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What happens after coding is solved? | Fiona Fung (Claude Code and 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 podcast@lennyrachitsky.com._ Lenny may be an investor in the companies discussed.

Lenny RachitskyhostFiona Fungguest
Jun 21, 20261h 38mWatch on YouTube ↗

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  1. 0:002:31

    Introduction to Fiona Fung

    1. LR

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

    2. FF

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

    3. LR

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

    4. FF

      It's always something we ask ourselves, what's better than me doing it? Have a bot do it

    5. LR

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

    6. FF

      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 a hypothesis of what you're trying to solve?

    7. LR

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

    8. FF

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

    9. LR

      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

    10. FF

      In terms of the 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?"

    11. LR

      Today my guest is Fiona Fung. Fiona leads the teams behind Claude Code and Cowork at Anthropic. She oversees both Boris Cherny and Kat 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. 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 Kat Wu, Boris Cherny, and Mohammed Hegazy 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

  2. 2:319:28

    How the engineering role has transformed over 25 years

    1. LR

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

    2. FF

      Thanks so much for having me, Lenny.

    3. LR

      So I was at the Claude, uh, Code with Claude event, uh, I don't know, a month ago at this point. I was-- And I went to your talk, and I, 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 what, where people are at with AI. So you've been an engineer for 25 years. I was browsing your LinkedIn. Uh, you started at, at IBM, of all places. [chuckles]

    4. FF

      [laughs]

    5. LR

      Such a different place to be these days.

    6. FF

      Yes.

    7. LR

      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. Uh, as Boris, uh, famously said, "Coding, coding is solved." Along these lines, there's just this tweet that you guys put out yesterday where you showed, uh, 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 kinda 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?

    8. FF

      Oh, I, 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, uh, 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 like more hardcore and you, you'll learn more. So that was, uh, I was really fortunate to gotten into the IBM internship. Um, 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've been an, an Eclipse license, but for some reasons most of us didn't use it. So I remembered it was mainly like Vim and, and, uh, you know, like kind of terminal 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, 'cause, uh, 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, or were hiring 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 'cause I came from like a Unix school. So I remembered asking, "Oh, Vi-" 'Cause I was thinking, "Well, the name Visual Studio." I'm like, "Oh, is this like a, a better paint program?" And I could tell the look on my manager's face like, "What is going on?" [laughs] But then it ended up becoming like the love of my life for the first, you know, 11 years of, 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 break points and do multi-threaded debugging. Like, that was also always mind-blowing for me to think about the, the stepwise change. Um, so yeah, like that was kind of the, the story going from IBM to Visual Studio. And then what I really loved actually about Visual Studio is, uh, I was on the Visual Studio editor team. So I used the VS editor to build the VS editor, and that's where my whole love of dogfooding comes from. Like I, I remembered I wanted to first and foremost create a delightful experience not only for myself, but for my teammates. 'Cause also, if we go back in that time, if you remember... I mean, when did Twitter come out? Like, was it two- 2006 or something? [chuckles]

    9. LR

      Feels like it's been around my whole life.

    10. FF

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

    11. LR

      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 upmarket 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 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. Uh, so I love that sh- I love that you're reminding us of these moments in, uh, the history of software engineering that, that have changed the, the work in a big way.

    12. FF

      Yeah, when I worked on Visual Studio. Back then, we also shipped software on CDs. Uh, I mean, before-

    13. LR

      I remember that

    14. FF

      ... like, and, and, and that's why there were really hard deadlines, 'cause you had to make sure the software was ready for us to give to manufacturing to then, you know, put on the CDs for this to then put on the shelves. And, uh, 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 an 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 on CDs. And so back then, you would do a lot more planning 'cause you just wanted to make sure given the time you have, you, you make the best of it. And that's a shift that, you know, like we're seeing with, with, uh, Claude Code and Cowork is coding is no longer the bottleneck. And so now, like, you know, you showed up the, you showed the, the tweet and that graphic. So but now it's all about, like, where has that shift happened? Like now, not only engineers with... 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.

    15. LR

      Maybe just

  3. 9:2812:26

    What an AI-pilled software team looks like in 2026

    1. LR

      kind of set this theme that I wanna have for this conversation. A lot of people are just wondering, what is, what is software engineering, managing software engineers, s- managing software and product teams look like in the future? And you are living through that right now. So you mentioned this, um, point about a more focus on verification, making sure the quality of the code being, uh, 8X'd is actually high and something, uh, that sh- that, you know, will work. So just, like, let me ask this broad question. Let's kind of see where this conversation goes. What does a, what does an AI-pilled software team look like in 2026?

    2. FF

      Because the roles are blurring, it's shifting more to this builder. Uh, like ev- everybody starts being a, a, 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, it also has access to all our Slack channels, and, and I'll, I'll have access to, like, how, how are the metrics of, of everything we track. And so ev- every month, like I 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, uh, you know, I share my screen, then we, we, we do a Claude Code session. And it's just about, hey, what were the focus areas? Like, what were some of the, the products that got shipped? How did it do? Oh, what were the feedback channels? And, and so I even though, like, before I would've just used these sessions to, like, generate PRs and bug fixes, I actually have these sessions, uh, to enable me to have conversations with folks that I support.

    3. LR

      Say more about that. So this is, this is, uh, like a management technique, let's say, to help people, uh, 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.

    4. FF

      Exactly. So like, yeah, outside of just, you know, the action of shipping is how'd it do in market? Or hey, did we have, you know, like, did we cause some bugs? And it's okay to have... Like, I have this 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 j- 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? I think th- that used to be just a much more manual- A process, I would say. Like, if I look back a year ago, I don't think I would've been able to, you know, have some of these insights with Claude.

    5. LR

      Yeah. Well, partly it's 'cause, like, there's that, and also people weren't shipping as much, so you could just make a little bulleted list.

    6. FF

      [laughs]

    7. LR

      Here's the things I shipped last quarter, this feature, that feature, this feature, that feature. So-

    8. FF

      That's right

    9. LR

      ... 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

  4. 12:2614:40

    Using Claude to manage and review team output

    1. LR

      is shipping.

    2. FF

      Mm-hmm.

    3. LR

      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.

    4. FF

      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 what I could, like, see some gaps. Like, that just used to be something I would do every morning, and, uh, yeah, I think maybe a month or two ago, we, 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 gerate the, like, generate the prompts and the PR. 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. Um-

    5. LR

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

    6. FF

      Uh, [laughs] our feedback channels are definitely, like, we have a lot from internal and-

    7. LR

      I see

    8. FF

      ... but also, like, emails, channels. Actually, everybody, uh, 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, and we also have, like, of course, partnerships, and so we have different channels, uh, for, for all the various sources. But, but that's what I mean of I need Claude's help to help me stay on top because there is so much incoming feedback.

    9. LR

      Got it. Okay, so this is cool. So this is a, uh, 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/routine where you as a manager look at what people are saying about the current state of, uh, 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."

  5. 14:4016:55

    The evolution of code review and verification

    1. FF

      Mm-hmm. That's right.

    2. LR

      Awesome. 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?

    3. FF

      Yeah, and honestly, it's crazy when, you know, 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 wanna make sure we have the proper, uh, you know, like, humans still reviewing. I would say what helps us, though, is the more that we can automate to almost, uh, 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, our, like, you know, like, r- recently we just updated the content design to have a skill in it. Like, my, like, I... And this is why, like, um, I think if you have specs 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 Claude code review can make sure it's still matching what you set out to do.

    4. LR

      And basically it's like e- the evolution of test-driven development.

    5. FF

      Yes. For TDD it's... 'Cause I remember that was, like, a, a big thing, my gosh, maybe, like, in the 2000s of write 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 remembered I myself struggling a bit because it was almost like you have to eat the broccoli first. 'Cause I was like, "Ah, 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 wanna do test-driven development. Help me write the test first. Make sure it's fails, and then we'll actually, you know, do the fix and then, and then now the test pass." 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 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.

    6. LR

      Yeah. Like, that's, that's so unfair. It just writes the test for you first.

    7. FF

      [laughs]

  6. 16:5518:18

    Who to hire: creative builders and deep systems experts

    1. LR

      [laughs] So on this point of builders, one of my favorite slides from your talk that, um, I wanna ask 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 wanna 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.

    2. FF

      Yeah, the deep subject matter expertise. Like, for example, when I first joined Claude Code, we had really great, um, kind of like product generalists, and then I realized, oh, we were missing folks with a systems background. And so that was definitely an area that we, we needed more folks with, uh, kind of like systems and distributed systems expertise. Um, and so I would say whatever are the parts that... It's all about trust but verify. 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, uh, subject matter expertise, I would say that's, you know, an area to definitely still invest in. Um, and the other one is kind of like the, the, the product, uh, the product sense folks, 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 end, uh, th- that's- That's like a, another skill set that served

  7. 18:1819:40

    The shift to ambitious thinking

    1. FF

      us really well on Claude Code.

    2. LR

      This super resonates. There's this word ambition, and 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, um, in the podcast and, and other work I've been doing. There's this 10XC 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,' [chuckles] and it just does it."

    3. FF

      Yes.

    4. LR

      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, does that resonate? Is that something that you think about?

    5. FF

      Yes. Actually, I was just catching up with an engineer, uh, yesterday, and, um, uh, he actually is not a mobile engineer by trade, but we really needed to, uh, update this feature to also have a, a mobile footprint, and it was just amazing. Like, he's like, "You know what?" 'Cause it, it, it... And it's common 'cause 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, it's like the, it's lifted the ceiling of what an- anyone is able to do.

    6. LR

      So let me follow that thread.

  8. 19:4025:52

    The growth mindset required to thrive in AI-native teams

    1. LR

      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, you know, even outside engineering that are just, like, frustrated and having a bad time?

    2. FF

      I would say a growth mindset really, really helps. Like, actually, even before, um, AI tooling, I found that has been just so valuable, and I, I learned that a lot. Actually, it was the shift from Me- um, Microsoft to Meta. That was where I first real- 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 be-- and also what served you to get you to this point may not, uh, may serve you no longer. But it's really hard because o- of course, everybody, like we all, you know, we've all gotten to this state by acting or, you know, like operating in a certain way. And so sometimes it is a little bit scary to think, wait, you're ask- like, but I've been successful so far. You're asking me to change what has made me successful. And so I, I would say, like, the growth mindset is, is really, really, has, has really served me well, and I think it's also served others well, um, that, that I noticed. Like, always leaning in with curiosity and always being able to learn. Um, and then in terms of, like, 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... 'Cause we all have-- And fear is, of course, an evolutionary, like, I'm, I, 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 and, you know, uh, by, by larger predators. But for anything that, you know, that, that there is a fear, my advice is kind of lean in and ask, "Okay, is there some-- What can I do about it? What is within my control?" 'Cause 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, um, i-i- instead of happening to you, is it happening for you? And then what's, what's something that you might be able to kind of like do and change? Like, I felt that's been helpful, 'cause if not, it, it, it, it is super frustrating to have the fear and then feeling like everything's outside of your control. Like, I actually remembered, um, when I was in, actually, when I was in high-- It's funny when we were going back to IBM. Uh, when I was in high school, I actually didn't, uh, 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 wa- uh, access to computer was grade nine, I think, in high school. I don't even know if this happens in high school anymore. My high school had a typing class where you [chuckles] would take class just to learn how to type on a keyboard and learn to be really proficient, and that was my first time. And then, you know, the next class was maybe like, um, some HTML programming. So anyways, it, it, it... But the reason why I fell in love with it was while what I love about art is creating and being able... 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, um, 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. I knew there was an Ontario, you know, School Assistance program, like OSAP, 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 remembered, oh, that, like, I... And of course, it was gonna be minimum wage, but I, I, I, I thought that, that could be a lifeline. But it was funny 'cause the class I hated the most in high school was accounting, so I don't know if I would 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 'cause I worked all summer, saved up, and then, then actually I was able to work as a bank teller on the weekends. So, like, yeah, while I went to, I would go to school Monday to Friday, and then on Saturdays I'd be a bank teller, and that ended up being this lifeline that enabled me to, you know, like pay for all my school expenses. Um, and you know, we talked about the, the year 2000 dotcom crash. Then when folks weren't hiring as much interns, actually, I continued being a bank teller for For two, two years. Uh, 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 gonna go down this path, I don't even know if I could have afford 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 from, you know, the... Like, see is there some- is there one action that's within your control that you can take, um, to, you know... So it, it, it, like... 'Cause I think there's, and, you know, there, there was a saying, like, do something. 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, 'cause that's also usually how we grow. Um, I found that when you're, when you're really good and proficient at 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 k- have a dip because you need to learn. But that's kind of how you, um, keep pushing yourself to learn.

    3. LR

      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."

    4. FF

      Oh, I love that. [chuckles]

    5. LR

      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.

    6. FF

      Mm.

    7. LR

      In terms of career-

    8. FF

      I'm, I'm gonna steal your quote

    9. LR

      ... like, yeah. Please do. Like, you know, there's- like, don't do all the scary things. Like, maybe don't jump off a cliff. But maybe-

    10. FF

      [chuckles]

    11. LR

      ... in career, in career moves, it's probably a good, a

  9. 25:5231:46

    Helping small businesses adopt AI tools

    1. LR

      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, uh, new world that is emerging. Uh, 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 we should be thinking about to help folks, you know, stay, not, not fall behind, basically.

    2. FF

      Oh, I, I, I love this. Yeah, it's one of my passion topics 'cause, uh, I kind of mentioned, you know, like, growing up in Canada. Um, and I, I moved there when I was a kid. Uh, 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, uh, 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, uh, very alienating for her to be, you know, in a count- new country where, and, you know, back then it wasn't as walkable. Um, but one summer, I remembered we just happened to find this little yarn shop, uh, 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, and my grandma found her knitting circle, and then I think I learned how to do, like, macramé, [chuckles] which I think is having a comeback, by the way. It's al- it's always funny to see what's-

    3. LR

      Macramé coming back

    4. FF

      ... you know, like... Macramé, I think. Yeah. [chuckles] Heard it here first on Lenny's Podcast.

    5. LR

      [chuckles]

    6. FF

      I think macramé's coming back.

    7. LR

      All right.

    8. FF

      Um, but, but that was prob- 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, that I love. So that, that's kind of, like, where the passion comes from. And then, um, what, how it happened was I was using Cowork for my own, uh, business, uh, expensing travel. I don't know what it is. I really don't like doing business expensing. And when I was using Cowork, it was magic. I'm like, [gasps] 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. Um, and they're us- you know, like sometimes might be operating on really small margins. And so I thought, if it's, if Claude Cowork is so good at helping me do my little, you know, business travel expense, this would be huge for... 'Cause I, I see my friends sometimes sitting at the bar with stacks of bills, and all they're doing is invoicing and expensing, and, and I think nobody actually really likes to do it. So that's kind of, uh, where it came from. And then so yeah, I remembered, uh, ch- like helping, uh, a couple of them onboard, and, and, uh, it was also very humbling to, to see them go through our onboarding flow. Actually, they found some really good bugs. So it was really, like, a win-win. But it was also delightful for me 'cause they also use Cowork in, in ways that I, I wouldn't have thought about, 'cause I was all fixated on, "Look at how it is amazing with PDFs and invoice." And then, um, you know, one of my friends who, who runs two restaurants, she's like, "Oh my gosh, this folder I have is like a junk drawer of..." Like, it, it's basically our, you know, documents folder just becomes this junk drawer of every... Or downloads, like just a y- 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 wanna 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." Um, so I learn something every time. And, uh, and yeah, they've been, like, giving me great feedback as well.

    9. LR

      So the question then is just, like, how do we, how do we spread this to everybody? Because as you s- 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 wanna ignore it." Is it, like, talking, is it just talking about these, sharing examples? What do you think? How do, what's, like, a way to make a dent in this, uh, in this problem?

    10. FF

      For all of us, es- 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, um, has That you really have felt has made a meaningful life change, uh, for you with, with the AI tools, and then seeing if that is a conversation starter for... 'Cause 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 would s- that's something that I would love everybody's [chuckles] help with of if there's, whether it's a community member or even if there's a business you really like and you think, "Hey, have you ever..." It's, it's, it's a little awkward to start. Like, I remember when I first-

    11. LR

      Yeah

    12. FF

      ... reached out to my friends, I'm like, 'cause I don't talk about what I do, [chuckles] uh, with them a lot. But I'm like, "Hey, uh, kind of, you know, working AI. Can I, can I sh..." It, it sounds... It's, it's even unnatural for me to do it 'cause I'm, you know, like, I'm like, "Hey, can I show you what, you know, Cowork is possible?" And, and, uh, y- and then, uh, but it end up, we end up having a lot of fun. So yeah, I would love for, like, that, that conversation starter, um, would be great of... Yeah, 'cause I just wanna make sure we keep sharing the, the knowledge and, you know, making the tool equitable, 'cause if not, I'm concerned that the divide grows larger and larger.

    13. LR

      Me too. I find that sharing use cases, as you said, is, like, so powerful. I was just using Cowork the other day to fill out my s- 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."

    14. FF

      Mm-hmm.

    15. LR

      And it's just, like, these little things you don't think about that Cowork and

  10. 31:4635:08

    How Anthropic spots latent demand and builds for it

    1. LR

      Claude Code 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, uh, it was just like, whoa, that's maybe the biggest [chuckles] new business opportunity in history. Uh, and then Cowork is a great example of just leaning into knowledge 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 y'all were very early on, just how important that is, not just for the experience, but just also the intelligence and, 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?

    2. FF

      Well, I haven't worked in any other labs, so [chuckles] I'm not sure how other labs operate. But I, I will share, like, yeah, with, um... 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, our own first customers, and we're able to do, like, really rapid feedback. And, and so I think, um... But latent demand has, has been like a... Like, for example, like Cowork, we noticing a lot of folks that were not necessarily coders were, were using Claude Code. Can we make that experience better? Um, I think that's actually even outside of Anthropic, that served me well in, in all the different products I've worked on. Um, but, uh... And, and actually, it's funny you mentioned, like, you know, the, the Claude for, uh, you know, my passion with small business. After I, you know, had, had a few of those visits, we ended up now launching Claude for small business, which is really cool 'cause I... And, and it totally didn't come from me, so I'm not taking credit.

    3. LR

      Mm-hmm.

    4. FF

      But I noticed it too of, like, when I was working with... And they, because they were asking me, "Oh, does it have this plugin or 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 with small business bundles it all up. So inside Cowork, you just have this little toggle. And, uh, there were, there were, there was a wonderful team that's been kind of like, uh, you know, doing, uh, Cowork sessions with small businesses that probably found, "Hey, we could have, like, an efficiency gain here," um, [lip smack] or, like, make the experience better. And so I w- I would say, like, always, uh, not only for products that you're on, like making sure you're always s- 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? Um, it's, it's interesting. Like, after, like, you know, i- 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, um, is really, like, it's all about the iteration, learn, and, um, keep close to the feedback.

    5. LR

      Latent demand. That's a, that term's come up a bunch on this podcast.

    6. FF

      [chuckles]

    7. LR

      There's something there. Might be something there. So essentially it's just watching closely for behavior that you may not have expected or that-

    8. FF

      Mm-hmm

    9. LR

      ... is just kind of emerging, and then just going big on that, essentially.

    10. FF

      Yeah.

    11. LR

      Exploring it, building something awesome.

    12. FF

      Yeah. 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, and better experience?

  11. 35:0838:06

    The next frontier: asynchronous work with AI routines

    1. LR

      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 gonna 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?

    2. FF

      I would say we're shifting more towards async, like asynchronous. And so to your point, the, the fleets of agent. Like, that, that's why routines is so interesting, 'cause it's almost like I used to be like, you know, doing a prompt and synchronously, and then, uh, I would like maybe, like, kick off different prompts asynchro- 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 str- abstraction keeps pulling up a little bit. And so I, I would s- yeah, I, I wish I have a crystal ball to see what this is gonna look like. It'll be fun actually for you and me to revisit a year from now. [chuckles]

    3. LR

      [chuckles] No, I wa- I wanna hear more about this. This is... So help us understand what is, what is routines, and then what is... When you say asynchronous, you're writing a prompt, and it just kind of goes off, and is it writing it immediately? Talk about what this actually looks like.

    4. FF

      Ah, g- yeah. So, uh, routines is, like, how you can au- Like, so if you remember, I was sharing about my... What I used to do is always, like, uh, you know, wake up with my morning cup of coffee and, "Hey, look it through this Slack channel for me." But then now, like, I have a routine, uh, that I set to run every morning at a certain time-

    5. LR

      It's like a cron job

    6. FF

      Mm-hmm. That's right. Uh, but then it's able to actually go and kick off agents on your behalf.

    7. LR

      Mm.

    8. FF

      And so that... 'Cause like that's what like in, you know, even, you know, before it, it would be, oh, y- you could like, yeah, do a cron job to automate. Like, but now it's, "Hey, look at this 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 have different agents that... 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 the prompts for me for spawning different agents? Uh, so I think we'll, we'll move more towards that kind of like asynchronous style of working.

    9. LR

      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 unblock? Who is, uh, who's struggling? 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," or, "Here's what I, here's what there is to review."

    10. FF

      And then it's, it's even like then giving even more autonomy at some point of, uh, you know what, like go for it. Like if, for example, a-

    11. LR

      Then just ship it

    12. FF

      ... verification is really good-

    13. LR

      Yeah

    14. FF

      ... go, [chuckles] go for it.

    15. LR

      I see. So you give it like a little bit of freedom to do more of this.

    16. FF

      Yeah.

  12. 38:0639:40

    Agency and accountability in AI-native teams

    1. LR

      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 Cowen have this awesome talk about just like what's happening. I don't know if you know Tyler Cowen. He's a really smart dude. [chuckles] "The Economist" has a podcast. Uh, and he just had... Like, there's so much talk of the people that are doing best in this world, uh, his term is, um, initiative. They have initiative. Uh, another term people use, agency. 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?

    2. FF

      Actually, that's, uh, agent, it, it's... I love that word agency. That's what we really hold important on the Claude Code and Cowork team. Um, but it's interesting. I say along with high, 'cause like we really, it's about like, "Hey, here's a problem," and then it's really everybody, uh, 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, 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 of the same kind of agency, and then accountability, I think has served our team really well.

    3. LR

      [chuckles] Such an important element [chuckles] of a k- agency. Okay, cool. Everyone's off doing stuff, but okay, what have you actually-

    4. FF

      [laughs]

    5. LR

      ... what have you busted up? [chuckles] What have you done? So kind of along those lines,

  13. 39:4044:24

    The vibe shift from token-maxing to ROI measurement

    1. LR

      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 is it costing? What's the ROI? Uh, interestingly, Boris was actually like head of productive, eng productivity at Meta. That was like his job, is measuring eng 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? How do you... Like, you know, you guys have the unfair advantage of getting free, free tokens working at Anthropic. With that in mind, what, what have you learned about just how to measure, say, ROI of engineers in today's world?

    2. FF

      This eng productivity is such a fascinating topic. Um, yeah, 'cause 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 of it's always been whichever metric, it's, it's, um... Like, if, if you're really focused on the out- Like, my advice here is, one is output, like is the output really going towards the outcome? 'Cause yeah, like the, the, the, the token maxing, it's kind of like a, a, a... It's almost like the lines of code [chuckles] that we used to have. But I'm really much more about a, um, 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, like don't forsake motion for progress. Um, 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 the end outcome of yours like important? Um, and so I, I really, uh, 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, uh, that's what we b- we focus mostly on versus kind of like the, the, the productivity measurement. Um, 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, um, on a listening tour for, for, for the leaders listening to a podcast. Especially, you know, um, 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? 'Cause they will also help you multiply and scale that out across a full engineering team. And sometimes it's those conversations where you might get, spark an idea that comes up, and also really good shared learning versus, um, you know, like metric dashboards. It, it's very interesting. I've learned some good lessons for metrics. I'm all about like it's really great when you have, uh, 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, uh, still serving the outcome that you were aiming for? Um, 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, o-one thing we would keep an eye on is kind of, like, number of sellers. And I remembered after launching to our first region, I'm like, "Huh, 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, 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've 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, uh, so then we updated the, the metric to go, oh, you know, like it's not a number of seller, 'cause it didn't factor in power sellers. And so that's the advice I have, too. Like, whatever metric, whether for productivity or even for 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, 'cause sometimes the landscape can change so fast, uh, even the metrics themselves might need to be adjusted.

    3. LR

      And this comes back to your, uh, 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 did this have, what was maybe-

    4. FF

      Mm-hmm

    5. LR

      ... some bugs that happened, and that being a really powerful way of understanding how, what's going on with this engineer.

  14. 44:2449:34

    The “bad vs. sad” quality framework

    1. LR

      Awesome. Let me come back to this, just this question of speed and quality and just, like, impact. Uh, 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 wrangle all this, all these PRs being shipped every day?

    2. FF

      I would say, and this is what, uh, honestly, we, we, we're, we wanna keep doing more of and, 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, uh, 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. Um, and so, like, on the quality front, we found, like, um... And this is, like, the more proactive we can be of, like, making sure we can get an earlier detection into, uh, quality. And, and so, like, um, that's been one thing that we've been paying a, a lot of attention to. Like, so, like, you know, I, I, I started this, "Hey, let's have a concept of, uh, what's bad versus what's sad." 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, you know, 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, a 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, uh, you know, like, reliability numbers, also having some framework of what we think is, you know, like a, 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.

    3. LR

      I like that. I like-

    4. FF

      That, that's helped us a little bit.

    5. LR

      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, or, or failures? Or what, what are, what sort of things are you measuring here?

    6. FF

      Uh, so for example, like, we, 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, what is... Like, so for example, on CLI could be crash rates. Like, a crash is pretty bad. You lost work.

    7. LR

      Mm.

    8. FF

      Um, and for example, sad might be, hey, is it flickering? Like, it might be recoverable. But we have each team... Like, and, and that's why it's been interesting, because before each, because surface areas are different, like, we would have all these dashboards of, but it's, 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, um, each team wants to take.

    9. LR

      One of the, like, the main takeaway I'm hearing here is, uh, one of the best tools for staying on top of quality is just, uh, 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, is part of this, and then just, like, monitoring failures and speed and things like that.

    10. FF

      That's right.

    11. LR

      Something, I think this is public. I, I know that you guys have this dashboard that tracks just, like, F words. Like, how often people are like, "F-"

    12. FF

      [laughs]

    13. LR

      ... 'cause they're so pissed and frustrated.

    14. FF

      [laughs]

    15. LR

      There's, like, a funny term for it, I think. I forget what it's called.

    16. FF

      Yes. Actually, I remember, yeah, that was last September, 'cause we were all, uh, we were all seeing some frustrations and, uh, yeah, that was an engineer on the team of, "Hey, we should maybe track swear words." I'm like, "Oh, [laughs] that's a great idea." I remember it. I had just, you know, joined, and we were having that really fun conversation. Um, yeah, so it's, it's, again, like, it- it's very interesting to kind of like look at, um... 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, the swear word dashboard is, is a fun one. [laughs]

    17. LR

      This episode is brought to you by Mercury. Radically different banking loved by over 300,000 entrepreneurs, and now with Command. I've been a customer of Mercury's for over six years. I have never once thought about leaving. Mercury is basically what happens when banking is built by product people, not by bankers. They make it so easy, dare I say fun, to send invoices, move money around, set up virtual cards for folks on my team. Does your bank have an API, a terminal-native CLI, or an AI-ready MCP server? I don't think so. And just recently, they launched Command, a conversational interface built directly into Mercury, which acts as your financial operator. I've been using Command to transfer money around, to figure out what categories I've been spending the most money in, analyze my cash flows, and just today, I used it to find out how much I've made from a specific sponsor over the past year. I just ask, "How much have I made from X over the past year?" 10 seconds later, I have an answer. It is so freaking cool. Visit mercury.com to learn more and apply online in minutes. Mercury is a fintech company, not an FDIC-insured bank. Banking services provided through Choice Financial Group and Column NA, members FDIC.

  15. 49:3455:24

    Why all managers start as ICs at Anthropic

    1. LR

      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, um, I've heard about a couple things that you've implemented that are pretty unique, I think, to, uh, how teams operate, and I think is something that has worked really well for you. One is making every manager start as an IC, and then just every manager has to continue being an IC part-time, kind of this player-coach approach. Talk about that, why that's so important in today's world.

    2. FF

      Mm. I love it. Um, it's funny, when I first joined, 'cause I, I, uh, and I have amazing recruiting partners, and I, I noticed we were... You know, this whole theme of, um, 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, recruiter's like, "Okay, yeah, we have these, um, couple, like, manager postings." And I'm like, you know... 'Cause actually how, it came from, like, a listening tour I did with, like, all the, all the, um, members on the team of... And I heard a lot of these, "Hey, I really appreciate the agency, but how can I make sure prioritization?" And, and so I kind of, of through that, I, I, um, I reali- And then there was some really good feedback too of making sure that, um, it's not too many layers of reviews. Like, there was good feedback. Some folks have, might have joined from other companies, they're like, "You know..." And, and then I'm like, "Hmm." When I actually think as a, as a leader, if you actually start as IC first, without the con- like, worry of supporting people, 'cause 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, uh, the code base, and I, I f- or, or, or the product. Like, whatever it is. It doesn't have to... Like, honestly, the, the PRs I do are like... But it, 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. So even me doing PRs, it's less about what it is I'm fixing. It's more about me using the, the product every day just to keep that touch. 'Cause as amazing as metrics and everything are, and I do look at those dashboards, if you, as a leader, if, if you're not, you know, like, living and breathing your, your product every day, you s- you sometimes kind of, like, lose touch of, uh, the touch and feel of the product. But anyways, on the manager front, I think cr- giving time for managers that join to be able to go deep and to do that before supporting people, and then they actually, like, end up building really great rapport with the team. Like, because if not, I, 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, and do managery things." 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, um, to, to building rapport. And, and in ter- and in terms of, like, using the product, I think that's, that's import- It's, 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 join, 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, it's refreshing to see, you know, you giving user feedback." Like, like, and, and so I think as leaders too, it's also a way for us to experience the work, uh, personally that the team does.

    3. LR

      Something that people may not realize, uh, you were overseeing a- 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.

    4. FF

      [chuckles] I started out, like, it was for a very short, short amount-

    5. LR

      Okay

    6. FF

      ... of time. But, but, um, 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 an IC, um, '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, uh, yeah, but it was so valuable to have the, the, those first months, like, actually learn what it's like to ship, uh, 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, um, the last time I shipped production software at Meta was probably 2017. And every year I might st- uh, like, I do a lot of dogfooding and a lot of, you know, like I, I also use dogfooding to help me, like, vet the quality of, of, of product as well. Um, 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, on Claude, I'm like, at, at first I almost, again, went, did my usual, let me go meet all the engineers and treat them to coffee, and then, and I'm like, "Oh, wait, wait, wait, let me ask Claude." And so Claude was this really good onboarding buddy of mine 'cause I was, like, curious about the code base, asking it questions. 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 a 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 PRs 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 manager 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, it's, it's just important to me as leaders to make sure you're kind of, like, using the product that your team builds.

    7. LR

      It's so interesting that you are overseeing the team As an eng leader that is most changing the role of an engineer, it's such a meta role. Like-

    8. FF

      Yeah

    9. LR

      ... the work of an engineer is transforming because of the software that you're building.

  16. 55:2458:43

    Preventing skill atrophy

    1. LR

      One question along these lines is just, do you worry about, uh, 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?

    2. FF

      It's, it's interesting 'cause we actually have this, uh, discussion o- 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 doesn't anymore, but he gained that knowledge from before 'cause he was in the code base. 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 that understanding of the architecture or the change because it goes back to that trust but verify. Maybe one day [chuckles] 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 dependencies, 'cause 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 'cause we all started just working with our agents so much. So recently we started, uh, maybe a, like, a pairwise programming lunch. Because what we also learned was on Claude Code, everybody uses, uh, Claude Code Cowork, everybody uses the flow so differently. And so we found that, wow, when we do pairwise programming, we actually learn so much from each other. Um, and, uh, but, and then the other thing 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.

    3. LR

      That is such a good point, just, like, the loneliness that emerges because it used to be eng teams building code together. Someone's doing backend, someone's doing frontend, someone's doing-

    4. FF

      Mm-hmm

    5. LR

      ... iOS app, probably a bunch of people, you know, on the backend, and now it's like [chuckles] you have all, we have 10 Claudes 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 [chuckles] 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.

    6. FF

      Yeah. And it's because our, our own tool chain is changing so fast as well.

    7. LR

      Yeah.

    8. FF

      But yeah, it's very interesting to me how, like, everybody on, on our team just uses Claude Code and, and Cowork in different ways. And so every time I watch someone work, then I, I learn something myself as well.

    9. LR

      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"?

    10. FF

      [laughs] You know, I, I haven't seen too many folks on our team... Like, it's, I think 'cause everybody is just real excited about, you know, either a, like, a, an architecture update that we think will be higher reliability or some product experience. So most folks, like, that's what we, we talk about a lot. Like, yeah, we, we, um, we don't over... It, it's fun lunchtime conversations, but I don't think we over-optimize-

    11. LR

      All right. All right

    12. FF

      ... because there's no, 'cause there's no perfect answer actually.

    13. LR

      Too much to do. There's too much to do.

    14. FF

      [laughs]

    15. LR

      [chuckles] Is there anything... These are really interesting insights,

  17. 58:431:00:08

    Managing context switching with 20 AI agents running

    1. LR

      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. Uh, and it was, like, so fun just to sit there in flow 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?

    2. FF

      Yeah, it's so funny. I just had that conversation with a engineer on the team of talking about flow. Like, remember the old days, you have this really gnarly problem, and you pop the music soundtrack in, and then you're just in the, in the zone. Um, uh, 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 we, 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... 'Cause I hear from other engineers as well of, "Well, I, uh, some of the hardest parts is what I used to enjoy." Um, uh, like, yeah, I heard that from another engineer as well. And so I think we're all just kind of, like, shifting, um, uh, but I, I, I do see, like, the, the thing most, and that's why I was, I, I was talking about, like, the pairwise programming and the hackathon. That did recently come up more. Folks were starting to feel like it's starting to be [chuckles] a lonely experience.

    3. LR

      So interesting.

  18. 1:00:081:03:40

    How PM and data science roles are transforming

    1. LR

      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 years ago, let's say?

    2. FF

      It's, it's all the coding-adjacent roles are shifting. Like, PM is, I know, like, you, you were chatting with Kai. I think PM is also transformed quite a bit because PM are no longer bottlenecked of if they have an idea waiting on engineering bandwidth. Um, so that's kind of, like, the, the next role that I saw 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, um, you know, like, when, when there wasn't, uh, when there was a, you know, something we wanted to do and an engineer wasn't able to. So I think, um, it's all the coding-adjacent roles are starting to shift. Um, but I think that's where, again, the verification is important, 'cause when you have more different disciplines checking in, how do we make sure everybody has higher confidence? 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 that I think are good opportunities for us to see how we can, yeah, like, um- Uh, start and im-improving kind of the experiences there as well.

    3. LR

      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 it, 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, now it's like, "All right. I'm just reviewing all this AI data science all the time. What the hell?"

    4. FF

      [chuckles]

    5. LR

      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 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?

    6. FF

      Oh, interesting. Well, definitely I think most commits are Claude-assisted.

    7. LR

      Mm-hmm.

    8. FF

      Uh, and so that was a shift. Um, 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 q- um, give to Claude. I think having engineers building, like, keep building that stronger product sense muscle is, I, I think also, like, another... And I think that i- in general helps kind of, uh, 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 a, like... And sometimes you're just blocked by, you know, waiting for a, you know, a cross-functional partner. I think there's, there's less of those blocks now just because, uh, the models are able to augment additional capabilities that you may not have as a, um, from a, as an engineer.

    9. LR

      So it's kind of interesting how it's both directions. Engineers becoming more product-minded and responsible for the quality and success of a product, and then everybody becoming an engineer more and more.

    10. FF

      Yeah. That's right.

    11. LR

      So interesting.

    12. FF

      Like, yeah, it's all blurring. [chuckles]

    13. LR

      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 about you? And that's kind of your role now, whatever it is-

    14. FF

      [chuckles]

  19. 1:03:401:08:36

    The importance of dogfooding and using your own product

    1. LR

      ... you happen to be.

    2. FF

      Yeah.

    3. LR

      Oh, man. I wanna come back to your point about obsession with the, the product. Living and breathing the product, dogfooding. 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, uh, this idea of dogfooding. Talk about just, like, why that is so important, why that's something you instill within your teams and, and, and reports.

    4. FF

      Oh, love it. Um, yeah, I think it's, it's really... And, and this has worked for me. Um, it's just been a really good way for me to keep a pulse on... You know, e- anytime you build product, there's, there's a dream. Like, you're really hoping to enable an experience or making an experience better. So I think, um, being able, like, like, that helps me keep really close to the pulse. I also think, uh, as may- and maybe some, like, for sure on Visual Studio, that was, like, you know, where I, where I got this love of it. Um, but it's interesting 'cause even Marketplace, I remembered every t- once in a while I'll do, like, even after I left the team actually, um, 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. Let me..." And I could not believe it, the minute I, I put it up for sale, a, a seller or, or a 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, uh, your products in ways that, 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, it's funny when it, when I was, uh, you know, supporting the VR and AR teams, somehow how I used VR, the setup, I would always be able to find these really weird, uh, floor height issues. So that ended up being a, "Oh, I took a, you know, like, I'm gonna help us," you know, like, 'cause somehow I got a good re-repro environment. Um, and so I think it's number one, like, making, that's how you keep, uh, your pulse on the product that you're building and don't get too lost in metrics and dashboards only or presentations.

    5. LR

      I think that's such an important point you're saying there that I just wanna 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 eng leader, there, uh, you found a lot of success in, like, the anecdotes, the specific, uh, little one-offs that you experience as a, as a, as a user versus, like, obsessing with the data only.

    6. FF

      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, I was, uh, s- you know, leading a VR team, and, you know, because, like, back then the, like, I, I, it, it would've been r- I w- I, I was n- I have not checked in any code into that code base just 'cause 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, uh, I was, I wanted to... I'm like, "Hey, you know what? I'll use my dogfooding 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, uh, and then, like I say, like, e- every team member usually just always really appreciates, uh, 'cause I, I think, um, 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, uh, yeah, just, just making sure that, you know, leaders use their product. I think folks feel, uh, the, the leaders then remain, like, really engaged and not too, um, distanced.

    7. LR

      And this connects a lot with your point that engineers need to become more product-minded, that engineers need to become more PM-y, 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, 'cause you're just using it.

    8. FF

      That's right. And, 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 that other avenue is that kind of, um, like I, I think that's also been really important too. Every time I've done customer visits, I always learn something new. Like, actually I remember that was, uh, Facebook Marketplace. We were trying to launch to, uh, Latin America, and so we had, you know, we were testing in Chile, and I remember it, it, it just wasn't doing as well as the other regions we'd done. And ev- everything else we've, we've tried. And then I remember I'm like, "Oh, yeah." 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 a very small crew, like just three of us. And upon landing, and upon me opening up these Android phones, and I'm like, "Ah," 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-

    9. LR

      That's right. Yeah

    10. FF

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

    11. LR

      I think it was Jeff Bezos that said, "If you have the data and you have an anecdote, trust the anecdote over the data."

    12. FF

      [chuckles]

    13. LR

      Surprisingly. And that's a great example. Okay, uh, just a couple more

  20. 1:08:361:12:48

    Outstanding questions

    1. LR

      questions. One is, in your talk, you had this really interesting slide at the end of what questions you're kind of re- thinking about right now that you haven't figured out how to solve with how much is changing. Uh, I'm gonna 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 auton- on- automated reviews? And which role... with role blurring, how do you ensure everyone's equally productive? Still problems? Is there anything else that you're thinking about like, "Okay, we need to crack this. We haven't figured this out"?

    2. FF

      You know, the iOS, Android one, like I think we're still... And actually, it's funny 'cause, uh, speaking of like the deep expertise, we definitely feel that, um, it's really import- 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 a f- um, you know, like the Android and iOS experts, but then less of a, the larger kind of like a mobile org one per. And so, but again, that's still a balance that we're trying to figure out if do, do we have, uh, the right and enough expertise? Um, the, the second one was, uh, sorry, what was the second one though? [chuckles]

    3. LR

      Oh, yeah. Uh, it is, uh, how far do you push fully automated review?

    4. FF

      Ah. Yes. Actually, well, this is a, 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? Um, and so I have a like, the, um, actually the verification is still one that we, I think, and that's kind of like the second and the third, but I think we, there's more, a lot more opportunities there for us. Um, but the how far to push, I think, uh, looking at where we think a expert 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, um, like looking across the whole end-to-end experience, like making sure we're not missing any... Like I think we, we come at it from like an engineering standpoint, but making sure on experiences, how we think about those other areas, um, I, I think there's definitely still more that we can do there.

    5. LR

      Basically it's how do you sol- how do you set up a verification that the experience is what you want it to be.

    6. FF

      Exactly. That, and I think that one is still a hard one to crack, as you kind of like mentioned evals, 'cause it's, it's, some of it for sure is accuracy, but it's also the experience. Um, so that's something that, uh, yeah, we're, we're still kind of thinking through.

    7. LR

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

    8. FF

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

    9. LR

      Yeah

    10. FF

      ... increasing. [chuckles]

    11. LR

      I can... Like, if you have 20 agents running, there's just-

    12. FF

      [laughs]

    13. LR

      ... endless checking in and reviewing, and you have to remember what you were 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 'cause you don't have to like re-learn everything. You don't have to like re-understand the code base and the, 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.

    14. FF

      Well, it's interesting 'cause I used to do, book out like focus time for like, you know, the focus time for coding 'cause 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.

    15. LR

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

    16. FF

      Yes. I agree. Like-

    17. LR

      All right. Open question

    18. FF

      ... definitely I haven't cracked it yet. [laughs]

    19. LR

      [laughs]

  21. 1:12:481:17:59

    The future of engineering jobs and education

    1. LR

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

    2. FF

      I'll, I'll, I'll sh- I'll actually, I'll, I'll, I'll share some vulnerability here. One, um, speaking of, like, big open questions, I really do think how we grow the, 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 it? But, but the important thing to me, but still understand kind of like, you know, that double-click I talk about to, to the, the layer beneath. Um, but that, that is a big question I have, and I wish I had the answers, but I, I wonder if it's, um, for software engineering, it's almost like you go more towards a fellowship or apprenticeship program. I know it's odd 'cause technically we have, like, in- internships that would... But those were, like, kind of, like, three months and, and little projects. But I, I do wonder if, um... And I, I wish I have a crystal ball here, but it's, it's, yeah, like, how do you almost, like, cram in some of the... And, and maybe it won't matter, but, you know, some of the life experiences that we all got, how do you actually enable, um, us to kind of, like, teach that to, you know, the next generation of builders?

    3. LR

      Right. Like, if you don't have to ever look at code, w- what's the incentive for a new software engineer to truly understand how infrastructure works and, and-

    4. FF

      Yeah

    5. LR

      ... memory allocation, all these things that are, like, kind of foundational.

    6. FF

      And, and it's interesting. Maybe the, the models will get good enough that it, it doesn't matter. But I do-

    7. LR

      You don't have to worry about it. Yeah

    8. FF

      ... you know, but I do think there's something about that, that double-click, 'cause 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, year, years of, uh-

    9. LR

      Of typing code.

    10. FF

      Yeah.

    11. LR

      Yeah. Like, somebody's gotta have to understand code at some level. [chuckles] Like, it's like some COBOL engineer they have to, like, pull out of their retirement one day. Like, "Do you remember how to write Python?"

    12. FF

      You know what actually what's really fun? One of my, uh, you know, previous managers, I mean, he started software engineering when it was punch cards, and is 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, seen this whole change. So maybe, I think for us to think 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, kind of gain... Like, I have a theory. Maybe, maybe that's 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?

    13. LR

      Of, yeah, just learn the things that really matter. Like-

    14. FF

      Yeah

    15. LR

      ... 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, uh, Claude's thinking, uh, you know, messages.

    16. FF

      Yeah. And it's maybe like, okay, what is a interesting problem, and what's the prioritization for experience to build? Like-

    17. LR

      Yeah

    18. FF

      ... it's, it's interesting.

    19. LR

      When building things.

    20. FF

      Maybe we're kind of... Yeah. And then when you build things, how do you know it's actually resonating and, and, and, uh, it's kind of like doing what you intended?

    21. LR

      And is good. Yeah. Like, is this gonna... Are we just building a bunch of slop here, or is this actually-

    22. FF

      Exactly

    23. LR

      ... architecture that will work?

    24. FF

      Yeah.

    25. LR

      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 longtime engineers like yourself have adapted and embraced this. It's, like, so hard to just change everything. Okay, let's do it.

    26. FF

      [chuckles]

    27. LR

      Everything.

    28. FF

      Well, 'cause the rate of change is also so fast. Actually, that-

    29. LR

      Yeah

    30. FF

      ... that was the one thing of, um, I remember the first time I, I... It was probably Sonnet 3.5 or, or 3.6. 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, um, always... And, and maybe that's another interesting thing that I myself am 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. Like, it might be worth the time to revisit 'cause y- you know, that now might be a new capability.

  22. 1:17:591:22:53

    What keeps Fiona up at night: team culture at scale

    1. LR

      Okay. Uh, final question. You may have already answered this with what you just said, but what keeps you up at, at night?

    2. FF

      You know, [chuckles] the thing that keeps me up at night is probably, um, is how we... So, you know, we talked about kind of like Claude Code and Cowork team culture. Uh, that's-- And the team culture is really important to me. Like, it's the one team mentality, and I, I, you know, I, I share with folks. And, 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 s- 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, uh, and since the culture shifts, like, making sure that maintaining the things are important, that we are, we still really, uh... Like, it, it's really important for me to have, like, diverse perspectives 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 have what I call that one team mentality, that when you get close to the finish line, look behind you and see these are some of our teams to have 'cause 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 hypotheses. Like, but, uh, the culture is, like, a human aspect that is, um- [laughs] Like, like I, I think that's the one that I, I always wanna make sure that we're... as we grow, we're still kind of like maintaining that culture 'cause it is kind of like the fiber, um, of the team. And it-- like when it starts drifting, it, it, uh, 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.

    3. LR

      Yeah. I imagine everybody is struggling with this considering the pace of change and the pace of hiring. Just like es- 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 [chuckles] uh, some- a, a challenge, uh, with so much change. So, uh, 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 co- topic of conversation, how do we maintain the culture?

    4. FF

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

    5. LR

      There's a, a couple things. One is just the... what worked well is the founders being obsessed with it. Like every con-

    6. FF

      Oh

    7. LR

      ... 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 re- 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 of 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 main- deal with all this change and culture and all these new people." And her advice was, "This is actually the, what, a problem you want to have because this means you're growing and doing well, and this is normal. Versus you can... n-nothing will change if you're doing badly." Like that's, that's the, 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 all, even more pain and suffering. So this is what, this is a good problem you're, you're, you're dealing with, is, is her advice, which has always stuck with me.

    8. FF

      Oh, that's great. Like it's interesting, like hearing you talk, I think one of the important things to kind of Claude Code and Cowork team is, um, whether, uh, an 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 well, but also just be open about what's not going well. Because then if we can actually have a 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 not..." And like, like it's that, that whole, like you know how there was this meme of the doctor, he had a cup of coffee in a room that's on fire.

    9. LR

      On fire.

    10. FF

      This is-

    11. LR

      Yeah

    12. FF

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

    13. LR

      I imagine that's 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, um, this awesome company or like just like everything. It's hard to, it's like hard to actually be honest and say-

    14. FF

      Mm-hmm

    15. LR

      ... "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.

    16. FF

      Mm.

    17. LR

      Yeah.

  23. 1:22:531:27:03

    From six-month roadmaps to JIT (just-in-time) monthly planning

    1. LR

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

    2. FF

      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, um, 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, working on a team or leading teams, like take 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, it, it... but or something that's just very manual. Like pick one thing and, um, first ask, is it still having its purpose? Like for example, when like even our planning, like work... [chuckles] Actually, that was my own big first learning when I first joined Claude Code. I'm like, "Hey, maybe we should, you know, do a six-month road map doc." And, and but we're gonna do it super lightweight 'cause I don't wanna waste a lot of time planning. And I, I felt we did a really lightweight process. But that was such a good learning for me 'cause, uh, the exercise was good to kickstart conversations and ensure we're aligned. But like three months into it, I'm like, "Wait, have we still referenced our..." [chuckles] Because so much has changed. So that was also something I like... and so that was also something I changed, uh, 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 this still serving its purpose? Just because the field is changing so fast.

    3. LR

      I love that advice. I gotta 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 road map? What's kind of like the simple way to explain where you're at with that?

    4. FF

      [laughs] Yeah. I, I, I call it JIT planning now, like just-in-time planning. So it, it is like around like... 'cause yeah, I think six months was too long. So now for sure pr- some projects will take more than a month, but we try to do like a, a month, uh, 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, I'm kind of thinking through, hey, like every week we should probably still keep a, like... w-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 wanna do really quick like, hey, just to check. Yep, th-this is the, still this month's priorities. Good. Um, but yeah, like n- but now we've, we've shrunk it to JIT monthly planning.

    5. LR

      So it's monthly, meaning for the next month, here's a little, uh, sheet/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?

    6. FF

      Yeah. It's-

    7. LR

      So cool

    8. FF

      ... it's, yeah, like, like very, very weird.

    9. LR

      Yeah, yeah.

    10. FF

      But even that one, I, I'm also still feeling, how can we even automate this more? 'Cause I don't-- I never want it to be feeling, like, attacked when someone has to, you know, up- update the spreadsheet. So this is actually... Yeah, like, just yesterday we were chatting, "Hey, how can we actually, uh, automate this?" So speaking to that question, always ask yourselves, "Can we actually automate this better?"

    11. LR

      Like, my PM brain is like, that's so... Like, how could you not do something like that? [chuckles]

    12. FF

      [chuckles]

    13. LR

      Like, okay, here's what we're thinking for the next month. Let's just check in once a week.

    14. FF

      [chuckles]

    15. LR

      Just make sure this is... Like, it's hard to imagine that not happening. Um, and you don't have a lot of items on the spreadsheet is what I'm hearing also.

    16. FF

      Yeah, but, like, we really try focus. So, like, we... we'll, we'll share out, like, here's what we think are the highest priorities.

    17. LR

      Yeah.

    18. FF

      And again, for that agency, given the priorities, them, like, everybody's, like, their kind of, like, item for how they think, uh, addresses those priorities.

    19. LR

      And 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?

    20. FF

      I... Like, so we'll usually, definitely there's themes of where we think the, the work, and so we'll, we'll definitely like, um... And actually the, the whole team will bring everyone together, uh, like, uh, 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... B- because again, like, even those themes change, you know, so fast when, uh, the landscape changes. Um, so-

    21. LR

      All right. Let's pull out the spreadsheet and let's take a look.

    22. FF

      [laughs]

    23. LR

      [chuckles] Oh, man. Man, this, this whole podcast could've been just talking about this planning stuff that you do. Okay, I'm gonna have to find someone else to talk about this 'cause this is so interesting-

    24. FF

      [chuckles]

    25. LR

      ... just how y'all plan. Uh,

  24. 1:27:031:38:42

    Lightning round

    1. LR

      yeah. Okay. Well, Fiona, with that, we've reached our very exciting lightning round. I've got five questions for you. Are you ready?

    2. FF

      Ready.

    3. LR

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

    4. FF

      Ooh, I will say for fiction, uh, actually two authors I recommend to everyone, Margaret Atwood and, uh, Har- uh, Haruki Murakami. Um, those are just two, like, I, like... I, I mean, I grew up in Canada, so, so I, I read a lot, a lot of Atwood growing up. But her books are fascinating 'cause it's almost like speculative fiction of... You can kind of squint and say, "Okay, c- could this actually, you know, like, happen to, to a society?" So, so I love her take on speculative fic- fiction. And Murakami, I love his, um, magical realism style. It's, it's, um... But then the one book, so those are authors, but the one book I always recommend to everyone to read at least once a year or, you know, um, The Little Prince. I, like, I, I think, I'm, I'm sure we probably all read it at, at some point in our lives, but I think it's a... I, 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.

    5. LR

      Wow. That hasn't come up a bunch.

    6. FF

      [chuckles]

    7. LR

      Okay. I love it. Uh, favorite recent movie or TV show you've really enjoyed?

    8. FF

      I haven't watched TV shows. [chuckles]

    9. LR

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

    10. FF

      [laughs]

    11. LR

      Common theme.

    12. FF

      But I will share with you what I always have downloaded on my phone so that if I'm-

    13. LR

      Yeah

    14. FF

      ... on, on the airplane... Um, so there's three movies that I'll always have on my phone 'cause I, I think they're just so, so fun to, to, to watch if I have time. One is Amélie. It's this, uh, 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, I loved Amélie. Super whimsical, so really highly recommend it to, um, anyone that haven't seen it. It's, uh... You know, if I, if you remember, I told you I was, you know, uh, 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 just... I, I have so many memories of that, and Amélie really captures the magic I felt at Paris. And the other two are, are Ghibli films. Uh, I love Spirited Away. That's, um... It's just such a fa- like, just such a fab... Like, 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 one's another Ghibli film, um, Nausicaä, Valley of the Wind. And, uh, I, I think about this one quite a bit because if anyone asks me, "Hey, how did you kind of think about, you know, all these leadership traits?" I think w- I watched that movie probably when I was eight or nine, and the, the heroine, Nausicaä, and how she, seeing how she leads just left such a, like, um, just left such a thumbprint in my heart, I guess you could say, that probably Nausicaä has inspired me to a lot in, uh, a lot of my different leadership principles.

    15. LR

      Wow. What, what is that book called again?

    16. FF

      Uh, the, the movie's called, like, Nausicaä-

    17. LR

      The movie. Sorry

    18. FF

      ... Valley of the Wind, but it was actually based on a-

    19. LR

      Nausicaä

    20. FF

      ... on a manga.

    21. LR

      On a book. Valley of the Wind.

    22. FF

      Yeah.

    23. LR

      So it's like High Output Management, Andy Grove, Valley of the Wind, Nausicaä.

    24. FF

      [laughs] That's right.

    25. LR

      Two top management books. So cool. Okay. Uh, do you have a favorite product you recently discovered that you really love? Could be an app.

    26. FF

      Ooh.

    27. LR

      Could be clothing, could be a gadget, could be kitchen equipment. I don't know.

    28. FF

      I'll, I'll share the product that I'm reminded of how much it's made a difference in my life recently.

    29. LR

      Yeah.

    30. FF

      Uh, 'cause I've been just traveling a l- a little bit, and so I don't... And, and I like to travel really light, so I, I use whatever shampoo and conditioner, you know, the, the hotel gives. And I forgot that, um... So the, the, the product that I l- And I actually have one of their hand... I promise this is not an infomercial, but [chuckles] Sweet Sisters Body Care, it's, you know, a, a, a local business on, on Whidbey Island. Um, but the reason why their product has made such a big difference in my life, uh, 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 o- 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." And they're like, "Maybe your body has now, um..." And it's, you know, like a generic, you know, brand shampoo that you could get anywhere. And they said, "Maybe your body's just started developing an allergy to, to it because of the chemicals, uh, in it that might-" I'm like, "What?" And so anyways, this was an organic shampoo that I found. Lo and behold, I use their shampoo, and then... It, 'cause I-- You don't think that when you wash your hair-

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