What happens after coding is solved? | Fiona Fung (Claude Code & Cowork)

Fiona Fung leads the teams behind Claude Code and Cowork at Anthropic (overseeing Boris Cherny and the entire engineering and PM team). Before Anthropic, she spent 11 years at Microsoft building Visual Studio and TypeScript and then moved to Meta, where she started Facebook Marketplace (now generating over $100 billion in GMV annually), worked on Meta’s first smart glasses and AR glasses, and led infrastructure, growth, integrity, and safety teams at Instagram. She’s been an engineer for over 25 years and has a unique perspective on how the role of building software is changing. *In our in-depth conversation, we discuss:* 1. What she’s learned about running a team that’s shipping 8x more code than before 2. Which roles AI will transform next 3. Specific ways her team uses AI 4. How Claude “routines” have changed how she operates as a manager 5. The context-switching problem no one has solved yet 6. The biggest unsolved problem in AI 7. What keeps her up at night *Brought to you by:* WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny Mercury—Radically different banking, now with Command: https://mercury.com/ *Episode transcript:* https://www.lennysnewsletter.com/p/building-the-most-ai-pilled-engineering *Archive of all Lenny's Podcast transcripts:* https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 *Where to find Fiona Fung:* • LinkedIn: linkedin.com/in/fionafung *Where to find Lenny:* • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ *In this episode, we cover:* (00:00) Introduction to Fiona Fung (02:31) How the engineering role has transformed over 25 years (09:28) What an AI-pilled software team looks like in 2026 (12:26) Using Claude to manage and review team output (14:40) The evolution of code review and verification (16:55) Who to hire: creative builders and deep systems experts (18:18) The shift to ambitious thinking (19:40) The growth mindset required to thrive in AI-native teams (25:52) Helping small businesses adopt AI tools (31:46) How Anthropic spots latent demand and builds for it (35:08) The next frontier: asynchronous work with AI routines (38:06) Agency and accountability in AI-native teams (39:40) The vibe shift from token-maxing to ROI measurement (44:24) The “bad vs. sad” quality framework (49:34) Why all managers start as ICs at Anthropic (55:24) Preventing skill atrophy (58:43) Managing context switching with 20 AI agents running (1:00:08) How PM and data science roles are transforming (1:03:40) The importance of dogfooding and using your own product (1:08:36) Outstanding questions (1:12:48) The future of engineering jobs and education (1:17:59) What keeps Fiona up at night: team culture at scale (1:22:53) From six-month roadmaps to JIT (just-in-time) monthly planning (1:27:03) Lightning round *Referenced:* • Running an AI-native engineering org: https://www.youtube.com/watch?v=igO8iyca2_g • Head of Claude Code: What happens after coding is solved | Boris Cherny: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens • Today, Anthropic engineers on average ship 8x as much code per quarter as they did compared to 2021-2025: https://x.com/AnthropicAI/status/2062568864240836995 • Visual Studio: https://visualstudio.microsoft.com • Joseph Campbell’s quote: https://www.goodreads.com/quotes/192665-the-cave-you-fear-to-enter-holds-the-treasure-you • Life-changing Cowork use case: https://x.com/lennysan/status/2059664455001334124 • Introducing Claude for Small Business: https://www.anthropic.com/news/claude-for-small-business • Conversations with Tyler podcast: https://conversationswithtyler.com • Sheryl Sandberg on Facebook: https://www.facebook.com/sheryl# • Amélie on Prime Video: https://www.amazon.com/Amelie-Jean-Pierre-Jeunet/dp/B0DQ4S3N45 • Spirited Away on HBO Max: https://www.hbomax.com/movies/spirited-away/3deab668-d0a4-4a8d-9bc8-0952a0ad836e ... References continued at: https://www.lennysnewsletter.com/p/building-the-most-ai-pilled-engineering *Recommended books:* • Margaret Atwood’s books: https://www.amazon.com/stores/author/B000AQTHI0?ccs_id=0027a474-cd59-4a3a-bcd7-9b173c27d530 • Haruki Murakami’s books: https://www.amazon.com/stores/Haruki-Murakami/author/B000AP7AFI • The Little Prince: https://www.amazon.com/Little-Prince-Antoine-Saint-Exup%C3%A9ry/dp/0156012197 • Nausicaä of the Valley of the Wind: https://www.amazon.com/Nausica%C3%A4-Valley-Wind-Box-Set/dp/1421550644 • High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884 _Production and marketing by https://penname.co/._ _For inquiries about sponsoring the podcast, email [email protected]._ Lenny may be an investor in the companies discussed.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Lenny Rachitsky?

  Anthropic engineers on average ship eight times as much code per quarter as they did compared to 2025.

• 0:05Speaker 01

  Coding is no longer the bottleneck. It's lifted the ceiling of what anyone is able to do.

• 0:10Lenny Rachitsky?

  Everything is now possible in theory. Now it's about how ambitious can you be?

• 0:14Speaker 01

  It's always something we ask ourselves. What's better than me doing it, having a lot to do?

• 0:18Lenny Rachitsky?

  The people that seem to be doing best are taking the most initiative, getting the most proactive, have the most agency.

• 0:22Speaker 01

  We say with high agency is also high accountability. So it's all about making sure folks have that freedom to cook. But then it's also like, okay, what's the accountability for it? What's the hypothesis of what you're trying to solve?

• 0:33Lenny Rachitsky?

  I'm curious what is lost in this new world of software engineering.

• 0:36Speaker 01

  It can start being a lonely experience because we all started just working with our agents so much. And on the Claude Code team, recently, we started a pairwise programming lunch.

• 0:44Lenny Rachitsky?

  Something you think about is this gap forming between people that are leaning into AI, killing it, and then people that are not, super frustrated, fighting, resisting.

• 0:52Speaker 01

  In terms of frustration, I think sometimes I also see a little bit of fear. For anything that there is a fear, my advice is lean in and ask, what can I do about it? What is within my control?

• 1:05Lenny Rachitsky?

  Today, my guest is Fiona Fung. Fiona leads the teams behind Claude Code and CoWork at Anthropic. She oversees both Boris Cherny and Cat Wu, both of whom who have been on the podcast and whose episodes are in the top 10 most listened to episodes of all time. Before Anthropic at Microsoft, Fiona ran the teams that built TypeScript and Visual Studio. After that, she went to Facebook, where she started the Facebook Marketplace team, which she took from idea to launch. Today, Facebook Marketplace generates over $100 billion in GMV every year. Also, while at Meta, she oversaw work on Meta's first smart glasses product, and then she helped build Orion, their first AR glasses product. Then she went to Instagram, where she led infrastructure, growth, integrity, and safety teams.

• 1:49Lenny Rachitsky?

  While at Instagram and at Meta, she oversaw an org of over 500 people. Fiona has been an engineer for over 25 years and as a longtime engineering leader, especially now at Anthropic, she has such a unique lens into where things are heading, what's worth paying attention to, and what teams should be thinking about right now as AI transforms the world of building. A huge thank you to Cap Wu, Boris Cherny, and Mohamed Hegazi for suggesting topics and questions for this conversation. Before we get into it, don't forget to check out lennysproductpass.com for a free year of the hottest and most well-crafted AI products in the world, available exclusively to Lenny's newsletter subscribers. With that, I bring you Fiona Fung.

• 2:35Lenny Rachitsky?

  Fiona, thank you so much for being here. Welcome to the podcast.

• 2:39Speaker 01

  Thanks so much for having me, Lenny.

• 2:41Lenny Rachitsky?

  So I was at the Claude, Code with Claude event, I don't know, a month ago at this point, and I went to your talk. And I was just like, holy shit, I gotta get Fiona on this podcast. She's thinking so far ahead of where everybody else is going and where people are at with AI. So you've been an engineer for 25 years. I was browsing your LinkedIn. You started at IBM of all places. Such a different place to be these days. And it's just insane how much the job of an engineer has changed over the past just like two years. It's like a completely different job. Like, people may forget 100% of code was written by humans not long ago. And now it's getting to 100% of code written by AI.

• 3:24Lenny Rachitsky?

  As Boris famously said, "Coding is salt." Along these lines, there's just this tweet that you guys put out yesterday where you showed, here's the tweet, "Anthropic engineers on average ship eight times as much code per quarter as they did compared to 21 to 2025." We'll show this chart on the screen. It's just like, stable, stable, stable, stable, boom, shooting off into the moon. So it's just insane how much this role has changed. I'm curious about your kind of path as an engineer, going, living through this, having been an engineer for a long time. What have been kind of like the big moments along the way where it's shifted your... Way of thinking and operating that have led you to what you do now and how you operate now?

• 4:03Speaker 01

  Oh, I love this kind of walk back in time. Yeah, like IBM, working on DB2, the operating system services team. Like, back then, I was thinking, oh, how can I, how can I be like the, like, what's a hard area of the stack? And I really thought, the lower level, you go closer to the OS, then it's more hardcore and you'll learn more. So that was, I was really fortunate to gotten into the IBM internship. But the funny thing was, I would, I think there's even a big shift from IBM to Microsoft. So at IBM, it was, I think Vim, like, I didn't have an IDE that we used. I think there might have been an Eclipse license, but for some reasons, most of us didn't use it. So I remembered it was mainly like Vim and, you know, like, kind of terminal

• 4:45Speaker 01

  debugging. And then when I joined Microsoft, I mean, this is how naive I was. I didn't even know about IDEs and such. And, and back then, you didn't really get to pick teams. Like, this was early 2000s. Actually, first off, I should say, I was so grateful that I landed the internship and the role, because to take us all the way back in time, the dot com bubble burst in 2000. And so for my graduating class, like, a lot of the companies weren't hiring or were having freezes. So I was so fortunate when Microsoft extended me an offer. And so they're like, you're gonna work on Visual Studio. I did not even know what Visual Studio was, because I came from like a Unix school. So I remembered asking, oh, because I was thinking, well, the name Visual Studio, I'm like, oh, is this like a better paint program? And I could tell the look

• 5:27Speaker 01

  of my manager's face, like, what is going on? But then it ended up becoming like the love of my life for the first, you know, 11 years of my career. But that was the first time I used an IDE. So joining the Visual Studio team, seeing, oh, wow, like, here's an IDE with like, debuggers, and you can set breakpoints and do multi-threaded debugging, like, that was also always mind-blowing for me to think about the stepwise change. So yeah, like, that was kind of the story going from IBM to Visual Studio. And then what I really loved, actually, about Visual Studio, is I was on the Visual Studio editor team. So I used a VS editor to build the VS editor, and that's where my whole love of dog feeding comes from. Like, I remembered I wanted to first

• 6:09Speaker 01

  and foremost, create a delightful experience, not only for myself, but for my teammates. Because also, if we go back in that time, if you remember, I mean, when did Twitter come out? Like, was it 2006 or something?

• 6:22Lenny Rachitsky?

  Feels like it's been around my whole life.

• 6:24Speaker 01

  But back then, like before social media, it was also harder for most engineers to hear fast customer feedback. Like for sure, there you would be use research sessions or we would have customers visit us. But you didn't get the rapid feedback that you do nowadays. But back then I was so lucky because I was on VS. We ourselves gave each other so much rapid feedback because we were all heavy VS users on the team.

• 6:49Lenny Rachitsky?

  This episode is brought to you by our season's presenting sponsor, WorkOS. What do OpenAI, Anthropic, Cursor, Vercel, Replit, Sierra, Clay, and hundreds of other winning companies all have in common? They are all powered by WorkOS. If you're building a product for the enterprise, you've felt the pain of integrating single sign-on, SCIM, RBAC, audit logs, and other features required by large companies. WorkOS turns those deal blockers into drop-in APIs with a modern developer platform built specifically for B2B SaaS. Literally every startup that I'm an investor in that starts to expand up market ends up working with WorkOS. And that's because they are the best. Whether you are a seed-stage startup trying to land your first enterprise customer

• 7:33Lenny Rachitsky?

  or a unicorn expanding globally, WorkOS is the fastest path to becoming enterprise-ready and unblocking growth. It's essentially Stripe for enterprise features. Visit workos.com to get started or just hit up their Slack where they have actual engineers waiting to answer your questions. WorkOS allows you to build faster with delightful APIs, comprehensive docs, and a smooth developer experience. Go to workos.com to make your app enterprise-ready today. People think about these milestones along the way of an engineer's journey and we forget there's also, there's been like a lot of transformation over the years. Not quite what we're living through, but just like IDEs, Visual Studio. So I love that you're reminding us of these moments in the history of software engineering that have changed the work in a big way.

• 8:16Speaker 01

  Yeah, when I worked on Visual Studio, back then we also shipped software on CDs. I mean, and that's why there were really hard deadlines because you had to make sure the software was ready for us to give to manufacturing to then, you know, put on the CDs for us to then put on the shelves. And then so once, that was another shift when we actually started to be able to, you know, ship software online. And I think that's the interesting thing, and I kind of mentioned this in my talk. It's before when you like- Engineering time was like, like really precious resource. But you also have these really hard deadlines, for example, like printing software CDs. And so back then you would do a lot more planning because you just wanted to make sure, given the time you have, you you make the best of it. And that's the shift that, you know, like we're seeing with with Claude Code and Co.

• 9:01Speaker 01

  Work is coding is no longer the bottleneck. And so now, like, you know, you showed up, you showed the tweet and that graphic. So but now it's all about like, where has that shift happened? Like now, not only engineers, we also have designers, PMs, everybody on the Claude Code team checks in code. So like when not only more people checking in code, but like kind of different disciplines, but also the throughput is so high. How do we think about verification? Like, that's kind of this other shift that I'm seeing.

• 9:27Lenny Rachitsky?

  Maybe just kind of set this theme that I want to have for this conversation. A lot of people are just wondering, what is what is software engineering managing software engineers, managing software and product teams look like in the future? And you are living through that right now. So you mentioned this point about a more focus on verification, making sure the quality of the code being eight X is actually high and something that that, you know, will work. So just like, let me ask this broad question. Let's kind of see where this conversation goes. What is a what is an AI pilled software team look like in 2026?

• 10:03Speaker 01

  Because the roses are blowing, it's shifting more to this builder. Like, everybody starts being a builder, I would say. The other shift that I've recently done is I actually have a Claude Code remote session that I enlist in all of our repos. And so this way I have full visibility into the work that everybody's doing. And this instance, he also has access to all our Slack channels and and I'll have access to like, how are the metrics of everything we track? And so every month, like when when like I'll be like, hey, you know what's fun? Like, let's let's take a look back like, and so we'll actually do it together. I'll share my, you know, like Claude Code, you know, I've shared my screen and we do our Claude Code. Session and it's just about, hey, what were the focus areas? Like, what were some of the products that got shipped? How did it do?

• 10:48Speaker 01

  Or what were the feedback channels? And, and so I, even though like before I would have just used these sessions to like generate PRs and bug fixes, I actually have these sessions to enable me to have conversations with folks that I support.

• 11:00Lenny Rachitsky?

  Say more about that. So this is, this is like a management technique, let's say, to help people not just ship, but actually ship better, understand if they're shipping things that have impact. Is that kind of the idea here? Just like use Claude to keep on top of all the things people are shipping and then make that a conversation with them?

• 11:20Speaker 01

  Exactly. So like, yeah, outside of just, you know, the action of shipping is how did it do in market? Or, hey, did we have, you know, like, did we cause some bugs? And it's okay to, like, I have the saying, make new mistakes. Like, it's okay to make mistakes, just make new ones so that we're always learning. Cause if you aim to make zero mistakes, like that probably means you're not, you know, moving fast enough or being a little bit too cautious. And so, yeah, by, by having Claude, like, so then it can also look at, like, some, like, for example, actually, yeah, we were, I was just looking at, oh, you know, given some of the, you know, incidents that we have, like, let's look across all this, can we generate a theme? Like, what's a good area investment for us next? Especially we think about like quality, like, are we seeing any hotspots of where there could be a gap?

• 12:01Speaker 01

  I think that used to be just a much more manual process, I would say. Like, if I look back a year ago, I don't think I would have been able to, you know, have some of these insights with Claude.

• 12:11Lenny Rachitsky?

  Yeah, well, partly is because like there's that and also people weren't shipping as much. So you could just make a little bullet list. Here's the things I shipped last quarter, this feature, that feature, this feature, that feature. So I think what I'm hearing here is this is like one of the only ways to stay on top of all the things a teammate is shipping. So this is a really cool thread of just like how you found ways to stay on top of this 8X increase in code. What else has worked in helping you and your team stay on top of and maintain quality of all the stuff that y'all are shipping? Cause that's obviously a challenge, a bigger challenge.

• 12:42Speaker 01

  Yeah. And so definitely like the feedback channels are really important to us, but then we also get a lot of feedback. And like, for example, even I myself, usually what my, my morning ritual would be, you know, I get my morning cup of coffee and then I look at the feedback channels and then I try to pick out what are, you know, if I have some maker time, what's something that maybe I would be able to help out? Or would I could like see some gaps? Like that just used to be something I would do every morning. And yeah, I think maybe a month or two ago, we launched routines. And that's also completely changed. Like now I just have a routine that automates all this for me. And then there's also, it's almost like before I would, you know, be able to kind of like, you know, generate some prompts, but now with routines, it's almost like I'm, you know, having an agent help me, Jerry, like generate the prompts and the PR.

• 13:25Speaker 01

  So for example, one is, hey, keep a look on this feedback channel. You know, what are some of the themes? And then like when I wake up, then, you know, I have a really good summary of that. And then even some like PRs that I'll be able to take a look and review.

• 13:38Lenny Rachitsky?

  And the feedback channel, where's that feedback coming from? Is that like, like emails, Twitter, or a combo of everything?

• 13:44Speaker 01

  Ah, our feedback channels are definitely like, we have a lot from internal ads, but also like emails, channels, actually, everybody, like when we all get feedback on even like when friends ping us or on LinkedIn or socials, we'll all actually like post all of that in Slack as well. And so, and we also have like, of course, partnerships. And so we have different channels for, for all the various sources. But, but that's what I mean. I need Claude's help to help me stay on top because there is so much incoming feedback.

• 14:14Lenny Rachitsky?

  Got it. Okay. So this is cool. So this is a, like a way of working that you've built to stay on top of all the stuff, shipping, which is this kind of daily ritual slash routine where you, as a manager, look at what people are saying about the current state of Claude Code and Cowork. And used to just like, okay, someone go fix this, go fix that. Now it's like, here's the PR that'll fix this thing. Check it out. We're ready to ship it if you want.

• 14:40Speaker 01

  That's right.

• 14:41Lenny Rachitsky?

  Okay. Like obviously a big challenge for people is also just code review. I imagine Claude is also doing a lot of its own code review. Is there anything there? You've recently figured out that allows your teams to ship faster stuff that they are confident is great.

• 14:54Speaker 01

  Yeah. And honestly, it's crazy when, you know, I think we didn't even have Claude code reviews last year. And so speak of bottlenecks, that, that was a really, really big bottleneck of, you know, the human reviewers. So we definitely for the important, like, like areas that need deep subject matter expertise, we definitely want to make sure we have the proper, you know, like humans still reviewing. I would say what helps us though is the more that we can automate to almost check in the framework for what good looks like. Claude is very good when you give it a framework to validate against those frameworks. So I had mentioned like, you know, or like, you know, like recently, we just updated like content design to to have a skill in it like my like I and this is why like, um, I think if you have specs

• 15:35Speaker 01

  or like or like like check those into the repo and then make sure the spec also keeps up to date with the code like frequently. But that's what I found like works really well of any time you have like a statement of what good looks like, get that into the repo and then code review can make sure it's still matching what you set up to do.

• 15:52Lenny Rachitsky?

  Basically, it's like the evolution of test driven development.

• 15:56Speaker 01

  Yes, for TDD, it's because I remember that was like a big thing. My gosh, maybe like in the 2000s of right, the test first and then and then you can like make sure the test fails. Then you do actually the code in principle is really good, but I think I know I remember it. I myself struggling a bit because it was almost like you have to eat the broccoli first. I was like, oh, you have to write this test first. And I just get so much thrill out of shipping and building product. So it's funny, actually, the first bug I fixed on Claude code, I remember asking Claude, hey, I want to do test driven development. Help me write the test first. Make sure it fails and then we'll actually, you know, do the fix and then and then now that has passed. And the fact that that used to be, you know, like that test generation used to just be this tax that I remember having to pay like the fact that that's now automated and you can

• 16:41Speaker 01

  even revisit all these principles that have been around for a while, but now they actually might be even more efficient just because you have the models that can do more of the work for you.

• 16:51Lenny Rachitsky?

  Yeah, like that's that's so unfair. It's just write the test for you first.

• 16:56Lenny Rachitsky?

  So on this point of builders, one of my favorite slides from your talk that I want to ask you about is who you are hiring and who what you look for in people. And so I'll read what you said there and I want to hear more here. So the two profiles that you now look for when you're hiring are creative builders with product sense and deep systems experts for the hard parts.

• 17:18Speaker 01

  Yeah, but deep subject matter expertise, like for example, when I first run Claude code, we had really great kind of like product generalists. And then I realized, oh, we were missing folks with systems.

• 17:29Speaker 01

  Background. And so that was definitely an area that we we needed more folks with a kind of like systems and distribute systems expertise. And so I would say whatever are the parts that it's all about trust, but verified. The models are really good, but there are definitely a lot of areas that still need, you know, the verification. And so wherever you need the deep subject matter expertise, I would say that's, you know, an area to definitely still invest in. And the other one is kind of like the the product, the product sense works almost like the dreamers. Like, these are folks that usually will be like, my gosh, I'm really passionate about a product and they have an idea, they build it. And then it's always like looking at the feedback and then iterating and polishing and making sure that the product is a delightful experience. Like owning that product end to

• 18:14Speaker 01

  end. That's, that's like another skill set that sort of does really well on Claude Code.

• 18:19Lenny Rachitsky?

  This super resonates. There's this word ambition. I don't know if you used it, but that's what I thought of as you were talking. That's been coming up a bunch recently in the podcast and other work I've been doing. There's this ten X C engineer I was talking to the other day, and he was just like, I used to, like, I heard about a feature idea, like I, someone's like, hey, we should build this. And I was like, no, that's really hard and complicated. And he's like, but now I'm like, no, no, that's so possible. I just ask Claude Code to do it. And it just does it. And it's this whole mindset shift. And he's just realizing now it's about how ambitious can you be? Like, everything is now possible in theory. Now it's about how ambitious and how big can you think versus just like, okay, it's all these stupid little features and things I have to unblock. Does that resonate?

• 19:04Lenny Rachitsky?

  Is that something that you think about?

• 19:06Speaker 01

  Yes, actually, I was just catching up with an engineer yesterday, and he actually is not a mobile engineer by trade. But we really needed to update this feature to also have a mobile footprint. And it was just amazing. Like, he's like, you know what? Because it, and it's common, because you might think, wait, but I don't, I'm not like an Android expert. But now, thanks to Claude, actually, I can actually have a partner and actually also do this on the mobile surfaces. And so that definitely resonates. It's like, it's lifted the ceiling of what anyone is able to do.

• 19:38Lenny Rachitsky?

  So let me follow that thread. As the role has transformed in such a crazy way, some people are thriving, some people super frustrated, unhappy, fighting, resisting. What do you see common across the people that are doing really well? The engineers that have adapted and are thriving versus the engineers and even outside engineering that are frustrated and having a bad time?

• 20:04Speaker 01

  I would say a growth mindset really, really helps. Actually, even before AI tooling, I found that has been just so valuable. And I learned that a lot, actually, it was the shift from Microsoft to Meta. That was where I first, that first year, I'm like, oh, this is what having a growth mindset really means. It's really this concept of always be learning. Also, what served you to get you to this point may not, we serve you no longer. But it's really hard because, of course, everybody, like, we all, you know, we've all gotten to the state by acting or operating in a certain way. And so sometimes it is a little bit scary to think, wait, you're, but I've been successful so far. You're asking me to change what has made me successful.

• 20:48Speaker 01

  And so I would say the growth mindset is really, really, has really served me well. And I think it's also served others well that I noticed, like always leaning in with curiosity and always being able to learn. And then in terms of the frustration, I think sometimes I also see a little bit of fear. And so my advice there is, at least this is how, just in life, I've, because we all have, and fear is, of course, an evolutionary, like, I didn't study anthropology, but I think it, you know, it makes sense, right? It helps us make sure we were able to survive and not get eaten by larger predators. But for anything that, you know, that there is a fear, my advice is kind of lean in and ask,

• 21:33Speaker 01

  okay, is there some, what can I do about it? What is within my control? Because sometimes the frustration comes from fear and feeling like, but everything is outside of my control. And so it's happening to me. And so if you think about, okay, what is in your control?

• 21:49Speaker 01

  Instead of happening to you, is it happening for you? And then what's something that you might be able to do and change? I felt that's been helpful because if not, it is super frustrating to have the fear and then feeling like. Everything's outside your control. Like, I actually remembered when I was in, actually, when I was in high, it's funny when we were going back to IBM. When I was in high school, I actually didn't go into computer science or engineering. Like, I really wanted to be a visual artist. And this is how far back we go back, then computers were really expensive. So I actually didn't even have access to a computer. My first computer, uh, access to computer was grade nine, I think, in high school. I don't even know if this happens in high school anymore.

• 22:32Speaker 01

  My high school had a typing class where you went to class just to learn how to type on the keyboard and learn to be really proficient. And that was my first time. And then, you know, the next class was maybe like some HTML programming. So anyways, it, it, but the reason why I found love with it was why, what I love about art is creating and being, if you have an idea, you can go ahead and create and tell a story. And then I realized, oh, computers and programming, you know, that, that's, that's enables me to do that. So anyways, I, I tried to really fast, try to make up for all the, you know, science classes for me to get into university. But I had this fear of, oh, but how will I afford to get into an engineering school? And it was this big unknown. I, I grew up in Ontario, so I was very grateful.

• 23:15Speaker 01

  I knew there was an Ontario, you know, school assistance program, OSAF, I think it's called, which I'm very grateful for. But I didn't know how much of that would cover my tuition or like expenses. And it was just this unknown and it would be like a year, a year out. And I remember thinking, okay, what can I, what can I do about it? And then as, as luck would have it, the National Bank of Canada just posted this flyer in our high school saying, hey, we're hiring high school interns to be a bank teller. And I remember, oh, that like, I, and of course it was going to be minimum wage, but I, I, I, I thought that, that could be a lifeline. But it was funny because the class I hated the most in high school was accounting. So I don't know if I'd be any good at it at all. But I signed up to be a bank teller and that ended up being such a great decision because I worked all summer, saved up.

• 24:00Speaker 01

  And then actually I was able to work as a bank teller on the weekends. So like, yeah, well, I went to, I would go to school Monday to Friday and then I'm tired to be a bank teller. And that ended up being this lifeline that enabled me to, you know, like pay for all my school expenses. And, you know, we talked about the, the year 2000 dot com crash. Then when folks weren't hiring as much interns, actually I continued being a bank teller for, for two, two years. And, and so, but. But like that was the one action I felt I could take that was within my control to try to counter this fear I have of if I'm really going to go down this path, I don't even know if I could have afforded to go to school. So that's probably my other advice of like growth mindset and the source of, you know, frustration or anxiety, if it's coming

• 24:45Speaker 01

  from, you know, the like, see, is there some, is there one action that's within your control that you can take to, you know, so it like, because I think there's, and you know, there was a saying like, do some things, what would you do if you're not afraid, actually? Those were my two favorite sayings before, like, what would you do if you're not afraid? And do something scary once in a while, because that's also usually how we grow. I found that when you're, when you're really good at perfection, what you do, you're kind of at peak, you know, like maximum efficiency. But then how do you keep growing is you then do something scary that you might not have done before. And yeah, you will have a dip because you need to learn. But that's kind of how you keep pushing yourself toward.

• 25:22Lenny Rachitsky?

  The quote that I have probably used the most on this podcast of all quotes is, "The cave you fear contains the treasure you seek."

• 25:30Speaker 01

  Oh, I love that.

• 25:32Lenny Rachitsky?

  Yeah. And it's so true. Just like, like, I forget who put this, but just the thing that is scariest is like, that's a compass towards that's what you should be doing.

• 25:40Speaker 01

  Hmm. I'm gonna steal your quote.

• 25:43Lenny Rachitsky?

  Yeah, please do. Like, you know, there's like, don't do all the scary things. Like, maybe don't trip off a cliff. But maybe in career, in career moves, it's probably a good, a good choice. So kind of following this path, something that I know that is important to you, something you think about that I also think about is this kind of gap that is forming between people that are just like leaning into AI, killing it, doing super well, and then people that are just like not. And this is like a scary time for people that may be left behind in this new world that is emerging. I know you spend a lot of time with small businesses. That's a big passion of yours to help people learn how to use AI in their work. Talk about just like how you think about that and what maybe

• 26:25Lenny Rachitsky?

  we should be thinking about to help folks, you know, stay, not, not fall behind, basically.

• 26:30Speaker 01

  Oh, I love this. Yeah, it's one of my passion topics because I kind of mentioned, you know, like growing up in Canada and I moved there when I was a kid. I was born in Hong Kong. So I didn't speak any English and my parents had to work all the time. So my grandma, who is the best grandmother anyone could have ever asked for. I know everybody thinks their grandma's the best, but I really was so lucky. I had the best grandma. She moved with us just to take care of me while my parents were working. But neither of us spoke English, but I was able to learn how to speak English by, you know, going to school and speaking with classmates. And when I think about my grandma, it was very alienating for her to be, you know, in that country, new country where, and, you know, back then it wasn't as walkable. But one summer, I remember we just

• 27:14Speaker 01

  happened to find this little yarn shop that was owned by a lady that also spoke Cantonese. And so that became every week, we would go to this yarn shop this summer. My grandma found her knitting circle and then I think I learned how to do like macrame, which I think is having a comeback, by the way. It's always funny to see.

• 27:31Lenny Rachitsky?

  Macrame coming back.

• 27:33Speaker 01

  Macrame, I think, yeah. Heard it here first on Lenny's podcast. I think macrame's coming back.

• 27:38Lenny Rachitsky?

  All right.

• 27:39Speaker 01

  But that was probably where my love came from. I'm like, oh, wow, this little small business created this wonderful sense of community. And I've been really fortunate to, you know, become friends with all of the small businesses that I love. So that's kind of like where the passion comes from. And then what, how it happened was I was using cowork for my own business, expensing travel. I don't know. It is, I really don't like doing business expensing. And when I was using cowork, it was magic. I'm like, oh, all these things that I don't like to do, like cowork is doing for me. And I'm like, wait a minute, all my friends and honestly, small business owners, they really bust their butt. Like they work incredibly hard and they're usually, you know, like sometimes might be operating on really small margins. And so I thought,

• 28:21Speaker 01

  If Claude Cowork is so good at helping me do my little business trial expense, this would be huge for it because I see my friends sometimes sitting at the bar with stacks of bills and all they're doing is invoicing and expensing and I think nobody actually really likes to do it. So that's kind of where it came from. And then so yeah, I remembered helping a couple of them onboard. And it was also very humbling to see them go through our onboarding flow. Actually, it found some really good bugs. So it was really like a win-win. But it was also delightful for me because they also use Cowork in ways that I wouldn't have thought about because I was all fixated on, look at how it is amazing with PDFs and invoice. And then, you know, one of my friends who runs two restaurants, she's like, oh, my gosh,

• 29:06Speaker 01

  this folder I have is like a junk drawer of like, it's basically our documents folder. It just becomes this junk drawer of every, or downloads, like just, you know, like the kitchen junk drawer. And she's like, I know I have a few menus in here and I can't find it. And I'm like, well, let's ask Cowork. So we gave Cowork access to the directory, found the menus. And then she's in a really unique way. She goes like, I want to make sure I keep my prices reasonable for locals and tourists. So she goes, hey, Claude, look across my style of cuisine in this area. Is it comparable? And it came back with really cool, almost like market analysis. And she goes, hey, I actually just went to that restaurant in Seattle and that was pretty good. So I learned something every time. And yeah, they've been like giving me great feedback as well.

• 29:48Lenny Rachitsky?

  So the question then is just like, how do we, how do we spread this to everybody? Because as you see, you know, there's like, like a lot of people are just like, I don't have time for this or I hate AI. It's just like, I want to ignore it. Is it like talking, is it just talking about these sharing examples? What do you think? What's like a way to make a dent in this, in this problem?

• 30:07Speaker 01

  For all of us, especially to your listeners are probably very AI-pilled. If there's anyone either in their community or their family that, that has like, I would start with, what has something that really you felt has, that you really have felt has made a meaningful life change?

• 30:25Speaker 01

  For you with the AI tools and then seeing if that is a conversation starter for because for me, AI is a tool. Again, it's the whole light in the dark. I totally understand the frustrating part as well. But for me, I'm also felt like knowledge is power, like have to learn how to use the tools because it could actually, you know, be the light part of that light and dark equation. So I think that that was that's something that I would love everybody's help with if there's whether it's a community member or even if there's a business you really like and think, hey, have you ever it's it's it's a little awkward to start. Like, I remember when I first reached out my friends, I'm like, because I don't talk about what I do with them a lot. But I'm like, hey, I kind of, you know, working AI, can I can I it sounds it's even unnatural for me to do because I'm, you

• 31:08Speaker 01

  know, like, I'm like, hey, can I show you what, you know, cowork is possible and and then but it ended up, we end up having a lot of fun. So yeah, I would love for like that conversation starter would be great of yeah, because I just want to make sure we keep sharing the the knowledge and, you know, making the tool equitable because if not, I'm concerned that the device grows larger and larger.

• 31:29Lenny Rachitsky?

  Me too. I find that sharing use cases, as you said, is so powerful. I was just using cowork the other day to fill out my my son's camp forms and just sharing that on Twitter, just like a lot of people are like, oh, wow, I didn't think about that. It's just like these little things you don't think about that cowork and clock out can do kind of along those lines. Speaking of cowork, if you think about it, Anthropic has been super early on uncovering these really big opportunities ahead of everyone else. For example, coding so far ahead, like realizing this is a huge market, whether it was intentional or not, it was just like, whoa, that's maybe the biggest new business opportunity in history. And then cowork is a great example, just leaning into knowledge

• 32:13Lenny Rachitsky?

  work. Let's just make let's just solve all the knowledge work. Why not? So far ahead of everyone else. Another element is it feels like a focus on the personality of the model, something you all were very early on, just how important that is, not just for the experience, but just also the intelligence and success of the model. What is it that you think Anthropic and the teams do? differently that allows you to uncover these opportunities and then just go big on them before other labs, let's say.

• 32:43Speaker 01

  Well, I haven't worked in any other lab, so I'm not sure how labs operate, but I will share like, yeah, with and like actually on the Claude code team as well and cowork like we also keep an eye on like latent demand. Now, we're very fortunate with coding as a use case because so many ants that we were, you know, like our own first customers and we're able to do like really rapid feedback. And, and so I think, but latent demand has, has been like a, like, for example, like coworker, we noticed a lot of folks that were not necessarily coders were, were using Claude code. Can we make that experience better? I think that's actually even outside of Anthropic, that served me well in, in all the different products I've worked on. But, and, and actually, it's funny. You mentioned like, you know, the, the cloud for, you know, my passion with small

• 33:27Speaker 01

  business after I, you know, had a few of these visits, we ended up now launching Claude for small business, which is really cool because I, and, and it totally didn't come from me. So I'm not taking credit, but I noticed it too of like when I was working with, because they were asking me, oh, does this plugin, right? This plugin? I'm like, I think it does. And then we have to, you know, go and search for it. So actually now Claude was small business bundles it all up. So inside cowork, you just have this little toggle and there were, there were, there was a wonderful team that's been kind of like, you know, doing cowork sessions with small businesses that probably found, hey, we could have like an efficiency gain here or like make the experience better. And so I would, I would say like always, not only for products that you're on, like making sure

• 34:08Speaker 01

  you're always, you know, listening to feedback and always iterating, trying to make a delightful, reliable, high quality experience, but then also keeping an eye out for, oh, what are these other use cases that, that are popping up? And can we also make that experience better?

• 34:23Speaker 01

  It's, it's interesting. Like after like, you know, in software, I've learned that customers will use your product in ways that you did not intend for good or for bad. And so the, the best way is really like, it's all about the iteration, learn and keep close to the feedback.

• 34:40Lenny Rachitsky?

  Weight and demand. That's a, that term's come up a bunch on this podcast. Some there, might be some there. So essentially just watching closely for behavior that you may not have expected, or that is just kind of emerging, and then just going big on that, essentially exploring it, building something awesome.

• 34:57Speaker 01

  And having a hypothesis for, hey, like, because actually, when you see people jumping through hoops to make something work, can you actually make that an even, like, a smoother and better experience?

• 35:08Lenny Rachitsky?

  Yeah. Coming back to the way that your teams operate, you guys are so at the edge of what's possible, and the role of just engineering has changed so much. I'm curious what you think is the next kind of frontier of how engineering in particular is going to change? Is it like, you know, fleets of agents? Is it something else? Just like, what's like the next big shift to how engineers operate? That either you're already working on or implementing, or just like is starting to happen?

• 35:36Speaker 01

  I would say we're shifting more towards async, like asynchronous. And so to your point, the fleets of agent, like that, that's why routines is so interesting, because it's almost like, I used to be like, you know, doing a prompt synchronously. And then I would like maybe like kick off different prompts asynchronously. But now I can actually have a routine that actually generates, you know, these, these prompts for me. So it's almost like the level of abstraction keeps pulling up a little bit. And so I would, yeah, I wish I have a crystal ball to see what this is going to look like. It'll be fun, actually, for you and me to revisit a year from now.

• 36:09Lenny Rachitsky?

  No, I want to hear more about this. This is, so help us understand, what is, what is routines? And then what is, what do you say synchronous? You're writing a prompt and it just kind of goes off and isn't writing it immediately? Talk about what this actually looks like.

• 36:21Speaker 01

  Ah, good. Yeah. So routines is like how you can, like, so if you remember, I was trying about my, what I used to do is always like, you know, wake up with my morning cup of coffee and hey, look at through this Slack channel for me. But then now like I have a routine that I set to run every morning at a certain time to say, hey. That's right. But then it's able to actually go and kick off agents on your behalf. And so that's because like that's what like, you know, even you know, before it would be, oh, you could like, yeah, do a cron job to automate like, but now it's, hey, look at these feedback. And then if you're seeing some of these bugs that what are some polish fixes that you might be able to to knock out? And then it would like go kick off. And then I wake up and I end up having PRs that I could review versus before, which is still more of a, I can have different agents.

• 37:04Speaker 01

  And then it's still, I'm still thinking about, okay, now what do I do with this information? So it's like that higher level abstraction of, okay, now how can I actually write a routine that also basically does prompts for me for spawning different agents? So I think what will move more towards that kind of like asynchronous style of working.

• 37:22Lenny Rachitsky?

  So interesting. So like, in a sense, as a manager, you have these kind of things you do daily. And what you're saying here is you can set up these prompts that kind of check in every day on the things you would be be doing. Like, how are the projects going? What's falling behind? What should I imply? Who is, uh, who's struggling? And, uh, what's, how do I fix some, improve some, some polish? And so the idea here, what you're describing here is kind of write these things that you almost do as a manager daily. And have Claude essentially do them for you and then show you, here's what I'm doing. Here's what, here's what there's to review.

• 37:53Speaker 01

  And then it's, it's even like then giving even more autonomy at some point of it. You know what? Like, go for it. Like, for example, a verification is really good.

• 38:01Lenny Rachitsky?

  Yeah.

• 38:01Speaker 01

  Go, go for it.

• 38:02Lenny Rachitsky?

  I see. So you give it like a little bit of freedom to do more of this. Okay, that is so interesting. That reminds me, speaking on this idea of go for it, I don't like, I wasn't planning to talk about this, but I just watched Tyler Cohen have this awesome talk. About just like, what's happening? I don't know if you know Tyler Cohen is really smart, the economist as a podcast. And he just had, like, there's so much talk of the people that are doing best in this world. His term is initiative. They have initiative. Another term people use, agency.

• 38:33Lenny Rachitsky?

  Is that something, just like, you know, people hear this a lot, just like the people that seem to be doing best are taking the most initiative, getting the most proactive, have the most agency? Does that, does that kind of spark any thoughts to you, just what people may need to, I don't know, think about or improve on?

• 38:47Speaker 01

  Actually, that's agent, it's, I love that word, agency. That's what we really hold important on the Claude Code and Cowork team. But it's interesting, I say along with high, because like we really, it's about like, hey, here's a problem. And then it's really, everybody on the team has ideas for how to address the problem. So it's really high agency. And then we say with high agency is also high accountability. So it's all about like, making sure folks have that freedom to cook. You know, they, and but then it's also like, okay, what's the accountability for it as well? And that's where, and again, it goes back to like, what's a hypothesis of what you're, you know, like trying to solve? So I think, yeah, the, the balance, like, we're, you know, almost like two sides are the same kind of agency. And then accountability, I think, has served our team really well.

• 39:29Lenny Rachitsky?

  Such an important element of agency. Okay, cool. Everyone's off doing stuff, but okay, what have you actually, what have you brushed it up? What have you done? So kind of along those lines, it feels like there's this vibe shift recently from token maxing, just go crazy, spend as much as possible, just see what's possible. To like, wait, what are we actually getting out of this? How much does it cost staying with the ROI? Interestingly, Boris was actually like head of productivity, inch productivity at Meta. That was like his job is measuring inch productivity. And, uh, and then also just this like tweet of lines per code, like code shift, like there's this like interesting discussion of just, how do you actually measure productivity increase and ROI of AI tools in spend?

• 40:13Lenny Rachitsky?

  How do you, like, you know, you guys have the unfair advantage of getting free, free tokens working in Anthropic. With that in mind, what, what have you learned about just how to measure, say, ROI of engineers in today's world?

• 40:27Speaker 01

  This end productivity is such a fascinating topic. Yeah, because I remember, you know, like, like even Boris mentioned, like, you know, we'll first start with like lines of code. And then that's throughput. And then I remembered once, then there was a debate of, well, lines of code, this engineer had this crazy lines of code, but they just took some library and then just was porting it. So they checked it in. And then I was like, well, maybe it's significant lines of code. And then it's, well, but what if we're, you know, updating our frameworks and now we're generating less code, but like the output's still the same. So now I was like, okay, maybe it's, it's like time to land PR. Like, but, but it's very interesting if it's always been whichever metric, it's, it's like, if, if you're really focused on the, like, my advice here is,

• 41:10Speaker 01

  one is output, like, is the output really going towards the outcome? Because, yeah, like the, the, the token maxing, it's kind of like a, it's almost like the lines of code that we used to have. But I'm really much more about a, what is it that we're trying to, to do? Like, all, all of this, you know, there, there was another saying, I really, like, don't forsake motion for progress. Because if you're measuring like, you know, like tool user usage, then you're, you're measuring the action. But is it really making whatever that end outcome of yours like important?

• 41:42Speaker 01

  And so I, I really try to zoom out and focus on what is the problem we're trying to solve? What's a good way to measure that? And then that's what we, we focus mostly on versus kind of like the, the productivity measurement. I would say though, like outside of metrics, especially if on teams, as you're having more people adopt AI tooling. I would say definitely go on a listening tour for, for, for the leaders listening to a podcast, especially, you know, I, I love to focus on the senior engineers as well, like hear from them on what's working, what's not, how can we actually make it better? Because they will also help you multiply and scale that out across a full engineering team.

• 42:20Speaker 01

  And sometimes it's those conversations where you might get spark an idea that comes up and also really good shared learning versus, you know, like metric dashboards. It's very interesting. I've learned some good lessons for metrics. I'm all about like, it's really great when you have a, a metric that you can actually hill climb on. But always keep in mind of is, you know, kind of my whole growth mindset of, is it still serving you? Always keep in mind, like, is that metric really still serving the outcome that you were aiming for? Like a fun example I have of this is in the early. Facebook Marketplace days, we were kind of like launching by region and we really wanted to make sure we're building a delightful product before we expand. And I remember in the early days, one thing we would keep an eye on is kind of like number of sellers.

• 43:05Speaker 01

  And I remembered after launching to our first region, I'm like, oh, in this area, the number of sellers is low, but actually people are like, people are finding items that they're looking for, which is what we're aiming for, like helping people find items that they need. And then I realized in that region, it wasn't a large number of sellers, but there were power sellers. But our first gate before we expand would have just been like, you know, factoring heavily number of sellers. And I remember that quick conversation of, hey, and this goes back to that whole people will use things in ways you may not expect and shift iterate learn. And so, so then we updated the, the metric to go, oh, you know, like it's not a number of sellers because it didn't factor in power sellers. And so that's the advice I have to like whatever metric, whether for productivity or even for

• 43:49Speaker 01

  product, always keep an eye and make sure that you're not just having blinders on that's blindly following a metric that used to make sense because sometimes the landscape can change so fast, even the metrics themselves might need to be adjusted.

• 44:01Lenny Rachitsky?

  And this comes back to your process that you shared of having Claude watch all the PRs shipping per engineer, let's say, and then not focusing on the metrics, but focusing on that leading to a conversation about what impact does have, what was maybe some bugs that happened? And that being a really powerful way of understanding how, what's going on with this engineer? Awesome. Let me come back to this, just this question of speed and quality and just like impact. Is there anything else you've learned about just how to balance those things, just like this crazy velocity of code that's being generated and just staying on top of quality and impact? Is there anything else there that might be helpful to other teams that are trying to

• 44:44Lenny Rachitsky?

  wrangle all this, all these PRs being shipped every day?

• 44:47Speaker 01

  I would say, and this is what honestly we, we're, we want to keep doing more of and being better at it too, like the proactive quality. So especially for quality, making sure that what are the experiences that are key and making sure you actually, as you know, actually speaking of metrics, those are really good things that you make sure you can like, kind of like see trends over time. And so like on the quality front, we found like, and this is like the more proactive we can be of like, making sure we can get an earlier detection into quality. And so like, That's been one thing that we've been paying a lot of attention to. Like, you know, I started this, hey, let's have a concept of what's bad versus what's sad.

• 45:30Speaker 01

  And bad is like a very bad irrecoverable error. And sad is something that's kind of like a pain point recoverable. But it's interesting when you stack up sads, it could generally go to bad. But even having a, like, starting with a high level framework like that. And because if not, like, I think sometimes with dashboards, you can have, you know, like, time to load or all these other. But when you're dealing with a lot of different product surfaces, it's harder to go, wait, is that a good number or not a good number? And so one thing that's helped us is versus just raw, you know, like, performance or, you know, like, reliability numbers. Also having some framework of what we think is, you know, like, a bad experience and making sure we're focused on addressing those. And then also keeping an eye on where we're seeing in terms of the sad.

• 46:12Lenny Rachitsky?

  I like that. Yeah, I like the bad and sad. So these are kind of like thresholds of this is bad. Okay, this is serious. And this is in terms of like performance or failures? Or what sort of things are you measuring here?

• 46:24Speaker 01

  So for example, like, we allow each team, like, speaking of agency. So knowing that bad is like a really bad irrecoverable error. We enable each team of further surface areas, or it could be services that, you know, they lead. What is, like, so for example, on CLI, it could be crash rates. Like, a crash is pretty bad, you lost work. And for example, sad might be, hey, is it flickering? Like, it might be recoverable. But we have each team, like, and that's why it's been interesting, because before each, because surface areas are different. Like, we would have all these dashboards, but it's harder to zoom out and go, okay, what's the overall theme of the experience? So to your point, we give high agency to each team of what we think constitutes a bad and what's a sad. And then what's the goal that each team wants to take?

• 47:06Lenny Rachitsky?

  One of the, like, the main takeaway I'm hearing here is one of the best tools for staying on top of quality is just monitoring and tests versus spending more time reviewing, which makes sense because the speed is just impossible to stay on top of. And it almost speaks to this idea of closing the loop for agents to be able to kind of figure things out themselves. They know what success looks like, cool, we'll fix it ourselves. So that's a really interesting takeaway is just invest more in the tests, evals, I imagine, as part of this. And then just like monitoring failures and speed and things like that.

• 47:38Speaker 01

  That's right.

• 47:39Lenny Rachitsky?

  Something, I think this is public. I know that you guys have this dashboard that tracks just like F-words, like how often people are like, because they're so pissed and frustrated. There's like a funny term for it, I think. I forget what it's called.

• 47:50Speaker 01

  Yes. Actually, I remember. Yeah, that was last September because we were all, we were all seeing some frustrations. And yeah, that was an injury on the team of, hey, we should maybe track swear words. I'm like, oh, that's a great idea. I remember it. I had just, you know, Joey and we were having that really fun conversation. Yeah. So it's, it's again, like, it's very interesting to have like, look at, and, and that's why like evals is hard too, because it's going back to like that user experience and how we can make sure it's a delightful experience and less frustrating. But yeah, the swear word dashboard is, is a fun one.

• 48:22Lenny Rachitsky?

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• 49:05Lenny Rachitsky?

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• 49:35Lenny Rachitsky?

  Kind of going back to the way you operate and ways that you've figured out to work in this crazy new world that we're in. I've heard about a couple of things that you've implemented that are pretty unique, I think, to how teams operate and I think is something that has worked really well for you. One is making every manager start as NIC and then just every manager has to continue being NIC part-time, kind of this player-coach approach. Talk about that, why that's so important in today's world.

• 50:00Speaker 01

  I love it. It's funny, when I first joined, because I have amazing recruiting partners and I noticed we were, you know, this whole theme of kind of growth mindset, it's just because the landscape is changing so fast. Like what worked well before like may not make sense and even what makes sense today may need to change tomorrow. Right? Like that's what I have to keep reminding myself. So yeah, when I first joined recruiters, like, okay, yeah, we have these couple of manager postings. And I'm like, you know, because actually how it came from like a listening tour I did with like all the, all the members on the team. And I heard a lot of these, hey, I really appreciate the agency, but how can I make sure prioritization? And so I kind of through that, I realized, and then there was some really good feedback too of making sure

• 50:43Speaker 01

  that it's not too many layers of reviews. Like there was good feedback, some folks might have joined from other companies or like, you know, and then I'm like, hmm, when, I actually think as a leader, if you actually start as IC first, without the worry of supporting people, because that's a very heavy responsibility that, you know, I think like managers, but like that, but before you have to take on that full responsibility, give yourself that maker time to actually dive deep into the code and learn the code base and I, or the product, like whatever it is, it doesn't have to, like honestly, the PRs I do are like, but it's more about for me, it's important because it keeps me in the flow because we're making so many changes to cowork and code.

• 51:26Speaker 01

  So even me doing PRs, it's less about what it is I'm fixing, it's more about me using the priority data just to keep that touch, because as amazing as metrics and everything are, and I do look at those dashboards, if you, as a leader, if you're not, you know, like living and breathing your product every day, you sometimes kind of like lose touch of the touch and feel of the product. But anyways, on the manager front, I think giving time for managers that join to be able to go deep into do that before supporting people. And then they actually like end up building really great rapport with the team. Like, because if not, I think sometimes as managers, you know, you might come and join a new team and you instantly think, I have to manage, let me dig into my manager toolbox and do managerial things.

• 52:10Speaker 01

  But if you actually give yourself time to not have to worry about that first and actually learn what it's like to be an engineer and teammate on the team, that also goes really far to building rapport. And in terms of like using the product, I think that's important. It's interesting, every team I've joined, one of the first, actually across all the different products, it could be VR, it could be smart glasses, it was like Instagram. Usually when I first joined, one comment that comes back to me is, hey, you know what? I really love how you're actually using what we build. It's refreshing to see, you know, you giving user feedback like, like, and so I think as leaders too, it's also a way for us to experience the work personally that the team does.

• 52:50Lenny Rachitsky?

  Something that people may not realize, you were overseeing an org of like 500 people at Meta before you moved to Anthropic, right? And you moved to IC, IC engineer, basically, at Anthropic from that.

• 53:03Speaker 01

  I started out like, it was for a very short, short amount of time, but, but actually this was my journey between Microsoft and Meta. So at Meta, I interviewed as a manager, but I think at least for the first quarter, I was also in IC. Cause I really wanted to learn what it's like to be a Meta engineer. Cause before then I was at Microsoft, kind of like cut my teeth on engineering at Microsoft. So I knew all the code bases, the tools, the languages. And yeah, but it was so valuable to have the, those first months, like actually learn what it's like to ship as a Meta engineer. Plus it was also fun, like I think sometimes we forget if we like, and but that's, by the way, what I love about Claude Code. Because the last time I shipped production software at Meta was probably 2017.

• 53:48Speaker 01

  And every year I might start, like I do a lot of dog fooding and a lot of, you know, like I, I also use dog fooding to help me like vet the quality of, of product as well. But it's been a very long time since I shipped production software. It's because part of it is I don't, I don't wanna screw something up. Like, I'm always, I'm always so scared of, what if I do something and then I cause a bug and then am I verifying everything properly? Or am I wasting someone's time? Because, you know, like also the, the, the tool flows would change. But I remember that first week on Claude, I'm like, at first I almost again went to my usual, let me go meet all the engineers and treat them to coffee. And then I'm like, oh, hey, wait, wait, let me ask Claude. And so Claude was this really good onboarding buddy of mine, because I was like curious about the codebase, asking questions.

• 54:33Speaker 01

  And, and then it also really, um, you know, uh, helped me like, you know, do the automated test, but I also want to still do some manual testing. And I, I asked Claude, hey, help me come up with like, what's the way for me to manually test this to make sure I cover all the case? But all that then gives me confidence that, okay, I can ship peers again. And then I got like kind of more comfortable with it again. And, and so, um, I've, I've actually had a lot of friends reach out to me that have been managing for a while that's like, hey, I'm shipping code again. Thanks to Claude. And so, um, but in, in general, it's, it's, yeah, like it's, it's just important to me as leaders to make sure you're kind of like using the product that your team built.

• 55:09Lenny Rachitsky?

  It's so interesting that you are overseeing the team as an engineer leader that is most changing the role of an engineer. It's such a meta role, like the work of an engineer is transforming because of the software that you're building.

• 55:25Lenny Rachitsky?

  One question along these lines is just, do you worry about engineers' skills to code atrophying from not actually writing code anymore? And does it even matter? Is this like something you think about? Is it a big deal?

• 55:38Speaker 01

  It's, it's interesting because we actually have this, uh, discussion on the team a bit like there, like, are there things that we miss? Or like, actually, to your point, I'm always like thinking about like when someone's onboarding and ramping, like you have Boris who hand rolled the code in the early days. And of course now does anymore, but he gained that knowledge from before because he was in the code days. So for especially all the engineers that join, I'm also like, make sure you're like taking the time too to all the work that you do, still get the understanding of the architecture or the change, because it goes back to that trust but verify. Maybe one day it won't matter anymore, but at the, at the pace that we're going, I actually still think understand, like it's always double clicking on that layer that you depend on. Like may, maybe that to me is a meta, like it's, um, it's always take that time to learn about your

• 56:22Speaker 01

  dependencies, because this way when your dependencies change, like you're kind of like more aware, or you might not be taking advantage of changes to, you know, dependencies. So I think it's always about kind of like, uh, doing that double click. But the other thing that we found interesting on the Claude code team is after a while, we felt, uh, it could start being a lonely experience because we all started just working with our agents so much. So recently we started up maybe like a pair wise programming lunch. And because what we also learned was on Claude code, everybody uses a Claude code work, everybody uses a flow so differently. And so we found that wow, when we take pair wise programming, we actually will learn so much from each other. Um, and but, and then the other thing

• 57:03Speaker 01

  too, is we, we make sure that like, we also, uh, have the maker time together too. So like, for example, hackathons is, is another thing we really like to do, just to make sure we're kind of like interacting together as a team.

• 57:15Lenny Rachitsky?

  That is such a good point, just like the loneliness that emerges because it used to be ench teams building code together. Someone's doing backend, someone's doing frontend, someone's doing iOS app, probably a bunch of people, you know, on the backend. And I was like, yeah, well, if 10 clods running in parallel, doing all these things, that is such a good idea of just like finding ways to connect engineers. So the idea here is like almost pair programming, but not, it's like parallel, it's like parallel play when kids are growing up. Like you're kind of working next to each other, but building your own things. But even just watching how other people build is, you're finding is really valuable.

• 57:51Speaker 01

  Yeah. And it's because our, our own tool chain is changing so fast as well. But yeah, it's very interesting to me. I like everybody on, on our team just uses Claude code and co-work in different ways. And so every time I watch someone work, then I, I learned something myself as well.

• 58:05Lenny Rachitsky?

  How do you manage people getting over like obsessed with their optimizing their workflows? Is there anything you're just like, okay, it's fine. Just, just keep going.

• 58:14Speaker 01

  You know, I haven't seen too many folks on our team. Like, I think everybody is just really excited about, you know, either a, like, an architecture update that we think will be higher reliability, or some product experience. So most folks, like, that's what we talk about a lot. Like, yeah, we, um, we don't over... It's fun lunchtime conversations, but I don't think we over-optimize. Because there's no, because there's no perfect answer, actually.

• 58:38Lenny Rachitsky?

  There's too much to do.

• 58:41Lenny Rachitsky?

  Is there anything? These are really interesting insights. Just like, as the role transformed, things come, things go. So I'm curious what else is kind of lost in this new world of software engineering. I used to be an engineer. I don't know if you know this. I was an engineer for 10 years. And it was like, so fun just to sit there, inflow coding. You know, this feeling, just like, oh, wow, it's working. Look at it compile. It's amazing, I'm making progress. And now it's like, you don't do that anymore. You just sit there and kind of wait for agents to build the thing. What else, what else is kind of lost in this new world for engineers?

• 59:12Speaker 01

  Yeah, it's so funny. I just had that conversation with an engineer and the team of, talk about flow. Like, remember the old days? You have this really gnarly problem and you pop that music soundtrack in and then you're just in the, in the zone. So, yeah, there is a little. And then there was always that big aha moment at the end, I would remember. Like, is it, yeah, you remember, you're like, you finally cracked it. You know, that, yay! So what we do, uh, but it's like, I think now we get a lot of joy from, like, the product. But I do think there is, because I hear from other engineers as well of, well, I, some of the hardest parts is what I used to enjoy. Like, yeah, I heard that from another engineer as well. And so I think we're all just kind of like shifting.

• 59:55Speaker 01

  But I, I do see like the, the thing most, and that's why I was, I was talking about, like, the pair-wise programming in the hackathon. That did recently come up more. Folks were starting to feel like it's starting to be a lonely experience.

• 1:00:07Lenny Rachitsky?

  So interesting. Within Anthropic, I'm curious, so engineering, like, the most transformed, I think, of any role right now. What other, what's like the second most transformed role so far, would you say, within Anthropic? That's most different from how it was like a couple of years ago, let's say?

• 1:00:23Speaker 01

  It's all the coding adjacent roles are shifting. Like PM is, I know, like you were chatting with Kat. I think PM is also transformed quite a bit because PM are no longer bottlenecked if they have an idea, waiting on engineering bandwidth. So that's kind of like the next role that I've seen shift. Like, actually, our PMs have also helped us roll up sleeves and help shift, you know, like some features when we, when we were, you know, like when, when there wasn't, when there was, you know, something we wanted to do and an engineer wasn't able to. So I think it's all the coding adjacent roles are starting to shift. But I think that's where, again, the verification is important because when you have more different disciplines checking in, how do we make sure everybody has higher confidence?

• 1:01:05Speaker 01

  I also think we need to do more to keep automating these other portions of the workflows. Like, for sure, we focus a lot on coding, but next, when you think about like design or data science, like, those are starting to be the next areas, I think, are good opportunities for us to see how we can, yeah, like, start improving kind of the experiences there as well.

• 1:01:26Lenny Rachitsky?

  Yeah, I have a, speaking of data science, I have a data science friend and he was just saying how data science is so different now, where now, most of their job is people doing their own, like, not amazing data science work using AI and then, and then just like showing it to the data scientist, "Here, here's the analysis I did. Can you just make sure it's right?" And half the time, it's not right. And so the job is just like a whole different job now. Instead of doing the work that they thought they wanted to do, and that's like, alright, I'm just reviewing all this AI data science all the time, to hell.

• 1:01:58Lenny Rachitsky?

  Kind of along the lines, coming back to just how your team operates and how things are changing. Let me see if something comes with this question. What should an engineering manager expect from their team now? Versus like a couple of years ago, what's like a normal, I don't know, baseline expectation of how things should work? Is it, other than just, you know, we're shipping faster, is there anything else?

• 1:02:20Speaker 01

  Oh, interesting. Well, definitely, I think most commits are Claude assisted. And so that was a shift.

• 1:02:29Speaker 01

  I think, you know, I kind of like mentioned, we have like Slack channels with all the feedback and also our dashboards that we have give to Claude. I think having engineers building, like keep building that stronger product sense muscle is I think also like another. And I think that in general helps kind of be these really trauma minded product engineers. I would say more of these roles that were traditionally non-engineering. You do now see engineers being like, and sometimes you're just blocked by, you know, waiting for, you know, a cross-functional partner. I think there's, there's less of those blocks now just because the models are able to augment additional capabilities that you may not have as an engineer.

• 1:03:12Lenny Rachitsky?

  So it's kind of interesting. It's both directions. Engineers becoming more product minded and responsible for the quality and success of our product. And then everybody becoming an engineer more and more.

• 1:03:23Speaker 01

  Yeah, that's right. Like, yeah, it's all blurring.

• 1:03:25Lenny Rachitsky?

  Yeah. I forget who said this, but there's this like, like, what is a role anymore? And this, this guy said that it's like, what's the average of what you do? What's like the highest percentage of you? And that's kind of your role now, whatever it is. Oh, man. I want to come back to your point about obsession with the, the product, living, breathing the product, dog fooding. I talked to a bunch of people that work with you about you. And that's the thing that came up most, just like your obsession with living and breathing the product, using the product constantly, whatever it is you're building, this idea of dog fooding. Talk about just like why that is so important, why that's something you instill within your teams and reports.

• 1:04:06Speaker 01

  Oh, I love it. Yeah, I think it's, it's really, and this has worked for me. It's just been a really good way for me to keep a pulse on, you know, anytime you build product, there's, there's a dream. Like, you're really hoping to enable an experience or make an experience better. So I think being able, like, like that helps me keep really close to the pulse. I also think, and maybe something like for sure on Visual Studio, that was like, you know, where I, where I got this love of it.

• 1:04:35Speaker 01

  But it's interesting because even Marketplace, I remembered every, once in a while I'll do, like even after I left the team, actually. One time I had like a MacBook Air I wanted to sell. I'm like, oh, you know, I haven't sold anything on Marketplace lately. And I could not believe it. The minute I put it up for sale, a seller or buyer tried to scam me. And it was an interesting like new scam vector I didn't detect. And so, but that goes to again, like people will use your products in ways that you may not expect. And so, especially as leaders or even like anyone on the team, we all have different like life, like actually, it's funny when I was, you know, supporting the VR and AR teams, somehow how I used VR,

• 1:05:17Speaker 01

  the setup, I would always be able to find these really weird floor height issues. So that ended up being a, oh, I took a, you know, like I'm going to help us, you know, like, because somehow I got a good repro environment.

• 1:05:30Speaker 01

  And so I think it's number one, like making, that's how you keep your pulse on the product that you're building and don't get too lost in metrics and dashboards, only your presentations.

• 1:05:40Lenny Rachitsky?

  I think that's such an important point you're saying there that I just want to make sure people hear is just like, like there's always this idea of anecdotal evidence and just like examples versus the data. And what you're saying here is as a product leader, as an engineer leader, you found a lot of success in like the anecdotes, the specific little one offs that you experience as a, as a, as a user versus like obsessing with the data only.

• 1:06:02Speaker 01

  Yeah. And, and actually sometimes it's also how I've been able to most effectively help the team. So for example, the last team I was on, I, I was, you know, leading a VR team and, you know, because like back then, the like I, it would have been, I was, I have not checked in any code into that code base just because I was really worried about like messing up the operating system. But what was a gap, we were doing a lot of polish fixes and I was, I wanted to, I'm like, hey, you know what? I'll use my dog baiting time to actually vet how the experience looks. And, and so that was also probably a way that I felt I could still meaningfully contribute to help hold the quality bar for the team. And, and then like I say, like every team member usually always really appreciates, because I think.

• 1:06:47Speaker 01

  As a lead, like, you know, leader, you're supporting folks on team that outside of metrics and everything, everybody really wants to make sure their work matters. And yeah, just just making sure that, you know, leaders use your product. I think folks feel the leaders remain like really engaged and not too distanced.

• 1:07:05Lenny Rachitsky?

  And this connects a lot with your point that engineers need to become more product minded, that engineers need to become more PME, PMs need to become more. But this is like as an engineer, this is one way to do it. Use the product constantly and that'll help you understand what is missing in the product as a user, because you're just using it.

• 1:07:21Speaker 01

  That's right. And I would say if you're leading a team where it's really hard for you to use a product, then meet with customers. Like whatever the other avenue is that kind of like, I think that's also been really important to you. Every time I've done customer visits, I always learn something new. Like, actually, I remember that was Facebook Marketplace. We're trying to launch to Latin America. And so we had, you know, we were testing in Chile and I remember it. It just wasn't doing as well as the other regions we've done. And everything else we've tried. And then I remember I'm like, and we had a really small research trip where I went to Chile. I remember getting us a whole bunch of Android phones for us. It was for a small crew, like just three of us. And upon landing and upon me opening up these Android phones and I'm like, ah,

• 1:08:04Speaker 01

  you know, the LTE connection was real, was much slower than what we were used to in the US. And so I'm like, oh, the marketplace feed didn't even load very well on these low LTE situations. What a, what a growth blocker.

• 1:08:15Lenny Rachitsky?

  That's my idea.

• 1:08:16Speaker 01

  You know, you can't even load. But again, that's why it's so important to always, you know, like, listen to customer feedback and, and get that fast feedback loop.

• 1:08:24Lenny Rachitsky?

  I think it was Jeff Bezos that said, if you have the data and you have an anecdote, trust anecdote over the data, surprisingly. And that's a great example. Okay, just a couple more questions. One is in your talk, you had this really interesting slide at the end of what questions you're kind of thinking about right now that you haven't figured out how to solve with how much is changing. I'm going to read the three. I'm curious, just like if it's still these three, if there's anything else like current problems we need to figure out that we haven't solved in how we operate. What you shared in your talk was, do we still need separate iOS and Android orgs? How far do you push fully automated reviews? And which role, with role blurring, how do you ensure everyone's equally productive?

• 1:09:10Lenny Rachitsky?

  Still problems? Is there anything else that you're thinking about? Like, okay, we need to crack this. We haven't figured this out.

• 1:09:15Speaker 01

  You know, the iOS, Android one, like, I think we're still, actually, it's funny because speaking of like the deep expertise, we definitely feel that it's really important, like, it's really important to still bring on folks with those expertise, but we probably don't need like as large, because people are flexing. So it's, again, making sure we have, you know, like, the Android and iOS experts, but then less of a, the larger, kind of like, mobile or one per. And so, but again, that's still a balance that we're trying to figure out if do we have the right and enough expertise? The, the second one was, sorry, what was the second?

• 1:09:52Lenny Rachitsky?

  Oh, yeah. It is, how far do you push fully automated review?

• 1:09:57Speaker 01

  Yes. Actually, well, this is a fun one, like, you know, with the content design check. I think we're, we're looking for across all of it, like, how do you actually get what good looks like? And so I have, like, actually, the verification is still one that we, I think, and that's kind of like the second and the third, that I think we, there's more, a lot more opportunities there for us. But the how far to push, I think, looking at where we think experts still matters. And then also, again, have to keep asking ourselves, okay, is there a way to leverage our expertise to also automate? Like, I think, like, looking across the whole end-to-end experience, like, making sure we're not missing in, like, I think we, we come at it from like an engineering standpoint, but making sure experiences, how we think about those other areas.

• 1:10:41Speaker 01

  I, I think there's definitely still more that we can do there.

• 1:10:44Lenny Rachitsky?

  Basically, how do you solve, how do you set up a verification that the experience is what you want it to be?

• 1:10:49Speaker 01

  Exactly. But, and I think that one is still a hard one to crack, as you kind of like mentioned, Evals, because it's, some of it for sure is accuracy, but it's also the experience. So that's something that, yeah, we're, we're still kind of thinking through.

• 1:11:03Lenny Rachitsky?

  Awesome. Is there anything else that's like, oh, this has changed recently. We got to figure out how to rethink the way we operate, or is this kind of the, the big ones?

• 1:11:11Speaker 01

  You know, I think because with Routines and everything being more async. I think there is starting to be a high load on our context switching. Cause I even remember myself was like, oh, like I kicked like, I kicked off like, and so I think that's probably another thing we have to think about of how to be, you know, whether for team members or as our users, like, how can we actually make the experience better to reduce that load? Cause I do see the context switching.

• 1:11:37Lenny Rachitsky?

  Yeah.

• 1:11:37Speaker 01

  Increasing.

• 1:11:38Lenny Rachitsky?

  I could like, if you have 20 agents running, there's just endless checking in and reviewing, and you have to remember what you're doing there. It's like such an interesting world where like the idea of flow, we talked about before, like engineers and most people, like there's less of the just hours of flow. But now the agents can kind of just remind you, here's where you're at, like the reset to switch almost is easier because you don't have to like relearn everything. You don't have to like re-understand the code base and the architecture. You can kind of just like, okay, but here's what we're trying to do. It's kind of like both got better, got worse.

• 1:12:12Speaker 01

  Well, it's interesting because I used to do book out like focus time for like, you know, the focus time for coding, because you want that dedicated and then the whole context switching. And then it's interesting now that because I can context switch more with more async agents, I'm noticing I do actually have to go back and block like a focus time for me to catch up on all the, you know, different async work that I've kicked off.

• 1:12:32Lenny Rachitsky?

  Yeah. Do you have any thoughts on the solution there? Cause that's hard. Just like there's like, people just want to do more and more and just how do you do that without constantly context switching? It's really hard and annoying.

• 1:12:42Speaker 01

  Yes, I agree.

• 1:12:44Lenny Rachitsky?

  All right.

• 1:12:44Speaker 01

  Definitely haven't cracked it yet.

• 1:12:48Lenny Rachitsky?

  So interesting. Okay. There's a question I thought of as we were talking that I'm like so excited to hear your answer on that. I wasn't even planning to ask this, but it's so important these days, which is just like end jobs and hiring. So interesting that you would think AI would make engineers less necessary. On the other hand, it feels like you guys are hiring engineers like crazy, OpenAI is hiring engineers like crazy, just like there's so much demand for engineers. Where do you think this goes? What do you think about just the future of the end role? And this is a big question, but just. Thoughts?

• 1:13:20Speaker 01

  I'll actually, I'll share some vulnerability here. One, speaking of like big, open questions, I really do think how we grow the next generation, just because how you and me got to our engineering path is just so different. It's almost like, okay, now when you graduate from school, it's like, how do you kind of fast forward? But the important thing to me, but still understand, kind of like, you know, that double click I talked about to the layer of need? But that is a big question I have, and I wish I had the answers. But I wonder if it's for software engineering, it's almost like you go more towards a fellowship or apprenticeship program?

• 1:14:03Speaker 01

  I know it's odd because technically we have like internships that would, but those were the kind of like three months and little projects. But I do wonder if, and I wish I have a crystal ball here, but it's, yeah, like, how do you almost like cram in some of the? And maybe it won't matter, but you know, some of the life experiences that we all got? How do you actually enable us to kind of like teach that to, you know, the next generation of builders?

• 1:14:28Lenny Rachitsky?

  Right, like, if you don't have to ever look at code, what's the incentive for a new software engineer to truly understand how infrastructure works and memory allocation, all these things that are like kind of foundational?

• 1:14:42Speaker 01

  And it's interesting, maybe the malls will get good enough that it doesn't matter.

• 1:14:46Lenny Rachitsky?

  You don't have to worry about it, yeah.

• 1:14:47Speaker 01

  You know, but I do think there's something about that double click because I think that's where there might be an opportunity to improve the product or the system. But figuring out how to learn that, not necessarily by, you know, like years of.

• 1:15:02Lenny Rachitsky?

  Of typing code.

• 1:15:03Speaker 01

  Yeah.

• 1:15:03Lenny Rachitsky?

  Yeah, like, somebody's got to have to understand code at some level. It's like some Cobol engineer, they have to like pull out of retirement one day, like, do you remember how to write Python?

• 1:15:13Speaker 01

  You know, actually, what's really fun, one of my, you know, previous managers, I mean, he started software engineering when it was punch cards. And it's so fabulous, like he's been messaging me, everything he's been building with Claude code. And I'm like, wow, what a career that you go from like, he's really like, he, you know, he's really kind of like seeing this whole change. So maybe I think for us, the thing about is like, when I think about his career, how he got started with punch cards was also totally, totally different than than now. And so it it might be that um, I I think it'll be interesting for us to see what remains important. And then what changes in terms of importance. And then it's like, how do you um, have gained, like, I have a theory, maybe, maybe that's

• 1:15:55Speaker 01

  the, the, what is important will shift over time. And then how do you kind of uh, kind of build the proficiency in doing that?

• 1:16:02Lenny Rachitsky?

  Yeah, just learn the things that really matter. Like the argument that I constantly hear is just like, it's a new level of abstraction, just like assembly and binary, like it just keeps going up and up. And now, okay, we don't need to actually look at the code. It's like a new layer of abstraction, prompts and and Claude's thinking, uh, you know, messages.

• 1:16:20Speaker 01

  Yeah. And it's maybe like, okay, what is the interesting problem? And what's the prioritization for experience to build? Like, it's interesting. Maybe we're kind of, yeah. And then when you build things, how do you know it's actually resonating? And and and it's kind of like doing what you intended.

• 1:16:34Lenny Rachitsky?

  And it's good. Yeah. Like, is this gonna, are we just building a bunch of sloppier, or is this actually

• 1:16:38Speaker 01

  Exactly.

• 1:16:38Lenny Rachitsky?

  architecture that will work. I think the advantage, though, for young people is they are so, it's so much easier to just lean in and work in this new way versus being stuck in the way that things used to be. It's like rare. It's like amazing how many long time engineers like yourself have adapted and embraced this. It's like so hard to just change everything. Okay, let's do it.

• 1:16:59Speaker 01

  Well, because the rate of change is also so fast. Actually, that that was the one thing of um, I remember the first time I, it was probably Sonnet three, five or or three, six, like, and I I remembered it was still like making some mistakes when I was doing things on the side. I'm like, hmm, what are you? And and and then what I noticed was some of the engineers that were resisting AI tooling, they're like, ah, but see, it's, you know, like, look at all of these. But then I think it was hard to understand of how kind of like the exponential rate of improvements. And so I'm always, and and maybe that's another interesting thing that I myself, I'm learning too. Like, there might have been something I tried to automate that Claude wasn't quite good enough. And then actually in the next model, oh, well, now it is good enough. So it's always also thinking about what may have not worked.

• 1:17:44Speaker 01

  Like, it might be worth a time to revisit because, you know, that now might be a new capability.

• 1:17:50Lenny Rachitsky?

  Yeah, that comes up a lot in this podcast. Just build something that is almost working that is at the edge. Because once the model gets there, you'll be so far ahead of everybody else. Okay, final question. You may have already answered this with what you just said, but what keeps you up at night?

• 1:18:06Speaker 01

  You know, the thing that keeps me up at night is probably it's how we. So, you know, we talked about kind of like Claude Code and Co work team culture. That's and the team culture is really important to me. Like, it's the one team mentality and I, you know, I share with folks. And by the way, culture is like a living, breathing thing. It's not just a poster you slap on a wall and it changes over time. And it's, it shows up in how we treat each other, how we, how we're there for each other. And so the culture of the team is important to me because we are, we are growing. And, and, and since the culture shifts, like making sure that maintaining the things are important, that we are, we still really, like, it's really important for me to have like diverse perspectives.

• 1:18:47Speaker 01

  So then we can have, you know, like good, healthy, open, honest debates out in the open. And we kind of like welcome those and kind of what I call that one team mentality. That when you get close to the finish line, look behind you and see is there someone from your team to help because we kind of finish as a team. That's probably the thing that keeps me up at night. And it's, it's like, you know, there's so many other hard problems, right? But I think maybe a lot of the other ones are product or engineering challenges that, yes, we have, you know, like dashboards or theories or hypothesis like. But the culture is like a human aspect that is.

• 1:19:25Speaker 01

  Like, like, I, I think that's the one that I, I always want to make sure that we're, as we grow, we're still kind of like maintaining that culture. Because it is kind of like the fiber of the team and. Like when it starts drifting, it it's it. I'm always worried of it, you know, like if it if it drifts, are we catching it? And having conversations as a team together to to to make sure we're kind of all wanting the culture to grow in the right direction.

• 1:19:49Lenny Rachitsky?

  Yeah, I imagine everybody is struggling with this, considering the pace of change and the pace of hiring, just like, especially at a company like Anthropic, that's in this crazy, like the most unprecedented growth trajectory in history. I could see how that could be a some a challenge with so much change. So it makes sense. Like even, you know, at Airbnb, when I was there, like, that was quite a growth trajectory, and that was nothing like what you guys are going through. And that was a constant topic of conversation. How do we maintain the culture?

• 1:20:19Speaker 01

  Actually, I'm curious, what was your experience at Airbnb to maintain the culture as we're growing?

• 1:20:24Lenny Rachitsky?

  A couple of things. One is just the what worked well is the founders being obsessed with it, like every call, every all hands, every, every big meeting is just like reminding of like the culture and the value of the culture and what the values are. Just the founders, top down, being obsessed with it was a real big part of it. You just like couldn't have a meeting without that coming up as a as a thing. The other is a memory I always come back to is we had Sheryl Sandberg speaking at Meta come to come do a fireside chat. And somebody asked her, just, how do you maintain culture as you scale? Because we're just growing so fast and it's so hard to, I mean, deal with all this change and culture and all these new people. And her advice was, this is actually the problem you want to have, because this means

• 1:21:09Lenny Rachitsky?

  you're growing and doing well, and this is normal versus you can, nothing will change if you're doing badly. Like, that's, that's, that's a much worse situation when you're not growing and you're not hiring like crazy. That's a much worse situation that will cause even more even suffering. So this is what this is a good problem you're you're dealing with, is her advice, which has always stuck with me.

• 1:21:32Speaker 01

  Oh, that's great. Like, it's interesting, like, hearing you talk. I think one of the important things to kind of Claude Coad and Co work team is whether ICs or managers, but this is a thing I especially ask for managers on the team, is really important that we all talk about for sure what's going out, but also just be open about what's not going well. Because then if we can actually have the conversation of what's not going well, that's how we can actually go ahead and address it. Like my, my, my, speaking of what keeps me up at night, my nightmare is especially if someone's in a manager position and, and I'm like, hey, how are things going? Everything's fine. I'm like, oh, my gosh, I'm not doing fine. I know this thing's on. And like, like it's that, that whole, like, you know how there was this meme of the doctor, care, a cup of coffee in a room that's on fire?

• 1:22:14Speaker 01

  This is like, that, that is my, my nightmare. So that's actually a, a discussion I have with a lot of, uh, folks on the team, but special managers, especially when they first join up. Hey, let's always have these open conversations so that we can solve problems together.

• 1:22:28Lenny Rachitsky?

  I imagine this is something a lot of people struggle with, seeing so many people around them doing super well, at least seemingly doing well. Everything's going great. I'm growing this, some of this awesome company or like just like everything, it's hard to, it's like hard to actually be honest and say, okay, it's not going great. I'm struggling here. I'm falling behind. Cause everyone around you is just like on the surface, feeling like they're killing it.

• 1:22:50Speaker 01

  Hmm.

• 1:22:51Lenny Rachitsky?

  Yeah.

• 1:22:53Lenny Rachitsky?

  Before we get to our very exciting lightning round, is there anything else that you either want to leave listeners with, anything else that we didn't cover, anything else that's important that you wanted to share?

• 1:23:03Speaker 01

  Maybe one thing is like, but just a suggestion of, cause you know, we talked about how, you know, how can Claude do like automate? Like one other thing that's really big on Claude code and cowork team culture is explicit permission to kill processes that no longer serve us. And so maybe a suggestion is for, you know, any, anyone, you know, like on, I'm working on a team or leading teams like, pick your, like, what's one process that you either dread doing? Or is really highly noisy? Or is like really expensive in terms of like, just a lot of like, it, it might, but, or is something that's just very manual? Like pick one thing and first ask, is it still having its purpose? Like, for example,

• 1:23:44Speaker 01

  When like even our planning like, actually, that was my own big first learning when I first joined Clockcut. I'm like, hey, maybe we should, you know, do a six-month roadmap doc and but we're gonna do it super lightweight because I don't want to waste a lot of time planning. And I felt we did a really lightweight process. That was such a good learning for me because the exercise was good to kickstart conversations and then share our lines. But like three months into it, I'm like, wait, have we still referenced? Because so much has changed. So that was also something I like. And so that was also something I changed to that I myself brought in thinking, hey, maybe this will, this will help. So always be open to learning and always ask yourself, whatever process you have, is it still serving its purpose? Just because the field is changing so fast.

• 1:24:25Lenny Rachitsky?

  I love that advice. I got to follow up on this real quick. So what is it? How do you think about planning now? Do you do any planning? Is it just like a month-long roadmap? What's kind of like the simple way to explain where you're at with that?

• 1:24:36Speaker 01

  Yeah, I call it jit planning now, like just-in-time planning. So it is like around like, because yeah, I think six months was too long. So now for sure, some projects will take more than a month, but we try to do like a month of planning, like really lightweight. Actually, there's not even docs. It's really just us aligning on a, on a little spreadsheet of what we think is important. But even that one, I'm kind of thinking through, hey, like every week, we should probably still keep a like, what we're trying is here are the the month's priorities. And we're gonna try it out. But I have a feeling like every week, we'll probably want to do really quick, like, hey, just to check. Yep, this is the still this month's priorities? Good. But yeah, like, but now we've shrunk it to jit monthly planning.

• 1:25:17Lenny Rachitsky?

  So it's monthly, meaning for the next month. Here's a little sheet slash Excel spreadsheet of what we're planning to do for the next month. And then every week, check in, is this still what we're planning to do for the next month?

• 1:25:28Speaker 01

  Yeah, it's like, very, very weird. But even that one, I'm also still feeling, how can we even? Automate this more because I don't, I never wanted to be feeling like attacked when someone has to, you know, update the spreadsheet. So this is actually, yeah, like just yesterday, we're chatting, hey, how can we actually automate this? Well, speaking to that question, always ask yourselves, can we actually automate this better?

• 1:25:50Lenny Rachitsky?

  Like my PM brain is like, that's so, like, how could you not do something like that? Okay, here's what we're thinking for the next month. Let's just check in once a week. Make sure this is, like, it's hard to imagine that not happening. And you don't have a lot of items on this spreadsheet is what I'm hearing also.

• 1:26:05Speaker 01

  Yeah, like, we really try focus. So like, we will, we'll share out, like, here's what we think are the highest priorities. And again, for that agency of, given the priorities, then, like, everybody's, like, they're kind of like item for how they think addresses those priorities.

• 1:26:19Lenny Rachitsky?

  Is there anything that's like, here's for the next, like, six months, bigger bets kind of stuff? Or is it just like, let's just think one month ahead?

• 1:26:26Speaker 01

  I like, so, well, usually, definitely, there's themes of where we think the work. And so we'll, we'll definitely like, and actually, the, the whole team will bring everyone together, like, every, every six months. So there, we'll usually kick off, like, some themes. But then, it's really the, making sure we keep the pulse of what, because again, like, even those themes change, you know, so fast when the landscape changes.

• 1:26:49Lenny Rachitsky?

  All right, let's pull up the spreadsheet and let's take a look.

• 1:26:54Lenny Rachitsky?

  Oh, man. Man, this, this whole podcast could have been just talking about this planning stuff that you do. Okay, I'm gonna have to find someone else to talk about this because this is so interesting, just how you all plan. Yeah, okay. Well, Fiona, with that, we reached our very exciting, lightning round. I've got five questions for you. Are you ready?

• 1:27:10Speaker 01

  Ready.

• 1:27:11Lenny Rachitsky?

  Okay, first question, what are two or three books that you find yourself recommending most to other people?

• 1:27:17Speaker 01

  Oh, I will say for fiction, actually, two authors I recommend to everyone, Margaret Atwood and Haruki Murakami. Those are just two, like, like, I mean, I grew up in Canada, so, so I read a lot, a lot of Atwood growing up. But her books are fascinating because it's almost like speculative fiction of

• 1:27:41Speaker 01

  You can kind of squint and say, okay, could this actually, you know, like, happen to to a society? So I love her take on speculative fiction and Murakami, I love his magical realism style. It's, it's, but then the one book, so there are authors, but the one book I always recommend to everyone to read at least once a year, or, you know, The Little Prince. I like, I think, I'm sure we probably all read it at some point in our lives, but I think it's a, I read it at least once a year, just, you know, to, to remind me to, to think about like, kind of like, what's truly important.

• 1:28:17Lenny Rachitsky?

  Wow. That hasn't come up a bunch. Okay. I love it. Favorite recent movie or TV show you've really enjoyed?

• 1:28:25Speaker 01

  I haven't watched TV shows.

• 1:28:27Lenny Rachitsky?

  That's very common across anthropic people I have on the podcast.

• 1:28:31Speaker 01

  But I will share with you what I always have downloaded on my phone so that if I'm on, on the airplane. So there's three movies I'll always have on my phone because I think they're just so, so fun to, to, to watch if I have time. One is Emily. It's this French movie that, oh my gosh, all of these movies are gonna be very old, by the way. It's gonna be like vintage movies. But I, I loved Emily, super whimsical. So really highly recommend it to anyone that haven't seen it. It's, you know, if I, if you remember, I told you I was, you know, going on a, I thought I was gonna be a visual artist. So when I was 16, my high school, we took a, a trip, a high school trip to Paris. And that, that

• 1:29:12Speaker 01

  just, I, I have so many memories of that. And Emily really captures the magic, I felt, at Paris. And the other two are, are Ghibli films. I love Spirited Away. That's, it's just such a, like, just such a fab, I just love that story. I, I, I love the, yeah, like, I, I just love every, everything about Spirited Away. It's probably one of my favorite Ghibli films. And then the third was another Ghibli film, Nausicaä: Valley of the Wind. And I, I think about this one quite a bit because if anyone asked me, hey, how did you kind of think about, you know, all these leadership trades? I think, I watched that movie probably when I was eight or nine. And the the hero in Nausicaä and how she seeing how she leads just left such a like

• 1:29:58Speaker 01

  just left such a thumbprint in my heart, I guess you could say that probably Nausicaä has inspired me to a lot in a lot of my different leadership principles.

• 1:30:08Lenny Rachitsky?

  Wow, what what is that book called again?

• 1:30:10Speaker 01

  Uh, the the movie is called like Nausicaä Valley of the Wind, but it was actually based on a on a manga.

• 1:30:15Lenny Rachitsky?

  Valley of the Wind, so it's like high output management and it grew Valley of the Wind, Nausicaä.

• 1:30:20Speaker 01

  That's right.

• 1:30:21Lenny Rachitsky?

  Two top management books. So cool. Okay. Do you have a favorite product you recently discovered that you really love? Could be an app, could be clothing, could be a gadget, could be kitchen equipment.

• 1:30:32Speaker 01

  I'll I'll share the product that I'm reminded of how much has made a difference in my life recently. Cause I've been just traveling a little bit and so I don't and I like to travel really light. So I I use whatever shampoo and conditioner, you know, that the hotel gives. And I forgot that um, so the the the product that I I actually have one of their hand. I promise this is not an infomercial.

• 1:30:58Speaker 01

  Sweet Sisters Body Care, it's, you know, a a local business on on Whuppi Island. But the reason why their product has made such a big difference in my life. It's a full line of organic hair, body, skincare. But a few years ago, I started getting this rash on my nose right here that was really painful, like actually bleeding. And I could not for the life of me figure out how to stop it. Like I tried not using any lotions. Like I cut everything on on my face and it was still really hurting. And then somebody says, what's the shampoo you're using? I'm like, it's the same shampoo I've used since I was, you know, like a teenager. Now, like, maybe your body has now, um, and it's, you know, like generic, you know, brand shampoo they could get anywhere. And they said, maybe your body is just.

• 1:31:40Speaker 01

  Start developing an allergy to it because of the chemicals in it that night.

• 1:31:45Lenny Rachitsky?

  Wow.

• 1:31:46Speaker 01

  I'm like, what? And so anyways, this was an organic shampoo that I found. Lo and behold, I use our shampoo and then, because you don't think that when you wash your hair, it actually then, you know, like goes, goes over to the, to the rest of your body. But so since then, I've switched everything that I used to be sweet sisters. But I'm recently reminded of how important this is because after a week of hotel shampoo, I, I actually started having some skin reactions again. I'm like, ah, maybe I should get like travel sized bottles that I could bring with me.

• 1:32:18Lenny Rachitsky?

  This is an awesome pick. I love local, local business picks, even big bonus points for that. And by the way, this travel you're doing, just for folks that may not know this, there's a, there's these Code with Claude events that are happening all over the world. I went to the one in SF, there's one in London, you're going to one in Tokyo. Is that the end of it or is there more after that?

• 1:32:36Speaker 01

  Tokyo is, so the, yeah, that's next week and that's the last leg of the trip.

• 1:32:40Lenny Rachitsky?

  Okay. And then probably, probably more in the future. So cool. I love that that's happening. Okay. Two more questions. Do you have a favorite life motto that you find yourself coming back to often in work or in life?

• 1:32:51Speaker 01

  Oh, so in work, I really love to remind folks, keep it simple. Like what is the, the thing that you're really trying to do well and, and focus on that? Do, you know, like keep it simple because I think sometimes we could overthink. So it's always a good mantra to think about that. And then in life, you know, probably in a world where you can be anything, be kind.

• 1:33:11Lenny Rachitsky?

  I love that one. We were at a, at a Montessori school tour and that's what the teacher had up on the wall.

• 1:33:19Speaker 01

  Oh, like it's, you know, we have, we have so many things going on that you never know what's going on in someone else's life. And that one small act of kindness can make the biggest difference. Like for, for me, actually that was when, do you remember COVID? We were all like working from home during, you know, the COVID.

• 1:33:39Speaker 01

  It just always really struck with me because I was in these back to back meetings. And I always, one on ones are really important to me because, you know, that actually that time is usually also really important for the other person. It's something that, you know, they've been looking to. They might have things to discuss. So I always try, like, I always really prioritize one on ones. But during that time, my grandmother wasn't doing well and she was in a home in Canada because of COVID, I couldn't go visit. And actually, even my aunt and mom couldn't go visit. And it was this very rare of if they have a helper that can help, we could do FaceTime. But you never know what time that is going to be because, you know, there's so many people that take care. And all of

• 1:34:22Speaker 01

  a sudden, I got a message from my aunt going, Grandma can FaceTime at like 12:00 PM today. I'm like, oh, no, there's this one on one that I I've been meaning to have. And I just messaged, you know, my reporter, I'm really, really sorry. It's the last minute. Is it okay to? And I know now it's when I say it, it doesn't seem like it's a big thing because it's like, but to me, it's always really important to keep. But he was like, yeah, totally. No problem at all. And for me, that was just a small after kindness. He doesn't, and he totally didn't make it into a big deal. But that made the biggest difference to me that I got to, you know, say hi to my grandmother on FaceTime.

• 1:34:53Lenny Rachitsky?

  I love that. Okay, final question. So Boris Cherny, when I asked him about you, when he had this interest at you and say where he said in very important meetings, you can often hear Fiona, you can hear the click clack of Fiona knitting in the background. Maybe talk about just what's going on there. And what's, what are a couple of things you knitted recently?

• 1:35:17Speaker 01

  Oh, my gosh. Well, I knitted this top recently.

• 1:35:22Lenny Rachitsky?

  You make your own clothing. This is very meta for Claude Code building itself.

• 1:35:27Speaker 01

  You know, we're always, actually, this is whole fun thing. I think between knitting and programming, because it's kind of like two stitches knit in a pearl. So zero and one. Anyway, so many concepts of stacks and keys, you actually could, like, I'm kind of like a compiler. I'm kind of like, you know, generating a next a key bowl when I knit.

• 1:35:49Speaker 01

  Yeah, actually, it was my grandma that taught me to knit when I was eight. I kind of mentioned her and I going to that yarn shop. And so every time I knit, I think of her. But I always like to multitask, as you could see, like, yeah, kick off multiple agents. And so anytime I'm sitting and because I practice enough and got proficient, I have to, I don't have to look at what I'm doing. So it's almost, almost like how, you know, sometimes people have like fidget spinners and such. Knitting is just, so anytime I'm sitting still, I'm like, oh, this is time to, you know, like, generate more knitting executable. Because I got so much yarn that if I don't do this, yeah, my yarn, I might have a slight yarn addiction problem.

• 1:36:28Lenny Rachitsky?

  I love this. When I, when I asked Boris what he would do when AGI hits, when we don't have to work, he said he's gonna make me so. I'm guessing your answer would be just knit and make beautiful clothing.

• 1:36:37Speaker 01

  Oh, my gosh, my dream is to actually open up a yarn store in my grandmother's name and, and create that community.

• 1:36:44Lenny Rachitsky?

  Wow. And then cowork would help out you automate everything.

• 1:36:46Speaker 01

  That's right, especially invoicing.

• 1:36:50Lenny Rachitsky?

  Oh, my God. Fiona, you're awesome. It's just incredible, the work that you and your team are doing, just changing the world in such profound ways. And there's no, it's clear why it's growing so fast. So, good job, good job over there.

• 1:37:05Speaker 01

  Well, I'm just so. Well, I'm just really honestly lucky and humbled that I get to work with such an amazing team. Like, I know how lucky I am, I am, and I'm so grateful. But thanks a lot for having me on the podcast as well. This was a lot of fun.

• 1:37:19Lenny Rachitsky?

  Two final questions. Where can folks find you online if you are online? If they want to follow up on anything? And how can listeners be useful to you?

• 1:37:26Speaker 01

  Oh, so definitely, so I'm on LinkedIn. And I'm sure most people have shared this already, but would love feedback of what's going well, what's not going well. Also, any latent demand that you are all using that might be interesting use cases. You know, I had a friend message me recently to go, oh, I'm using Claude to help me generate a building plan for my shed. And he actually showed me his whole, his whole shed, which was cool. So would love to hear about that. And then, yeah, maybe also, you know, we talked about reaching out across, so there's someone, whether a small business that you love, or, or someone that you feel like hasn't, you know, assuming all the listeners are super AI-pilled, yeah, maybe take a time to hold somebody's hand to show what's. AI might be able to help him with.

• 1:38:11Lenny Rachitsky?

  Such a good one. That is such a good answer to this question, especially coming from you. Fiona, this was awesome. Thank you so much for being here.

• 1:38:19Speaker 01

  Thanks so much for having me, Lenny.

• 1:38:20Lenny Rachitsky?

  Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.