example of someone in

[00:49:30] design that has a like what’s what’s a skill that they’re really good at sometimes there’s

[00:49:33] designers who are just like really technical in a way where they could be like 50 percent of

[00:49:37] their they’re basically a software engineer like that’s really interesting especially because

[00:49:41] right now like a lot of it is at least for us it’s like you know you’re working with directly

[00:49:46] with the model so it can it helps when you have just like deep engineering expertise uh but

[00:49:50] another like deep kind of like specialist t is just you know maybe they’re just really good at

[00:49:55] like visual design or just like designing icons or something where things like that given that

[00:50:01] everybody can anybody can make anything you know having that deep specialist slant feels like oh

[00:50:07] they can really help differentiate the things that we’re building awesome okay and then this

[00:50:12] block shape ed mark andresa in the podcast we kind of called it the f f shape or e shape or

[00:50:17] there’s like multiple t things sideways f sideways e i guess is that what you’re describing where

[00:50:21] there’s like many things you’re really really good at yeah yeah and like basically like i don’t know

[00:50:26] if you almost had their skill set it would it would look like a block you know because there’s

[00:50:30] so many skills that like the t is spread out yeah okay and the correct new grid so this is just like

[00:50:37] open-minded gritty very smart i imagine is a big part of it yeah awesome yeah yeah if someone’s

[00:50:45] like a new design like a young designer trying to break in trying to be successful what would

[00:50:51] your advice be to them to help them have a shot at and ends up joining anthropic for example i

[00:50:56] would just say there’s like build a bunch of stuff like try a bunch of stuff out build build actual

[00:51:01] things i i think that is that can feel i don’t really know what the state of like design

[00:51:07] or education is these days but at least from like back when i was in school like everything was

[00:51:12] very like theoretical and like here we’re going to teach you some approaches and whatnot but like

[00:51:19] the best the best kind of like cracked new grad folks i know are just like people who just like

[00:51:24] use the technology build actual things don’t feel like limited by you know how little experience

[00:51:32] they might have i think that sometimes they’re actually unburdened by that because like we have

[00:51:36] expectations of ourselves and we don’t have expectations of ourselves and we don’t have

[00:51:37] expectations of ourselves after being in industry for so long but they actually don’t and they sort

[00:51:42] of feel like anything is possible and so just like building a bunch of stuff and sharing it with

[00:51:46] people and finding a community of folks that uh that also do that um yeah i think my my one call

[00:51:52] here too is like i went to a school that started something called socratica like much about a few

[00:51:58] years after actually a while after i graduated and basically their whole thing is like building

[00:52:04] stuff and showcasing it almost like a science project

[00:52:07] yeah i think there’s just been a really cool movement there of folks who just like

[00:52:12] build things and do things like for example somebody builds this like clod robot project

[00:52:18] this was like a few years ago too where they were uh just assembling robots that were running on

[00:52:24] clod and then somebody else did something where she just wanted to put googly eyes on a bus

[00:52:28] in boston or something and there’s just like a sense of of both like agency in terms of like

[00:52:33] yeah we can just do stuff but then also this community where people were just trying to like

[00:52:35] and then sort of like kind of like you know like making that internet community into this

[00:52:37] you know just sort of like yeah like you know just practicing in that way but like she’s not

[00:52:37] She found a bunch of small communities she’s also relatively enough of a demand in the Isso

[00:52:37] and building things and sharing things with each other.

[00:52:40] So whatever that looks like,

[00:52:42] given the school that someone’s from or graduating from,

[00:52:46] yeah, doing that kind of stuff

[00:52:47] is the stuff that will make people stand out.

[00:52:51] For current designers that are in a career,

[00:52:54] awesomely senior,

[00:52:56] do you think you need to get technical

[00:52:58] and learn to code, at least build?

[00:53:00] Or do you think you could be really successful

[00:53:02] and just not lean into that and get better at other stuff?

[00:53:04] I think it definitely helps to

[00:53:07] maybe not learn how to code so much

[00:53:11] that you’re building something from scratch.

[00:53:14] But it does feel like more and more

[00:53:15] of the designer’s vocabulary right now

[00:53:17] is implementing some stuff.

[00:53:19] I wonder though, as the models,

[00:53:22] both the models and the products get better,

[00:53:24] if like, I mean, we probably will continue

[00:53:28] to move up the abstraction layers

[00:53:29] and you won’t have to actually know

[00:53:31] how each single line of code will work.

[00:53:34] But I think what I would say is like,

[00:53:37] start to bring that into your toolkit,

[00:53:39] the coding tools,

[00:53:40] whether or not it’s like

[00:53:40] you’re actually becoming technical.

[00:53:42] I think any designer should just be really aware

[00:53:45] and know how to use the tools that are at hand

[00:53:48] as opposed to maybe like learning

[00:53:50] and like going off and learning React

[00:53:52] or et cetera, et cetera.

[00:53:53] How good of a designer is Claude, would you say?

[00:53:56] Or Claude Code, would everyone describe?

[00:53:57] Like, would you hire Claude as a designer

[00:54:00] or is it like not there yet?

[00:54:01] I don’t think Claude is there yet.

[00:54:02] I don’t think Claude is there yet

[00:54:03] in terms of a designer.

[00:54:04] Yeah.

[00:54:04] I think it is not yet the strong generalist

[00:54:08] or the deep specialist

[00:54:10] or the crack new grad.

[00:54:11] I think it’s pretty good at a first pass

[00:54:14] and at presenting a bunch of different ideas to you,

[00:54:17] but nothing there quite feels like,

[00:54:20] yeah, special and hireable yet.

[00:54:22] Which is good news for designers for now.

[00:54:24] It sucks at this for now.

[00:54:26] And I’m so curious to see

[00:54:27] how good it could get at this.

[00:54:28] That’s like such a big open question is,

[00:54:30] can it pump out amazing, novel,

[00:54:33] unique creative experiences?

[00:54:34] Or is this, it’s just never going to be that good

[00:54:37] as a human designer.

[00:54:38] I mean, it’s gotten a lot better

[00:54:40] in the last year or so, even.

[00:54:42] So, yeah.

[00:54:43] There’s a couple of management,

[00:54:44] I don’t know, rituals or takes you have

[00:54:47] that I’ve heard from folks that you work with

[00:54:49] that I want to touch on.

[00:54:50] One is that you have this hot take

[00:54:53] that low leverage time for managers

[00:54:54] is just not a thing that there’s a lot of benefit

[00:54:58] you can get out of things

[00:54:59] that people consider low leverage.

[00:55:01] You talking about that?

[00:55:02] Yeah.

[00:55:03] Yeah.

[00:55:03] I remember like first becoming a manager

[00:55:05] and I think one of the pieces like of advice

[00:55:10] that I either got from a course or a book

[00:55:12] or something is like, yeah,

[00:55:13] now that you’re a manager,

[00:55:15] you have to like really prioritize your time

[00:55:18] and categorize your work.

[00:55:19] And there was like this two by two of like,

[00:55:21] I don’t remember what it was in it,

[00:55:22] but you essentially say like,

[00:55:23] oh, these are the things that only I can do.

[00:55:25] These are the things anybody else can do

[00:55:26] and everything else, you know,

[00:55:29] like it’s low leverage

[00:55:30] and you shouldn’t do that anymore.

[00:55:31] And a lot of the low leverage things

[00:55:33] were just like,

[00:55:33] you know, like things that are really nitpicky

[00:55:36] in the weeds or just like literally,

[00:55:38] yes, probably somebody else could do those tasks.

[00:55:41] But when I think about like leaders and managers

[00:55:44] that I have respect the most,

[00:55:46] I actually think some of their best traits

[00:55:49] is that they choose like low leverage tasks

[00:55:52] that they take on themselves.

[00:55:54] And that actually ends up being actually

[00:55:56] a very high leverage thing

[00:55:57] because it’s them who’s doing it.

[00:56:00] So one example is whenever you have

[00:56:03] like senior leaders who just like test the shit

[00:56:05] out of the product

[00:56:06] and they’re just like so in tune with it

[00:56:08] and they dog food it,

[00:56:10] they repur the bugs,

[00:56:10] they spend a bunch of time with like engineers,

[00:56:13] like sharing the logs

[00:56:14] and like nitpicking and stuff like that.

[00:56:16] And I think that ends up being like

[00:56:17] super actually high leverage,

[00:56:19] even though it’s a lot of time

[00:56:20] of like nitty gritty time

[00:56:22] because it creates this like familiarity

[00:56:25] with the product,

[00:56:26] which I think is really good.

[00:56:28] It also creates this vibe where it’s like,

[00:56:30] oh yeah, this senior leader really cares deeply.

[00:56:33] And they actually know the ins and outs of the product

[00:56:34] and they’re rolling up their sleeves

[00:56:36] and they’re giving this feedback

[00:56:37] and working with the team on it.

[00:56:40] And I think similarly to what I’ve seen is like

[00:56:42] when a senior leader is able to like fix a bug now,

[00:56:47] you know, even like,

[00:56:48] I think I’ve actually seen like Mike Krieger before,

[00:56:50] like put in PRs himself.

[00:56:53] And it’s really nice because it’s like,

[00:56:55] okay, cool.

[00:56:56] Like we’re all on this team together

[00:56:57] and nothing is like below this person.

[00:56:59] And I think another thing that I love

[00:57:01] that’s like a little bit more cultural

[00:57:02] is when somebody like goes out of the way

[00:57:06] to like make somebody’s like anniversary card or something

[00:57:09] and like vibe code them something super nice

[00:57:12] or make them something, a super nice card.

[00:57:14] Cause I think it just shows that,

[00:57:15] yeah, it’s like an EA or somebody

[00:57:17] can put together the card,

[00:57:18] but this leader is just somebody

[00:57:20] who cares so much about their team

[00:57:22] that they put in the effort.

[00:57:23] So that’s something I try to embody

[00:57:24] is like choosing the like,

[00:57:27] the seemingly low leverage tasks

[00:57:29] that are like worth my time.

[00:57:32] Yeah.

[00:57:32] That is so interesting.

[00:57:33] Like what you’re saying there is in a sense,

[00:57:35] like the low leverage stuff is the one,

[00:57:37] is the stuff that often has the most impact

[00:57:39] because your reports wouldn’t expect you

[00:57:42] to spend time on this thing.

[00:57:43] And there’s like the low leverage

[00:57:45] ends up being high leverage.

[00:57:47] Yeah.

[00:57:47] And I think it’s what makes

[00:57:48] like your style of leadership stand out

[00:57:50] or feel special to a certain person.

[00:57:52] Amazing.

[00:57:53] Another, I don’t know,

[00:57:55] ritual and kind of way of running teams

[00:57:57] that I heard about you

[00:57:58] is you encourage team members roasting each other.

[00:58:02] Which on the surface doesn’t sound

[00:58:04] like a wonderful environment.

[00:58:05] But on the other hand,

[00:58:07] I hear constantly that the teams that you’ve built

[00:58:09] are just the happiest,

[00:58:11] the highest performing teams.

[00:58:13] Talk about, I guess,

[00:58:14] this idea of roasting and encouraging that

[00:58:15] and just what you’ve learned

[00:58:16] about building awesome teams.

[00:58:18] Yeah, I think it’s not that I’m like,

[00:58:20] yo, you should roast each other.

[00:58:21] You know, like I’m not like forcing it

[00:58:23] in that way or anything.

[00:58:25] But when I think about

[00:58:26] the sort of psychological safety

[00:58:29] and teams and like people

[00:58:31] that just get along with each other,

[00:58:32] like when you think about your friends,

[00:58:34] you know, you’re always sort of willing

[00:58:35] to like push the boundaries a little bit

[00:58:37] and like roast them.

[00:58:37] Like you’re roasting your friends a lot,

[00:58:39] but you actually might not be roasting

[00:58:40] your coworkers a lot because you,

[00:58:42] it’s all just about like comfort and safety, right?

[00:58:45] So it’s not that I’m like,

[00:58:46] oh, I want my teams to roast each other.

[00:58:48] But I think it can be a really good sign

[00:58:51] when the people on your team

[00:58:53] kind of feel comfortable,

[00:58:55] just like kind of poking fun

[00:58:56] at each other a little bit.

[00:58:58] And I think that also can be a good sign

[00:59:00] when folks also feel the same way

[00:59:02] about like, you know,

[00:59:02] like you as a leader,

[00:59:04] where it’s like,

[00:59:05] there’s just an element of like,

[00:59:07] they don’t, they don’t fear you as much,

[00:59:09] but they, and they feel like

[00:59:10] there’s a sense of safety

[00:59:11] where if they say something,

[00:59:12] they’re not going to get fired.

[00:59:14] So an example of this is like

[00:59:16] with my last team,

[00:59:17] I feel like they would make fun of things

[00:59:19] that I would say at crits sometimes,

[00:59:21] like certain phrases I would say.

[00:59:23] What’s an example of that?

[00:59:25] I don’t know.

[00:59:25] Like, oh, I would always be like,

[00:59:27] okay, like what are next steps?

[00:59:29] And like, how do we follow up on this?

[00:59:30] And then they’d be like,

[00:59:31] okay, like what are next steps?

[00:59:32] And they would sort of channel me in that way.

[00:59:36] Yeah.

[00:59:36] I just think it shows a level of like,

[00:59:38] okay, these people are like,

[00:59:40] not necessarily afraid of me.

[00:59:42] They know that they trust me.

[00:59:44] They can trust me.

[00:59:46] And it’s, it’s,

[00:59:48] and then they sort of like know enough

[00:59:49] about each other and me,

[00:59:51] like personally in our personal lives

[00:59:53] to be able to like know

[00:59:54] sort of where those boundaries are.

[00:59:56] But at the same time,

[00:59:57] I think the thing that you sort of err into

[01:00:00] in that territory is like,

[01:00:02] are you,

[01:00:02] as a manager,

[01:00:04] are you friends with your reports?

[01:00:05] Which is, I think,

[01:00:06] the thing people tell you like not to do.

[01:00:08] And so the way I think about balancing this out

[01:00:10] is like,

[01:00:12] this creates like the,

[01:00:13] you have to create this sort of like

[01:00:14] baseline of psychological safety

[01:00:17] and people feel comfortable

[01:00:18] both with each other and with you.

[01:00:20] But you also have to make sure that you,

[01:00:22] they know that you have really high standards.

[01:00:24] And I think these two things

[01:00:26] can feel like they’re at tension,

[01:00:27] but I think they’re actually,

[01:00:29] they work really well together.

[01:00:30] Cause it’s like,

[01:00:31] once you have that psychological safety,

[01:00:32] you know,

[01:00:32] you have people trusting each other

[01:00:34] and you applying the high standards

[01:00:37] actually I think becomes potentially easier

[01:00:41] because you can do it without fear,

[01:00:43] I think.

[01:00:44] And I sort of think about this

[01:00:45] from the approach of like,

[01:00:46] kind of like being a tough parent a little bit,

[01:00:48] you know,

[01:00:49] it’s like,

[01:00:50] oh yeah,

[01:00:50] like they,

[01:00:51] my team,

[01:00:52] I work with them in a way

[01:00:53] where they know I’m always going to be there

[01:00:55] and I’m not just going to fire them

[01:00:58] on a whim or something.

[01:01:00] But at the same time,

[01:01:00] they also know that I want the best for them.

[01:01:02] You know,

[01:01:03] and that I have high standards

[01:01:04] and that,

[01:01:06] you know,

[01:01:07] I’m working with them

[01:01:08] to make the best work possible.

[01:01:10] And so,

[01:01:11] yeah,

[01:01:11] that’s the balance I think you just write.

[01:01:12] Cause like,

[01:01:13] can you create this environment

[01:01:14] of one where your team feels comfortable

[01:01:17] like roasting you,

[01:01:18] but at the same time,

[01:01:19] like they know they have to be doing great work

[01:01:21] and they will do great work with you.

[01:01:24] That is awesome advice.

[01:01:25] It’s interesting how often this,

[01:01:27] this just like management style comes back

[01:01:30] or management,

[01:01:31] good management.

[01:01:32] It comes back.

[01:01:32] Reminds me of what was a candid red radical candor.

[01:01:36] Just this combination of caring deeply

[01:01:38] and challenging directly.

[01:01:39] Yeah.

[01:01:40] And that’s kind of what I hear here

[01:01:41] is just make sure people know

[01:01:43] that you care deeply about them,

[01:01:44] but also be very direct and have high standards.

[01:01:47] Yeah.

[01:01:48] So interesting.

[01:01:49] Okay.

[01:01:49] Maybe a final question.

[01:01:51] I’m always looking for interesting frameworks

[01:01:52] and methods and processes

[01:01:54] that people have found useful in their work.

[01:01:56] And I hear you’re a big fan of something

[01:01:58] called the legibility framework.

[01:02:00] Talk about this.

[01:02:01] Talk about how you use it,

[01:02:02] why it’s so valuable.

[01:02:03] Yeah.

[01:02:03] This framework,

[01:02:04] I think I saw it on Twitter

[01:02:07] of maybe last year or something.

[01:02:09] And it was Evan Tana,

[01:02:11] who is a partner at SPC.

[01:02:13] He’s a BC.

[01:02:14] So it basically is this like two by two.

[01:02:17] I don’t think it like got so much attention,

[01:02:19] but once I started seeing it,

[01:02:21] I actually couldn’t stop thinking about it.

[01:02:23] So on the two by two,

[01:02:24] he basically has like founders,

[01:02:26] like founders can be either illegible or legible.

[01:02:30] And then ideas can either be,

[01:02:32] like, illegible or legible.

[01:02:34] And basically he was saying that,

[01:02:36] like, okay, if both the founder and idea

[01:02:38] is like super legible,

[01:02:40] the idea is probably not that novel.

[01:02:41] And somebody is already like,

[01:02:43] they’re already going to implement it or do it.

[01:02:45] And you’re actually not finding something new.

[01:02:47] But then where it gets really interesting

[01:02:49] is where like the idea itself is illegible.

[01:02:51] And by illegible, he means like,

[01:02:54] oh, it’s sort of like really,

[01:02:55] you know, on the frontier,

[01:02:57] people might not get it yet.

[01:02:58] Or like the way it’s being told,

[01:03:00] it just doesn’t,

[01:03:01] it’s not like,

[01:03:02] being told in the way

[01:03:04] that makes the most sense to people.

[01:03:06] And I think this is obviously a good way

[01:03:08] for a VC to operate

[01:03:10] because you’re trying to look for the opportunities

[01:03:11] that people don’t see

[01:03:12] and put them out there in the world.

[01:03:14] But I also think that like,

[01:03:15] part of the role of the designer,

[01:03:18] at least at a frontier lab at Anthropic

[01:03:21] is kind of spotting the ideas that are illegible

[01:03:25] and trying to understand what’s there

[01:03:27] and how to take that and like transform it,

[01:03:30] whether it’s through storytelling,

[01:03:32] or whether it’s through like the actual UX

[01:03:34] and the form factor and put it out there.

[01:03:37] And I think there’s like,

[01:03:39] like when I mentioned, you know,

[01:03:41] going through Slack and like looking at all the stuff

[01:03:43] that people are making,

[01:03:44] like that’s kind of what I’m doing.

[01:03:45] I’m trying to see like,

[01:03:46] oh yeah, what are the ideas that are really,

[01:03:49] that like there’s like some energy there around,

[01:03:52] but like might not make sense yet

[01:03:53] that are worth me like thinking about more in my work.

[01:03:57] There’s one good example actually

[01:03:59] that like ties to co-work.

[01:04:02] Where there was this internal prototype

[01:04:05] that we called like Cloud Studio

[01:04:06] that I think somebody built like partway through last year.

[01:04:11] And it essentially was this like really kind of like dense,

[01:04:15] powerful interface that was built on top

[01:04:18] of some agent like Harness.

[01:04:20] It might’ve been Cloud Code at that point in time too.

[01:04:23] And it had all these like displays

[01:04:25] where it’s showing you like all this knowledge

[01:04:26] and all these skills and things Cloud was doing

[01:04:29] and like previewing its outputs.

[01:04:31] And I think,

[01:04:32] like to a designer I looked at it and I was like,

[01:04:34] this is like, I don’t know what’s going on.

[01:04:36] I don’t really get it.

[01:04:38] But then I sort of saw the folks in research,

[01:04:41] the folks building it and just folks internally,

[01:04:43] there’s just a lot of energy around it.

[01:04:45] And I was like, cool.

[01:04:46] Like, I think there’s like something here,

[01:04:48] but I just don’t understand it yet.

[01:04:50] I think that really was an example of an illegible idea.

[01:04:56] And ultimately what came from it was like the skills framework

[01:05:00] and-

[01:05:00] Mm-hmm.

[01:05:02] Like the sort of like markdown files

[01:05:03] that sort of that instruct Cloud on how to do something.

[01:05:06] So that came out of that specific prototype.

[01:05:08] That was not something I was directly involved in.

[01:05:10] And that was more of like,

[01:05:12] you know, the folks working on this prototype

[01:05:13] extracted that out of it.

[01:05:14] But when it did come to work on Cloud Co-Work

[01:05:17] and I was thinking about like,

[01:05:19] oh yeah, what is the form factor for those things?

[01:05:21] Seeing that prototype and seeing the kinds of information

[01:05:24] that people found really helpful,

[01:05:25] like seeing Cloud’s plan and to-dos,

[01:05:28] seeing Cloud’s like context and the files that it was,

[01:05:31] it was going through,

[01:05:33] like those kinds of things are things

[01:05:34] that I ended up pulling out of that prototype

[01:05:36] into Cloud Co-Work.

[01:05:37] So yeah, I think about like,

[01:05:40] how can designers almost be more like VCs in this way

[01:05:44] internally when we’re looking at prototypes?

[01:05:46] This is super interesting.

[01:05:48] I did a research project recently

[01:05:49] where with this guy, Terrence Rohan and VC actually,

[01:05:52] we looked at what are patterns across people

[01:05:56] that have joined companies very early

[01:05:58] that ended up being massive successes

[01:06:00] like Palantir and Stripe.

[01:06:01] And Linear and Notion, all these companies,

[01:06:04] like people that have joined many of these companies early,

[01:06:06] what were they looking for?

[01:06:08] And one of the factors was the idea is like so crazy

[01:06:12] that everyone’s laughing at this.

[01:06:14] This is impossible.

[01:06:16] You’re never gonna do this.

[01:06:17] This is the craziest thing.

[01:06:18] Why would you even think like Palantir?

[01:06:20] Like OpenAI actually was one of them,

[01:06:22] just like some research lab doing some stuff.

[01:06:24] So it’s interesting that,

[01:06:26] and it’s not like every time this will work

[01:06:28] and it’s not like every crazy idea that sounds,

[01:06:30] makes no sense will be good.

[01:06:32] But I think what you’re saying is pay attention to stuff

[01:06:35] that’s like interesting to you and isn’t totally clear.

[01:06:38] Maybe you can be the person that helps pull it together.

[01:06:41] Yeah, yeah.

[01:06:41] That, but also like if there is some energy around it,

[01:06:45] but I don’t quite always understand what the energy is,

[01:06:49] it’s to like dive deeper and try to understand what that is.

[01:06:52] Yeah, yeah.

[01:06:53] Because I think people who often gravitate

[01:06:54] towards these early ideas,

[01:06:56] they can’t always articulate why.

[01:06:59] And it’s sort of up to you to like dive,

[01:07:00] dive deeper and understand that.

[01:07:02] That’s one of, that was,

[01:07:03] so there’s three patterns we found.

[01:07:04] One of the other ones was,

[01:07:05] there’s just pay attention to people getting very excited

[01:07:08] about this thing, even if you don’t get it.

[01:07:11] And it’s like, sounds crazy.

[01:07:13] That’s so interesting.

[01:07:13] Okay.

[01:07:14] And then what was the other one?

[01:07:15] Oh, the founders are just like top 1%

[01:07:18] was the other piece there,

[01:07:19] which everyone at Anthropic already.

[01:07:21] So you got that one.

[01:07:23] Oh man, Jenny, what a crazy time we’re living through.

[01:07:25] What a world.

[01:07:26] How much, how much change.

[01:07:28] Okay.

[01:07:29] Before we get to our very exciting,

[01:07:30] lightning round,

[01:07:31] is there anything else that I should have asked you

[01:07:34] that you want to leave listeners with

[01:07:35] that you want to double down on?

[01:07:38] I think I just want to call out

[01:07:40] the Anthropic design team and shout them out

[01:07:44] just because it’s a team of folks

[01:07:46] that are just really humble

[01:07:47] and they’re not always the loudest on social,

[01:07:49] but they’re doing a lot of really great work.

[01:07:52] And especially through this time,

[01:07:53] our jobs are changing so much.

[01:07:55] The team is so resilient

[01:07:57] and they’re,

[01:07:59] they’re, they sort of span

[01:08:00] this whole spectrum of people

[01:08:02] who are really technical and prototype-y

[01:08:03] to all the, all the way to folks

[01:08:05] that are really high craft

[01:08:07] and, and, and delivering stuff

[01:08:09] that’s, that’s going out the door

[01:08:10] and is fabulous.

[01:08:12] And we are hiring throughout the year.

[01:08:14] So I just wanted to call that out.

[01:08:15] If I didn’t scare you

[01:08:16] with the way that we work internally at Anthropic,

[01:08:18] if that sounds more exciting than terrifying,

[01:08:21] would love to connect.

[01:08:23] What sounds exciting is getting access to these slacks

[01:08:25] or however all the features are being built.

[01:08:27] Yeah, that’s the core benefit.

[01:08:28] Let’s talk to super intelligence,

[01:08:30] right now and tell me where I should invest.

[01:08:32] I’m just joking.

[01:08:33] And then in terms of hiring,

[01:08:34] is there anything specific

[01:08:35] that people should think about to,

[01:08:37] if they want to play?

[01:08:38] Think a little bit about the,

[01:08:41] the archetypes that I mentioned,

[01:08:43] especially the strong generalists

[01:08:44] and the deep specialists.

[01:08:45] Those folks were really excited about,

[01:08:47] but generally folks who are-

[01:08:49] The block and the deep T.

[01:08:50] The block, the block and the deep T.

[01:08:53] What could we be talking about?

[01:08:56] Yeah, folks who feel like they,

[01:08:58] you know, they,

[01:09:00] those archetypes resonate with them,

[01:09:01] but also folks that are just really excited

[01:09:03] about the technology,

[01:09:04] have been building a lot

[01:09:06] and sort of want to be on the frontier.

[01:09:10] Amazing.

[01:09:11] Well, with that,

[01:09:12] we’ve reached our very exciting lightning round.

[01:09:14] I’ve got five questions for you, Jenny.

[01:09:16] All right, I’m ready.

[01:09:18] Here we go.

[01:09:19] What are two or three books

[01:09:20] that you find yourself recommending most to other people?

[01:09:22] The first one is The Power Broker by Robert Caro,

[01:09:26] which is an incredibly aggressive,

[01:09:28] incredibly aggressive book.

[01:09:29] It’s an aggressive recommendation

[01:09:30] given that it’s like 1,100 pages.

[01:09:34] But I think in this era

[01:09:36] when our attention spans are so short,

[01:09:39] I think this is actually worth reading end to end

[01:09:41] because I think there are very few

[01:09:44] collections or memoirs

[01:09:46] where it spans through someone’s entire life

[01:09:49] and you sort of see

[01:09:50] how somebody changes throughout those decades.

[01:09:54] And it’s also something

[01:09:54] that’s really controversial too.

[01:09:56] And it’s nice to sort of like read

[01:09:58] a really nuanced view.

[01:09:59] If somebody, Robert Moses,

[01:10:01] and I think we just lose out

[01:10:04] on some of this like long arc thinking

[01:10:05] because we’re thinking so much about right now.

[01:10:08] So it’s just an important reminder

[01:10:10] that careers are long

[01:10:11] and is also really good for kind of understanding

[01:10:14] how somebody just gets things done really well.

[01:10:17] So Power Broker.

[01:10:19] The second one that I recommend to a lot of people

[01:10:21] is a book called Insomniac City,

[01:10:24] which is written by Bill Hayes,

[01:10:25] who was the partner of the scientist,

[01:10:29] Oliver Sox,

[01:10:31] around the time that Oliver Sox died.

[01:10:33] And it’s just this like really beautiful

[01:10:34] kind of like ethereal memoir

[01:10:36] of Oliver Sox’s last days

[01:10:38] and their sort of love story.

[01:10:41] I think this has like very little to do

[01:10:43] with the stuff on your podcast, Lenny,

[01:10:44] but it’s just like,

[01:10:45] it’s just a book that I really love

[01:10:47] and just like makes you think about mortality,

[01:10:50] but also like love and life and stuff like that.

[01:10:52] So that’s one of my favorite books.

[01:10:54] My goal here isn’t, you know,

[01:10:55] I’m trying to create,

[01:10:56] we’re trying to create renaissance humans.

[01:10:57] All of this,

[01:10:59] other stuff is excellent.

[01:11:01] Cool.

[01:11:02] Interestingly,

[01:11:03] I saw Julie Zhu,

[01:11:04] famed design leader,

[01:11:05] was reading the Power Broker recently.

[01:11:07] I don’t know what’s going on over here.

[01:11:10] Spreading in design land.

[01:11:12] Okay.

[01:11:12] Do you have a favorite recent movie or TV show

[01:11:14] that you really enjoyed?

[01:11:16] I watched A Sentimental Value recently.

[01:11:19] I watched it on a plane,

[01:11:20] which is, you know,

[01:11:20] how directors want you to watch their films.

[01:11:23] But it’s a Norwegian film

[01:11:26] by the same director

[01:11:27] who did The Worst Person in the World,

[01:11:29] I think just the pacing,

[01:11:31] the writing,

[01:11:31] the relationship between the characters

[01:11:32] is just really subtle and beautiful.

[01:11:35] It’s basically about this family,

[01:11:37] sort of a family drama,

[01:11:39] but also about this house

[01:11:40] that they lived in their entire lives.

[01:11:42] It’s beautiful

[01:11:43] because like the house is sort of a character.

[01:11:45] So I don’t know what else to say about that,

[01:11:47] but that was a really good movie.

[01:11:49] And then I would also recommend,

[01:11:50] obviously, The Pit season two.

[01:11:52] I know we’re on that.

[01:11:54] We’re on that.

[01:11:55] I think everybody just likes to watch people

[01:11:56] who are really competent at their jobs

[01:11:58] do something.

[01:11:58] I think that’s a really good movie.

[01:11:59] I think that’s a really good movie.

[01:11:59] So, yeah.

[01:12:00] Mention being an actor on that show,

[01:12:02] just like how much you have to learn

[01:12:03] and memorize all these terms.

[01:12:05] Yeah, yeah.

[01:12:06] It just also seems really fast-paced too.

[01:12:08] Like they do so much stuff in like one shot

[01:12:10] and there’s just so much like movement

[01:12:12] and stuff like that.

[01:12:13] It seems really, really hard to be an actor on.

[01:12:15] And I only recently realized

[01:12:16] Noah Wiley was in ER as like a younger person

[01:12:18] and now he’s like the head of this thing.

[01:12:20] Yeah, yeah.

[01:12:21] Oh, man.

[01:12:22] Okay.

[01:12:22] Favorite product you recently discovered

[01:12:23] that you really love cannot be co-work.

[01:12:26] Not one that I’ve actually discovered recently.

[01:12:28] But Retro, I’ve been using it

[01:12:31] for basically two years now since it came out.

[01:12:35] And I think I discovered new benefits of it recently.

[01:12:39] So for folks who don’t know about Retro,

[01:12:41] it’s sort of like this small community photo sharing app

[01:12:44] in which you can only share photos from each week,

[01:12:48] from a given week as opposed to like all time.

[01:12:51] And it basically has like none of the social media stuff.

[01:12:54] Like you can’t really see like counts.

[01:12:57] It’s not.

[01:12:57] There’s no ads, et cetera.

[01:12:59] But one really nice thing is now

[01:13:01] that I’ve been using it for two years,

[01:13:03] I can now look back at each year and see like,

[01:13:05] oh yeah, this week, two years ago, I was doing this.

[01:13:08] And it’s become this really special way

[01:13:10] to like live through each week of my life, basically.

[01:13:14] Wow.

[01:13:14] And it’s also a beautifully crafted app

[01:13:17] if you’re looking for building your own taste in design.

[01:13:20] Yeah, designers love Retro.

[01:13:22] I could see, I could see that.

[01:13:24] Okay.

[01:13:24] Do you have a favorite like motto

[01:13:25] that you often come back to in work or in life?

[01:13:28] Yeah.

[01:13:29] Not sure if it’s my favorite life motto,

[01:13:31] but one thing I do catch myself saying a lot

[01:13:33] is just it is what it is.

[01:13:36] My dad says that all the time.

[01:13:38] I love it.

[01:13:38] Yeah.

[01:13:39] Yeah.

[01:13:39] It sounds super defeatist,

[01:13:41] but I promise it’s not.

[01:13:42] I think just given how much stuff

[01:13:44] is going on in the world right now,

[01:13:46] and especially with the industry and whatnot,

[01:13:48] you can’t control everything.

[01:13:50] And so sometimes it is what it is,

[01:13:52] just like brings the levity you need to move forward.

[01:13:55] I went to, I did a 10 day meditation retreat a while.

[01:13:57] And I came back from it.

[01:13:59] And it’s like, dad, you’ve been right all along.

[01:14:02] This is the whole, the answer to it all.

[01:14:04] It is what it is.

[01:14:05] You can’t, don’t cling.

[01:14:06] Don’t try to change.

[01:14:07] Just it is what it is.

[01:14:08] It is what it is.

[01:14:10] There’s so much depth to that.

[01:14:11] I was like, okay, smarter than I even thought.

[01:14:15] Okay.

[01:14:15] Final question.

[01:14:16] Coming back to cowork.

[01:14:18] Is there a, I don’t know, mind blowing use case,

[01:14:21] something just like, wow, that’s so cool.

[01:14:24] That cowork can do that.

[01:14:25] Either something you use it for,

[01:14:26] or you’ve heard somebody,

[01:14:27] using it for one thing I really like is just like introspection.

[01:14:31] And so I have this,

[01:14:34] this folder basically of like local notes that I have from that.

[01:14:37] I use like IA writer for,

[01:14:39] and I basically just like write whatever.

[01:14:40] And over the years have collected it with a bunch of different notes.

[01:14:44] And they span like all different things,

[01:14:47] like one-on-one notes,

[01:14:48] like random thoughts,

[01:14:49] like kind of like tiny memos,

[01:14:50] interview notes,

[01:14:51] et cetera.

[01:14:52] And my favorite,

[01:14:54] like it makes it’s,

[01:14:55] it’s cool to me.

[01:14:57] It’s just like,

[01:14:57] it’s like,

[01:14:58] it’s just so cool.

[01:14:59] Like,

[01:14:59] it’s just so cool.

[01:15:00] And I’ve been using cowork to like analyze that and have insights out of it

[01:15:05] and actually create things out of it.

[01:15:06] Um,

[01:15:06] so like anything I,

[01:15:08] anytime I can like learn something new about myself,

[01:15:10] like,

[01:15:10] I love that,

[01:15:11] but I think a very practical thing I did with it the other day was

[01:15:14] like,

[01:15:14] all along the lines of hiring.

[01:15:16] I was like,

[01:15:16] oh yeah,

[01:15:17] I want to sort of articulate.

[01:15:18] Like what it is that I look for,

[01:15:20] why I look for a design craft.

[01:15:21] Cause I think actually a lot of people struggle to articulate that.

[01:15:24] And I just had it read through all of my notes,

[01:15:26] both like interview notes,

[01:15:27] have written in in the past and then it made me this rubric uh for for evaluating that so um that

[01:15:33] kind of introspection where it’s like oh i don’t even i wouldn’t have realized even these things

[01:15:38] about myself that i’ve been putting out there implicitly that’s been really cool for me that

[01:15:42] is so cool so just to make this very clear for people you have a folder with all these things

[01:15:46] you’ve written one-on-ones meetings like you could do i don’t know if y’all are allowed to use

[01:15:50] granola something like that like meeting transcripts and ask it and it’s like i was

[01:15:55] gonna ask what prompt you use but it’s just like read all these things i’ve written and help me

[01:15:59] probably just like understand how i feel about what is design craft yeah basically i think it

[01:16:04] was like hey i have a bunch of interview notes and a bunch of notes related to design craft in

[01:16:09] this folder um read it and then help me craft a uh like a memo slash rubric for how i assess craft

[01:16:18] in interviews so cool yeah jenny this was awesome what a what a time to be alive

[01:16:25] you

[01:16:25] what a time two final questions where can folks find you online if they want to reach out and

[01:16:29] how can listeners be useful to you yeah um i’m on twitter slash x is what we’re calling it these

[01:16:34] days um it’s at jenny underscore when that’s probably the best place not really on linkedin

[01:16:40] as much so that’s that’s the best place um and how can folks be helpful to me send us your product

[01:16:45] feedback you know like we’re working on co-work uh or anything cloud related really just send us

[01:16:50] your feedback we’d love to make it better for you jenny thank you so much for being here

[01:16:55] yeah of course it was great chatting lenny it was wonderful jenny thank you bye everyone

[01:17:00] thank you so much for listening if you found this valuable you can subscribe to the show

[01:17:05] on apple podcast spotify or your favorite podcast app also please consider giving us a rating or

[01:17:12] leaving a review as that really helps other listeners find the podcast you can find all

[01:17:16] past episodes or learn more about the show at lenny’s podcast.com see you in the next episode

Vox

Explorador