Claude's Head of Design: Full Claude Cowork Tutorial in 40 Min | Jenny Wen

Summary

Behind the Craft – Claude’s Head of Design: Full Cowork Tutorial in 40 Min | Jenny Wen

Host: Peter Yang
Guest: Jenny Wen, Head of Design at Anthropic
Date: March 29, 2026

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Episode Overview

This episode offers a deep dive into Anthropic's product development workflow as seen through the eyes of Jenny Wen, design lead for Claude Cowork and Claude Code. Jenny walks Peter through a real-time tutorial of how she leverages Claude Cowork to research, design, prioritize, and prototype features—revealing a modern, highly iterative, and AI-integrated design process. The conversation also covers the inside story of Cowork’s origin, the evolution of its UI/UX, and the shifting role of designers as AI transforms product development.

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Key Discussion Points & Insights

1. Jenny’s Day-to-Day as Head of Design (01:00)

• No “Typical” Day: Jenny describes her work as highly variable—much of it spent “jamming with engineers and product people…in a less formal way” rather than following rigid processes.
• Multi-Project Focus: She often consults across 5-6 projects at once, balancing hands-on prototyping, user feedback analysis, and casual yet effective collaboration.
• Less Formal Docs & Specs: Detailed specs are less common now. Instead, priorities are often just “a few bullet points”—helpful mostly for coordination with stakeholders like security or legal.

2. Live Walkthrough: Claude Cowork in Practice (04:30)

• Garbage In, Treasure Out: Jenny uses Cowork as an “insight refinery,” aggregating vast user feedback from interviews, social channels, internal Slack, and more.
  • She points out, “It’s just really good at taking things from a lot of different sources and then finding and picking the gems out of it…" (07:06)
• Automated Insight Reports: Jenny demonstrates how she prompts Cowork to scan user interviews, Reddit, X (Twitter), and generate insight summaries for weekly team kickoffs.
• Parallelized Tasks & Presentation Generation: She spins up sub-agents to create presentations and product ideas simultaneously, scheduling them for recurring meetings (12:48).

3. How Anthropic Stays Close to Users (08:25)

• Internal Dogfooding: The team depends heavily on feedback from internal power users and passionate external users in Slack and social media.
  • “[People internally] are really willing to be honest with you, and they're often pushing the capabilities furthest.” (08:46)
• Iterative Decision-Making: Fast-paced, feedback-driven cycles replace exhaustive up-front planning.

4. From Insights to Prototypes (11:56)

• AI as Co-Designer: Jenny lets Cowork draft specs and even generate scratch wireframes based on summarized insights, which she then feeds into Figma or Claude Code for higher fidelity work.
  • “I always let AI take a first cut at everything and then I just kind of react to it.” – Peter ([15:08])
  • Jenny confirms: “That’s how I operate too…having Claude…jog my mind…helped evolve my thinking instead of just like being stuck there with the blank page problem.” (15:30)
• Scheduling as Ritual: Regularly auto-generating team kickoff materials shrinks the feedback-to-execution loop dramatically.

5. Working with Claude’s Memory and Skills ([17:32]–[19:03])

• Personalized Knowledge Base: Rather than relying solely on explicit “skills,” Jenny’s workflow involves Cowork learning from folders of her ongoing notes and personal artifacts.
  • “It’s sort of like learning about me from those folders has been really useful to a…point where I feel the need less for skills because it sort of has this knowledge base about me already.” (18:10)

6. Democratizing the Design Process ([20:15]–[22:58])

• Empowering the Whole Team: Instead of a top-down approach, the democratized workflow means “anybody can do this…not just the designer.”
• Designers as Curators: Jenny values seeing multiple AI-generated options, curating and refining before bringing them into production.
  • “…I like to just, like, see a lot of options, even if they're, like, not super high fidelity…helps me decide, like, what to actually do.” (22:18)

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The Origin and Evolution of Cowork

1. The Myth of the “10-Day Build” ([23:14]–[26:30])

• Long-Term Vision, Fast Execution: Cowork was not truly built in 10 days; it was “about a year in the making” with ongoing prototyping and learning.
  • The 10-day sprint was about capturing the right market moment, based on enthusiastic internal adoption and promising signs of product-market fit for non-technical users.

2. Iterative Design History ([27:17]–[32:32])

• Early Prototypes:
  • Early versions were overly structured—requiring users to specify detailed workflows and inputs, which proved unintuitive.
  • Moving toward a chat-based, freeform interface proved more successful.
  • “We stripped most of [the opinionated UI] back…so now…if you look at the current UI…it feels more like the traditional…chat box. But we reformatted the homepage to feel more almost like…Claude’s active to-do list.” (29:56–31:54)
• UI Evolution: The UI changes rapidly in response to user feedback—“The UI looked so different, just like, you know, maybe like four or five weeks ago…” (32:12)

3. Balancing Power and Flexibility ([32:32]–[34:00])

• Slash Commands & Skills: While these advanced features exist, they are not required for most workflows. Power users can go deep, but Cowork aims to onboard beginners without overwhelming them.
  • “You shouldn't have to know all the commands in order to use it.” (33:58)

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Modern Product Planning & Culture at Anthropic

1. Adapting to Change ([34:00]–[37:30])

• Flexible Planning: Monthly, loosely-structured spreadsheets replace traditional annual planning and vision decks.
• Short-Term “Vision”: With rapid technology shifts, visions are set only 3-6 months out—often as prototypes or visual documents.
  • “I think there's no such thing as a one year vision, let alone a two or five year vision for us because there's so much that's unknown out there.” (36:09)
• Design’s Role: Design provides cohesion and clarity when multiple teams’ work risks overlap or diverge.

2. Product Reviews ([37:20]–[38:03])

• Still regularly conducted for major projects, but less frequent and less bureaucratic than at traditional companies.

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Navigating the New Era of Design

1. Advice for Designers [(38:03)–(39:56)]

• Embrace the Change: Jenny underscores that feeling instability is normal—“If you feel like the ground is shifting beneath your feet, it's because it is.”
• Adapt and Learn: Draw inspiration from engineers who have already navigated this shift. AI won’t eliminate designers but will change their role—freeing them from drudgery and requiring new collaborations and curatorial skills.
  • “…my engineering peers…have already adapted…they're producing even better and more work today. And so I look at them as inspiration…if all these people that I really respect can do it…I can too.” (38:54)

2. Higher Output, Less Drudge Work ([39:32]–[40:27])

• Not Less Work, Just Higher Impact: AI accelerates the work, but ambition fills the time saved with new and better projects.
  • “They're creating entire features in days, not weeks, these days.” (39:42)
  • “…it's like a high. You're like, oh my gosh, I can get so much done now and I don't have to do the stuff that I didn't like doing before and so let me do more, you know?” (40:07)

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Notable Quotes

• “If you feel like the ground is shifting beneath your feet, it's because it is.”
  – Jenny Wen, [38:15]

• “My secret is that I actually use Cowork for most things now. I start every Monday morning at 10am with this presentation and with like three different product ideas that I can use and kick off the week.”
  – Jenny Wen, [00:11]

• “The UI looked so different just like four or five weeks ago and now it's like we're constantly learning, like what's working and isn't working. If you feel like the ground is shifting beneath your feet, it's because it is.”
  – Jenny Wen, [32:12]

• “The actual story is that Cowork…has been something that the company has been…thinking about…for…basically ever since I joined Anthropic about a year ago…[the] 10 days [story]…is one of those things that I think got pulled out of a quote somewhere…”
  – Jenny Wen, [23:18]

• “It's all about the iteration. It's all about the iteration.”
  – Peter Yang, [15:08]

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Timestamps for Key Segments

• Jenny’s Day and Workflow – 00:56–03:25
• Live Cowork Tutorial – 04:30–12:48
• Turning Feedback into Features – 12:48–15:30
• Design Culture & Democratization – 20:15–22:58
• Cowork’s Origin and Iterative UI – 23:14–32:32
• Planning & Cultural Shifts at Anthropic – 34:00–37:30
• Advice for Designers in the AI Age – 38:03–40:27

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Tone & Style

Jenny’s style is reflective, candid, and iterative—open about uncertainty and the fact that processes, priorities, and workflows are all in rapid flux. Both speakers are informally conversational, favoring practical detail over hype or jargon.

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Summary Takeaways

This episode offers a vivid, practical glimpse into how a top design leader at one of tech’s most innovative companies harnesses AI—both as a tool and a collaborator. Jenny demonstrates that speed, feedback loops, and democratized design sit at the heart of modern product strategy at Anthropic. Her openness about constant change is both reassuring and galvanizing for designers wrestling with the future of their craft.

Transcript

[A]

They're creating entire features in days, not weeks. These days, I think about the specs that we used to make six months to a year ago and, you know, be like, milestone one. We have these P zeros, we have these P1s. We still do that prioritization, but it's usually just like a few bullet points. My secret is that I actually use Cowork for most things now. I start every Monday morning at 10am with this presentation and with like three different product ideas that I can use and kick off the week. 4. The UI looks so different just like four or five weeks ago and now it's like we're constantly learning, like what's working and isn't working. If you feel like the ground is shifting beneath your feet, it's because it is.

[B]

Hey, everyone. I'm super excited today to welcome Jenny, design lead at Anthropic. Jenny is going to show us how she uses cloud cowork and cloud code to design and ship products and give us the inside story of Cowork and also maybe what's next for the product. So welcome Jani.

[A]

Thanks, Peter. So good to be here.

[B]

Yeah. All right, so I'm just really curious, like, what is a typical day, like at work for you? Like, what tasks take up most of your time?

[A]

I'm like, is there a typical day? Like, I don't know if there is a typical, typical day, but a lot of the things that I spend time doing is it's like to get product out the door. Right. But I think that maybe looks different from what it looked like a year or two ago. And a lot of that is. A lot of it is just actually just like jamming with engineers and product people and whatnot in a less formal way. It's often looking at a prototype together and then pointing out and thinking about the ways that it could evolve. It's sometimes just talking about the behavior of things and then sometimes it's me implementing stuff. I think there's also still a big portion of the time that is know me designing stuff, prototyping and stuff like that. But it feels like a lot of the way that design works these days is kind of loose. Like it is in. In the. It's. It sounds so like, like non tangible. It's like, oh, it's a conversation or it's just like jamming with people. Um, but that is kind of what I, I find a lot of the work to do because. To be. Because it's less. You know, I spend less of my time just focused on one single project. But, but I feel like I'm consulting on five or six different projects at any given time.

[B]

Interesting. Okay, so basically you have a bunch of prototypes that generate through cloud code or something and then you just kind of jam the engineers, give some feedback and they just prompt AI to improve it. Right? Is that how it works?

[A]

Basically. And they're not even often prototypes like that, they're working prototypes. They're things that are in our internal builds and instances of, of Claude or cowork. And usually like I've spent some time using the feature, you know, pushing the feature, seeing what it's capable of and forming opinions. And the next step on iterating with on them is often like me just sitting down with the engineer and be like, hey, here's what I think. These are the things I should change. I think part of there is still time where I feel like, you know, being in the, in the design tools and iterating on it and like getting down to polish and to iteration is like still really, really important. So that part hasn't like gone away. It just, I think, I think since I'm like operating on more projects at any given time feels more effective to sort of just like do it really casually and informally.

[B]

Okay. I mean that's always been like the most fun part of just like, you know, being a PM or designer to me. Just like getting designer and engineers and just like looking at product and iterating. Yeah. So there isn't a lot of like, do you guys still make like specs and figmas and like, you know, these planning documents or is it just like in the code iterating on prototypes?

[A]

I mean, I still make figmas. I don't, I think we haven't, we don't make specs as often. Like they're. And they're not as detailed usually. Yeah, like we still do that prioritization and it like exists as a document. It's actually really good for us to like hand off to security or legal and stuff like that so they understand what's happening in the launch. But it's usually just like a few bullet points. It's not this like beautiful table that's over engineered. And I think the same thing goes for our FIGMA files.

[B]

Okay, so why don't we get into it? So like now anthropic and by the way, like I spent my whole life on cloud, like I live in cloud these days. But like now you guys have like three separate products, right. You have cloud cowork and cloud code. And maybe you can kind of like, show us how you use some of these products or like how. What do you use each one for?

[A]

Yeah, I will show you Cowork. Because my secret is that I actually use Cowork for most things now, aside from like the. The very nitty gritty production code stuff. So like when I'm polishing, I will. You still use like cloud code. But I. For, for all. For all purposes of chat, I actually fully use Cowork now. So I will show you some things there. Okay, I'm going to show you this account that I'm using with Cowork. There's no tasks there because this is sort of like not my burner, but it's my. It's my external account. But trust me, like my actual Cowork has like many different sessions that I'm often like running in parallel and whatnot. And so one thing that I find Cowork really helpful for is I just generally call it sort of like garbage in, treasure out. It's just really good at taking things from a lot of different sources and then like finding and like picking the gems out of it and also making it something really productive. So right now I've actually like hooked it up with a folder of. They're. They're not real user interviews. I like actually cut and clawed to generate them, but they're, let's just say they're like a bunch of like transcripts from user interviews that we've done from uxr. And I think the thing that we try to do, at least on the Cowork team, is we try to stay super close to the ground both through like traditional sources of like UXR and like talking to people, but also through like internal dog fooding, through things like just this running Slack channel of all this feedback, but then also, you know, social and people who are using it and passionate users there. And so like, I think that's actually been a big part of our somewhat success so far is that we have just been like staying super close to that and iterating really quickly. So what I will do here is I will say like, cool, I have this folder of interviews, but I also will tell Claude, like, hey, can you look on social and customer reviews and whatnot of Cowork and tell me what the biggest insights are. So look in this folder of UXR interviews and on social like X and Reddit and other reviews for Cowork, or else I'll say like cloud cowork, tell me what the main insights are and I'll have Claude do that. It might take a little bit of time because it's like going. It's truly just going through so much data and processing it. But yeah, it'll do things like it'll sometimes like spin off subagents to do that in parallel and it'll search the web for a while and do that. But yeah, it's basically just pulling from a wide variety of sources.

[B]

This episode is brought to you by replit. Replit's new Agent 4 is the best way for teams to collaborate with AI agents. There's a new infinite canvas where you generate design directions, compare them, and take your favorite straight into a working app. From there, you can spin up multiple AI agents in parallel to build different features at the same time and track them on a task board where you can review and approve what ships. And once your app is built, the agent can generate slide decks, animations and more from the same process project. Because slides, animations and documents are all just code under the hood. Check out Replit via the link in the video description and use my code, PYAN26 to get three months free. That's P Y A N G 26. Now back to our episode and in your real job, do you have some sort of a, like weekly insight report, something that, you know, gets sent to you and your team or something that aggregates all this stuff automatically?

[A]

I mean, we can make that right now through cloth, through coworkers. So I'll show you the flow for that. Yeah, we do in that. I think one of our researchers has one that they'll send out and then we have one that sort of like pings us in slack as well that will send that out. And then we also just like listen to the slack, like the internal slack. We have really been relying on our internal and like most powerful users to sort of like be the people that gives us the sort of bleeding edge feedback. Because, um, people internally are really willing to be honest with you, and they're, they're often pushing the capabilities furthest and it's easiest to follow up with them too because they are just, you know, so close to you and like, and willing to participate. So we rely on internal feedback a lot, which might be counterintuitive.

[B]

I mean that, that, that that's what should happen. Like, and I, I feel like most companies like the, this like so siloed that like the teams don't dog for each other's product, but like it feels like anthropic. That very much happens, right? Both for Cork and Kako Y like

[A]

it was a big part, I think of cloud code success too is just like listening to your frontline users. And that was the thing too that we did a lot at Figma too was a lot of internal dogfooding. Yeah. Because a lot people will point out things that, especially when it comes to things like interaction design and polish and whatnot, people internally will really poke at that stuff versus people externally tend to give you feedback often about does it work for their user flow. So it could just be a very different altitude of feedback.

[B]

Let me ask you this. While this thing is generating. So I know that anthropic marketing pm, everybody is basically using cloud code to also do stuff. Now that codework is internally available. How do you see different types of functions or how are people using this versus cloud code? Or. It depends.

[A]

Yeah, I think we're seeing just like overall, like wider adoption of Cowork for similar use cases that some of like the bleeding, what I call the bleeding edge users of cloud code were like, for example, when we started working on Cowork, we had a few internal sales employees just be sort of our inputs into what we should build. And there were a few people who were like, oh, we're like, they're like die hard cloud code users and they were using it to generate like leads lists and help them like come up with scripts and whatnot for calls. And it was like, it sort of blew my mind when I saw, because I at that point didn't even comprehend that you could use cloud code for those things. And those folks, they are, they're basically all on Cowork now and more of their sort of like their peers are actually using Cowork as well. Whereas before those people were like the

[B]

bleeding edge users just because like actually is nice to see a ui.

[A]

And I think, I think that's, that's what it, that's honestly what it takes. And, and I think also part of it is it's so close to the other work too that they're doing. You know, if they're already using chat and they can still use cloud code too from this desktop app too. So it just, I think it, it fits closer to their existing workflows then opening up the command line does.

[B]

Got it.

[A]

Okay.

[B]

Looks like it generates something. Yeah.

[A]

And it's generating stuff. Okay. Yeah. So it sounds like there is some, there's some insights there. Okay, cool. Like I can take these insights and there's like seven different themes here. They're different every week, which is great, but I can, I can basically tell it and say, you know, like, it's create this, it's created this docx for me, which actually is like, it will be, it's already like stored in a folder on my computer, which is great. And so what I can also do is like, I can spin off to parallel tasks. So here I can say like, okay, cool, like these are great insights, but what are product features I should actually build from this?

[B]

Yeah.

[A]

Then what I might also do in parallel is it's already attached this folder that this output has been dropped into. I could say, okay, given the insights in this folder from the Insights doc, you made me turn this into a presentation I can share with the team this week at our kickoff. In one thread it's making me an artifact. The other one, it's starting to actually figure out what to do next. This is going to run for a bit too. But ultimately what I can do from here is start the design process. Essentially it will give me options for what the features I can create. And from there I can even ask Claude to like create some wireframes for me for those given features. And that can be a really good place where it just shows me a bunch of different options. And I can take those, bring those with me to Figma and actually start to flush them out or like, or bring them with me to cloud code and start to make them like real with our real design system components and just get started from there. And then the other thing I can also do too is just take these and turn them both into scheduled tasks. Yeah, exactly. I can say, actually I probably wouldn't start from here. Once this is done running, I would say, okay, schedule this for me. I don't want to disrupt while it's doing this thing, but I would probably just have it structure, schedule this task for me to do it every Monday morning at like 10am or something. And then that way I start every Monday morning at 10:00am with this presentation and with like, you know, three different product ideas that I can use and can kick up, kick off the week for. And it just makes that sort of like iteration cycle between feedback to actually creating something that's tangible or an idea that the team can look at. Just really, it squishes that time to be really tight and it helps us just iterate on the product quickly and make it much better quickly. Play.

[B]

Yeah, it's all about the iteration. It's all about the iteration. Yeah, yeah, yeah, yeah. And you know what? Like I, I, I, I've also gotten so lazy. Like I always let AI take a first Cut at everything and then I just kind of react to it. Yeah, so. So if, if you actually want me to take those insights and try to draft like some sort of a feature prioritizing from scratch, it'll take me, like, way longer than it used to take.

[A]

Yeah, yeah. I mean, that's how I operate too. Like, even, Even when you start sent me over, like the notes for this podcast, I was just like, I, you know, I keep a folder of like all of my personal notes, whether it's like things from one on ones or things from just like random thoughts. And then I was just like, cool. Like, you know, read my personal notes and like, like come up with, with speaking points for this podcast and help me think about what I want to say here. And it, I mean, I'm not going to, I'm not reading it word for word or anything, but it just helped me jog my mind in terms of like, oh, cool. Like, these are the things that I, I care about. And, and I didn't have to think that hard to, to. To actually like or like, helped evolve my thinking instead of just like being stuck there with the blank page problem.

[B]

Yeah, yeah, yeah, yeah.

[A]

Okay. So it's doing the thing where it's, it's specking and telling me what the P zeros and P ones are. You know, so if I, let's say, like, I want to build up the step by step progress, task progress ui, I can just say, like, I like the step by step progress, the step by step progress UI idea. Make me an interactive prototype of that, of a few options of this and do it in a scratchy wireframe style.

[B]

Scratch your wire.

[A]

Yeah, yeah, got it.

[B]

Okay. Okay, so it has context of what cowork looks like now.

[A]

Or this probably doesn't because I haven't set it up to have that. But it will just, I think based on like, the context here and whatnot. It will, it will try its best. And it feels pretty isolated too. So I don't think I have to show it like, okay, this is what Cowork looks like. But I could, I could upload, you know, like an image and also, you know, give it this, like, anthropic branded skill that we have to. To make it look more on theme.

[B]

Do you have any. Yeah, like, that's my next question. Like, what kind of skills do you use? Or do you have any personal skills for, like, these docs and slide slides?

[A]

Yeah, we have a few internal skills that we use for some of these, like, docs and slides, because it helps Brand them. I actually don't have like, a personal skill like library that I use. I've been mostly borrowing from the ones that we have internally and using them for different purposes.

[B]

Okay.

[A]

Okay. Yeah.

[B]

Because. Yeah. So, like, for example, I have a skill, like a writing skill that just tries to tell them not to, like, make AI slop words.

[A]

Like. Yes.

[B]

Yeah, yeah. You know, so that helps a little bit.

[A]

But yeah, I've actually found that, like now with. This is probably not like the best practice and the most efficient thing to do, but with. With Cowork and some of these, like, folders I have with all these like personal notes and whatnot, it's sort of like learning about me from those folders has been really useful to a. In a way to me where it's like it. I feel the need less for. For things like memory and for skills because it sort of has this knowledge base about me already. Even though I think there's still. There's still a time and place for skills. But I personally, for the use cases that I've had, have felt like less of a need for them.

[B]

Oh. Because it just updates his memory every day based on what, your conversations?

[A]

Yeah. Or it's. It's. Yeah. And it's basically like that is like a memory that almost that I. I maintain of it because I'm taking notes in it all the time. Yeah. Got it. Yeah.

[B]

Yeah. This is great. It looks like your presentation is ready. Just like a thought.

[A]

My presentation is ready. Let's see if it is. Oh, it is. Okay, cool. So it's made this presentation. It will load a little bit. Um, yeah. So I think, you know, with this you could take it into. Into Keynote or whatnot. It did. I didn't ask it to use the anthropic skill here. So it's sort of generic, but I could. And then. Yeah. I think from here I would take this and I would say, like, let's schedule. Yeah. Do this every morning or every Monday morning

[B]

at 10am and you can set up in a way where. Can you set up in a way where it actually shares with your team too, not just you, like in Slack.

[A]

Yes. Like, I could. I could set it up with my like Slack MCP and have it just like send it out, basically. So it's like. I think I would. Yeah. So I think it. I also like how it asks me like, clarifying questions here. So it will push this money. Let's say it rebuilds the duck. Yeah. So it'll. It'll do that. Yeah. And then I could also ask it to, you know, using the Slack mcp, send it to a certain channel every, every week.

[B]

So, so where do you bring your team into this process? Or like, you know, like. Yeah, when do you actually. Because you're interviewing with AI and then you go iterate for team and you kind of go back and forth or how do you.

[A]

Yeah, I mean, here, like the, the, the actual like UXR interviews are like something that I probably, I wouldn't. You know, like either the PM or the researcher on the team or somebody else on the team would actually do. And then we would. And then through this, you'd probably just like share the artifact and bring them in. And, and then, and then I thought this actually could become the, the, the thing that the team operates off of. You know, like, it's like, oh, you know, the, the team, at least our team is pretty bottoms up and, and like democratic in that way. And so giving, the way we operate is like, we just give people the insights and the goals and then everybody sort of like goes off and like makes prototypes and try stuff out and ideas come from everywhere. And so that's what the, the handoff point is. It's like, it's like, it's less of like, oh, like me as the designer, I will come up with all the ideas, but it's like, hey, here are, you know, anybody can do this. It doesn't have. Just have to be the designer either. It's like, here are the insights, here's what we're trying to do this month and how can we all get there? Like, how can we all meet this goal together?

[B]

Yeah, maybe just give like half tasks to Claude to create a PR for and then with the more complicated ones, you can like try to handhold it.

[A]

Yeah, I mean, yeah, I think with this we, we still wouldn't hand it like directly to Claude to, to. To do all the stuff. Like there. A lot of what we do is I think we rely on ourselves for a lot of our own judgment and our ability to like, curate and decide what to actually build and do.

[B]

And like, you know, people could talk about taste and stuff and judgment online. Like, I don't know about you, but like, I, I feel like the way to build this stuff is just to. Yeah. Like, just, just get the fire hose of product feedback from internally and externally. And then you just kind of develop the sense of like, what's broken and what needs to be fixed. Because just hearing feedback all day long, so you kind of know.

[A]

Yeah, yeah, yeah, yeah. So this one I Think. Yeah. You know, it will have created these, like, basically kind of wireframe Y type things and. Got it. Yeah. And I think it's like, it'll show you different options and stuff like that. And I think I am, as a designer, I like to just, like, see a lot of options, even if they're, like, not super high fidelity versus, like, imagine them. And that helps me decide, like, what to actually do. So, yeah, I think having Claude just, like, come up with the options saves me, like, a step from just having to mock them up. Even though from here what I would probably do is, like, choose one of these directions and then, like, start to, like, micro iterate on it or even take this and. And make a prototype of it in code and then iterate from there.

[B]

Got it. Okay.

[A]

Yeah. Yeah.

[B]

Well, it sounds like a fun job.

[A]

Yeah, it's a fun job.

[B]

Sounds fun. Let's switch topics a little bit and let's talk about how Cowork came to be. You know, so. So, like, there's a bunch of stuff out there about how it came together in 10 days.

[A]

Yeah, but.

[B]

But I think it's actually, there was a lot of iteration before that too, right? Or, like.

[A]

Yeah, that's a. That is one of those things that I think got pulled out of a quote somewhere on somebody else's, like, interview or press tour. And I think everyone's anchored onto it, like, oh, they made it in 10 days. And the actual, like, the actual story is that cowork or this, like, direction of Cowork has been something that the company has been, like, thinking about or, like, wanting to do for. Honestly, like, basically ever since I joined Anthropic about a year ago, like, just some way to help and be sort of like a thinking partner for, like, since we already have this basically for code, but for, like, all general knowledge workers. And I think a lot of it has just been, like, how do we execute on it and what is the right, you know, architecture for it and what is the right UX for it? And so even throughout last year, like, there's been, like, lots of different prototypes, some more ambitious than others. There's been a lot of different, like, technical experimentations around, like, different agent harnesses that we've used, a few that didn't pan out super well before we landed here. And we've seen prototypes from people in our sort of, like, labs wing, but also, like, prototypes that we've built on the product side of the house. And I think about, like, a lot of these things. It's just about, you Know if the idea keeps coming back and there's like energy each time, but then it's like the execution, often it is just about like timing and execution, just like the lightning striking really well. So when we did decide to ship this, it was basically 10 days from like, oh yeah, we should ship this to like, okay, it's shipped kind of thing. And a lot of that was like building on the momentum of what we were seeing with Claude code over the holiday break, where it feels like over the holiday break, everybody finally had the time to, to try out cloud code because they've been hearing about it, they're like, okay, it sounds great. You know, there's all these AI tools, I don't have any time to try it. But then for some reason everybody tried it out and then a lot of also like people with non technical use cases tried it out. Like people were using it to like do things like parse their podcast transcripts, or they were using it to do all these like complex analyses and stuff like that. And we were starting to see like, even like early product market fit of like the Claude code, basically agent harness with non technical people. And so we already had this sort of like working prototype of that internally and we were slated to launch it a bit later, but I think that gave us the. We were like, this is the moment, we need to meet it. And even if we don't have the perfect product yet, we should get something out there because we think that like the benefits and the usefulness and our moment to like capture this audience, it is right now. And so that ensued a really hectic 10 days, but it got us here. And now that it's out here, it's been really, really helpful for us to get the signal from people of how to, how they use it and iterate on it and keep making it better for people.

[B]

Yeah, you can learn way faster. I guess the research preview is like the new beta. You can learn way faster.

[A]

Yeah.

[B]

Okay. So basically, so if I understand, there was even over the past year, there's a bunch of like people sharing prototypes in Slack internally and then, you know, people leaving feedback and then eventually you had a working prototype and then because the market kind of demanded it, you kind of just like rushed. You kind of just like did a sprint to make it happen.

[A]

Yeah, basically. And like we were originally going to launch this a few weeks later anyway, but it felt like, oh, this is the moment. And it sort of forced us to scope it in a way that was a little bit more realistic and just put energy behind IT and staffing behind it.

[B]

And can you share some early iterations or any kind of work in progress stuff?

[A]

Yeah, I pulled together a few screens of what it actually looks like or some design iterations too, of it. Obviously there's a lot more, but this is what I can show you. Okay, so we had an earlier prototype in the year, and this is actually something that another designer and I collaborated on, but we actually tried to make this sort of feel a little bit more like, task oriented or, like, workflow oriented. And I think also we were really worried at that time, like, oh, like Claude is. Or people are not going to understand that with a product like Cowork that they're going to be able to, you know, do certain things or, like, make certain basically outcomes, like make a dashboard or something and gather sources from a bunch of different places. And so we actually made this, the, the. The UI much more structured and almost like you would like a workflow tool where it's like, hey, add these things. Like, this is. These are the inputs and these are the outputs. And then we made chat sort of secondary here. And I think when we did this, like, one Claude was like, not great at sort of following the workflow exactly at that point, given the technology that we had. And it felt like way too structured. Like, I think seeing this UI on the left, where you sort of have to fill it out and like, add all these different sources, it didn't feel good, you know?

[B]

Yeah, yeah.

[A]

And it was just felt like a lot of work. And it was like, why do we have to do this in this day and age, in 2025, when we could just, like, ask Claude to do something for us? And so that was one iteration that was actually a part of, like, a different prototype. Yeah. And then we originally were just like. We eventually were like, okay, cool, it's going to be a chat box. And we tried to do a thing where we guided people towards, like, more specific outcomes, like whether it was like, analysis or documents. And we built this, like, this working prototype that I wish I had a screenshot of where each of these, like, when you clicked into them, they almost had, like, different dials for you to, like, adjust the length of the document or I see. Or, you know, like the type of document, like memo presentation, whatever. And that felt, like, really overwhelming as well, I think. And so a big thing we were trying to balance with a lot of these explorations was, like, how prescriptive of the use cases are we versus, like, freeform, like a chat box.

[B]

Got it.

[A]

And then what we actually ended up shipping with just a few weeks ago, a few months ago was something like this, where again, we did have this, like, sort of like, almost wizard like, experience. We would click through and it'd be like, oh, create a doc, make it three to five pages, etc. Etc. And we also just showed a bunch of the UI up front because we wanted it to feel really differentiated from chat. But then I think when you come here, it just felt like there was a lot of competing visual elements. And so over time, we stripped most of this back and we went away from this actually really opinionated UI because it was actually not helpful to show all of these things. It's this constant balance of how much do we tell people how to use, what to use it for versus, like, leave it really free form for them. And so now actually, like, if you look at the current ui, which I'm just going to switch if you look at the current ui. Yeah, like, a lot of it is really peeled back. We don't have. We don't. We're not showing these heavy sidebars and it feels more like the traditional, like, sort of chat box. But we, we sort of have. We reformatted the homepage to feel more almost like a. It's Claude's active to do list. So here I only have, like, one active task. But, you know, at any given time, I could have, like, many more. You know, like, if I'm really asking Claude to do stuff or if I've, like, you know, given Cloud a bunch of tasks and come back, I'll have a bunch of these where it'll be like, okay, there's an extra message or I could review this. And here I can actually just like, approve and triage these tasks. So it's like, yeah, let's schedule that and then I'll see my scheduled tasks here. And the idea is that it just feels much more like a shared to do list between you and Claude as opposed to this chat box with a bunch of overwhelming suggestions and UI to sort of show you how to use it.

[B]

Got it.

[A]

Yeah.

[B]

That's awesome. That's awesome. And maybe in the future it can be like, you have multiple agents and they can be like a treadle board. You can move tasks around and stuff like that.

[A]

Yeah, I mean, maybe,

[B]

yeah, Maybe by the time this podcast come out, you have updated the UI again.

[A]

Yeah, maybe, maybe. Yeah. But I think that also shows. Hopefully that shows too. Like, the UI looked so different, just like, you know, maybe like four or five weeks ago, and now it's like we're constantly learning, like, what's working and isn't working, but we're also learning best about how to like, display this technology to people.

[B]

Yeah. You know, it's really interesting, like for clock code, like, I've been leaving, I've been tweeting some feedback about, like, because there's so many different, like slash commands and stuff that you can just like learn. It's almost like going to Costco to do like a treasure hunt. Like, you never know what you find. But, like, it's not very beginner friendly. Right. It's like a game where you learn more and more. You kind of master it. I think maybe for Cowork, you're trying to find the middle ground between the regular chat and the cloud code. So it's not like all the things are hidden, but you try to guide people in some way.

[A]

Yeah, I mean, you're still able to use slash commands in Cowork, but they're not the primary way in which you interact. And I think the way that at least I personally think about it is at least Cowork is also a tool for professionals. And we sort of see a bunch of people use it in very power user ways, and there are already power users of it. So a lot of people will be motivated to learn much more complex capabilities. Right. Like, they will be willing to create their own skills, share them with their team, etc. And also want shorthand commands for things. But all these things should be possible without having to do that learning as well. And those sort of commands should be a secondary way to interact with Claude. And you shouldn't have to know all the commands in order to use it.

[B]

Yeah, that makes sense.

[A]

Yeah.

[B]

Okay. All right, just a couple of closing questions, I guess. So how does planning work at Anthropic? It seems like a pretty chaotic place. Do you guys do annual planning and setting goals and stuff, or is it more just like prototyping and trying it out?

[A]

I mean, it also changes every time we do planning. Like, I feel like every time we've done it, it's been very different. On the team that I am on, we do monthly planning. We. We just, we have a spreadsheet. And I think it, at least in. In the co work section, there's maybe like Max, like 12 things in that list and it's really truly our p zeros. And then for each of them, they just have one single DRI and it's like. And then we just come back each week and we're like, are we on track or not there is some amount of like quarterly or half planning that we'll do where I think usually one of the leads will be like, hey, this is like generally where I think we should go and these are the things that we should work on. But it's not so structured where it's like we absolutely have to do these things and these are the projects. It's sort of like just giving everyone a picture of how things might fit together. Okay. Yeah, yeah. So it's pretty loose.

[B]

It's pretty loose, right? Yeah. You know, you know, that's the funny thing I find because like, you know, Anthropic is one of the most innovative companies, but I find at the most innovative companies it's less about trying to do this annual planning theater and more just about like iterating and like learning from the users. Like do you still make like at some point in your career you're probably like a North Star Vision deck or something, right? Like, do you think that stuff is useful?

[A]

Yeah, yeah. I mean I like, I think we did. I made a North Star Vision deck maybe last year.

[B]

Yeah.

[A]

So we, I think there is still room for these visions in that they point people towards something and make quick clarity around what we're going to do. I think given the where at least I work, you know, like we. This technology like literally changes all the time and there's new models all the time and the rate at which new models is coming out is just faster and faster. Basically. I think there's no such thing as a one year vision, let alone a two or five year vision for us because there's so much that's unknown out there. But what actually is helpful still is pointing people towards the same direction, especially when anyone can build anything. So what I think about as visions now is just more like, yeah, it's like three maybe maximum six months. But a vision can be, it can be a document. I think it's more helpful when it is visual. So I do think this is where design still has a ton of power, is being able to piece things together and make it coherent in a story for that period of time. But it can also be a prototype. It doesn't need to be this deck that's static. It can be a prototype that, that just sort of helps us. I think often what it helps us do is we often have five teams working on something very similar or things that collide or might feel duplicative. And what design can really do is curate and help bring cohesion to those ideas and show us a path towards making that an ideal experience as opposed to five disparate ones.

[B]

Yeah, that makes sense. That makes sense. And how about with. Do you guys have like, reviews of army and like, for folks like that? Like, is there like former reviews or they're also, like, playing with the prototypes too?

[A]

No, we do still have reviews. We don't have them for, you know, I've been at companies where we have them for like every single feature and whatnot. It happens for sort of like, bigger, you know, higher priority projects. But it doesn't feel like it is. It is a big sort of like, thing you have to prepare for and spend so much time on. It's mostly for that visibility and for that feedback. And if there's things that sort of cross are big and have like, big company wide implications, we'll have those reviews. Yeah, got it.

[B]

Okay. Well, I mean, do you have any closing words of advice for designers who maybe like, you know, they kind of feel like the ground is shifting under defeat? Like, should it, should they start, like, submitting PRs or like, what should designers do?

[A]

Yeah, I mean, if you feel like the ground is shifting beneath your feet, it's because it is. You know, it's because it is. And I think at this point you have to just accept that, you know, and then. And sort of adapt to it and just be really open towards, like, questioning the way that we work already. I, I think it's, it's coming for, it's coming for designers right now. And I think we're feeling it today a lot because a lot of, like, the roles around us have changed already and we're like the second tier effect for it. But also I think the, the tooling for us is also changing. And whenever I feel sort of like sometimes I am like, sort of threatened, I'm like, oh, my gosh, my job is. Change is changing a lot. Like, I. People don't value me in the same ways that I used to be valued. But then I think about, like, my engineering peers and how much that they have already adapted towards how much their job has changed and how like, valiantly they've. They've. They've gotten through it and how much they are still. They're producing even better and more work today. And so I look at them as inspiration. I'm like, oh, if all these people that I really respect can do it and do it in a way with such humility, then I can too. And I sort of see them as a model for what's coming next for me.

[B]

Yeah. In some ways, to get rid of. There's a lot of mundane and busy work, like moving boxes around that you don't have to do anymore. Right. So you can actually focus on a higher level thinking and that kind of work.

[A]

Yeah, or it just producing more work too, you know? Like, I think I. I think about how much my engineers are capable of right now and I'm like, yeah, that's, that's wild. Like they're, they're, they're creating entire features in days, not weeks, these days. So. Yeah.

[B]

Yeah. But the funny thing is you don't actually get more free time. You actually work harder.

[A]

I mean, like, it's because I think we're all really ambitious and we like

[B]

so much good time.

[A]

It's like a high. You're like, oh my gosh, I can get so much done now and I. And I don't have to do the stuff that I didn't like doing before and so let me do more, you know?

[B]

Yeah, yeah, yeah, yeah. No, that's good. That makes more job more fun. Okay, well, thanks so much, Jenny. This is awesome. Awesome. I feel like we've been talking online for a lot and I finally got to talk to you. Yeah, it's been great.

[A]

It's been great to have this conversation.