The Pragmatic Engineer - The revised rules of engineering management with Will Larson

0:00How has injury management changed in the last few years? Will Larson is one of the best people to talk about this. He's been an engineering executive for the last 10 years at four different companies, wrote some of the most widely-read books on injury leadership and sapless levels, and I really appreciate how deep and thoughtful of a thinker he is. Today we cover how zero interest rates heavily influence a decade of management habits in the 2010s, many of these habits no longer helpful.

0:24how the role of engineers is changing and why solving problems that the business cares about is becoming much more important to thrive inside of companies. The path to becoming a CTO today and why line managers often make better engineering executives than middle managers do, and many more. If you're an engineer or engineering manager and are wondering what your query path could look like with AI changing the industry and how the path to CTO looks like today, this episode is for you. This episode is presented by TurboPuffer, a ridiculously scalable fast and cheap hybrid search engine built on top of object storage by an engineering team that I've really gone to like after spending time with them. The TurboPuffer engineering team is doing something really cool. They are completely redesigning their storage architecture from first principles to make church faster, cheaper, and more reliable at scale. The new system, called TurboPuffer V3, is not yet in prod, but it already passes CI. Still, it's not nearly as performant as the current production version, V2, and so the TPUF team is now

1:19perfmax in query plans until they are as fast or faster than v2. They are doing all of this in public documenting how they increase performance all the way up to the v3 production launch. And it's so cool to follow along and see the different performance wins and how they did it. For example, we see how full text search, the red line, started out as 129 times slower than the current system. But now it's only four times slower.

1:43And in the development log, we can also see that the team used things like batch scoring or batch reads to increase performance. A lot of these wins are basic foundation work right now, but the team will be sharing some very cool systems work over the next few weeks. But hang on, why is the team doing a Flurry write? It's because search is changing and so is trouble buffer. TPuff started as a vector database, but it's no longer a vector DB. It has evolved into high performance database for search.

2:07The V3 discards the vector primary index, and all indexes will share the same columnar source system. Every query will run on vectorized query engines, which is something you don't usually see in search databases, but which will result in both very fast search and just generally a very fast database. The TurboPuffer team is keeping a work log of their journey, and you can follow along at TurboPuffer.com. It's a blast to see how it's being built.

2:37Finally, in person, because we know each other for so long, both started writing, we will talk about that writing as well. And also just hung out before, but this is nice. I want to jump in to the beginning. How did you get interested in computers? Were you interested in computers to start with?

2:53From the time I was five, we had like a Mac 2C or something like that. This was like, uh, not, not black and white, not the very earliest one, but it was pretty basic. And I think it had like one thing that I understood how to use as a four and a half or five year old, which was like kid pics, which you've maybe, I don't, did you ever use to see kid pics? I didn't, I know of it, but I never use it. It wasn't like a super sophisticated thing. I don't even know if you could save files, but it was basically like a graphical program for, for children. And you could make squares and circles and little like.

3:20graphics, but that was kind of the introduction to me. And I remember using that computer a lot and like that this is an era ones are really no internet to speak of really no way to figure out how to do anything other than just banging on it, which is sort of the fundamental of writing software in some ways is just banging until you figure out how to make it work. I think that was a great introduction. But to be honest, I wasn't doing a whole lot in like software other than, you know, multi-user dungeons. Did you ever like play a mud growing up?

3:49Multi-user dungeon. What's a no? What's a mud? It's a text-based game and so basically the idea is that World of Warcraft is actually a graphical text-based game that we basically derive from these ideas of muds or multi-user dungeons But when I was a kid in high school, that's when I started doing more software So a little bit you start with Urk IRC internet relay chat and and Merck, which I don't even know what the M stood for to be totally honest was a client could do a little bit of scripting with regexes, but then a lot of the mud clients as a kid could do a ton of triggers, regexes, and that's where I got it a little bit further into it. Learned my regexes there, but really I didn't start writing software at all until I got to college. And then at college, what did you start writing? How did you get into a more serious level? So I came into college not really knowing what I wanted to study and I thought I might do physics or English or, you know.

4:44economics. My father was professor of economics, so there's some family lineage to try to live up to. But ultimately, I kind of fell in the computer science at my school, which was like a small kind of private school in Kentucky. There were, I think, 13 people in the computer science program the year that I graduated. And that was like the entire program. So I think there were four graduates my year, and then like the juniors and sophomores in total were like 13. And so it was quite small.

5:12So I think there were four that graduated my year, but, um, yeah, really that was when I got into it. And why? I just enjoyed had an intro course that we're required to take. And it's kind of funny, um, with a lot of American colleges, especially smaller private ones, they have random kind of requirements. So I was required to take a introduction to Christianity course, like at the history of Christianity, but also required to take like an introduction to computer science or some of our course. I forgot what the other alternative was. So I.

5:38really enjoyed computer science one. Did you decide that you're probably going to be a professional software developer, engineer, programmer, whatever we call it back then? So I think one of the interesting things when you talk a lot about careers is like a lot of folks go to like elite school. So you talk to someone from Waterloo and they go, how did you get your job? They're like, well, literally everyone at Waterloo is coached on how to do software. They're literally trading the answers to interviews with each other. So they know the interviews and drill on the interviews before they go in.

6:08They also, like, amazing program. They've been doing co-ops for years. Like, they're great. They're great candidates. They tend to do really well. But go to Waterloo. You go to MIT. You go to Stanford. You really, there's, like, this path. And you just kind of put your foot on it, and you do well, and it carries you there. And these are amazing students. It's like an escalator, almost. But it is an escalator. If they're good enough to stay in the program, they tend to kind of get there. Going to a small school with, again, like, four-ish folks that graduated my year in computer science, there really was no path.

6:36I remember one of the folks that graduated the year before that was working in software. He went to go work on a horse racing betting software company in Lexington, Kentucky, which I don't think there were more than like five engineers there. And this was like a really talented, really capable person. And this is kind of what they knew how to find. And so for me, it actually was interesting. I wasn't quite sure what I was going to do. I actually ended up teaching English and Japan on the chat program.

7:04the Japanese exchange teaching program. And so I was in the middle of nowhere in Japan in the Gifu prefecture for a year. But that's when I really started writing a lot because I was like, hey, I'm definitely not going to be an English teacher for more than one year. It's a one year contract. I did that one year. I had no thoughts about doing a second year. And I came back and started trying to figure out how to actually break into Silicon Valley from there. And you had the goal, break into Silicon Valley already. Why Silicon Valley? Can you take us back to what Silicon Valley was like back then?

7:33First of the time, I didn't know what Silicon Valley was, right? I just wanted a job that paid well. And I think, you know, this was so I graduated in 07. And then the next year I was teaching English. And then I actually started working for Yahoo in, I guess, maybe early 09, something like that.

7:52Really interesting time though. So initially I was working for Yahoo from the East Coast as a remote contractor. It was an interesting moment. So I started working with Yahoo because I wrote a series of blog posts on something called Yahoo Boss. Just build your own search service. And this was a product that they had launched on this one team. I think it wasn't getting a lot of kind of traction in the industry. But when it launched, I was writing a lot. So I did three or four tutorials on building...

8:18boss things in Python, boss things with Django kind of made a Django forget the name might have been Django Springsteen was like the name of the search library to use Yahoo boss with Django. And so I think they got excited because someone was writing about it, which also got me excited. And that ended up ultimately in this contract job. And then ultimately they had the policy where you had to move after a year as a contractor and go full time.

8:42And the reason I was hired as a contractor, though, is they had a hiring freeze for basically that entire year. Because this was right after a financial crisis. And so they're just going through layoff after layoff. And so they could hire a couple contractors, couldn't hire anyone full time. And then at 12 months, they are like, hey, now you have to go full time or you're not employed, because there's kind of the compliance obligations to it to avoid. And so they're like, hey, and if you go full time, you got to move. And so basically I.

9:08had a job at Yahoo, if I moved, or I didn't have a job at all. And so I moved from the East Coast out to California pretty easy at the time. Didn't have a lot of obligations other than, you know, employment. Yeah. And back then Yahoo, I guess their, their star was kind of fading with, with Google, but they're still pretty good company, right? I'm good at engineering talent. Like what's up founders famously came from Yahoo. I think Yahoo honestly is a really interesting company, right? And so I think one of the challenges for Yahoo is if you, if you came into tech in 2007, 2008, a lot of open source sort of

9:38made things easy. Yahoo, though, is a company that predated all these open source libraries. And so how do you run a server at Yahoo in 2007, 2008? You run Y Apache. So they had their own fork of Apache with a Y in front of it. What programming language do you run on Y Apache? Well, of course, you would run YPHP, which was their fork of PHP. And what UI library would you use? You might know this one, but it's YUI.

10:07And then how do you install things? So if you think about like, you know, a month to you'd have kind of like APT or whatnot, well, you'd use why inst, which was this Perl script that would navigate kind of the dependencies for installation. And so it's like really, really fascinating place to come up. But every single thing there they made from scratch, even they had like a precursor to Kafka, which I think was called why repel, which basically would be like a read log to do replication kind of.

10:35Outside of a database and that that was like a core tool for managing state Just like a fascinating place and I think if I just had like one quick Yahoo story that I loved So David Filo kind of famously approved every server that was allocated in the company And so one of the founders like would review and so that the theory was this would drive Accountability right you had to prove you needed more servers What it actually did is it created like the black market of servers? And so on my team there was like one engineer that had 30 servers from a prior canceled project, he never gave back. And so he would basically sell them to you effectively, right? And so if you couldn't get approval for like favors and IOU and that kind of stuff. And so it actually meant they had massive numbers of outdated servers that were like using like inefficient like power wattage because people would never give servers back. And so you had to find like someone who liked you with servers to loan for your projects to launch. Like a fascinating how these incentives drive just like wild.

11:35wild situations. I guess that's one thing you remembered for when you later became an engineering leader. Yeah, it was very instructive, right? And I'm sure I'm curious, like, did David Filo know that people literally had a black market of servers? Like, I assume he probably did know, but didn't didn't change the kind of the top down mandate. After Yahoo, is that when you ended up at Dig at the time? Very famous company for a very amusing story.

12:03Okay, can you tell us about like how we decided to switch because it was a startup, right? Dick was a startup back then. So depending who you talk to, there's gonna be different narratives. But I think the the dig narrative is basically it was like the before Reddit, it was the big community site, but it was centrally curated. And so Reddit had these sub communities where the communities kind of voted with the algorithm on what they wanted, the Reddit algorithm. Dick was actually centrally curated on what but went on to the front page. And so I had like a very different experience. But it also meant that the quality was consistent and you had less of kind of the bias and subreddit problem. Instead, you had a bias and central moderation problem. And there were, you know, communities, there are IRC channels where people would basically trade favors trying to get things on to the red, the, the dig front page. And in fact, for dig before we changed the algorithm and I had people saying they had come murder me.

12:58for stealing their livelihood because their entire livelihood was selling access to the front page, the new algorithm didn't support that. And they were literally threatening our lives. And so it was a fascinating place. But dig was a really important website. And when I joined Yahoo, this wasn't true. But a little bit before I joined Yahoo, literally the front page of Yahoo was a static file on a net.

13:24a net scaler, which was basically like a filer, which is like a way to store files. And Yahoo Sports was just like a static page, right? And so Dig in that era, like early on, was like a very important static page, but then it became not a static page, like a dynamic of sorts community. I think really was extremely important to folks at the time, though it's faded into slightly less relevancy over time. And it's been restarted a couple of times since, but never really picking up the traction once did. I think it was a top 10.

13:53website at one point. Yeah, it was top 10. And that's why the story that I remember is they did a big rewrite. I think it might have been the v4 one, right? And from the outside, what I remember is well, well, Dick was doing good. It was popular. There were complaints a bit like with Stack Overflow maybe a few years ago. And then Dick did this massive rewrite and disaster followed. And it was like a very juicy story. Everyone was talking about it. What can you tell us like what Actually happened and what did it look like from the inside because you were building this thing? Yeah, so I was there I was there for that launch and I was there after that launch and so I joined dig about three to six months before that launch went out and it was a fascinating time so I joined and then on the Friday before I started the CEO got Removed and then Kevin Rose came back in as he was founder, right Kevin Rose was the founding CEO He was there for a while and then he kind of stepped back and then he then he came back in

14:49But it came back in and we had this very hard deadline to launch Digv4, which was a rewrite. And so Digv3.5 was the prior version before Digv4, basically entirely a PHP software running on distributed MySQL. And this was like a different era, right? So Digv4 was running on hardware that we owned in like a colo. And so it wasn't like just spin up some capacity or whatnot. But Digv4 was trying to solve a bunch of problems.

15:19First and foremost, the internet was changing at that time. So this dig at one point, a top 10 website was starting to lose traction to Facebook. And it was starting to lose search traffic as well. And so there were a series of large Google changes. And I think we don't hear about Google search algorithm changes that much these days. But back then, there was the Google Panda algorithm change. And there were a handful of others. And they were starting to really reshape how traffic flowed through.

15:46So for a company like Dig, a substantial amount of the traffic, I want to say like 60 to 70%, the traffic was actually coming in via search. Oh, into something called the permalink. And so the permalink pages would be like, say you write a great blog post, that would then get posted to Dig. And then we'd have the reference to the permalink and also like a small link to your site, of course, and comments about it. But we would take a ton of traffic through these permalink pages that would be higher page length than the original source themselves.

16:14And you can argue, now maybe we shouldn't have been. Probably not. I think that would be kind of the perspective today. But from the perspective of that moment, we were actually creating the discoverability and the conversation around it. This was before Twitter. This was before Facebook got substantial distribution. This was really early moment. And so for us, that was the core of where people came into.

16:38Also, it was really where we sold the most ads. And so losing that traffic was basically tanking the company's financial prospects. And so Digv4, from the outside, Digv4 was working pretty well. It seemed like Navy was growing. But really, what we knew was Digv4 was shrinking. We had one beautiful month of profitability, and then an algorithm change hit. And we started shrinking.

17:03And we knew that this is existential for us. We were going to simply not exist, not that far down the path. And when I joined, I want to say like 110, 120 people, something like this. But this was in 2010 when funding rounds were $1 million or $3 million or something. It's not like today when people are raising.

17:27500 million dollars and you can have a team of however many or it was a very different moment So even with 110 people that was pretty substantial when we were we were running down with um, you know the remaining uh coffers pretty pretty fast the the launch In turn, did it go poorly? Did it go well? Because from the outside again, there was a perception that it went terribly and people there was a bit I think a lot of it was the community was upset And then there was a bit of celebration as well, like, well, they messed it up, like they kind of deserved it. You know, the mob, the people, especially, who were very involved, they didn't like change. First, there's like a really fascinating set of cartoons someone made, which is like dig versus reddit, and like dig is like blue, and then like reddit's red, and there's this like giant war that someone did like a four or five part. It's like this very intricate.

18:13comics someone wrote around around this time and it is kind of interesting to see how much energy people put into it But yeah, there was a lot of passion and I think it's one of the challenges of like a really passionate community is like when you foster passionate community then you change what you are Community doesn't like that because I mean there were literally these folks like mr. Baby man was like a really big one like one of the top did kind of curators unsolicited curators of content getting to the front page and and he you know he and many others were they lost kind of their their business right but the launch were pretty poorly and why did they go poorly? I went poorly for a lot of reasons. So first the launch technically wasn't really ready and so we made a lot of really aggressive technology decisions and again I came in about three months before this went went live so I I don't personally take a ton of responsibility. I also again think about where I was in my career I was basically

19:08was my second job. I had been at Yahoo for two years. So I won't own this one. I later in my career, I'll own anything that happened, but this one wasn't really by fault. But basically we made the decision to launch on Cassandra. And there's like a joke at the time, which is that Cassandra was a Trojan horse that had launched to basically ruin competition in the industry. Because anyone who launched on Cassandra was basically screwed afterwards, which I think certainly was true for Dig.

19:36And so running to standard replaced the shard of my SQL system. The shard of my SQL system was pretty complicated, but it definitely worked. And to Sandra, I would argue like basically didn't work, but I remember there was a team response for load testing to Sandra before our launch. And two days before the launch, this other guy, Rich, who was fantastic, he and I were pulled aside and like, hey, well, they never did the load testing. We need the two of you to do the load testing before, you know, in the next two days.

20:04And so Rich was just like a software engineer like me. And so we're like, well, I guess we'll like install JMeter and try to figure out how JMeter works to do some load testing. And we had this like really interesting conversation with Chris, who's kind of the head of the Cassandra initiative is like, Hey, like I can't do the reads on Cassandra. He's like, that's not true. I was like, well, I can't do the rights. He's like, that's also not true. I'm like, okay, Chris, if I'm writing to Cassandra, I can't read from Cassandra. If I'm reading Cassandra, I can't write to Cassandra. He's like, that is true. It's like, we're supposed to launch in two days.

20:34And then we launched and we didn't fix it. We just launched. And so I think the company thought that we were literally dying. And the company was, the company literally was done. It was running out of money. But it was like the most interesting day I've ever had professionally. Can't remember when I got to the office, probably around 8 a.m. When you say interesting, even stressful. You can judge. Let me like paint the scene a little bit. So it was a launch, but they also decided to have a launch party. So the entire day there were caterers kind of in tuxedos.

21:03with like sushi trays, champagne. Oh, wow. And so like the entire office is there to have this like kind of like celebration. And then in the center of the room, there was this like table that might have been like a boardroom table or something and pulled out this giant table, maybe three or four times the size of this where the engineers were sitting. And we didn't have enough hardware to run the new system and the old system concurrently. And again, this was hardware we owned. So they were literally wiping the old servers and installing the new software.

21:32So we couldn't roll back. We didn't didn't have the money to or the end because again, we were running out of money, but enough budget for the party, but like not enough budget for the servers, right? So we were wiping server by server, spinning it up. And ultimately, like the damn thing didn't turn on. It was functionally what what happened, right?

21:51And so we had this, you know, like down for maintenance page up for I think roughly 24 hours. And then we're able to scrap it. While the champagne and the tuxedos are coming around surreal. And there were people upstairs getting massages. There were, you know, I remember certain groups who won't be named playing ping pong while we're trying to get this up.

22:12And it was, it was just like, it was sort of like a magical realism. I see what you mean by interesting. This is not how I imagined a launch like this. You can never imagine a launch like this. It was just, it was so, it was so surreal. True, like a magical realism moment where there's kind of all this normalcy happening while this like site's literally imploding. And it was just, it was unlike anything I've seen, but it's also like a moment I take a lot of pride in. And so I'd been there three months. I think interesting thing is we did get the site kind of working.

22:41But there were a lot of issues. And so people just gave up and like day by day, like people just stopped showing up. And like a small group was really the only group left of maybe like six people trying to keep it working. And we did. And so we, in the first two days, like the same guy, Rich and I wrote like a caching system from scratch on top of Redis, which helped the site stay on for hours. But we're still had huge memory leaks. And so we're actually like restarting every process every, you know, like hour or two.

23:11And the only way to keep it up was rolling restarts of every process. And so it took us like a full month to debug. And I have like a blog poster right a long time ago about it. But basically the core bug was we created an API service that could be used for like third parties. And it was in Python. The people writing it didn't know Python very well.

23:32And this was Python then calling like another Python gRPC that was hitting Cassandra. And basically in Python, when you instantiate a default parameter, if it's mutable, I don't know if this is still true, by the way, I hope it's not so true. But at the time it was true, where if you basically put a list as a default parameter, and then you mutated it like appended IDs into it, it would persist in memory. And so each time that function was called, it would have the same dictionary or the same list.

23:59And so the memory of the user IDs, basically every time they call this API to look up user IDs, they get the user objects back. All the users that were ever passed into it would still be there. And so it just cascaded over and over and over until we restarted and be installed memcache kind of in between these. And the memcache would start falling over and then it would, you know, destroy Cassandra. So really finding that bug, it took me, I think, four weeks to actually find it once you found it.

24:28Trivial to fix but we got it up and then our new CEO started I think that basically the same day that I fixed that and Then then we you know basically the entire company got laid off of the next year So yeah, pure victory in the sense that we did saw them it was working But I think you can't really have the central site be hard to use or down for like a month But like if you go to the counterfactual what would the company have done differently if they had simply kept up the old site, they also would have died, right? And so I don't know that they made the wrong choice, but at the time I certainly was pretty, pretty salty about it. Yeah. How did you eventually get into enduring leadership? I know you and me overlapped a little bit at Uber. Actually we both worked there, but we never worked together. So the kind of the end of the dig story was we got aqua hired. And so they sold the patents for, they did a lot of like innovation. So like in ad, in stream ad units.

25:24basically like you see it on X now where they'll have like an ad that kind of looks like the stories from people that are posting. They did own the patents of that. They were the first company to do it. They own like a variety of other patents. And so the patent portfolio got acquired by one company, digi.com, like the actual like brand of the website got acquired by I think Betaworks at New York at the time. I think they've sold it.

25:46Subsequently a few years ago and then the team that acquired by social code Which is like a third company a subsidiary of the Washington Post company from the time when that was a holding company that owned owned the post Kaplan and this company social code Which basically did advertising on Facebook and so the team went there and I was there for a couple of years But when I when I left I was thinking about okay I want to be kind of in engineering leadership But I can't get hired into a really large role because at that time I was managing maybe a team of 12 engineers something like that So I can't get hired in this big role because I haven't done the big role. Like how do we get hired in this big role? And so if you're at a small startup, like you just, there's, the scale is not there. Even if you go be ahead of engineering at this 15% startup, there's just five engineers there. And so you can never get at this scale. They're looking for it for these large roles. And so my, what I was looking about at the time and my thoughts on this topic changed a lot since then, but that's just like honestly where I was. It's like, well, if I want to manage a large team, I got to join a company that's growing really quickly.

26:45I kind of looked around like where's growing really quickly like uber uber was growing really really really quickly 16 i think this is 2014 this was early 2014 this is one growth just start to kick off. Like this was very early. This is pretty early. You had to be in San Francisco to know that Uber was doing really well. Like outside of SF, I think, I think news started to spread in 2015. And then by 2016, it was a global news. That sounds right. But the way I knew is that one of the engineers, Jeremy Grocer from Dig, who was on infrastructure there left and joined Uber. And actually, this is like an interesting technology adoption curve, because Dig made all these technologies. One of them is called Clusto, which I think

27:25Dig I'm uber and then like a second life that that company I forget their their actual name But whatever it is maybe the only three companies in the world that ever adopted this tool cluster But it managed basically a key value store to manage kind of state or infrastructure a little bit like a console from from a Hashi Corp. It's very very similar years before console was out Yeah, it was probably made originally in like 2008 2009 something like that and so he had actually brought like a ton of the dig stack over into Uber, because he was one of the first infrastructure engineers there. And so, you know, his team was hiring. And I really was like a generalist engineer, like I got who was actually hired to do front end engineering, which I don't know if I super qualified for. And then at, at dig, I was doing, you know, front end, Cassandra were back in just like everything. And then they hired me to kind of run this SRV team, but it wasn't.

28:19really an SRE team. It was just like an infrastructure team that they called SRE. You know, I read like an SRE book like the week before trying to figure out what the job was. You probably read the SRE book that existed, which is the Google SRE book, right? I don't think that book existed then. It might have. What book did you have access to? I think there was a DevOps book, might have been what I was reading on.

28:40And it might have been like the, um, the Phoenix project might have been out around then. I'm forgetting if that the exact timeline, but there was something like the Phoenix project. Maybe there was one other and I just showed up. And then of course, like a classic interview, I remember doing the traveling salesman's problem on a whiteboard and Python stuff, stuff like that, which didn't really evaluate my, my DevOps acumen very well. But, but he somehow, I think the company was, was a little bit desperate on hiring at that point, but, but did, did get the job and started.

29:08And then you were leading a team, already you were growing a team. So the team when I joined, I probably was managing like six people, but it was managing like an incredibly broad range of responsibilities. So Uber when I joined was 2,000 people, it was 200 engineers, and this team of about six was managing our databases, our Kafka, like our actual servers.

29:31Well, the management of the servers, there was a tech ops team that managed literally racking them and installing them, but once they were racked, we managed that. Our service provisioning, like we owned basically everything other than there was like a two person developer experience team. There was this tech ops team that actually like racked and installed the servers, but we owned all the other infrastructure and it was quite an experience. And then.

29:55in terms of just focusing on your your leadership journey or your management journey so at uber you started at this team how far did it go and then what were the next steps between stripe carada yeah absolutely so when i joined that team was i think a roughly five or six folks when i left two years later that team was 70 and that was all external hiring and i think that that was like the most kind of amazing thing about Uber at that point is like Uber doubled and she had count every six months. And so you can't just like steal people from other teams because those teams are hiring a ton too and also really underwater. And so I really learned how to hire at Uber. I had no idea how to hire before I joined Uber.

30:35but they were just hiring so many folks. I think one of my favorite stories was there's this guy out of a Vembrite that I managed for a year and a half that would give him an offer at like 4.30 p.m. on a Friday and he started Monday at 8. But I have so many like Uber hiring stories, like some of them like funnier than others. I remember someone who interviewed with Uber four times and I saw him interviewing a fifth time. They got rejected four times and the team interviewed him a fifth time as like we cannot hire this guy.

31:02We've already interviewed him like four times like stop wasting his time. But he got an offer for that team. And he joined and then he quit within six hours and took a different offer that because he got an offer from Twitter, which was right down right a block, a block away, a block away or somebody was also. He spent, he spent more time interviewing for Uber than working there despite accepting the job. And they're just like so many, so many wild stories from the Uber experience there. But that team six to 70 over two years.

31:31And our scope increased a lot in that time, but it was just like a really wild time. And it's hard, you know, some of the companies today, I think remind me a lot of that Uber experience. But Uber, when I joined basically every Friday, we were literally manually reallocating software between servers, trying to keep the servers up. Because typically Friday rush hour was our peak time of the week. Though a Saturday, you might have more volume, but that would be like spread over more hours because people aren't all leaving work at the exact same time.

31:59So many kind of wild stories of just like what a manic place that that was to work at. But I was there for a couple of years, then I went to Stripe. I was at Stripe for about four years from 2016 through early 2020. Then I was actually at Calm for three and a half, three years. That was my first CTO job. It was really kind of deliberate at that point. I think I was really worried. So I'd been at Stripe for four years, you know, Stripe had done really well. I think I joined at...

32:26Five and a half billion and I think it was at 96 billion four years later company valuation. Yeah, it really came together But the also I think the quality of the work we were doing was going really well And I want to say I was roughly someone that joined the day I joined at stripe was employee 500 I don't know if that was me or someone else in the batch But I think by the time I left it was 1.5 to 2,000 folks something of a company so stripe grew about 70% year over year the period that I was there Which is a lot less than uber which doubled every six months And obviously Uber subsequently contracted much more aggressively than Stripe ever did, which is the natural consequence of doubling every six months. But at that point, I was just worried that my entire savings were all in one company that was never going to go public, which I think has been true. And so it was a bit of a diversification play, but also the desire to, what does it actually feel like to fully lead? And so for my entire time at Stripe, I was basically...

33:26one step away from the CEO's reporting into Jeff Winter for my first year, then into David Singleton, who was my manager for the rest of the time. Oh, Stripe's CTO later, or maybe at that time as well. He joined as a CTO. No, that's not true. He joined as the head of engineering. And then it became a CTO maybe a year or two later, something like that. But I was reporting to him from when he joined through the time I departed in early 2020. So I was only one step away, but I was like, what if I could get into that seat? Could I do things some better? And that seemed like the the right thing to try for anyway, and has been educational ever since. And then you have had several CTO gigs and so it was calm, three and a half years CTO, then you were at Cardo? So I was at Com for I think three and a half years, then I was at Cardo for two years, and then I joined Imprint a year, year and a half ago, something like that, which is where I am today. Okay, so now I, three times CTO, I need to ask you, what does a CTO do? As an engineer, like,

34:23If you put yourself back as being an engineer, of course, I think I myself had aspirations when I was an engineer like, oh, it could be nice to want to be a CTO because in your mind it's like, well, it has some management, but it's also a lot of CTOs you see are technical and close to the thing. How do you find the CTO? I know you have a book on this as well on engineering executive careers and there's a lot of answers, but what is your mental model? How was it and how is it now especially?

34:50with AI, I think your role has changed. I think one of the worst parts of being an engineering manager in the 2010s is I think like when you joined the ranks of engineering management, like one of the first lessons you'd get is like, hey, you need to never make a technical decision again. That's what it used to be, right? I remember. That is, that's like literally, you know, what I was told. And I think you'd see people like the most important thing is to let go about technology decisions. And this was the ethos then.

35:18And that's definitely not the ethos today. But I think the thing that I kind of aspiration and really loved is the CTO was like the only place where this like engineering kind of career, this technical-arranged one and this managerial one converged. And so one of the things I've believed strongly in and continue to do today is having both engineering managers but also like individual contributor engineers report directly into me and CTO roles. And so today I have 14 direct reports right now. And I think four or five of them are ICs and then the rest are our managers. But having that balance is like really for many roles in management, you're just not allowed to be a technical leader or you weren't for a long time. And so to me, actually getting to the level where they converged again and you were allowed to be a leader on the technology and the management side was like one of the big appeals. But also, there's so many like

36:10bad CTO decisions out there. And I don't, I don't mean this to reflect on any of the individuals I've talked about. I think David in particular was like really excellent. And the decisions that strike were generally decision quality at stripe was pretty high. And so sometimes you could be like, I disagree, but you couldn't be like, this makes literally no sense. But often like, you know, especially outside of the stripe experience, there were just decisions that like just didn't make sense.

36:34And I thought, like, maybe I could do it better. But I think the thing that I've really loved in the most recent kind of era is, like, you're really, like, not just allowed to be in the details again. Like, you're really sort of required to be. And that to me has been, like, the very most fun part of being back in software in this era is, I think, you know, I've done over 500 pull requests in a year and a half at imprint, going all the way to production.

37:01which is substantially more than I did in my prior career combined. And that's pretty cool. And then you didn't imprint that CTO, or are you more than CTO at imprint? So I joined as the CTO and right now I'm also kind of leading the product design teams. So product design and engineering all reporting into one person. Yeah, it's like a unified EPD structure. Is this a new trend, one person?

37:25Because CTPOI started to hear about two years ago Chief Technology and Product Officer two or three years ago and now I'm starting to hear design also going into one person a little bit. I don't know if it's a trend or not. I do think that for one challenge I've been seeing with like the agents kind of getting more mainstream is you actually have to be able to make decisions and make them quickly. And how do we do things? How do we not do things? How does agent adoption work for products?

37:52How does it work for design? Hey, design, if they aren't using the, you know, new tools like cloud design or the figment MCP or whatnot, then they're really the bottleneck. How do you kind of split the responsibility there on who owns to sign now? And so imprint, for example, has been experimenting with this developer led design model for kind of second tier features. And it's created a ton of friction. Like it, it's solved this bottleneck. It's also created a lot of like who's responsible for these design gaps that show up when engineers do.

38:21lead design and sometimes like don't follow the design system properly. And so having a unified kind of point that can actually make these tradeoffs, I think this moment of like immense change I think is pretty powerful. I do think just in my core, I believe the industry is changing more in terms of how we create software than it ever has in my career. And, you know, I started in, you know, late 2008, I've never seen a change like this. A lot of the changes I've seen were more subtle or more kind of cultural or social.

38:50just how I create software is really different than it was even a year ago. And having a centralized kind of mechanism during this moment of immense change, I think it's been really helpful for us. But I don't personally think it's like a long-term trend, but I don't know. I'm trying to avoid predictions about too deep in the future at this point. Everything's changing a lot. Will just said how he's never seen the way we will software change this much in his whole career. One thing that is changing is the fact that we forget hosting, which brings us nicely to our seasonal sponsor Entire.

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41:45To see more case studies and details, head to antithesis.com slash pragmatic. And with this, let's get back to Will and what changes he's observed across the industry. But why don't you go back to like from when you started in the industry? Can we talk about the changes you've seen in software engineering? Let's just focus on your experience. So let's talk about the Silicon Valley companies. They we know they're bubble, but they're useful bubble to talk about. How did building software change? Leading teams change over, you know, like starting from like what, like 2007.

42:14All the way to today. I don't know what your first experience was like, kind of as an engineer. But when I was first engineer, first as a contractor, I was like 22 for Yahoo working remotely. No one else on the team was remote. And then when I went full time, I had the same manager. So I had the same manager for two years. I had two one-on-ones with that manager over two years. Yep. I had no one-on-ones or like once a year or for performance, not even performance, for pay conversations. And then they would say, yeah, good job. Here's your raise.

42:43They're like, oh, and then promotions used to be like congratulatory since you're now promoted. And it was more about like, yeah, you're making more money. Cool. And I didn't have any explication that I'd have more than two. And the first one was basically he wanted to talk about another employee's performance, trying to get like some signal about whether they were doing poorly. So it wasn't like feedback from me or something. And the second one was like, oh, you like gave notice. You're leaving. Like, what's what's going on? Right. And so, and that was just kind of normal.

43:10And so his job, the way he saw it, and I think he was like really good at it, was his job was to go find an opportunity in the company for the team to have impact. So he was going around the company, searching for something we could do that was really valuable. And he kind of like brought that back. And then our job was to implement it and make it work. And that was just like how the work was done. And there was no idea that he was like helping me have a rewarding career or something like that. That like, I think was irrelevant to him. We were talking pre 2010.

43:40Pretty much. Yep. And then when I, you know, got to dig, I think all the managers basically got fired. I actually became a manager at dig because I was the only one dumb enough not to say no when they asked me. But, but, you know, I had, I had like two and a half, three years of experience tops at that point. And I knew nothing about management. Right. And again, I never interacted with my manager at my prior job. I interacted with like a tech lead to kind of set technical direction.

44:06and then got upset if I screwed something up. But that was kind of the entirety of like the leadership model there, right? So I came in and I was a manager, but there was really no management at Dig other than, you know, me for the last year. And I didn't know what I was doing whatsoever. So really, I learned a lot at Uber. But again, at Uber, everyone was so busy, there was no management there either. It was really a sink or swim and either you figured it out and your team really struggled because if you didn't get the decisions right, Scale of the growth around that you would just crush your your team and so again like really really know no support It was interesting because by 2017 when I became manager uber put together his first apprentice manager program Which actually talking with people so when I became a manager there I had like a few days of getting together mentors assigned all that Most injury managers never ever had that and uber it was brand new at uber they made it more formal so they actually did some internal

45:03DIY training honestly, but yes before that nothing Oh, and they did it because I think they realized that bad managers were coming a really big problem. Yeah, which makes sense I think people were just figuring it out and I think the uber I worked in was extremely kind of myopic So one of the kind of like values I might get it wrong was basically Solve it yourself. That's like not literally on the stated values, but people didn't go get blocked in other teams. They just get it themselves And maybe let builders build might have been like a variant of this. Yeah, there was the let builders build be an owner, not a renter. And when you combine the two, there was sort of something of principled, but it was like just just roam your way and don't ask for forgiveness. I just get it done. And there was sort of like a no dependencies culture, which I found really empowering where it's like, oh, I'm blocked. It's like, you're not blocked. You need to go figure it out. And that, that was really painful sometimes, but it really meant you could always

45:59take responsibility and just figure it out yourself. Sometimes I remember signing purchase orders for Uber, China, where we couldn't get anyone to sign it. And I ended up signing like a multi $10 million purchase order. And I was probably like 27 or just there was no one to approve it. And we had to get done. And so Amir, the head of Tuck Ups and I were just kind of staring at each other and was like, I guess we'll just sign it.

46:24And like the thing that I loved about Uber of that era is like, no one ever talked to me about it. Like there was never, there was never like a follow up, probably not good either. The surgeon in a corporate governance perspective, that's like maybe like a little bit like ad hoc, but we really didn't get each other's way and we're able to do like amazing things. Also extremely challenging place to work in its own right. Yeah, but people left and burned out for a reason, a lot of them.

46:46100%. But really, so all the way through then, I finally get to Stripe around 2016. And Stripe sort of famously didn't have a management culture either. So when I joined, there were I think three managers, one of them who I really loved working with. Raylene I think had somewhere between 40 and 50 direct reports because Stripe had read the paper from Google when they used to have basically no managers for some period of time. And that didn't work.

47:12They initially followed the model where there were no managers for a long time. And so I kind of joined in the wave of managerization as one of the early managers in that wave. But I think there were three or four managers, Raylene, Jorge, and there were like one or two others. Jorge was managing a team of, I think, 30 with maybe one manager underneath him. For those 30 folks, Raylene, I think, and no managers. It was just like a very...

47:41It was a very chaotic time as well. But again, kind of coming out of the Uber experience, I was very, very familiar with chaos at that point. But the rest of the business was growing really, really fast. And so I think really that period at Uber though is when the cultural change around what is the role of manager, I think started to like cement itself a little bit and kind of this role of manager, not as a kind of a core viewer or a decision maker, but as a facilitator really started to take hold. And that was like, pretty, pretty fascinating to watch. And one of the reasons why I wrote staff engineer, which I think came out in 2021, was actually like collecting feedback for some of the staff engineers I worked with. Cause one of the, one of the ideas that I was really frustrated with at the, at the time was this idea that staff engineers principally got to work on interesting fund problems that they found personally rewarding, which wasn't what I needed for my staff engineers at all. Like I needed them to go work on.

48:39the business problems and the scalability problems that I, as like a leader, and when I left Stripe, I want to say my team was like 250, 260, something like that. I had all these problems. And so some of my very best engineers were like, I want like a more interesting problem is like, I only have suffering to offer, but this suffering will make is what's going to make the business succeed. And so how do I refocus them? And I think many of them at the time felt like that was a violation of the management contract, like my goal and my obligation was to give them interesting work they wanted. Oh, interesting how when we look back just how it changed from like 10 years before. Totally. Right. And so I think that that was like a fascinating time to be in, but I don't think that perspective was ever really right. If you look at the people who were really senior at Stripe, but also everywhere I've worked, those folks were doing the really valuable work that the company needed.

49:34You never saw that perspective like really take hold in the executive ranks. But a lot of the folks coming in really had that belief. And I'd say like without naming names, certain companies that they came from had very strong versions of that were kind of the obligation to the manager for senior hires was to give them fun work. And I think the industry is really reverted on that one for sure. Was this something to do with zero interest rates? We often come back to this, which is so.

50:01curious. I wrote about this as well, how an interest rate, which feels so abstract, and we sometimes hear about it, how it probably impacted funding in tech for a very long time, probably hiring startups, startups that were funded that maybe didn't have a business model, but they were still funded. And ultimately, software engineering, archetypes, manager types, management decisions. And then the music stopped sometime around 2022, where efficiency became more important. And now we're kind of seeing this And now I think a lot of us are asking and I'm also asking myself the question like, everything that we did during that time, was it right at the time? Did you ever read? I'm going to get his name wrong. The thing was like Ron John Roy's like a Zerp explains everything. Log posts from the margins. Yes. The margin. We'll also link that. I love his writing. Yes. One of my colleagues I dig who then I hired at Uber was John Derrick, who's the other writer on the margins, along with, I think it's Ron John Roy. But so I read that piece.

50:59And it really resonated, right? I do think that Zerp has explained the entire like 2010s in terms of how management styles changed, salaries went up, then competition for hiring became your ability to hire and close and retain became the differentiator between these like successful companies, the less successful because you simply couldn't retain great people. And that like pulled kind of leverage back into the engineer's hands.

51:26and created a very different environment. And so part of the way companies were pitching themselves was more relaxed, more focused on you, more career development in ways that I think were often self-defeating. So I think there's this kind of broad judgment of the Google Perk culture. And I don't think any company that did incredibly well other than maybe Google and Metta had that level of Perk orientation. But I do think ignoring the Perks, there are many other ways that companies try to focus on.

51:55Reloading work interesting work, you know companies like oh engineers maybe shouldn't be on call That's right. That's the second tier SREs to be on call And which was interesting because that was actually a place where Every single person I've worked with knows engineers being on call for the work makes the software better Yep, and yet companies were still kind of like oh maybe for the enjoyment of it We should let folks not be on call for the work they're doing and instead page other people that aren't involved in the creation of the software And that orientation really reveals, I think, that the shift in priorities in those companies. Well, I also wonder if that was a time where managers were rewarded for having low attrition on team, meaning few people left, being able to hire on the team to fill headcount. Because often there was a time this might sound crazy, but filling headcount was difficult. You were given, let's say, you had a team of 30 as a director or senior injury manager. You had 10 headcount this year.

52:53And if you couldn't fill that meaning you couldn't hire the right people and this was like that's a senior and above so it was like you can just get new grass because that would be too easy. Then it kind of counted a little against you or someone else would get that headcount which might help their promotion because it was kind of obviously if you have 40 plus people you're now there might be senior manager that's your director title and so managers.

53:16who did well in this environment became a bit of people pleasers and also they started to shield their engineers from the business for example and I wonder if this shielding from the business has bitten back a lot of people because now as engineers you're increasingly expected to be savvy about the business understand the business that's when you're going to be in demand that's when in a startup or other places you get hit the ground running and I still hear stories from people who worked at this big company the Let's say a big observability company at any of them and they want to start up 7% start up and they say it's terrible like I'm They're not letting me do things and I'm like hang on you're a 7% company like How is it and you're an experienced person? How is it that you're not asking? What does the business need to do? Let's do it boom and they've been socialized in different place for a while Yeah, I think I think that is like a huge part of it in terms of the incentives I do think the orientation around like headcount filling

54:10team kind of management, like the employee kind of survey results. These are really valuable tools. I get like a lot out of them, but I remember spending a lot of time at these faster growing companies, like analyzing the quality of manager based on the survey results. But survey results are like, you have to really interpret them. Like high scores or low scores don't mean good or bad manager. There's like context to ask other questions about like, Hey, why, why is your team all upset about this?

54:39that doesn't mean you're a good manager or not, right? And I think these became a little bit a goal of their own rather than an interpretation mechanism, which, you know, in a lot of ways it's just like lazy kind of middle management in terms of how these are deployed. But I definitely, definitely saw that. And I think in general, I think I hate headcount conversations, right? And I think they're, they're almost never the most interesting conversation. But I think in a world where managers are not allowed to make technology decisions, the only lever they have to actually execute faster is headcount for prioritization. Oh, so are you saying that at that time and during zero for managers where the conventional wisdom was do not make technical decisions this forced savvy and smart managers to put way more focus on the non-technical side potentially under investing in the technical things maybe just not making decisions that should have been done and over indexing on the soft side or maybe shielding their team from the business or all these things because they put their energy there?

55:37Oh, 100%. I think that's very true. Like for most, like what I tell my teams that I work with now is like the hiring is the least interesting way to solve every problem. Like we almost always should never talk about hiring. But the corollary to that is like, if you have open headcount, and that's for more headcount, we shouldn't talk about headcount either. Cause like what matters then is like the hiring throughput and you actually like can't use more headcount anyway. But yeah, I think we basically told managers they couldn't think about technology solutions. And then what do they have? They have like process solutions.

56:07They have scheduling or they have people. And so I do think this was the natural consequence of the bifurcation of these two roles, which isn't to say we shouldn't bifurcate at all. But I do think we need effective leadership to have both or they over anchor on kind of hiring. And that drives a lot of the bloated orgs we saw in the past. Let's talk about careers, career development. Let's start with individual contributors. How do you think career opportunities have changed for?

56:35software engineers working at start-ups, mid-sized companies that you see. Because we used to have a pretty good career ladder. Eng1, Eng2, senior Eng, staff Eng. It was clear on how you get promoted. To start with, you know, AI tools are out. You know, they're writing the code, which used to be like Eng1 and Eng2. They're now getting better at like architecture. We're talking about loops. Do we have a career ladder? Should we have a career ladder? If you are a manager at a company, should you be worried about putting together a career ladder right now?

57:02It's a good question, right? And I do think the expectation is certainly from the teams that we should have career ladders, right? And that is, so the belief, which I think is like backed up in research is that like having rubric strives more fairer decisions than not having rubrics. And so I think this anchoring on career ladders is like something that's here to stay. And I do think if you don't have that, then you do undervalue certain things, right? And so maintenance work, blue work, gel work, whatever you want to call it, I think gets like under emphasized and flashy things that actually work and get over emphasized. I think that's definitely true. So I'm still a believer in career laddering, right? I think it's still valuable. But what you'd be there, I think is like complicated. And I think it's like much less clear about what should be it. I think I don't know which consultancy has been selling on some of these career ladders. We kind of small company by small company, you see the exact same career ladder from some like kind of like

57:55I don't know, like the packet you can buy somewhere. And so I think all of those are just really outdated, but we don't have like the next version of it. That said, when I think about folks getting to like staff or principal these days, like what I really care about is I've been thinking about doing like an add on to staff engineer, I'll get to it in like, I don't know, the next decade sometime. But it's really about decision-making and complicated situations. And so first this idea of navigating ambiguity.

58:22And so at Stripe, I remember working on this project where we wanted to go multi-region and I kept getting from the engineers trying to lead it. Like we need a product to decide how on cross-region replication works or what's the product behavior that we support if there is like only the consistency and availability, but no partition ability. They wanted the product team to make these like cap theorem trade-offs, which the product team can't possibly make cap their own trade-offs, right? And what they were doing is they were finding a way to get stuck. When instead, like what you need, like somewhat at the staff or principal level to do is to navigate an ambiguity by making some trade-offs, build the conviction, figuring out how to like make a prototype that like tests, like whether the prediction, the assumptions that made are valuable and workable or not. And so I think these ambiguous problems are still a really challenging one. And to me, like a strong marker even today.

59:17Even with agents, you still have these complicated trade-offs that you have to make. And some of the trade-offs to your point about kind of understanding the business earlier do come from not just understanding like how the technology works, but the product implications. And to understand product implications, you have to understand what your users are actually trying to do. You have to understand the unit economics of like the product that you're offering and the cost to the service it and to actually what you're charging. And so increasingly, I think you have to think be quite broad to actually work these ambiguous problems.

59:46But I do think decision-making has always been where staff and principal engineers have to make the impact. And that hasn't changed at all. I don't actually think agents are exceptionally good at making these trade-offs. I think the agents often don't even recognize the trade-offs because they're not in the context window. Kind of subtle, implicit things that live kind of outside of the software. What about Eng1, Eng2 careers? I just had a senior engineer ask me saying, so, you know, like...

1:00:13AI clearly has gotten as good as an Eng1-Eng2 writing code because that's what we expected a lot of times from them. And then this person was saying that, well, somebody will come to Senior but it's not there right now, but I still remember this one because obviously there's truth to it, but I, in your org, how do you think of Eng1, Eng2, NewCrad, or people who are under the Senior, they don't yet have the battle scars or the expertise or the judgment that you can fully trust them both in terms of hiring but also developing them.

1:00:41So one of the things I try to stay away from is I call artificial specificity. And so what's the difference between an edge one and an edge two? And I think that's actually pretty hard to be super concrete about it. And I think a lot of companies successfully say the difference is three years of work experience. And they say, is that equitable? And I don't know if there's any super equitable way to evaluate edge ones versus edge two. And again, a really bad edge one, you can identify.

1:01:07But there was something like a really good edge one and edge two often is time and roll in terms of just like building more kind of context over time. But it's not like, it's not like super like they can do this or can't do this, especially with, you know, that the coding harnesses, like they can do anything, but actually deciding whether they should be doing it increasingly, increasingly tricky. And in the wrong situation, we're getting a lot of direction. You can't even perceive their judgment in a lot of cases, right?

1:01:35So I actually like hear less and less about some of these things where I think just general things like time and level stuff like that is probably good enough for a lot of these. I do worry that getting incredibly detailed on these criteria is like a bit of a like a fake victory where it's like, oh, it's made it really precise. But often you've been in like calibration meetings.

1:01:59where there are people who played to the rubric. I remember at one company I worked at, we had to get to like staff. There was like a mentoring requirement. And so we'd have people that literally went out and like would talk to someone and then be like, report them as like a mentee. And they were like collecting mentees. And then you talk to that person that like, I didn't know why I was talking to them. They just talked to me once. And so like, this is where if you actually create like the, you know, like you get what you measure. So I really think.

1:02:27For promotions, there's always been a lot of judgment. Whenever you try to remove the judgment, I actually don't think you get good outcomes there either. And so having the rubric to help guide people, I think that's useful. But ultimately, it's like pretty subjective. And for a lot of these things, I think it actually having kind of constraints is more interesting than having really comprehensive rubrics that are used to make judgment. So here's an example. So something you did at CARTA. Well, at CARTA, there's a lot of cost pressure.

1:02:54cost pressure, meaning that like to reduce costs of the let's say org or to reduce our managed costs. Yes. Exactly. And so I actually had like a ratio who can't have more than this number of staff engineers relative to the number. And they're just, you was not possible to exceed that ratio. That was very annoying to a lot of folks, right? But I think it actually is more honest where the industry was like 15 years ago, 15 years ago, I think there are.

1:03:22wasn't a role past senior in most companies. Like senior really was the ultimate role for almost every company. And so, you know, as people have gotten like further along in their careers and we have more people with like 20, 30, 40 years of software experience, they have opened up more of these levels. But like a lot of these levels are like ultimately more like time and role kind of titles rather than like really like a definitive, like obvious like change in the capabilities of the individuals that are that are doing it.

1:03:51I try not to worry quite as much about like the details. And I do think having like a hard block of like one or one to eight or whatever it is is really helpful. If like what you're trying to do is manage costs because when you're managing costs, what you have to be honest about is that you're managing costs. And so at Carta, that was kind of the situation we're in now at imprint. Like we're not trying to manage costs. We're trying to manage velocity and quality level. And so we haven't thought about that at all.

1:04:19But this is where I think part of leadership is knowing what you're doing, explaining how you're doing it, and then letting people accept the consequences of that. And so because of CARTA, we were going to have a fixed ratio that meant we had to start shifting hiring to be less senior, so we could actually have more of a pipeline of folks coming in and filling those levels. From that fix, a lot of things came from it, which worked really well. But it wasn't if we had just tried to fix it without figuring out the other parts of the hiring earlier in the funnel.

1:04:48wouldn't have worked, but I don't know, I'm less of a believer and kind of like a perfect description of things that are true than I was earlier in my career. Just so many exceptions to everything. The thing with like the rubric sound and with expectations, like it used to be, you know, when both of us worked at Uber, you later worked at Stripe, it was pretty well understood what was expected of the role. And you know, with the levels like, yes, I agree that I inch one inch to senior, at least can be murky, but there was a pretty clear expectation at some point. For example, a senior you could trust them typically I think the industry started to understand at some point for like closer to a decade a senior could trust them with a project if they had junior engineers they would mentor them, a staff you could trust them with to set the direction of a unit or multiple projects and so on. And the NJ1 and NJ2 is they could execute well coding without too many issues took feedback they were kind of like almost like they were like apprentice levels like I think NJ1 and NJ2 it wasn't a serious

1:05:45Promotion in terms of it was just it wasn't a destination. It was just they're growing Some companies even had the expectation as you were that you need to grow to a certain level But but they were like almost like apprentice honestly like they were just kind of getting getting to that that to have good judgments and all these things now that We're all using a harness is a lot more Including for reviews code reviews are slowly going away as well We're doing a less of the the what we used to do which is coding and the very visible feedback between each other How would you define what the role of a software engineer is and is it different from before is it more ambitious? Is it how do you think about it because it is it is changing like I feel is getting more ambitious somehow, but I'm not sure

1:06:28I'm able to put my finger on exactly how, especially from a CTO perspective. And is this like the general rule or is this like the level three? No, no, this is the general software engineering rule. Because I think I feel each role has changed a lot. Maybe the staff role of staff engineers never did too much writing code at like mid-size and above companies because they were busy making sure we're building the right thing. So maybe it's hard to separate because now no one is writing too much code and even the smallest roles, they will have they will just need to decide, are we doing the right thing? Am I doing it right? First, I think we're still like early days in terms of where we're going. And there's certainly people you're going to talk to. They're like, Hey, like the, the software teams, the future are five people for any size company. And maybe, maybe that's true. Maybe we'll get there at some point, but we're definitely not, we're definitely not there right now. And I, I don't know if we're going to get there soon, but there certainly are companies that are.

1:07:19you know, have a small number of engineers spending with a staggering number of tokens in productive lists. And that's like a pretty, a pretty cool thing to see. Where is the role of software going? I think we're going to find out. And this is actually why it's such a fun time to be in the industry right now, right? The most fun thing is like, I think our profession is changing in a much more extreme way than anything I've seen since I entered the industry. And for me, like someone who's always been very oriented around.

1:07:48the outcomes of the work I'm doing. It's just been like the most fun time I've had. But I've also spoken to folks who got basically joy from, you know, being in the zone, being in that flow state. And they like have fallen out of love with software. So what they loved was like the actual art of doing it. And for them, like, you know, a few folks, like one person I've spoken with recently, he actually, he's retiring. It's like, I just don't enjoy writing software anymore. And he's lost this flow state.

1:08:17it's more productive, but like I just don't enjoy it. And so I think the role is shifting, but I think it's shifting in a really interesting way. And I, to me, I have this kind of idea of software where the time to actually implement is approaching zero. These systems are still very slow in terms of like, you know, okay, let's say you can instantly implement stuff, you still have to make all these decisions. It still doesn't work in all these ways. It still is going to scale poorly in all these ways. It's still going to break the user expectation.

1:08:45still going to have like the wrong unit economics to actually be like a profitable business. And so I do think even if software were like literally free to write, it's still really, really, really hard. And so like today you'll see this like if software is free, then all of a sudden engineers are running ahead of the PRDs from product and running ahead from the high fidelity mocks from design. And that's creating a ton of issues for design teams trying to work with this engineering led model.

1:09:13something we're still trying to figure out at imprint totally, totally honestly, right? That also could create opportunities where like, well, if if an engineer also puts on a design hat or a business domain hat and now and now like runs an experiment full on. And obviously now you get to like, there's only so many experiments you can run without confusing you customers, which now it goes back to strategy. Someone having to say no. And also like, who are you building with? Like if it's for people, like they will have the need number of attention like Netflix has. I don't know how many new movies they bring out, but I know that when I open Netflix, they don't overload me. I mean, they do, but they have, they have, they don't show me all 8,000 movies. They, they figure it out. And so I wonder if, if software is becoming faster, like as engineers, we will need to discover the constraints of the other parts of the business that the main, the, the customers, the, the reality, like you say unit economics, how, how money can be made.

1:10:11I think something I thought about a lot working at CARTA. So CARTA is a low scale business by which I mean, there's not like hundreds of thousands of requests per second coming in. There's no like massive infrastructure problems there, but it's incredibly detailed business. How cap tables work is really, really, really specific. And it's very complicated. And there are tons of exceptions.

1:10:34And then doing accounting. And it's important, right? It's a little thing, but you need to get that right. And the accuracy is really important from like an audibility perspective. You're also working with law firms that have like a real strong point of view about how everything should be done very particularly as well. And you could be in a legal battle between two founders who are arguing about how much equity was actually vested or something like that. Similarly, the other businesses Carter went into like the fund administration also incredibly detail-oriented.

1:11:01And so there are a lot of businesses out there where the domain context has always been the hard thing. And it's not super clear to me if businesses where the domain context is really the hard part have benefited that much yet from kind of all the AI tools. It's still incredibly hard to do cap table management because of the details, the laws, the relationships, the law firms in terms of training like the paralegals there. There's like all these little pieces that I think domain like complex domain businesses.

1:11:31still have a lot of sensibility in this day and age. And I don't know if that's how that's going to change. I think it will change. Every two to three years, there's this kind of like the product engineers are the new king. Product engineers are the new superhero kind of like meme that comes around. No, it's the AI engineer. No, it's the AI engineer. Who really are like product engineers that use like AI techniques, right? And so the question is pretty much every product insurance these days. 100%, right? So it's like, it's unclear. I mean, I've never really quite understood what AI engineer means. I think it means.

1:12:00someone who uses harnesses and wants to get paid a lot of compensation as I think what it means. But it probably means something else too that I've just sort of missed the nuances on. But like, can you actually get individuals to hold all this context in their head? So even today, you know, people used to talk about like the front engineer who's actually a good designer or the designer who could actually write production front end code, that person's always been rare. And now a designer with like a little bit of taste can write production code.

1:12:27Right. And vice versa. A front engineer with a good design taste can do design. Why aren't we seeing more of that yet? And so I think that's like a social constraint. Well, it's a really good question because I was asking the same thing. I saw some data from Linear showing that PRs for designers and product managers are up. And I was like, oh, actually, someone messaged this to me, a fellow engineering manager said like, hang on, I've been asking around. Like we should be seeing more designers push.

1:12:56to production right or product managers asked around 10 companies i asked around another 10 including the likes of linear ramp open ai i have yet to hear except for like some exotic edge cases or like i just one example of designers pushing production code they will find bugs they will identify them but they will still get an engineer involved who confirms this this approach works in the coal base especially when we're talking about outside of prototyping they do prototype more but Even if we're not there it's I wonder if it's an accountability thing. It's a you know, like when Even though like I can change a light bulb I will still call the electrician when I need to do something a bit more on my house because it's electricity, right and and I can read the book I wonder if it's this or specialization I don't know, you know one of the things that I think a lot about is like there's there's one worldview right now Which is like if you have a great design system

1:13:50and you've actually used that design system, you don't need product designers anymore. That's like a viewpoint that a few people have. I haven't found that to be true though. Even with a good design system, understanding how all these different components fit together, understanding the missing components in your design system, figuring out when you have like trade-offs across different screens, how you manage those trade-offs while presenting like the unified experience for the user.

1:14:15These are still really hard things to do. And so, you know, I know attention is all you need is actually not about human attention at all. But do you think there's some dimension where like people are still constrained on attention and great designers and great product designers and great design system, the designers as well are all so constrained on like the details of what they're doing to do it well that they just don't have a ton of time to also be branching out? It does that inherently have to be true?

1:14:42I don't think it's inherently has to be true and I do think in theory if you have a great design system and you have a ton of consistency and a ton of linters in terms of like it has to be used this way, all of a sudden your design system folks, your product designers can be just looking at the exceptions much more aggressively. That is where we're trying to get to at imprint for what it's worth, where the base case is just done by engineering using the stock design system and product design is more working on the really complicated.

1:15:10kind of versions of it, along with extending the design system of the design system of folks. It's not working that way yet though. Like it's still, it's still a little bit tricky, but you know, as, as like the folks deep in AI say, like I kind of do assume this is like a quote unquote skill issue. And now we will like get, get to the other side of it, but I, it's still a skill issue for, for us. We're still figuring that out.

1:15:30One thing related to this is you wrote revised rules of engineering management, a really nice article, we'll link it in the show notes below. And one of the rules that I want to highlight, you say we wrote durable high ownership teams, I'm quoting you, durable high ownership teams with domain context are even more important. One of my biggest lessons that you were was that persistent durable teams work magic by accumulating domain context, building a sense of camaraderie and feeling increasingly strong sense of ownership over an area as they continue to work on it.

1:15:57Now this was from Uber, like what, like 2014, 15, so like more than 10 years ago. And you're saying that you feel this is very relevant, right? I think this is the only way to build skilled organizations. And it's interesting though, I think this is, this seems kind of like obvious, but it's actually a bit of like a, a non-consensus take if you will. And so a lot of times you're at a company, say there's 50 engineers and you have a really important project for a partner that projects late. There's still the mythical man month thing that I keep.

1:16:25removing 15 more people to work on this key project. And, you know, the Mythical Man Month, I want to say was written in like 80, 84, 75. 75, 1975. And the second version, 95. And it's, that's a while ago. And so. More than 50 years. We know this doesn't work. And so like, first, like when people do things like this, a lot of it's like optics and creating the perception of doing everything possible. Yes. So that when you miss, it's not, it's not your fault. But actually not only does.

1:16:53doesn't not work. It also destroys thing that does work, which is creating little pods that are able to own areas. And so when I joined Stripe, I had, you know, I took over kind of the team, Jorge was leading up the time and he moved on to a different part of the company. I think to lead connect. And so I had 30 people and one manager was managing like four or five of them. And then I was directly managing say like 23, 24 people.

1:17:18The first thing I did was like, all right, what are some pods? And figuring out like some areas I could put together who could own areas. And then once I saw some progress, I just stopped thinking about them entirely till something went really wrong. So I could focus on the bigger priorities for me, which is like the problems you couldn't solve. This works so well. And so at Uber did the same thing. I came into imprint, did the same thing as well, same at com.

1:17:45Cardo is like a really well kind of scaled organization by the time I joined it. So I didn't need to do the same thing there. I think this just works incredibly well. I think if you do this well, that people actually do better work than you will from top down dictation, simply because they understand it really well. And it gives you the ability to actually put your attention on the highest leverage or most painful parts of the company. And so, yeah, I think this is a strange non-consensus take, but it just works incredibly well. But Optically, it almost always looks wrong. And that's like one of the reasons it's hard to do where you have like a partner launch and you're like, Hey, I'm not going to, I'm not going to move these folks. I'm going to let them say on what they're doing. It's really important. Instead, the team that's on the critical path, we're going to work hard as hell together. But like, we're going to burn to get through it. We're not going to pull everyone over because if you don't do that, or what you might have done in the past is especially in syrup where it was.

1:18:43You have meetings, recruitment, all that. You would say like for this team on a critical path, we removed them from all of the BS. Totally. The recruitment, the university trip, you don't need to attend all hands and all these things. So you can be, which actually by the way, works so much better than adding people. And also sometimes telling people like, look, this will be a two week push. Anyone who can commit to it, please do so, including putting extra hours. And in return, you can take time off afterwards or.

1:19:10or you create incentives and you just treat them as adults and you're saying like, oftentimes people will like, I know in my life outside of work, sometimes you are okay taking a thing for this one thing, especially when you know that I will repay you in kind somehow. And if you don't do that, the thing that happens is actually at a real growing company, there's a crisis every day. And that means if you rotate people to crises, there's a crisis for everyone.

1:19:39Every day and it creates the sense of like devastation and so I remember talking with someone at Stripe one or two years in We were talking about this and he's like the the way Stripe had run up to that point His metaphor was like it was like people on a wall trying to defend a castle And they were always running to the place where they're about to get like overwhelmed But they just couldn't be everywhere because they were they were getting faster and faster at running But they still were not everywhere all at once and what we were trying to do was switch this metaphor was like we had many people many places

1:20:07And so the people working in one spot had to solve that spot, but it meant they didn't have to be everywhere. And those are kind of the two trade-offs. But to be a successfully scaling company that's growing quickly, you do have to get to a mode where it's not the same people running everywhere at once because those people just completely burn out over time. And there's a certain point where they just can't manage the coverage anymore, no matter how amazing they are. Although I think the question with AI is that point much further than it was before.

1:20:37But I'm not sure if it is, I still think their attention runs out before their ability to write code does. Also recently, something I was thinking about this with the durable high and ownership teams is just an example with Slack on how we have Google, Google Chat, you have Mattermost, you have Microsoft Teams and Slack. Let's say these are for big competitors for the chat market and it's pretty well understood was there and oh and you have AI.

1:21:03your startup, you could also instruct an AI to like copy Slack. And here's the interesting thing, you know, if you do have the AI would copy Slack's UI and or find open source things. First of all, there's a lot of decision that have never been documented that are behind the scenes that people at Slack will know and they take it takes years, which if you build it, you'll figure it out if you're big enough from the concurrency, deliverability platforms, yeah, yeah, yeah. But taking that aside, Slack launched Slack agents, which was a super sweet integration with coding agents and that do the work inside of Slack. It just works beautifully. It's been well thought out clearly. Like this is a team that has a domain context and they've clearly been working behind the scenes with teams partners. I'm kind of like, hang on, why has none of the other competitors launched it? Why has Google chat who have amazing people as well? These are all people had that have the domain. And I think this is where I'm starting to

1:21:54This one example just started to realize like there is probably value in like slack having all these people who are working I'm sure there's would be horrified of how many people work there I notice from Uber like why does Uber have this many people? But they're working on this but they're they're not only able to operate what they have But they are they keep reinventing what customers will want as the world changes You know no data companies seem to have not been it responded even though agents have been here for a while They just haven't responded slack has not only responded. They did something that is objectively good

1:22:24And now it's copyable, but how did you get there, right? There's some paper about the size of the bureaucracy of managing like the British kind of empire and the size of bureaucracy. The number of bureaucrats kept growing even as the territory getting managed kept shrinking. And there's sort of this inherent kind of thing where companies do just expands and create like bureaucracy and create like more kind of overhead. There's something there where like sometimes companies have just kind of like lost the plot and their ability to actually move.

1:22:54But my assumption, I think this is true for the Muse work on Fermetta, my impression is that when really interesting good products come out, there is one or two highly empowered people that are connected to the founder, the CEO, the executive team that are pushing it through and that are able to make painful trade-offs that are not well liked.

1:23:15And those can be like legal versus like company trade-offs. Those can be product trade-offs. Those can be there are, you know, the sacred kind of elements of how things have to be done, not doing it that way. And so like my guess is like for Slack, there was some sponsor and look, people hate overemphasizing executives, but I do think executive sponsorship to actually empower folks to do something difficult. Imprint moved over to linear, you know, like three or four months ago from JIRA. We did it in like less than four weeks.

1:23:45And there were basically zero people that thought it was a good idea when I decided to do it. We still did it in less than four weeks, and now people are really glad we did. It solved a lot of problems you had about having centralized issue management so the agents could actually know where tasks were, pull them down, work them, actually do kind of task unification, et cetera. We're having a really hard time managing workloads of tasks without that. But there were like maybe three people out of like 230 that thought it was a good idea before I did it.

1:24:14And that one, I just, you know, pushed through. And I think now people are like, oh, that was a good idea. But they just didn't think it was. And sometimes you do have to have someone who's willing to take the risk. And then, you know, the flip side is we then need to judge execs and other senior leaders on are the risks they made us take good. And so I think three months into the linear migration, I think, you know, no one talks about your anymore. But certainly no one's upset about the change. People are really glad with it.

1:24:42But conversely, if people had hated it, like they should be like, you know, rallying to get me fired, right? But I think a lot of times people don't get held accountable to this. And so that's the flip side of that highly empowered executive sponsor that does make these great products. Sometimes we let them do incredibly boneheaded things and don't hold them to account. Which is great segue to talk about executives. You've been a CTO, which is a former executive. Can you tell me what in your integration executive is?

1:25:11And how, what is the career path today to get to that level from an engineer? Like, okay, like I like the executive. I like that to have be able to make decisions, including unpopular ones, helping people, helping companies. What was the old path and what's the new path? If there's any. So I think the old path, your, your software engineer for some number of years could be pretty short. Then you get into management.

1:25:34and then you climb through middle management and then you get to the CTO role. And middle management, end manager, senior end, director. Exactly. And so I think there are a lot of problems with that. First, it means that often the people that were selected for management initially weren't like the most focused on the technical pieces of the work because they're trying to get promoted to management. And then the selection bias is really towards people that are able to operate well, which doesn't necessarily have a whole lot in common with technology side. Often they happen to be really good.

1:26:01technology, but there wasn't like a strong kind of selection bias for it. But you really do have to be a good bureaucrat to be an executive. And this is like one of the interesting challenges where a lot of my work is incentive management. It's knowing, hey, if we roll out this sort of performance review, here's how it's going to fail. And so we just shouldn't do that. We should do this other thing instead. And so if you haven't done the reps of being like a bureaucrat, you actually like.

1:26:22can't run a function because a lot of running a function is, in fact, being a bureaucrat. You learned to be a good bureaucrat. I was a bureaucrat, right? And so, I mean, out of necessity, so at Uber, we don't really like rubrics. There wasn't like an interview. We didn't have any structure of how we interviewed when I was there. So you had to make it all up yourself for your function. And again, we were doing tons of interviews. And each time we didn't give an offer out, I was like so pained because I was doing so many interviews.

1:26:50So I had to figure that out. And then at Stripe, Stripe was like a much more structurally cohesive company. And so we did have a lot of structured process. And then I got to work on a lot of that and learned a lot there. You kind of got pulled into it. You picked the pace. 100%. And a lot of the structure, I thought, wasn't working well at the point that I joined to kind of work to try to iterate and improve little pieces of it, because we were growing pretty quickly. And so really working these middle management jobs, I think.

1:27:16did educate me on how to be a good bureaucrat, which is part of being an effective executive. You can just allocate processes that work and avoid processes that don't work. Think about incentives that work and don't work, structure that does work and doesn't work. You know, the Gephard Reed scene, like a state, like you're not allowed to be in Silicon Valley if you haven't read seeing as like a state, but it's basically a book about how states see citizens and accomplishments and how that shapes how policy works.

1:27:43And it's the same thing, like if you've never been a bureaucrat, you don't know how to see things as a bureaucrat. But also, like if you can only be a bureaucrat, you don't know how anything actually works. You don't know how software actually gets made. And so it's like very damaging to you. Am I getting this right that you're saying to be a good engineering executive, so VP engineering or CTO, you want to be excellent at technology knowing how it works being hands-on if you need to or just be hands-on and also be a good bureaucrat where you can manage it and you need one both and you're saying that if you go the middle man of his route oftentimes it might happen that you either never were a good technologist or you stopped becoming that by the time you get up there so you're a great bureaucrat but not technology but if you just go from like an engineer great technologist straight up here let's say like you're a startup tomorrow congrats you're the CTO you will not be a good bureaucrat

1:28:33I think that's exactly right. And it's interesting. Oftentimes, I think line managers are better instinctual executives than middle managers because they're used to working the detail. So they can make better calls for the team or the company. Their judgment's just better on all these non bureaucratic dimensions of the job, but then their judgment's terrible on the bureaucratic dimensions of the job. And so this is why I think being an executive is hard and why it's a hard career path.

1:28:59is that it was, you know, in the 2010s in particular, you had to climb these like layers of middle management to learn this kind of bureaucratic component of it. And that was the only way to get scale to actually understand that. Now those layers are kind of gone. But the interesting thing is like the other half of the job is now really emphasized in terms of better decision making, understanding the actual product, understanding the actual business, understanding how software is shipped in a way where we kind of de-emphasize that. So I think, you know, people are like, is it easier? Is it harder? I don't think it's like.

1:29:27any easier or any harder. It was it's all harder to become like a bureaucrat now, which again, like negative connotations, right? But this is like learning how to actually operate a function is really difficult work. And as like a C level, like you'll often end up running three or four functions, often one you don't know much about yourself. So for example, at imprint, I was running the customer operations team for, you know, much of the last year, which is not something I am.

1:29:53incredibly detailed on. I have like some exposure to and had like an amazing leader in place. But I've had to learn how to do that. And I've had to do that, you know, a number of times at Stripe, I was managing support engineering, which is not something I've done personally myself, I was running data engineering, it's not something I've personally done myself. And so, you know, you learn how to run that way when you have to. It's really hard to get the jobs to learn how to like operate a function that way where you don't actually know the details of the work.

1:30:20but you get to be a much better, more detail-oriented leader for longer. And that's really where I think the best future executives are, are line managers, because middle management has historically selected for a totally different set of skills. How do you get both? It's incredibly hard now, and it was always hard in different ways. And what's your take on middle management solely dying? You agree?

1:30:43It's definitely a hard time to be a middle manager right now, especially if you came up in the 2010s, you were kind of selected and trained in this more of this empowerment model, more of this like functional like bureaucracy model. And now people are like, we don't want it and we don't need it. And so you've kind of risen to this pinnacle, but you can't get to the next step because of these other skills that are more kind of in the details execution.

1:31:04really de-emphasized and kind of people have changed the rubric on you, which is like super, super frustrating for folks to kind of get trapped by that. That's definitely the challenge that folks are in now. And I don't know how this wave of execs are going to happen, but it's always been a hard roll to get. Well, and I do want to ask you, two people asked me for advice and I'll share both of their stories and you can decide if they're similar or different. One is the head of engineering who has about seven people reporting to them.

1:31:34at a company and was thinking, I wonder about my future because I'm seeing about this middle management. The other one was a story from another head of engineering who has three EMs reporting to them and three ICs reporting to the VP of engineering. They've been shifting to AI transformation in the end department, also doing some other things. The VP of engineering is satisfied with their work, but they're under the VP of engineering. And this person also wondering like, hmm.

1:32:01Both people are wondering, am I in a bit of a career trap? And they asked me to ask you, well, you have a lot of experience. What tactics would you be able to suggest to them to figure out what career path could be for them to figure out what they might want, what is possible? And again, I think the tricky thing in both cases, both people have spent a bunch of time in middle management. There's not that they're not technical, but you know, they They had this path and it was pretty clear where they would go next will be VP of engineering for both of them. But in the current company clearly will not happen or unlikely. So it's a hard time in middle management, right? There's a lot more competition for these roles. And so I think what I found personally very rewarding is kind of getting back into the details of writing software. And so when I left CARTA, my team was 250, maybe something like that. When I joined Imparant, the team I was leading was I think 25.

1:32:57And so for me, this is kind of like a unique moment to actually reskill it. Well, if you're in management, I think right now either you have to like get back into the details or the world is changing so radically that like you, the profession you know will not be valued in three years. And I think you sort of have to decide like, am I retiring now? Or am I reskilling? And I thought about that too. Like, I, you know, a card is like, I could just, I could just be done, right? Is this, is this is what I want?

1:33:25But it's not what I want, right? I really want to still be participating. And I really genuinely believe the way that we work has radically changed in the last year. It hasn't changed everywhere. There's like a long tail that's going to take a long time to catch up. But in the places I work, it's changed a tremendous amount. And for me personally, it's a lot more fun. So first, I think there has to be some like openness to like taking a backward step or a lateral step. Just what people want.

1:33:54is very different and you have to be open to getting a different look at it. And so I think going back into a line management position, for example, is actually much more educational than a middle management. The tools for line management and writing software are so good. The tools for headcount planning or doing performance reviews are basically terrible. All LLM applications for these things are not good. So I do think you're missing a lot in middle management right now.

1:34:23try to find my way out of it, but thinking a little bit about some folks that I hired at Imprint. One of them that comes to mind is Jasmine, who I worked with at CARTA, came over and she was hired as a VP, but she was a VP that was hiring or managing a team directly. She was a line manager. She was a line manager, a really experienced line manager. I was running engineering at Unlux some time ago and she came in to line manage and she's doing just a tremendous amount of software.

1:34:51which she would have never done at Carta because she could have never gotten time to do it. And at MUX, she was also like way too busy like running the function to actually be in the details of writing. Those people that are willing to actually go back and get their hands onto it are so valuable. And if that is who you are, you have to let people know because other guys people think you would never take that opportunity, but I would hire more people like this all day long. You know what we're talking about in the 2010s on the reserve?

1:35:19how engineers got a got a little bit too used to like oh yeah my my company and manager is here to do what i would like to do i would like to do platform nope no products are even if the business needs it just not for me you know i'd rather quit and sometimes they quit i wonder if there's a little bit of this with management we're like look again i don't mean to imply too many things for these folks but generally i have been i have this path.

1:35:44I thought I would be VP of engineering soon and I want to get there, but is that what the industry wants? Is that what the other companies want? No, right now they want really good, let's say, line managers. And either similar to those engineers, the best engineers I know, they kind of put their ego on the back and when the business said, look, we need product to build, they're like, look, I'm great at platform. You know what? Let me be the best product engineer I can be. I felt with you as well that you had 250 people, I assume, you know, compensation, equity, status.

1:36:13And you went down to lesser known startup with not as a well-known brand yet, or at the time, taking a lot smaller teams, smaller responsibility. You let the ego at the door if you know what I mean. And then you learned so much more. I think in a lot of ways it was...

1:36:30just like a much better situation for me. And so like, there are a lot of pieces that weren't like kind of like, this is a hit. That's not really how I thought about it. It was the perfect situation for me because what I knew what I wanted was getting back into the details, relearning how to do software in the current age. That's what I believe is going to be the unlock to kind of the longevity of my career. Also, though, it's just like much more fun. And so like to me, it's just like much more energizing. And I've always been someone who kind of got.

1:36:58tricked into management going back to the story where they just needed a manager and so I I said yes You've been tricked ever since and then they made a director so it looked like they had a director and the acquisition conversations So they that was more palatable, but I didn't know how to line manage letter on direct I just they kind of needed one on paper. Um, so, you know Very kind of them though. So for for me, this has been kind of what I wanted and this has been like a unique opportunity But I think for a lot of folks there is this since the industry has betrayed them and that they're owed something that they've worked for. And the thing is, they're right. They have worked incredibly hard, but the rules have changed. And so I think that at certain moments, the world looks very stable and our industry looks very stable. And I think in the 2010s, we forgot that our industry is actually very volatile. Our industry has changed just a staggering amount.

1:37:54in the last every decade, things are just radically different than they were in the decade before. And we've sort of like lost sight of that. And I think that people that kind of came up in the era of a lot of stability don't remember that sometimes. And so I do think we have to be willing to kind of take lateral moves. We have to be willing to be a little bit humble. But if doing the actual work, that's like the thing that matters to the company is humility, then we've sort of like lost track of what we're doing here because we really do just get paid to do things that are valuable to the companies, right? Like they don't, there's no like entertainment orientation to why these companies employ us. Yeah. What about the TLM role, tech lead manager? This was a role that we declared dead. You and me both declared dead as a dead end. It is there, but this was back in, you know, like the tech leads who were given a very small team to manage as well.

1:38:45And we were clear, like in Zerp, that it's just a career rut. And if your experience is great, I think you also made it clear that it's a trap. I think you have an article. What do you think about this role now?

1:38:56It's funny, it's still a trap, but it's a highly demanded trap. And so, and I think in many cases, there's no way to actually, there's no alternative. So kind of it's less a trap than simply what's there. And so I think in a lot of companies, management is getting flat ends. So we're starting to see like a director, let's say have a bunch of like tech tech leads and like a org of like 30 people and a couple of tech leads here and there. Yep.

1:39:19I think you're either seeing kind of two models, you're seeing that there are engine managers, but they're managing much larger scopes. And so they're actually like less kind of hands on the individuals than they were before, because they're managing say like 12, 13, 14 people before instead of like, you know, like four to four to eight. And then we're also seeing kind of directors are then managing tech lead managers instead of managing kind of these line managers. And different companies are trying different things. But I think this is where I see the industry kind of asking for folks right now.

1:39:48And I do say like some of the best folks we've hired at Imprint have been folks that were in like more pure management roles that came in but really wanted to be writing software. And I've just been doing an amazing job of kind of like doing a blend of both. It is hard to find those folks where it's almost like interview them to be a great EM and then like do you just get frustrated you're not writing more software. It's really that person is kind of what you want.

1:40:14But it's hard, not how we've been interviewing them so far. I think we've just done a few great folks. But that is the role that we really want. And again, it kind of goes back to this thing where you want people who have the capability to do the bureaucratic parts, but don't want to. Like the capability but not the desire. Because those are really the folks that I see super effective these days. They can use that when they need to. But they default to actually writing software, which is really where most of the value is. As a closing topic, I wanted to ask you about how you write. You've been such a perfect writer. Still, I really enjoy your blog whenever there's a new article. I check it out. There's also, you can subscribe. There's an email that I subscribe to and I actually get it in my inbox. How you approach writing and what you think about AI. And also, what is your take on, there's a lot of AI writing going on, not just for social media on LinkedIn, we know that, but also for some authors who, before AI, they didn't write with AI, but now they're starting to a little bit.

1:41:10So I've been writing for about 20 years online in my blog. And I founded Irrational Zuberance in 2007. And then, you know, in next year, I actually might have been like May or June or something when I started writing it. So I'm getting close to this 20 year anniversary. And when I first started writing, I was simply trying to figure out how to network my way into a job, basically. But I did a ton of tutorials just like, here's how I did this. And this was a different era.

1:41:39Now the sort of thing that you just ask, you know, in AI, like how do I do X and it would write a great tutorial just for you or maybe just do it for you directly, right? Then as I started working at Uber, I started writing a little more of like the things I've been learning in hyperscale. And then it really took off when I was writing at Stripe because I think Stripe was a place that both had a lot to learn but a real like love of writing and that to me like really energized my work.

1:42:04and then wrote my first book, kind of the culmination of the things I had written at Stripe and Elegant Puzzle and then got a lot of momentum. I think a total of four books. Probably not writing another book for at least a decade, maybe not ever. But I think it's just been, it's been so transformational for me. I think like so much of like when people know me, which is not that very often really, but like when they people know me, it's exclusively from the books that I've written or the blog.

1:42:33And I really do believe writing is like a unique way that we as individuals can actually change the shape of the industry. And I think when you've done that, there's like little things that kind of pop up. So for you, like the tri-modal kind of salary piece, right? And that is first like a memorable name that helps. But also like, I think it was like a really important observation that a lot of people didn't understand. I think you've changed a lot of people in how they approach compensation.

1:43:01And then Patrick McKenzie has his work on negotiations. So impactful. Probably created so much wealth for people in the world. I think he might try to track how much he's created on it, but I'm not sure if that's still true. But for my books, I really think I've changed the industry with I think staff engineer. I think notably, I think like the staff plus kind of concept that that book created staff plus as like a concept, right? And there's other things that I think are like less like quotable, but have been mattered. And there's just like, there's nothing I could have done in my work in any company that could have impacted the industry in this way. There's many people. And so positively, or I remember the both the elegant puzzle and the SAP engineer I read it, and I took, I took a lot of guidance from it. And that's just so powerful. And then I think about writing with AI. And like, I've spent tens of thousands of hours over 20 years creating this.

1:43:56Writing this stuff. I'm not like super craft-oriented in my writing by which I mean I'm really trying to get ideas out more than I'm trying to write like the best blog post that I've never been Craft-oriented in terms of writing great blog posts somewhere to try to get the ideas out risen somewhere I think I like what I like about your writing is there are very punchy ideas It's it's not about the writing per se like you're you're I would say you're a decent writer or you get enjoy But it's not it's not like I don't like it because it's enjoyable to read the idea comes and it's there, and it makes me thinking, and I'm not thinking because of how you presented it. And again, the presentation is fine, but the idea is what brings me home. Yeah, it's pretty minimal writing. Some of your articles are short. It's not even about the length. I'm way more worried about writing than you are, which you will know, but it's just my natural side. But in yours, it doesn't have to be. What I like about yours, you don't waste a breath in your writing when there's not much, and that's complete.

1:44:56And then I think about that, all the stuff I put together, all of the things I've tried to change people's minds on. And to me, writing with AI would just be like throwing that away. And so I think I've never done a newsletter trying to collect a huge number of folks. It's more if you want to read what I'm writing. This is what it is. It's not like my business, like it is for you.

1:45:18But still, I've gathered some number of folks, and I think they read what I write. And that's really powerful. And I know if I write something, often there'll be hundreds of companies talking about the idea there in the next week. And that's just such a privileged thought to be in. If I just wrote swap, I would just throw it away. And I could never get it back. I'll never spend another 20 years doing this. And so when I think about...

1:45:47the advantages I have that I've kind of carefully built over like two decades, why would I throw that away? And so if I don't have something to say, I just don't say something. I'm not trying to manufacture content or something like that. I think it would be such like a devastating moment to me to throw that all away for nothing. Like if I was throwing it away for something, I could maybe get there, but I think it would just be like an uncompensated loss. If I were to write AI slop articles, like I don't think anyone would read them.

1:46:14Then I would throw away this this thing that I've spent so long putting together and I assume that you feel the same way as that true. Yeah, well, I feel that to me writing is how I think and When I write the drafts I often like a lot of my social media activity actually and I never talked about this before but Sometimes people ask me what is your social media strategy? I have a large number of followers Which is just a byproduct of doing things consistently and in my case honest this researching and thinking about like I almost do full-time or close to full-time thinking about stuff that's happening in industry and that I'm talking with engineers. Usually what happens is I start writing a draft about something and I have this idea. I put it in a tweet just like in another window and I keep writing it and then later look back it's now got it's gotten traction because I guess it was an interesting idea. Sometimes it's controversial. Sometimes I actually test them up. I'm not quite sure. I'll just put it out there.

1:47:09I call these a little bit like brain farts, which is not entirely true, because I am thinking about things, but I don't really care about them. And I've actually more interested in the conversation. So sometimes it then distracts me when I go back. But it then makes my ideas form. And a lot of my ideas are about observations. Is this happening? Are you seeing this, which just generates conversation? So and to me, that is that is the writing, like, and what I found with AI.

1:47:35there was a time where it was popular to like feed all your writing and have a bot that you can talk to and some people wrote a pragmatic engine and bot which I didn't like the idea to use but anyway I still tried it out and it was almost hilarious because for example it would my opinions change all the time my views change and it was kind of spit back something that I said you know like years back and I I know that we talked about TLM if you had a Will Larson bot it would say TLM is a trap and now we're talking about like well Actually, there's way more to it. I tell people like don't put your thinking whenever I see someone write on LinkedIn especially a fellow professional or they message me I'm They often comment with their real voice and I'm like why don't you just write that Imperfect that's you I like the you and I don't like the sterile thing and I also don't like how with AI

1:48:24It's got the same voice for millions of people using it, whereas millions of people talking have millions of different voices. So this connects to something I think is really related to this, which I think is a lot of people believe to be successful. They need to be writing content, but they don't really want to be writing content. And so they're like, I really hate writing content, but to get promoted, to get my next job, I need to be writing content. Like, how do I do that? And it's like.

1:48:49Obviously AI right and I think something I've been trying to push back on folks on for a while I wrote a piece of give the exact name but how to be like a tech influencer or something like that that we're gonna link that that post it's such a like not catchy but almost a click baiting name it is the single best post about how to be influential in tech and I will link it is one of my favorite articles I forward so many people So by the way, thank you for writing that. Of course. And the reason I read it was like these people were like, oh, I need to write 200 things, 300 things. I need to write every week. I need to do this. And it's like, well, if your goal is to be visible, what you need to do is write one thing that gets traction, spend a lot of time on it, test it, like figure that out. You don't actually need to write a ton of stuff. There's almost no value in writing a ton of stuff unless you are, you know, running a business that is based on a subscription.

1:49:40If you're just trying to get your ideas out, if you're just trying to be a little more visible, if you're trying to show proof of your ability to write co-gently, you can write like two things. You can write three things. You can write one thing every two years. And you don't have to write a lot. I think about Tanya O'Reilly, who has not written a lot on her blog, but when she writes something, it says something really interesting, right?

1:50:02And so she's not like a volume writer, but she's been able to have really impactful pieces that I think no glue is like the most obvious or one that has really been transformative. And so I think even for people that do write a lot, people don't remember the vast majority of the right. There's like a few pieces that stick out. So I really think that if people reoriented around the real goal, which is maybe to have some visibility, one or two good things matters so much more than volume. And so I wish people would Stop creating volume if they don't actually I think it doesn't serve their goals and in fact like I I've seen some candidates that have interviewed you know over the last year Where they have just like AI slop content and like a huge volume of it And I I don't know I'm pretty conflicted on those candidates because it's like hey people aren't reading it you keep doing it and it's sort of like Why are you continuing to do something that doesn't serve any purpose? Because it no one's responding to it

1:50:59So it just feels like people who are like running like a recipe but aren't tasting the product and aren't, it's cargo quilting, right? They don't actually know why they're doing it. And so to me it actually implies like poor judgment rather than showing like a sign of like, oh, this is an ambitious person trying hard. Yeah. This clothing, what's a book that you would recommend or books that you enjoyed reading? Certainly I think I would recommend kind of my books to anyone who enjoys spending money on things. Your books are...

1:51:29All excellence. Really. Thank you. And certainly I think crafting engineering strategy came out last year. And I think it's, you know, the newest one, but I think there's like a lot of interesting ideas in there for sure. I think, you know, thinking in systems of primer by Don Alamedos is like one that I think about a lot. I read it based on your recommendation. I think it's, it's honestly the book kind of formed my view about management and kind of operating and companies. I think that is not really about operating companies, but it's like a mental model you can use. That book I think is incredibly, incredibly helpful. But really like any book that forces you to have like a different perspective on something. And so I spent, you know, a decent enough time thinking about typing a couple years ago, like not typing like on a keyboard, but how to have like better type systems, which is not that relevant to my work on a day-to-day basis.

1:52:19And then there's another great book whose name I'm losing on TLA Plus and using that. Is that Hillel Wayne? Yeah, exactly. He was on the podcast. He has the famous TLA Plus. Fantastic book. And look, I'm not using a lot of TLA Plus on a day-to-day basis, but I think just the ideas there are incredibly powerful in terms of using languages to increase the verification or verifiability of your software, which is one of the biggest challenges of our time, right? If all of our software is getting written by someone else, which is an agent.

1:52:47Making verification cheap is really critical, and even FTLA Plus is not the tool for that in many cases. Thinking about that problem, and this is the same reason why typing is really interesting, really, really valuable. And so I think right now those are some useful ones. Thank you. Will, it was awesome to have you and finally have this super nice conversation. Likewise. Thank you for having me. I've known Will for so many years, and it was great to sit down in person.

1:53:12And we did it at a time when there's a lot of change happening with traditional best practices when it comes both to engineering management as well as engineering career progression. One really interesting topic was how farm managers used to bend backwards to find interesting projects for their engineers. We'll recall how at Stripe some of his best engineers asked him for more interesting problems.

1:53:31Back then, he already pushed back, saying that the only thing he has is suffering to offer, meaning not particularly glamorous problems. But that suffering is what's going to make the business succeed. But back in the 2010s and the early 2020s, lots of engineers saw this approach as not particularly great management behavior. And yet today, it's kind of a default. For career stability and promotions, as an engineer, especially the senior plus levels, you will want to help the business solve their most pressing problems.

1:54:00and this includes having empathy for those problems. I also found that Eyeopening how Will thinks about what it takes to be a great CTO. He thinks of it as unique to be two things. One, a great standout technologist who knows what to build and how to build, as well as a barocrat who can run a whole function, including a function you might not be an expert on like product or design. In the 2010s, lots of managers learned mostly about the bureaucracy part, and by the time they became CTOs, they lost the technology side.

1:54:28Today with smaller teams and less mental management, many CTOs will be technologists first, which Will thinks it might be better overall, and I have to agree with it. Finally, I appreciated Will's advice to middle managers, middle managers being injury managers who have teams that under managers report to them. Will did not beat around the bush. Yes, today it's a hard time to be in middle management.

1:54:47The two paths to seize looking forward are either you go back to being closer to where software is being built, work on a smaller team, or as a line manager role, or just accept that your expertise of mostly being a barracad but not a technologist could not be valued that much in a few years' time. Will himself took it backwards when he left the 250-person engineering team at CARTA to have a 25-person team at imprint. But he did it consciously to learn how to build with AI changing the engineering profession.

1:55:14I do find it inspiring that Will not only talks about the importance of learning the new rules of software ensuring, but also walks the walk. Do check out the show notes on related to pragmatic in your deep dives on zero interest rates and ensuring and EM careers. If you enjoyed the podcast, do subscribe in your favorite podcast player and a special thank you if you also leave a rating on the show. Thanks and I'll see you in the next one.