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

• 0:00
  SPEAKER_01: How has engineering management changed in the last few years?
• 0:02
  SPEAKER_01: Will Larson is one of the best people to talk about this.
• 0:05
  SPEAKER_01: He's been an engineering executive for the last 10 years
• 0:07
  SPEAKER_01: at four different companies,
• 0:09
  SPEAKER_01: wrote some of the most widely read books on engineering leadership
• 0:11
  SPEAKER_01: and SAP plus levels,
• 0:12
  SPEAKER_01: and I really appreciate how deep and thoughtful of a thinker he is.
• 0:16
  SPEAKER_01: Today we cover how zero interest rates heavily influenced a decade
• 0:19
  SPEAKER_01: of management habits in the 2010s, many of these habits no longer helpful.
• 0:23
  SPEAKER_01: How the role of engineers is changing and why solving problems that
• 0:26
  SPEAKER_01: the business cares about is becoming much more important to thrive inside
• 0:29
  SPEAKER_01: of companies.
• 0:30
  SPEAKER_01: The path to becoming a CTO today
• 0:32
  SPEAKER_01: and why line managers often make better engineering executives
• 0:35
  SPEAKER_01: than middle managers do.
• 0:37
  SPEAKER_01: And many more.
• 0:38
  SPEAKER_01: If you're an engineer or engineering manager
• 0:39
  SPEAKER_01: and are wondering what your career path could look like with AI changing
• 0:43
  SPEAKER_01: the industry and how the path to CTO looks like today, this episode is for you.
• 0:48
  SPEAKER_01: This episode is presented by TurboPuffer,
• 0:50
  SPEAKER_01: a ridiculously scalable fast and cheap hybrid search engine built on top
• 0:53
  SPEAKER_01: of object storage by an engineering team that I've really grown to like
• 0:56
  SPEAKER_01: after spending time with them.
• 0:57
  SPEAKER_01: The TurboPuffer engineering team is doing something really cool.
• 1:00
  SPEAKER_01: They are completely redesigning their storage architecture from first principles
• 1:04
  SPEAKER_01: to make sure it's faster, cheaper, and more reliable at scale.
• 1:07
  SPEAKER_01: The new system called TurboPuffer v3 is not yet in prod but it already passes CI.
• 1:13
  SPEAKER_01: Still, it's not nearly as performant as the current production version v2 and so
• 1:17
  SPEAKER_01: the tpuff team is now perf maxing query plans until they are as fast or faster
• 1:22
  SPEAKER_01: than v2.
• 1:23
  SPEAKER_01: They're doing all of this in public documenting how they increased performance all
• 1:27
  SPEAKER_01: the way up to the V3 production launch.
• 1:29
  SPEAKER_01: And it's so cool to follow along and see the different performance wins and how they did it.
• 1:33
  SPEAKER_01: For example, we see how full text search, the red line, started out as 129 times slow
• 1:40
  SPEAKER_01: But now, it's only four times slower.
• 1:42
  SPEAKER_01: And in the development log,
• 1:44
  SPEAKER_01: we can also see that the team used things like batch scoring or batch reads
• 1:47
  SPEAKER_01: to increase performance.
• 1:49
  SPEAKER_01: A lot of these wins are basic foundational work right now,
• 1:51
  SPEAKER_01: but the team will be sharing some very cool systems work over the next few weeks.
• 1:55
  SPEAKER_01: But hang on, why is the team doing a floor rewrite?
• 1:58
  SPEAKER_01: It's because search is changing and so is TurboPuffer.
• 2:00
  SPEAKER_01: TPuff started as a vector database, but it's no longer VectorDB.
• 2:04
  SPEAKER_01: It has evolved into a high performance database for search.
• 2:07
  SPEAKER_01: The V3 discards the vector primary index and all indexes will share the same column
• 2:12
  SPEAKER_01: or storage system.
• 2:13
  SPEAKER_01: Every query will run on vectorized query engines
• 2:16
  SPEAKER_01: which is something you don't usually see in search databases but which will result
• 2:20
  SPEAKER_01: in both very fast search and just generally a very fast database.
• 2:24
  SPEAKER_01: The TurboPuffer team is keeping a work log of their journey and you can follow along
• 2:27
  SPEAKER_01: at turbopuffer.com slash v3.
• 2:29
  SPEAKER_01: It's a blast to see how it's being built.
• 2:32
  SPEAKER_00: Will, welcome to the podcast.
• 2:34
  SPEAKER_00: Thank you for having me.
• 2:34
  SPEAKER_00: Excited to be here.
• 2:36
  SPEAKER_00: Finally chat in person.
• 2:37
  SPEAKER_02: Finally in person because we know each other for so long.
• 2:40
  SPEAKER_02: Both started writing.
• 2:41
  SPEAKER_02: We will talk about that writing as well and also just hung out before.
• 2:45
  SPEAKER_02: But this is nice.
• 2:46
  SPEAKER_02: I want to jump into the beginning.
• 2:49
  SPEAKER_02: How did you get interested in computers?
• 2:50
  SPEAKER_02: Were you interested in computers to start with?
• 2:53
  SPEAKER_00: From the time I was five, we had like a Mac 2C or something like that.
• 2:57
  SPEAKER_00: This was like a, not black and white, not the very earliest one, but it was pretty basic.
• 3:01
  SPEAKER_00: And I think it had like one thing that I understood how to use as a four and a half
• 3:05
  SPEAKER_00: or five year old,
• 3:05
  SPEAKER_00: which was like KidPix, which you've maybe, I don't, did you ever use to see KidPix?
• 3:09
  SPEAKER_00: I didn't, I know of it, but I never used it.
• 3:11
  SPEAKER_00: It wasn't like a super sophisticated thing.
• 3:13
  SPEAKER_00: I don't even know if you could save files,
• 3:14
  SPEAKER_00: but it was basically like a graphical program for children.
• 3:17
  SPEAKER_00: And you could make squares and circles and little like graphics.
• 3:21
  SPEAKER_00: But that was kind of the introduction to me.
• 3:23
  SPEAKER_00: And I remember using that computer a lot.
• 3:25
  SPEAKER_00: And this is an era when there was really no internet to speak of,
• 3:29
  SPEAKER_00: really no way to figure out how to do anything other than just banging on it,
• 3:33
  SPEAKER_00: which is sort of the fundamental of writing software in some ways.
• 3:36
  SPEAKER_00: It's just banging until you figure out how to make it work.
• 3:38
  SPEAKER_00: I think that was a great introduction.
• 3:40
  SPEAKER_00: But to be honest, I wasn't doing a whole lot in software.
• 3:44
  SPEAKER_00: And
• 3:49
  SPEAKER_00: so basically the idea is that World of Warcraft is actually a graphical text-based game.
• 3:59
  SPEAKER_00: We basically derive from these ideas of MUDs or multi-user dungeons.
• 4:03
  SPEAKER_00: But when I was a kid in high school, that's when I started doing more software.
• 4:07
  SPEAKER_00: So a little bit,
• 4:08
  SPEAKER_00: you start with IRC,
• 4:09
  SPEAKER_00: Internet Relay Chat,
• 4:11
  SPEAKER_00: and Merck, which I don't even know what the M stood for, to be totally honest.
• 4:14
  SPEAKER_00: So as a client,
• 4:15
  SPEAKER_00: you could do a little bit of scripting with regexes,
• 4:17
  SPEAKER_00: but then a lot of the Mudd clients as a kid could do a ton of triggers,
• 4:22
  SPEAKER_00: regexes, and that's where I got a little bit further into it.
• 4:25
  SPEAKER_00: Learned my regexes there,
• 4:26
  SPEAKER_00: but really I didn't start writing software at all until I got to college.
• 4:30
  SPEAKER_02: And then at college, what did you start writing?
• 4:32
  SPEAKER_02: How did you...
• 4:36
  SPEAKER_00: So I came into college not really knowing what I wanted to study,
• 4:39
  SPEAKER_00: and I thought I might do physics or English or, you know, economics.
• 4:44
  SPEAKER_00: My father was a professor of economics,
• 4:46
  SPEAKER_00: so there was some family, you know, lineage to try to live up to.
• 4:50
  SPEAKER_00: But ultimately,
• 4:50
  SPEAKER_00: I kind of fell into computer science at my school,
• 4:53
  SPEAKER_00: which was a small kind of private school in Kentucky.
• 4:55
  SPEAKER_00: There were, I think, 13 people in the computer science programs.
• 4:58
  SPEAKER_00: The year that I graduated.
• 5:00
  SPEAKER_00: So and that was like the entire program.
• 5:02
  SPEAKER_00: So I think there were four graduates my year and then like the juniors
• 5:07
  SPEAKER_00: and sophomores in total were like 13.
• 5:10
  SPEAKER_00: And so it's quite small.
• 5:11
  SPEAKER_00: So I think there were four that graduated my year.
• 5:13
  SPEAKER_00: But really, that was when I got into it.
• 5:16
  SPEAKER_00: And why?
• 5:17
  SPEAKER_00: I just enjoyed it.
• 5:18
  SPEAKER_00: We had an intro course that we're required to take.
• 5:20
  SPEAKER_00: And it's kind of funny with a lot of American colleges,
• 5:23
  SPEAKER_00: especially smaller private ones, they have random kind of requirements.
• 5:27
  SPEAKER_00: So I was required to take a introduction to Christianity course,
• 5:30
  SPEAKER_00: like at the History of Christianity,
• 5:32
  SPEAKER_00: but also required to take like an introduction to computer science
• 5:35
  SPEAKER_00: or some other course.
• 5:36
  SPEAKER_00: I forget what the other alternative was.
• 5:38
  SPEAKER_00: So I really enjoyed the computer science one.
• 5:40
  SPEAKER_02: Did you decide that you were probably going to be a professional software developer,
• 5:43
  SPEAKER_02: engineer, programmer, whatever we call it back then?
• 5:45
  SPEAKER_00: So I think one of the interesting things when you talk a lot about careers is like
• 5:49
  SPEAKER_00: a lot of folks go to like elite schools.
• 5:52
  SPEAKER_00: So you talk to someone from Waterloo and they go, how did you get your job?
• 5:55
  SPEAKER_00: They're like, well, Literally everyone at Waterloo is coached on how to go do software.
• 6:00
  SPEAKER_00: They're literally trading the answers to interviews with each other.
• 6:03
  SPEAKER_00: So they know the interviews and drill on the interviews before they go in.
• 6:07
  SPEAKER_00: They also like amazing program.
• 6:09
  SPEAKER_00: They've been doing co-ops for years.
• 6:10
  SPEAKER_00: Like they're great.
• 6:11
  SPEAKER_00: They're great candidates.
• 6:12
  SPEAKER_00: They tend to do really well.
• 6:13
  SPEAKER_00: But go to Waterloo,
• 6:14
  SPEAKER_00: you go to MIT,
• 6:16
  SPEAKER_00: you go to Stanford,
• 6:17
  SPEAKER_00: you really there's like this path and you just kind of Put your foot on it
• 6:21
  SPEAKER_00: and you do well and it carries you there.
• 6:23
  SPEAKER_00: And these are amazing students.
• 6:24
  SPEAKER_00: Like an escalator almost.
• 6:25
  SPEAKER_00: But it is an escalator.
• 6:26
  SPEAKER_00: If they're good enough to stay in the program, they tend to kind of get there.
• 6:29
  SPEAKER_00: Going to a small school with, again,
• 6:31
  SPEAKER_00: like four-ish folks that graduated my year in computer science,
• 6:34
  SPEAKER_00: there really was no path.
• 6:36
  SPEAKER_00: I remember one of the folks that graduated the year before that was working
• 6:41
  SPEAKER_00: in software,
• 6:41
  SPEAKER_00: he went to go work on a horse racing betting software company in Lexington,
• 6:46
  SPEAKER_00: Kentucky, which I don't think there were more than like five engineers there.
• 6:51
  SPEAKER_00: And this was like a really talented, really capable person.
• 6:53
  SPEAKER_00: And this is kind of what they knew how to find.
• 6:56
  SPEAKER_00: And so for me, it actually was interesting.
• 6:58
  SPEAKER_00: I wasn't quite sure what I was going to do.
• 7:00
  SPEAKER_00: I actually ended up teaching English in Japan on the JET program,
• 7:03
  SPEAKER_00: the Japanese exchange teaching program.
• 7:06
  SPEAKER_00: So I was in the middle of nowhere in Japan in the Gifu Prefecture for a year.
• 7:10
  SPEAKER_00: But that's when I really started writing a lot because I was like,
• 7:13
  SPEAKER_00: hey, I'm definitely not going to be an English teacher for more than one year.
• 7:16
  SPEAKER_00: It's a one-year contract.
• 7:17
  SPEAKER_00: I did that one year.
• 7:18
  SPEAKER_00: I had no thoughts about doing a second year.
• 7:20
  SPEAKER_00: And I came back and started trying to figure out how to actually break
• 7:23
  SPEAKER_00: into Silicon Valley from there.
• 7:25
  SPEAKER_02: And you had the goal, breaking Silicon Valley already.
• 7:29
  SPEAKER_02: Why Silicon Valley?
• 7:29
  SPEAKER_02: Can you take us back to what Silicon Valley was like back then?
• 7:33
  SPEAKER_00: First of the time, I didn't know what Silicon Valley was, right?
• 7:35
  SPEAKER_00: I just wanted a job that paid well.
• 7:40
  SPEAKER_00: And I think,
• 7:40
  SPEAKER_00: you know,
• 7:41
  SPEAKER_00: this was, so I graduated in 07, and then the next year I was teaching English.
• 7:46
  SPEAKER_00: And then I actually started working for Yahoo in, I guess, maybe early 09, something like that.
• 7:52
  SPEAKER_00: Really interesting time, though.
• 7:53
  SPEAKER_00: So initially, I was working for Yahoo from the East Coast as a remote contractor.
• 7:58
  SPEAKER_00: It was an interesting moment.
• 7:59
  SPEAKER_00: So I started working with Yahoo because I wrote a series of blog posts
• 8:03
  SPEAKER_00: on something called Yahoo Boss, which is build your own search service.
• 8:07
  SPEAKER_00: And this was a product that they had launched on this one team.
• 8:10
  SPEAKER_00: I think it wasn't getting a lot of kind of traction in the industry.
• 8:13
  SPEAKER_00: But when it launched, I was writing a lot.
• 8:14
  SPEAKER_00: So I did three or four tutorials on building boss things in Python,
• 8:19
  SPEAKER_00: boss things with Django, kind of made a Django script.
• 8:23
  SPEAKER_00: I forget the name.
• 8:23
  SPEAKER_00: It might have been Django Springsteen.
• 8:25
  SPEAKER_00: It was like the name of the search library to use Yahoo Boss with Django.
• 8:29
  SPEAKER_00: And so I think they got excited because someone was writing about it, which also got me excited.
• 8:33
  SPEAKER_00: And that ended up ultimately in this contract job.
• 8:36
  SPEAKER_00: And then ultimately,
• 8:37
  SPEAKER_00: they had the policy where you had to move after a year as a contractor
• 8:40
  SPEAKER_00: and go full time.
• 8:42
  SPEAKER_00: And the reason I was hired as a contractor,
• 8:43
  SPEAKER_00: though, is they had a hiring freeze for basically that entire year.
• 8:46
  SPEAKER_02: Because this was right after a financial crisis.
• 8:48
  SPEAKER_00: And so they're just going through Layoff after layoff.
• 8:52
  SPEAKER_00: And so they could hire a couple contractors, couldn't hire anyone full time.
• 8:55
  SPEAKER_00: And then at 12 months,
• 8:56
  SPEAKER_00: they are like, hey,
• 8:57
  SPEAKER_00: now you have to go full time or you're not employed because there's kind of
• 9:00
  SPEAKER_00: the compliance obligations to avoid.
• 9:03
  SPEAKER_00: And so they're like, hey, and if you go full time, Yeah.
• 9:05
  SPEAKER_00: And back then, Yahoo, I guess their Star Wars
• 9:20
  SPEAKER_02: It's kind of fading with Google, but they're still a pretty good company, right?
• 9:24
  SPEAKER_02: Good engineering challenge.
• 9:25
  SPEAKER_02: Like WhatsApp founders famously came from Yahoo.
• 9:27
  SPEAKER_00: I think Yahoo, honestly, is a really interesting company, right?
• 9:30
  SPEAKER_00: And so I think one of the challenges for Yahoo is if you came into tech in 2007,
• 9:35
  SPEAKER_00: 2008, a lot of open source sort of made things easy.
• 9:39
  SPEAKER_00: Yahoo, though, is a company that predated all these open source libraries.
• 9:42
  SPEAKER_00: And so how do you run a server at Yahoo in 2007, 2008?
• 9:47
  SPEAKER_00: You run Y Apache.
• 9:50
  SPEAKER_00: So they had their own fork of Apache with a Y in front of it.
• 9:53
  SPEAKER_00: What programming language do you run on Y Apache?
• 9:56
  SPEAKER_00: Well, of course, you'd run YPHP, which was their fork of PHP.
• 10:01
  SPEAKER_00: And what UI library would you use?
• 10:03
  SPEAKER_00: You might know this one, but it's YUI.
• 10:06
  SPEAKER_00: And then how do you install things?
• 10:08
  SPEAKER_00: So if you think about like, you know, Ubuntu, you'd have kind of like APT or whatnot.
• 10:13
  SPEAKER_00: Well, you'd use Yinst,
• 10:15
  SPEAKER_00: which was this Perl script that would navigate kind of the dependencies
• 10:18
  SPEAKER_00: for installation.
• 10:19
  SPEAKER_00: And so just a really, really fascinating place to come up.
• 10:23
  SPEAKER_00: But every single thing there they made from scratch.
• 10:27
  SPEAKER_00: Even they had like a precursor to Kafka,
• 10:29
  SPEAKER_00: which I think was called Y REPL,
• 10:30
  SPEAKER_00: which basically would be like a read log to do replication kind of outside of
• 10:36
  SPEAKER_00: a database.
• 10:36
  SPEAKER_00: And that was like a core tool for managing state.
• 10:40
  SPEAKER_00: Just like a fascinating place.
• 10:41
  SPEAKER_00: And I think if I just had one quick Yahoo story that I loved.
• 10:45
  SPEAKER_00: So David Filo kind of famously approved every server that was allocated in the company.
• 10:50
  SPEAKER_00: And so one of the founders would review.
• 10:52
  SPEAKER_00: And so the theory was this would drive accountability, right?
• 10:55
  SPEAKER_00: You had to prove you needed more servers.
• 10:58
  SPEAKER_00: What it actually did is it created like the black market of servers.
• 11:02
  SPEAKER_00: And so on my team,
• 11:03
  SPEAKER_00: there was like one engineer that had 30 servers from a prior canceled project.
• 11:07
  SPEAKER_00: He never gave back.
• 11:08
  SPEAKER_00: And so he would basically sell them to you effectively, right?
• 11:12
  SPEAKER_00: And so if you couldn't get approval.
• 11:14
  SPEAKER_00: For like favors and IOU and that kind of stuff.
• 11:17
  SPEAKER_00: And so it actually meant they had massive numbers of outdated servers
• 11:20
  SPEAKER_00: that were using inefficient power wattage
• 11:23
  SPEAKER_00: because people would never give servers back.
• 11:26
  SPEAKER_00: And so you had to find someone who liked you with servers to loan for your projects to launch.
• 11:31
  SPEAKER_00: It's fascinating how these incentives drive just wild things.
• 11:35
  SPEAKER_02: I guess that's one thing you remembered for when you later became an engineering leader.
• 11:40
  SPEAKER_00: Yeah, it was very instructive, right?
• 11:43
  SPEAKER_00: And I'm curious, did David Filo know that people literally had a black market of servers?
• 11:48
  SPEAKER_00: I assume he probably did know.
• 11:50
  SPEAKER_00: But it didn't change the top-down mandate.
• 11:54
  SPEAKER_02: After Yahoo, is that when you ended up at Digg?
• 11:57
  SPEAKER_02: Yeah.
• 11:58
  SPEAKER_02: At the time, a very famous company for a very amusing story.
• 12:03
  SPEAKER_02: Can you tell us about how you decided to switch?
• 12:05
  SPEAKER_02: Dig was a startup
• 12:06
  SPEAKER_00: back then.
• 12:28
  SPEAKER_00: Dig was actually centrally curated on what went on to the front page.
• 12:31
  SPEAKER_00: And so I had a very different experience.
• 12:33
  SPEAKER_00: But it also meant that the quality was consistent and you had less of kind of
• 12:37
  SPEAKER_00: the bias and subreddit problem.
• 12:39
  SPEAKER_00: Instead, you had a bias and central moderation problem.
• 12:44
  SPEAKER_00: You know,
• 12:44
  SPEAKER_00: communities,
• 12:45
  SPEAKER_00: there are IRC channels where people would basically trade favors trying
• 12:48
  SPEAKER_00: to get things onto the Dig front page.
• 12:51
  SPEAKER_00: And in fact,
• 12:52
  SPEAKER_00: for DigV4,
• 12:53
  SPEAKER_00: we changed the algorithm and I had people saying they had come murder me
• 12:57
  SPEAKER_00: for stealing their livelihood because their entire...
• 13:01
  SPEAKER_00: Livelihood was selling access to the front page.
• 13:04
  SPEAKER_00: The new algorithm didn't support that.
• 13:06
  SPEAKER_00: And they were literally threatening our lives.
• 13:08
  SPEAKER_00: And so it was a fascinating place.
• 13:09
  SPEAKER_00: But Dig was a really important website.
• 13:13
  SPEAKER_00: And when I joined Yahoo,
• 13:15
  SPEAKER_00: this wasn't true,
• 13:16
  SPEAKER_00: but a little bit before I joined Yahoo,
• 13:18
  SPEAKER_00: literally the front page of Yahoo was a static file.
• 13:23
  SPEAKER_00: And
• 13:26
  SPEAKER_00: Yahoo Sports was just like a static page, right?
• 13:32
  SPEAKER_00: And so Dig in that era,
• 13:34
  SPEAKER_00: like early on,
• 13:34
  SPEAKER_00: was like a very important static page,
• 13:37
  SPEAKER_00: but then it became not a static page,
• 13:38
  SPEAKER_00: like a dynamic of sorts community,
• 13:41
  SPEAKER_00: I think really was extremely important to folks at the time.
• 13:44
  SPEAKER_00: Though it's faded into slightly less relevancy over time.
• 13:47
  SPEAKER_00: And it's been restarted a couple of times since,
• 13:49
  SPEAKER_00: but never really picking up the traction once it did.
• 13:51
  SPEAKER_00: I think it was a top 10 website at one point.
• 13:54
  SPEAKER_02: Yeah, it was top 10.
• 13:55
  SPEAKER_02: And that's why the story that I remember is they did a big rewrite.
• 13:59
  SPEAKER_02: I think it might have been a V4 one, right?
• 14:01
  SPEAKER_02: And from the outside, what I remember is, well, Dig was doing good.
• 14:05
  SPEAKER_02: It was popular.
• 14:06
  SPEAKER_02: There were complaints a bit like with Stack Overflow maybe a few years ago.
• 14:10
  SPEAKER_02: And then Dig did this massive rewrite and disaster followed.
• 14:14
  SPEAKER_02: And it was like a very juicy story.
• 14:17
  SPEAKER_02: Everyone was talking about it.
• 14:18
  SPEAKER_02: Can you tell us like what actually happened and what did it look like from the inside?
• 14:21
  SPEAKER_00: Because you were building this thing.
• 14:23
  SPEAKER_00: Yeah, so I was there.
• 14:23
  SPEAKER_00: I was there for that launch and I was there after that launch.
• 14:26
  SPEAKER_00: And so I joined Dig about three to six months before that launch went out.
• 14:31
  SPEAKER_00: And it was a fascinating time.
• 14:32
  SPEAKER_00: So I joined and then on the Friday before I started, the CEO got removed.
• 14:39
  SPEAKER_00: And then Kevin Rose came back in as CEO.
• 14:42
  SPEAKER_00: Well, he was the founder, right?
• 14:43
  SPEAKER_00: Kevin Rose was the founding CEO.
• 14:45
  SPEAKER_00: He was there for a while, and then he kind of stepped back, and then he came back in.
• 14:49
  SPEAKER_00: But he came back in,
• 14:50
  SPEAKER_00: and we had this very hard deadline to launch Dig before, which was a rewrite.
• 14:56
  SPEAKER_00: And so Dig v3.5 was the prior version before Dig 4,
• 15:00
  SPEAKER_00: basically entirely a PHP software running on distributed MySQL.
• 15:06
  SPEAKER_00: And this was like a different era, right?
• 15:08
  SPEAKER_00: So Dig was running on hardware that we owned in like a colo.
• 15:12
  SPEAKER_00: And so it wasn't like just spin up some capacity or whatnot.
• 15:16
  SPEAKER_00: But Dig before was trying to solve a bunch of problems.
• 15:18
  SPEAKER_00: But first and foremost, the Internet was changing at that time.
• 15:22
  SPEAKER_00: So this Dig, at one point, a top 10 website was starting to lose traction to Facebook.
• 15:28
  SPEAKER_00: And it was starting to lose search traffic as well.
• 15:31
  SPEAKER_00: And so there were a series of large Google changes.
• 15:33
  SPEAKER_00: And I think we don't hear about Google search algorithm changes that much these days.
• 15:37
  SPEAKER_00: But back then there was like the Google Panda algorithm change and there were
• 15:41
  SPEAKER_00: a handful of others.
• 15:42
  SPEAKER_00: And they were starting to really reshape how traffic flowed through.
• 15:45
  SPEAKER_00: So for a company like Dig,
• 15:47
  SPEAKER_00: a substantial amount of the traffic,
• 15:49
  SPEAKER_00: I want to say like 60 to 70 percent, the traffic was actually coming in via search.
• 15:54
  SPEAKER_00: Oh.
• 15:54
  SPEAKER_00: Into something called the permalink.
• 15:56
  SPEAKER_00: And so the permalink pages would be like, say you write a great blog post.
• 15:59
  SPEAKER_00: That would then get posted to Digg.
• 16:01
  SPEAKER_00: And then we'd have the reference to the permalink and also like a small link
• 16:04
  SPEAKER_00: to your site, of course, and comments about it.
• 16:07
  SPEAKER_00: But we would take a ton.
• 16:08
  SPEAKER_00: A ton of traffic through these permanent pages that would be higher page rank than
• 16:12
  SPEAKER_00: the original source themselves.
• 16:14
  SPEAKER_00: And you can argue now, maybe we shouldn't have been.
• 16:17
  SPEAKER_00: Probably not.
• 16:18
  SPEAKER_00: I think that would be kind of the perspective today.
• 16:20
  SPEAKER_00: But from the perspective of that moment,
• 16:22
  SPEAKER_00: we were actually creating the discoverability and the conversation around it.
• 16:25
  SPEAKER_00: This was before Twitter.
• 16:26
  SPEAKER_00: This was before Facebook got substantial distribution.
• 16:30
  SPEAKER_00: This was really early moment.
• 16:32
  SPEAKER_00: And so for us, like that, that was the core of where people came into.
• 16:37
  SPEAKER_00: Also, it was really where we sold the most ads.
• 16:40
  SPEAKER_00: And so losing that traffic was basically tanking the company's like financial kind of prospects.
• 16:46
  SPEAKER_00: And so Dig before, from the outside, it was working pretty well.
• 16:50
  SPEAKER_00: It was, you know, seemed like maybe it was growing.
• 16:53
  SPEAKER_00: But really, like what we knew is like big was shrinking.
• 16:56
  SPEAKER_00: We had one beautiful month of profitability and then an algorithm change hit
• 17:01
  SPEAKER_00: and we started shrinking.
• 17:03
  SPEAKER_00: And we knew that this is existential for us.
• 17:06
  SPEAKER_00: We were going to simply not exist, not that far down the path.
• 17:11
  SPEAKER_00: And we were, when I joined, I want to say like 110, 120 people, something like this.
• 17:16
  SPEAKER_00: But this was in 2010 when funding rounds were $1 million or $3 million or something.
• 17:24
  SPEAKER_00: It's not like today when people are raising $500 million and you can have a team
• 17:29
  SPEAKER_00: of however many.
• 17:30
  SPEAKER_00: It was a very different moment.
• 17:32
  SPEAKER_00: So even with 110 people,
• 17:34
  SPEAKER_00: that was pretty substantial when we were running down
• 17:37
  SPEAKER_00: the remaining coffers pretty fast.
• 17:40
  SPEAKER_02: The launch internally, did it go poorly?
• 17:43
  SPEAKER_02: Did it go well?
• 17:44
  SPEAKER_02: Because from the outside, again, there was a perception that it went terribly.
• 17:47
  SPEAKER_02: And people, there was a bit, I think a lot of it was the community was upset.
• 17:51
  SPEAKER_02: And then there was a bit of celebration as well.
• 17:53
  SPEAKER_02: Like, well, they messed it up.
• 17:55
  SPEAKER_02: Like, they kind of deserved it.
• 17:56
  SPEAKER_02: You know, the mob, the people especially who were
• 18:00
  SPEAKER_00: very involved, they didn't like change.
• 18:01
  SPEAKER_00: First, there's like a really fascinating set of cartoons someone made,
• 18:04
  SPEAKER_00: which is like Dig versus Reddit.
• 18:05
  SPEAKER_00: And like Dig is like blue.
• 18:07
  SPEAKER_00: And then like Reddit's red.
• 18:08
  SPEAKER_00: And there's this like giant war that someone did like a four or five part.
• 18:11
  SPEAKER_00: It's like this very intricate thing.
• 18:13
  SPEAKER_00: Comics someone wrote around around this time.
• 18:16
  SPEAKER_00: And it's kind of interesting to see how much energy people put into it.
• 18:19
  SPEAKER_00: But yeah, there was a lot of passion.
• 18:20
  SPEAKER_00: And I think it's one of the challenges of like a really passionate community is like
• 18:24
  SPEAKER_00: when you foster a passionate community, they change what you are.
• 18:27
  SPEAKER_00: Community doesn't like that because I mean,
• 18:30
  SPEAKER_00: there are literally these folks like Mr.
• 18:32
  SPEAKER_00: Baby Man was like a really big one,
• 18:34
  SPEAKER_00: like one of the top did kind of Unsolicited curators of content getting to
• 18:40
  SPEAKER_00: the front page.
• 18:41
  SPEAKER_00: And he and many others were, they lost kind of their business, right?
• 18:46
  SPEAKER_00: But the launch went pretty poorly.
• 18:48
  SPEAKER_00: And why did it go poorly?
• 18:49
  SPEAKER_00: It went poorly for a lot of reasons.
• 18:50
  SPEAKER_00: So first, The launch technically wasn't really ready.
• 18:53
  SPEAKER_00: And so we made a lot of really aggressive technology decisions.
• 18:56
  SPEAKER_00: And again, I came in about three months before this went live.
• 19:01
  SPEAKER_00: So I don't personally take a ton of responsibility.
• 19:04
  SPEAKER_00: I also, again, think about where I was in my career.
• 19:06
  SPEAKER_00: I was basically, it was my second job.
• 19:08
  SPEAKER_00: I'd been at Yahoo for two years.
• 19:10
  SPEAKER_00: So I won't own this one.
• 19:12
  SPEAKER_00: Later in my career, I'll own anything that happened.
• 19:15
  SPEAKER_00: But this one wasn't really by fault.
• 19:18
  SPEAKER_00: But basically, we made the decision to launch on Cassandra.
• 19:20
  SPEAKER_00: And there's like a joke at the time,
• 19:22
  SPEAKER_00: which is that Cassandra was a Trojan horse Facebook had launched
• 19:25
  SPEAKER_00: to basically ruin competition in the industry.
• 19:28
  SPEAKER_00: Because anyone who launched on Cassandra was basically screwed afterwards,
• 19:32
  SPEAKER_00: which I think certainly was true for Dig.
• 19:35
  SPEAKER_00: And so running Cassandra to replace the sharded MySQL system,
• 19:38
  SPEAKER_00: the sharded MySQL system was pretty complicated, but it definitely worked.
• 19:42
  SPEAKER_00: And Cassandra, I would argue, like basically didn't work.
• 19:45
  SPEAKER_00: But I remember there was a team response for load testing Cassandra before our launch.
• 19:51
  SPEAKER_00: And two days before the launch,
• 19:53
  SPEAKER_00: this other guy, Rich,
• 19:55
  SPEAKER_00: who was fantastic,
• 19:56
  SPEAKER_00: he and I were pulled aside and we're like,
• 19:57
  SPEAKER_00: hey, well, they never did the load testing.
• 19:59
  SPEAKER_00: We need the two of you to do the load testing in the next two days.
• 20:04
  SPEAKER_00: And so Rich was just like a software engineer like me.
• 20:07
  SPEAKER_00: And so we're like, well,
• 20:08
  SPEAKER_00: I guess we'll install JMeter and try to figure out how JMeter works
• 20:11
  SPEAKER_00: to do some load testing.
• 20:12
  SPEAKER_00: And we had this really interesting conversation with Chris,
• 20:15
  SPEAKER_00: who was kind of the head of the Cassandra initiative.
• 20:18
  SPEAKER_00: I was like, hey, like, I can't do the reads on Cassandra.
• 20:21
  SPEAKER_00: He's like, that's not true.
• 20:22
  SPEAKER_00: I was like, well, I can't do the writes.
• 20:23
  SPEAKER_00: He's like, that's also not true.
• 20:24
  SPEAKER_00: I'm like, okay, Chris, if I'm writing to Cassandra, I can't read from Cassandra.
• 20:28
  SPEAKER_00: If I'm reading from Cassandra, I can't write to Cassandra.
• 20:30
  SPEAKER_00: He's like, that is true.
• 20:31
  SPEAKER_00: It's like, well, we're supposed to launch in two days.
• 20:34
  SPEAKER_00: And then we launched and we didn't fix it.
• 20:35
  SPEAKER_00: We just launched.
• 20:36
  SPEAKER_00: And so I think the company thought that we were literally dying.
• 20:40
  SPEAKER_00: And the company was.
• 20:41
  SPEAKER_00: The company literally was dying.
• 20:43
  SPEAKER_00: It was running out of money.
• 20:44
  SPEAKER_00: But it was like the most interesting day I've ever had professionally ever.
• 20:48
  SPEAKER_00: Can't remember when I got to the office, probably around 8 a.m.
• 20:50
  SPEAKER_00: When you say interesting, even stressful.
• 20:52
  SPEAKER_00: You can judge.
• 20:53
  SPEAKER_00: Let me like paint the scene a little bit.
• 20:54
  SPEAKER_00: So it was a launch, but they also decided to have a launch party.
• 20:59
  SPEAKER_00: So the entire day there were caterers kind of in tuxedos with like sushi trays, champagne.
• 21:06
  SPEAKER_00: Oh, wow.
• 21:07
  SPEAKER_00: And so like the entire office is there to have this like kind of like celebration.
• 21:11
  SPEAKER_00: And then in the center of the room,
• 21:12
  SPEAKER_00: there was this table,
• 21:14
  SPEAKER_00: it might have been like a boardroom table or something that had been pulled out,
• 21:16
  SPEAKER_00: this giant table,
• 21:17
  SPEAKER_00: maybe three or four times the size of this, where the engineers were sitting.
• 21:21
  SPEAKER_00: And we didn't have enough hardware to run the new system and the old system concurrently.
• 21:25
  SPEAKER_00: And again, this was hardware we owned.
• 21:28
  SPEAKER_00: So they were literally wiping the old servers and installing the new software.
• 21:32
  SPEAKER_00: So we couldn't roll back.
• 21:33
  SPEAKER_00: We didn't have the money to...
• 21:36
  SPEAKER_00: And again,
• 21:36
  SPEAKER_00: we were running out of money,
• 21:37
  SPEAKER_00: but enough budget for the party, but not enough budget for the servers, right?
• 21:41
  SPEAKER_00: So we were wiping server by server, spinning it up.
• 21:45
  SPEAKER_00: And ultimately, like...
• 21:47
  SPEAKER_00: The damn thing didn't turn on.
• 21:48
  SPEAKER_00: It was functionally what happened, right?
• 21:51
  SPEAKER_00: And so we had this, you know, like down for maintenance page up for, I think, roughly 24 hours.
• 21:57
  SPEAKER_00: And then we were able to scrap it.
• 21:59
  SPEAKER_02: While the champagne and the tuxedos are coming around.
• 22:03
  SPEAKER_00: And there were people upstairs getting massages.
• 22:06
  SPEAKER_00: There were,
• 22:06
  SPEAKER_00: you know,
• 22:06
  SPEAKER_00: I remember certain groups who won't be named playing ping pong while we're trying
• 22:10
  SPEAKER_00: to get this out.
• 22:11
  SPEAKER_00: And it was it was just like it was sort of like a magical realism.
• 22:15
  SPEAKER_02: I see what you mean by interesting.
• 22:17
  SPEAKER_02: This is not how I imagined a launch like this.
• 22:19
  SPEAKER_00: You could never imagine a launch like this.
• 22:21
  SPEAKER_00: It was just it was so it was so surreal.
• 22:24
  SPEAKER_00: True,
• 22:25
  SPEAKER_00: like a magical realism moment where there's kind of all this normalcy happening
• 22:29
  SPEAKER_00: while this like site's literally imploding.
• 22:31
  SPEAKER_00: And it was just.
• 22:32
  SPEAKER_00: It was unlike anything I've seen, but it's also like a moment I take a lot of pride in.
• 22:36
  SPEAKER_00: And so I'd been there three months.
• 22:38
  SPEAKER_00: I think interesting thing is we did get the site kind of working,
• 22:41
  SPEAKER_00: but there were a lot of issues.
• 22:42
  SPEAKER_00: And so people just gave up.
• 22:44
  SPEAKER_00: And like day by day, like people just stopped showing up.
• 22:48
  SPEAKER_00: And like a small group was really the only group left
• 22:51
  SPEAKER_00: of maybe like six people trying to keep it working.
• 22:53
  SPEAKER_00: And we did.
• 22:54
  SPEAKER_00: And so we,
• 22:55
  SPEAKER_00: in the first two days,
• 22:56
  SPEAKER_00: like the same guy,
• 22:57
  SPEAKER_00: Rich and I wrote like a caching system from scratch on top of Redis,
• 23:01
  SPEAKER_00: which helped the site stay on for hours.
• 23:04
  SPEAKER_00: But we still had huge memory leaks.
• 23:06
  SPEAKER_00: And so we're actually like restarting every process every, you know, like hour or two.
• 23:11
  SPEAKER_00: And the only way to keep it up was rolling restarts of every process.
• 23:15
  SPEAKER_00: And so it took us like a full month to debug.
• 23:18
  SPEAKER_00: And I have like a blog post I wrote a long time ago about it.
• 23:21
  SPEAKER_00: But basically the core bug was we created an API service that could be used
• 23:26
  SPEAKER_00: for like third parties.
• 23:28
  SPEAKER_00: And it was in Python.
• 23:29
  SPEAKER_00: The people writing it didn't know Python very well.
• 23:32
  SPEAKER_00: And this was Python then calling like another Python gRPC that was hitting Cassandra.
• 23:37
  SPEAKER_00: And basically in Python,
• 23:39
  SPEAKER_00: when you instantiate a default parameter,
• 23:42
  SPEAKER_00: if it's mutable,
• 23:42
  SPEAKER_00: I don't know if this is still true,
• 23:44
  SPEAKER_00: by the way, I hope it's not so true, but at the time it was true.
• 23:47
  SPEAKER_00: Where if you basically put a list as a default parameter,
• 23:49
  SPEAKER_00: and then you mutated it, like appended IDs into it, it would persist in memory.
• 23:54
  SPEAKER_00: And so each time that function was called, it would have the same list.
• 23:59
  SPEAKER_00: And so the memory of the user IDs,
• 24:01
  SPEAKER_00: basically every time they call this API to look up user IDs,
• 24:04
  SPEAKER_00: they get the user objects back.
• 24:06
  SPEAKER_00: All the users that were ever passed into it would still be there.
• 24:09
  SPEAKER_00: And so it just cascaded over and over and over until we restarted.
• 24:14
  SPEAKER_00: And we installed memcache kind of in between these.
• 24:17
  SPEAKER_00: And the memcache would start falling over and then it would destroy Cassandra.
• 24:22
  SPEAKER_00: So really finding that bug, it took me, I think, four weeks to actually find it.
• 24:27
  SPEAKER_00: Once you found it, trivial to fix, but we got it up.
• 24:31
  SPEAKER_00: And then our new CEO started, I think, basically the same day that I fixed that.
• 24:37
  SPEAKER_00: And then basically the entire company got laid off over the next year.
• 24:41
  SPEAKER_00: So pure victory in the sense that we did solve it.
• 24:45
  SPEAKER_00: It was working.
• 24:46
  SPEAKER_00: But I think you can't really have the central site be hard to use or down for a month.
• 24:52
  SPEAKER_00: But if you go to the counterfactual, what would the company have done differently?
• 24:56
  SPEAKER_00: If they had simply kept up the old site, they also would have died.
• 25:00
  SPEAKER_00: And so I don't know that they made the wrong choice.
• 25:02
  SPEAKER_00: But at the time, I certainly was pretty salty about it.
• 25:05
  SPEAKER_02: Yeah.
• 25:06
  SPEAKER_02: How did you eventually get into engineering leadership?
• 25:09
  SPEAKER_02: I know you and me overlapped a little bit at Uber.
• 25:11
  SPEAKER_02: Actually, we both worked there, but we never worked together.
• 25:13
  SPEAKER_00: So the kind of the end of the Dig story was we got Aqua hired.
• 25:17
  SPEAKER_00: And so they sold the patents for Dig did a lot of like innovation.
• 25:20
  SPEAKER_00: So like in ad or in-stream ad units,
• 25:24
  SPEAKER_00: basically,
• 25:24
  SPEAKER_00: like you see it on X now where they'll have like an ad that kind of looks like
• 25:28
  SPEAKER_00: the stories from people that are posting.
• 25:30
  SPEAKER_00: Dig owned the patents of that.
• 25:32
  SPEAKER_00: They were the first company to do it.
• 25:34
  SPEAKER_00: They own like a variety of other patents.
• 25:35
  SPEAKER_00: And so the patent portfolio got acquired by one company.
• 25:38
  SPEAKER_00: Dig.com,
• 25:39
  SPEAKER_00: like the actual like brand of the website got acquired by,
• 25:42
  SPEAKER_00: I think, Betaworks at New York at the time.
• 25:45
  SPEAKER_00: I think they've sold it subsequently a few years ago.
• 25:48
  SPEAKER_00: And then the team got acquired by Social Code,
• 25:50
  SPEAKER_00: which is like a third company,
• 25:51
  SPEAKER_00: a subsidiary of the Washington Post company from the time when that was
• 25:54
  SPEAKER_00: a holding company that owned the post.
• 25:56
  SPEAKER_00: Kaplan and this company, Social Code, which basically did advertising on Facebook.
• 26:01
  SPEAKER_00: And so the team went there and I was there for a couple of years.
• 26:04
  SPEAKER_00: But when I left,
• 26:05
  SPEAKER_00: I was thinking about, okay,
• 26:06
  SPEAKER_00: I want to be kind of in engineering leadership,
• 26:09
  SPEAKER_00: but I can't get hired into a really large role because
• 26:12
  SPEAKER_00: that time I was managing maybe a team of 12 engineers or something like that.
• 26:16
  SPEAKER_00: So I can't get hired in this big role because I haven't done the big role.
• 26:19
  SPEAKER_00: Like, how do we get hired in this big role?
• 26:20
  SPEAKER_00: And so if you're at a small startup, like you just, there's, the scale is not there.
• 26:24
  SPEAKER_00: Even if you Go be a head of engineering at this 15% startup.
• 26:27
  SPEAKER_00: There's just five engineers there.
• 26:30
  SPEAKER_00: And so you can never get into the scale they're looking for for these large roles.
• 26:33
  SPEAKER_00: And so what I was looking about at the time,
• 26:35
  SPEAKER_00: and my thoughts on this topic changed a lot since then,
• 26:38
  SPEAKER_00: but it's just like honestly where I was.
• 26:40
  SPEAKER_00: It's like, well,
• 26:40
  SPEAKER_00: if I want to manage a large team,
• 26:42
  SPEAKER_00: I got to join a company that's growing really quickly.
• 26:44
  SPEAKER_00: I kind of looked around and like, where is growing really quickly?
• 26:46
  SPEAKER_00: And like Uber, Uber was growing really, really, really quickly.
• 26:49
  SPEAKER_00: 15, 16?
• 26:50
  SPEAKER_00: I think this is 2014.
• 26:52
  SPEAKER_00: This is early 2014.
• 26:53
  SPEAKER_00: This is when growth just started to kick off.
• 26:56
  SPEAKER_00: Like this was very early.
• 26:57
  SPEAKER_02: This is pretty early.
• 26:58
  SPEAKER_02: You have to be in San Francisco to know that Uber was doing really well.
• 27:02
  SPEAKER_02: Like outside of that stuff, I think news started to spread in 2015.
• 27:06
  SPEAKER_02: And then by 2016, it was a global news.
• 27:08
  SPEAKER_00: That sounds right.
• 27:09
  SPEAKER_00: But the way I knew is that one of the engineers,
• 27:11
  SPEAKER_00: Jeremy Grosser from Digg, who was on infrastructure there, left and joined Uber.
• 27:17
  SPEAKER_00: And actually,
• 27:17
  SPEAKER_00: there's like an interesting technology adoption curve
• 27:20
  SPEAKER_00: because Digg made all these technologies.
• 27:22
  SPEAKER_00: One of them is called Clusto,
• 27:23
  SPEAKER_00: which I think Dig, Uber,
• 27:26
  SPEAKER_00: and then like Second Life,
• 27:28
  SPEAKER_00: that company,
• 27:29
  SPEAKER_00: I forget their actual name,
• 27:31
  SPEAKER_00: but whatever it is,
• 27:32
  SPEAKER_00: maybe the only three companies in the world that ever adopted this tool, Clusto,
• 27:35
  SPEAKER_00: but it managed basically a key value store to manage kind of state or infrastructure
• 27:39
  SPEAKER_00: a little But like a console from HashiCorp is very, very similar.
• 27:43
  SPEAKER_00: Just years before console was out.
• 27:45
  SPEAKER_00: Yeah, it was probably made originally in like 2008, 2009, something like that.
• 27:50
  SPEAKER_00: And so he had actually brought like a ton of the DIG stack over into Uber
• 27:54
  SPEAKER_00: because he was one of the first infrastructure engineers there.
• 27:56
  SPEAKER_00: And so, you know,
• 27:58
  SPEAKER_00: his team was hiring and I really was like a generalist engineer,
• 28:02
  SPEAKER_00: like I got who was actually hired to do front end engineering,
• 28:06
  SPEAKER_00: which I don't know if I super qualified for.
• 28:08
  SPEAKER_00: And then at Digg,
• 28:11
  SPEAKER_00: I was doing, you know, front end, Cassandra work, back end, just like everything.
• 28:15
  SPEAKER_00: Yep.
• 28:16
  SPEAKER_00: And then they hired me to kind of run this SRE team.
• 28:18
  SPEAKER_00: But it wasn't really an SRE team.
• 28:20
  SPEAKER_00: It was just like an infrastructure team that they called SRE.
• 28:23
  SPEAKER_00: You know, I read like an SRE book like the week before trying to figure out what the job was.
• 28:27
  SPEAKER_02: You probably read the SRE book that existed, which is
• 28:30
  SPEAKER_00: the Google SRE book, right?
• 28:31
  SPEAKER_00: I don't think that book existed then.
• 28:33
  SPEAKER_00: It might have.
• 28:34
  SPEAKER_02: What book did you have access to?
• 28:35
  SPEAKER_00: I think there was a DevOps book might have been what I was reading.
• 28:39
  SPEAKER_00: And it might have been like the Phoenix Project might have been out around then.
• 28:43
  SPEAKER_00: I'm forgetting if that the exact timeline, but there was something.
• 28:46
  SPEAKER_00: And then you were leading a team already.
• 28:47
  SPEAKER_00: You were growing a team.
• 29:11
  SPEAKER_00: So the team when I joined,
• 29:13
  SPEAKER_00: I probably was managing like six people,
• 29:15
  SPEAKER_00: but it was managing an incredibly broad range of responsibilities.
• 29:19
  SPEAKER_00: So Uber when I joined was 2,000 people,
• 29:22
  SPEAKER_00: it was 200 engineers,
• 29:24
  SPEAKER_00: and this team of about six was managing our databases,
• 29:28
  SPEAKER_00: our Kafka, like our actual servers.
• 29:31
  SPEAKER_00: Not, well,
• 29:32
  SPEAKER_00: the management of the servers,
• 29:33
  SPEAKER_00: there was a tech ops team that managed literally racking them in Installing them,
• 29:37
  SPEAKER_00: once they were racked, we managed that.
• 29:39
  SPEAKER_00: Our service provisioning,
• 29:41
  SPEAKER_00: we owned basically everything other than there was
• 29:43
  SPEAKER_00: a two-person developer experience team.
• 29:45
  SPEAKER_00: There was this tech ops team that actually racked and installed the servers,
• 29:49
  SPEAKER_00: but we owned all the other infrastructure, and it was quite an experience.
• 29:54
  SPEAKER_02: And then in terms of just focusing on your leadership journey,
• 29:58
  SPEAKER_02: your management journey, so at Uber, you started at this team.
• 30:01
  SPEAKER_02: How far did it go, and then what were the next steps between
• 30:04
  SPEAKER_00: Stripe, Carta?
• 30:06
  SPEAKER_00: Yeah, absolutely.
• 30:07
  SPEAKER_00: So when I joined that team was, I think, roughly five or six folks.
• 30:11
  SPEAKER_00: When I left two years later, that team was 70.
• 30:13
  SPEAKER_00: And that was all external hiring.
• 30:15
  SPEAKER_00: And I think that that was like the most kind of amazing thing about Uber
• 30:19
  SPEAKER_00: that point is like Uber doubled the edge headcount every six months.
• 30:22
  SPEAKER_00: And so you can't just like steal people from other teams
• 30:25
  SPEAKER_00: because those teams are hiring a ton too and also really underwater.
• 30:29
  SPEAKER_00: And so I really learned how to hire at Uber.
• 30:31
  SPEAKER_00: I had no idea how to hire before I joined Uber, but they were just hiring so many folks.
• 30:37
  SPEAKER_00: I think one of my favorite stories was there's this guy out of Eventbrite
• 30:40
  SPEAKER_00: that I managed for a year and a half that would give him an offer at like four
• 30:45
  SPEAKER_00: And he started Monday at 8.
• 30:47
  SPEAKER_00: But I have so many like Uber hiring stories, like some of them like funnier than others.
• 30:52
  SPEAKER_00: I remember someone who interviewed with Uber four times and I saw him interviewing a fifth time.
• 30:57
  SPEAKER_00: They got rejected four times and the team interviewed him a fifth time.
• 31:00
  SPEAKER_00: I was like, we cannot hire this guy.
• 31:02
  SPEAKER_00: We've already interviewed him like four times, like stop wasting his time.
• 31:06
  SPEAKER_00: But he got an offer for that team.
• 31:09
  SPEAKER_00: And he joined,
• 31:10
  SPEAKER_00: and then he quit within six hours and took a different offer because he got an offer
• 31:13
  SPEAKER_00: from Twitter, which was right down, right, a block away.
• 31:17
  SPEAKER_00: A block away or somebody was also a boat.
• 31:18
  SPEAKER_00: And so he spent more time interviewing for Uber than working there despite accepting the job.
• 31:23
  SPEAKER_00: And there are just like so many, so many wild stories from the Uber experience there.
• 31:28
  SPEAKER_00: But that team, six to 70 over two years, and our scope increased a lot in that time.
• 31:33
  SPEAKER_00: But it was just like a really wild time.
• 31:35
  SPEAKER_00: And it's hard,
• 31:36
  SPEAKER_00: you know,
• 31:37
  SPEAKER_00: some of the companies today, I think, remind me a lot of that Uber experience.
• 31:40
  SPEAKER_00: But Uber,
• 31:41
  SPEAKER_00: when I joined,
• 31:42
  SPEAKER_00: basically every Friday,
• 31:43
  SPEAKER_00: we were literally manually reallocating software between servers,
• 31:46
  SPEAKER_00: trying to keep the servers up.
• 31:48
  SPEAKER_00: Because typically, Friday rush hour was our peak time of the week.
• 31:52
  SPEAKER_00: Though a Saturday,
• 31:52
  SPEAKER_00: you might have more volume,
• 31:54
  SPEAKER_00: but that would be like spread over more hours because people aren't all leaving work
• 31:57
  SPEAKER_00: at the exact same time.
• 31:58
  SPEAKER_00: So many kind of wild stories of just like what a Manic place that I was to work at,
• 32:04
  SPEAKER_00: but I was there for a couple of years.
• 32:06
  SPEAKER_00: Then I went to Stripe.
• 32:07
  SPEAKER_00: I was at Stripe for about four years from 2016 through early 2020.
• 32:10
  SPEAKER_00: Then I was actually at Calm for
• 32:13
  SPEAKER_02: three
• 32:15
  SPEAKER_00: and a half, three years.
• 32:16
  SPEAKER_00: That was my first CTO job.
• 32:19
  SPEAKER_00: It was really kind of deliberate at that point.
• 32:20
  SPEAKER_00: I think I was really worried.
• 32:21
  SPEAKER_00: So I'd been at Stripe for four years.
• 32:23
  SPEAKER_00: Stripe had done really well.
• 32:25
  SPEAKER_00: I think I joined at And I want to say I was roughly someone that joined
• 32:28
  SPEAKER_00: the day I joined at Stripe was employee 500.
• 32:41
  SPEAKER_00: I don't know if that was me or someone else in the batch.
• 32:44
  SPEAKER_00: But I think by the time I left, it was 1.5 to 2,000 folks, something of the company.
• 32:49
  SPEAKER_00: So Stripe grew about 70% year over year the period that I was there,
• 32:53
  SPEAKER_00: which is a lot less than Uber, which doubled every six months.
• 32:56
  SPEAKER_00: And obviously, like Uber subsequently contracted much more aggressively than Stripe ever did.
• 33:01
  SPEAKER_00: Which is the natural consequence of doubling every six months.
• 33:05
  SPEAKER_00: But at that point,
• 33:06
  SPEAKER_00: I was just worried that my entire savings were all in one company
• 33:11
  SPEAKER_00: that was never going to go public, which I think has been true.
• 33:15
  SPEAKER_00: And so it was a bit of a diversification play,
• 33:17
  SPEAKER_00: but also the desire to, what does it actually feel like to fully lead?
• 33:21
  SPEAKER_00: And so for my entire time at Stripe, I was basically...
• 33:25
  SPEAKER_00: You know,
• 33:26
  SPEAKER_00: one step away from the CEO,
• 33:28
  SPEAKER_00: reporting into Jeff Winter for my first year,
• 33:30
  SPEAKER_00: then into David Singleton, who was my manager for the rest of
• 33:33
  SPEAKER_02: the time.
• 33:33
  SPEAKER_02: Oh, Stripe's CTO later, or maybe at that time as well.
• 33:36
  SPEAKER_00: He joined as the CTO.
• 33:37
  SPEAKER_00: Awesome.
• 33:38
  SPEAKER_00: No, that's not true.
• 33:39
  SPEAKER_00: He joined as the head of engineering,
• 33:40
  SPEAKER_00: and then he became the CTO maybe a year or two later, something like that.
• 33:44
  SPEAKER_00: But I was reporting to him from when he joined through the time I departed in early 2020.
• 33:48
  SPEAKER_00: So I was only one step away, but I was like, what if I could get into that seat?
• 33:52
  SPEAKER_00: Could I do things some better?
• 33:53
  SPEAKER_00: And that seemed like the...
• 33:55
  SPEAKER_00: The right thing to try for, anyway, and has been educational ever since.
• 33:59
  SPEAKER_02: And then you have had several CTO gigs,
• 34:01
  SPEAKER_02: and so it was Calm, three and a half year CTO, then you were at Carta?
• 34:06
  SPEAKER_00: So I was at Calm for,
• 34:07
  SPEAKER_00: I think,
• 34:07
  SPEAKER_00: three and a half years,
• 34:08
  SPEAKER_00: then I was at Carta for two years,
• 34:09
  SPEAKER_00: and then I joined Imprint a year,
• 34:12
  SPEAKER_00: year and a half ago, something like that, which is where I am today.
• 34:15
  SPEAKER_02: Okay, so now three times CTO, I need to ask you, what does a CTO do?
• 34:20
  SPEAKER_02: As an engineer,
• 34:23
  SPEAKER_02: if you put yourself back as being an engineer,
• 34:25
  SPEAKER_02: of course,
• 34:26
  SPEAKER_02: I think I myself had aspirations when I was an engineer, like, oh,
• 34:30
  SPEAKER_02: it could be nice to want to be a CTO because in your mind,
• 34:32
  SPEAKER_02: it's like, well,
• 34:33
  SPEAKER_02: it has some management,
• 34:34
  SPEAKER_02: but it's also a lot CTOs you see are technical and close to the thing.
• 34:38
  SPEAKER_02: How do you find the CTO role?
• 34:39
  SPEAKER_02: I know you have a book on this as well,
• 34:42
  SPEAKER_02: on engineering executive careers, and there's a lot of answers.
• 34:46
  SPEAKER_02: But what is your mental model?
• 34:47
  SPEAKER_02: How was it?
• 34:48
  SPEAKER_02: And how is it now, especially?
• 34:49
  SPEAKER_02: Because now with AI, I think your role has changed.
• 34:52
  SPEAKER_00: I think one of the worst parts of being an engineering manager in
• 34:55
  SPEAKER_00: the 2010s is I think when you joined the ranks of engineering management,
• 35:00
  SPEAKER_00: one of the first lessons you'd get is like,
• 35:02
  SPEAKER_00: hey, you need to never make a technical decision again.
• 35:05
  SPEAKER_00: That's what it used to be, right?
• 35:06
  SPEAKER_00: I remember.
• 35:07
  SPEAKER_00: That's literally what I was told.
• 35:10
  SPEAKER_00: And I think you'd see people like the most important thing is to let go
• 35:14
  SPEAKER_00: about technology decisions.
• 35:16
  SPEAKER_00: And this was the ethos then.
• 35:17
  SPEAKER_00: And that's definitely not the ethos today.
• 35:19
  SPEAKER_00: But I think the thing that I kind of aspirationally really loved is the CTO was like
• 35:23
  SPEAKER_00: the only place where this like engineering kind of career,
• 35:26
  SPEAKER_00: this technical oriented one and this managerial one converged.
• 35:30
  SPEAKER_00: And so one of the things I've believed strongly in and continue
• 35:33
  SPEAKER_00: to do today is having both engineering managers,
• 35:36
  SPEAKER_00: but also individual contributor engineers report directly into me in CTO roles.
• 35:40
  SPEAKER_00: And so today I have 14 direct reports right now,
• 35:44
  SPEAKER_00: and I think four or five of them are ICs, and then the rest are our managers.
• 35:49
  SPEAKER_00: But having that balance is like really for many roles in management,
• 35:53
  SPEAKER_00: you're just not allowed to be a technical leader or you weren't And so to me,
• 35:59
  SPEAKER_00: actually getting to the level where they converged again and you were allowed to be
• 36:02
  SPEAKER_00: a leader on the technology and the management side was like one of the big appeals.
• 36:07
  SPEAKER_00: But also there's so many like bad CTO decisions out there.
• 36:12
  SPEAKER_00: And I don't mean this to reflect on any of the individuals I've talked about.
• 36:15
  SPEAKER_00: I think David in particular was like really excellent.
• 36:18
  SPEAKER_00: And the decisions at Stripe were generally decision quality at Stripe was pretty high.
• 36:22
  SPEAKER_00: And so sometimes you could be like,
• 36:24
  SPEAKER_00: I disagree, but you couldn't be like, this makes literally no sense.
• 36:27
  SPEAKER_00: But often like,
• 36:28
  SPEAKER_00: you know,
• 36:28
  SPEAKER_00: especially outside of the Stripe experience,
• 36:30
  SPEAKER_00: there are just decisions that like just didn't make sense.
• 36:34
  SPEAKER_00: And I thought like maybe I could do it better.
• 36:35
  SPEAKER_00: But I think the thing that I've really loved in the most recent kind
• 36:39
  SPEAKER_00: of era is It's like you're really like not just allowed to be in the details again,
• 36:44
  SPEAKER_00: like you're really sort of required to be.
• 36:46
  SPEAKER_00: And that to me has been like the very most fun part of being back in software
• 36:52
  SPEAKER_00: in this era is I think I've done over 500 pull requests in a year and a half
• 36:59
  SPEAKER_00: at imprint going all the way to production,
• 37:01
  SPEAKER_00: which is substantially more than I did in my prior career combined.
• 37:05
  SPEAKER_00: And that's pretty cool.
• 37:06
  SPEAKER_02: And then you did Imprint at CTO.
• 37:09
  SPEAKER_02: Are you more than CTO at Imprint?
• 37:11
  SPEAKER_00: So I joined as the CTO.
• 37:13
  SPEAKER_00: And right now I'm also kind of leading the product design teams.
• 37:16
  SPEAKER_02: So product design and engineering all reporting into one person.
• 37:19
  SPEAKER_00: Yeah, it's like a unified EPD structure.
• 37:21
  SPEAKER_01: Is this a new trend?
• 37:23
  SPEAKER_02: One person,
• 37:25
  SPEAKER_02: because CTPO I started to hear about two years ago,
• 37:27
  SPEAKER_02: Chief Technology and Product Officer two or three years ago,
• 37:30
  SPEAKER_02: and now I'm starting to hear design also going into one person
• 37:34
  SPEAKER_00: a little bit.
• 37:34
  SPEAKER_00: I don't know if it's a trend or not.
• 37:36
  SPEAKER_00: I do think that for one challenge I've been seeing with like the agents kind
• 37:41
  SPEAKER_00: of getting more mainstream is you actually have to be able to make decisions
• 37:45
  SPEAKER_00: and make them quickly And how do we do things?
• 37:48
  SPEAKER_00: How do we not do things?
• 37:49
  SPEAKER_00: How does agent adoption work for product?
• 37:51
  SPEAKER_00: How does it work for design?
• 37:53
  SPEAKER_00: Hey, design,
• 37:54
  SPEAKER_00: if they aren't using the new tools like Claude Design or the Figma MCP or whatnot,
• 37:59
  SPEAKER_00: then they're really the bottleneck.
• 38:01
  SPEAKER_00: How do you kind of split the responsibility there on who owns design now?
• 38:05
  SPEAKER_00: And so Imprint,
• 38:05
  SPEAKER_00: for example,
• 38:06
  SPEAKER_00: has been experimenting with this developer-led design model for kind
• 38:10
  SPEAKER_00: of second-tier features, and it's created a ton of friction.
• 38:13
  SPEAKER_00: Like, it's solved this bottleneck.
• 38:15
  SPEAKER_00: It's also created a lot of, like,
• 38:17
  SPEAKER_00: who's responsible for these design gaps that show up when engineers do lead design
• 38:22
  SPEAKER_00: and sometimes, like, don't follow the design system properly.
• 38:25
  SPEAKER_00: And so having a unified kind of point that can actually make these trade-offs,
• 38:29
  SPEAKER_00: I think this moment of, like, immense change, I think, is pretty powerful.
• 38:32
  SPEAKER_00: I do think just in my core,
• 38:34
  SPEAKER_00: I believe the industry is changing more in terms of how we create software
• 38:38
  SPEAKER_00: than it ever has in my career.
• 38:40
  SPEAKER_00: And, you know, I started in late 2008.
• 38:43
  SPEAKER_00: I've never seen a change like this.
• 38:44
  SPEAKER_00: A lot of the changes I've seen were more subtle or more kind of cultural or social.
• 38:49
  SPEAKER_00: Will just said how he's never seen the way we build software change this much
• 38:53
  SPEAKER_00: in his whole career.
• 38:54
  SPEAKER_00: One thing that is changing is the stack that we use for Git hosting,
• 38:57
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• 39:19
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• 39:23
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• 39:36
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• 39:52
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• 39:59
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• 40:00
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• 40:04
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• 40:07
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• 40:11
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• 40:20
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• 40:24
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• 40:33
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• 40:36
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• 40:45
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• 40:49
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• 40:52
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• 41:48
  SPEAKER_01: And with this, let's get back to Will and what changes he's observed
• 41:51
  SPEAKER_02: across the industry.
• 41:53
  SPEAKER_02: But why don't you go back to like from when you started in the industry?
• 41:56
  SPEAKER_02: Can we talk about the changes you've seen In software engineering,
• 41:59
  SPEAKER_02: let's just focus on your experience.
• 42:00
  SPEAKER_02: So let's talk about the Silicon Valley companies.
• 42:03
  SPEAKER_02: We know they're a bubble, but they're a useful bubble to talk about.
• 42:07
  SPEAKER_02: How did building software change,
• 42:09
  SPEAKER_02: leading teams change over,
• 42:10
  SPEAKER_02: you know, like starting from like what, like 2007 all the way to today?
• 42:15
  SPEAKER_00: I don't know what your first experience was like kind of as an engineer,
• 42:19
  SPEAKER_00: but when I was first an engineer,
• 42:20
  SPEAKER_00: first as a contractor, I was like 22 for Yahoo working remotely.
• 42:24
  SPEAKER_00: No one else on the team was remote.
• 42:26
  SPEAKER_00: And then when I went full-time, I had the same manager.
• 42:28
  SPEAKER_00: So I had the same manager for two years.
• 42:30
  SPEAKER_00: I had two one-on-ones.
• 42:31
  SPEAKER_02: I had no one-on-ones or like once a year or for performance,
• 42:37
  SPEAKER_02: not even performance, but for pay conversations.
• 42:40
  SPEAKER_02: And then they would say, yeah, good job.
• 42:41
  SPEAKER_02: Here's your raise.
• 42:43
  SPEAKER_02: Or like, oh, and then promotions used to be like, congratulations, you're now promoted.
• 42:47
  SPEAKER_02: And it was more about like, yeah, you're making more money.
• 42:49
  SPEAKER_00: Cool.
• 42:49
  SPEAKER_00: And I didn't have any expectation that I'd have more than two.
• 42:53
  SPEAKER_00: And the first one is basically he wanted to talk
• 42:55
  SPEAKER_00: about another employee's performance,
• 42:56
  SPEAKER_00: trying to get like some signal about whether they were doing poorly.
• 42:59
  SPEAKER_00: So it wasn't like feedback from you or something.
• 43:02
  SPEAKER_00: And the second one was like,
• 43:03
  SPEAKER_00: oh, you like gave notice, you're leaving, like, what's going on, right?
• 43:07
  SPEAKER_00: And so, and that was just kind of normal.
• 43:10
  SPEAKER_00: And so his job,
• 43:11
  SPEAKER_00: the way he saw it,
• 43:12
  SPEAKER_00: and I think he was like really good at it,
• 43:14
  SPEAKER_00: was his job was to go find an opportunity in the company for the team
• 43:17
  SPEAKER_00: to have impact.
• 43:19
  SPEAKER_00: So he was going around the company,
• 43:20
  SPEAKER_00: searching for something we could do that was really valuable.
• 43:23
  SPEAKER_00: And he kind of like brought that back.
• 43:24
  SPEAKER_00: And then our job was to implement it and make it work.
• 43:27
  SPEAKER_00: And that was just like how the work was done.
• 43:30
  SPEAKER_00: And there was no idea that he was helping me have a rewarding career or something like that.
• 43:35
  SPEAKER_00: That, I think, was irrelevant to him.
• 43:38
  SPEAKER_00: We're talking pre-2010, pretty much.
• 43:41
  SPEAKER_00: And then when I got to Dig, I think, All the managers basically got fired.
• 43:46
  SPEAKER_00: I actually became a manager at Digg because I was the only one dumb enough not
• 43:50
  SPEAKER_00: to say no when they asked me.
• 43:51
  SPEAKER_00: But, you know, I had like two and a half, three years of experience tops at that point.
• 43:57
  SPEAKER_00: And I knew nothing about management.
• 43:59
  SPEAKER_00: Right.
• 43:59
  SPEAKER_00: And again, I never interacted with my manager at my prior job.
• 44:02
  SPEAKER_00: I interacted with like a tech lead to kind of set technical direction.
• 44:06
  SPEAKER_00: And then got upset if I screwed something up.
• 44:08
  SPEAKER_00: But that was kind of the entirety of like the leadership model there, right?
• 44:11
  SPEAKER_00: So I came in and I was a manager,
• 44:13
  SPEAKER_00: but there was really no management at Digg other than,
• 44:17
  SPEAKER_00: you know, me for the last year.
• 44:19
  SPEAKER_00: And I didn't know what I was doing whatsoever.
• 44:22
  SPEAKER_00: So really, I learned a lot at Uber.
• 44:23
  SPEAKER_00: But again, at Uber, everyone was so busy.
• 44:25
  SPEAKER_00: There was no management there either.
• 44:27
  SPEAKER_00: It was really a sink or swim.
• 44:29
  SPEAKER_00: And either you figured it out And your team really struggled because
• 44:34
  SPEAKER_00: if you didn't get the decisions right,
• 44:35
  SPEAKER_00: the scale of the growth around you would just crush your team.
• 44:40
  SPEAKER_00: And so again, like really, really no, no support.
• 44:44
  SPEAKER_02: It was interesting because by 2017,
• 44:46
  SPEAKER_02: when I became manager,
• 44:47
  SPEAKER_02: Uber put together its first apprentice manager program,
• 44:50
  SPEAKER_02: which actually talking with people.
• 44:51
  SPEAKER_02: So when I became a manager there,
• 44:53
  SPEAKER_02: I had like a few days of getting together, mentors assigned, all that.
• 44:56
  SPEAKER_02: Most engineering managers never, ever had that.
• 44:59
  SPEAKER_02: And Uber, it was brand new at Uber.
• 45:00
  SPEAKER_02: They made it more formal.
• 45:01
  SPEAKER_02: So they actually did some internal DIY training, honestly.
• 45:04
  SPEAKER_02: But yes, before that, nothing.
• 45:06
  SPEAKER_02: Oh, and they did it because I think they realized that bad managers were becoming
• 45:09
  SPEAKER_02: a really big problem.
• 45:10
  SPEAKER_00: Yeah, which makes sense.
• 45:12
  SPEAKER_00: I think people were just figuring it out.
• 45:15
  SPEAKER_00: And I think the Uber I worked in was extremely kind of myopic.
• 45:19
  SPEAKER_00: So one of the kind of values, I might get it wrong, was basically...
• 45:23
  SPEAKER_00: Solve it yourself.
• 45:25
  SPEAKER_00: That's like not literally on the stated values, but people didn't go get blocked in other teams.
• 45:29
  SPEAKER_00: They just did it themselves.
• 45:31
  SPEAKER_00: And maybe let builders build might have been like a variant of this.
• 45:34
  SPEAKER_02: There was the let builders build, be an owner, not a renter.
• 45:37
  SPEAKER_02: And when you combine the two, there was something about principles.
• 45:41
  SPEAKER_02: But it was like, just roam your way and don't ask for forgiveness.
• 45:45
  SPEAKER_02: Just get it done.
• 45:46
  SPEAKER_00: And there was sort of like a no dependencies culture,
• 45:48
  SPEAKER_00: which I found really empowering, where it's like, oh, I'm blocked.
• 45:51
  SPEAKER_00: It's like, you're not blocked.
• 45:52
  SPEAKER_00: You need to go figure it out.
• 45:54
  SPEAKER_00: And that was really painful sometimes,
• 45:57
  SPEAKER_00: but it really meant you could always take responsibility
• 46:00
  SPEAKER_00: and just figure it out yourself.
• 46:02
  SPEAKER_00: Sometimes,
• 46:02
  SPEAKER_00: you know,
• 46:03
  SPEAKER_00: I remember signing like purchase orders for Uber China where we couldn't get anyone
• 46:07
  SPEAKER_00: to sign it.
• 46:08
  SPEAKER_00: And I ended up signing like a...
• 46:12
  SPEAKER_00: And I was probably like 27 or just there was no one to approve it.
• 46:17
  SPEAKER_00: And we had to get done.
• 46:18
  SPEAKER_00: And so, you know, Amir,
• 46:20
  SPEAKER_00: the head of tuckups and I was kind of staring at each other and was like,
• 46:23
  SPEAKER_00: I guess we'll just sign it.
• 46:24
  SPEAKER_00: And like the thing that I loved about Uber of that era is like no one ever talked
• 46:27
  SPEAKER_00: to me about it.
• 46:27
  SPEAKER_00: Like there was never there was never like a follow up.
• 46:29
  SPEAKER_00: Probably not good either.
• 46:30
  SPEAKER_00: In a corporate governance perspective, that's like maybe a little bit like ad hoc.
• 46:36
  SPEAKER_00: But we really didn't get in each other's way and were able to do amazing things.
• 46:40
  SPEAKER_00: Also, extremely challenging place to work in its own right.
• 46:43
  SPEAKER_02: Yeah, but people left and burned out for a reason, a lot of them.
• 46:46
  SPEAKER_02: 100%.
• 46:47
  SPEAKER_00: But really, so all the way through then, I finally get to Stripe around 2016.
• 46:51
  SPEAKER_00: And Stripe sort of famously didn't have a management culture either.
• 46:55
  SPEAKER_00: So when I joined, there were, I think, three managers.
• 46:57
  SPEAKER_00: One of them,
• 46:58
  SPEAKER_00: who I really loved working with,
• 46:59
  SPEAKER_00: Raylene, I think had somewhere between 40 and 50 direct reports.
• 47:03
  SPEAKER_00: Because Stripe had read the paper from Google when they used
• 47:08
  SPEAKER_00: to have basically no managers for some period of time.
• 47:11
  SPEAKER_02: And how it didn't work.
• 47:13
  SPEAKER_00: No, they initially followed the model where there were no managers for a long time.
• 47:17
  SPEAKER_02: Yeah.
• 47:18
  SPEAKER_00: And so I kind of joined in that,
• 47:20
  SPEAKER_00: the wave of managerization as like one of the early managers in that wave.
• 47:25
  SPEAKER_00: But I think there were three or four managers,
• 47:27
  SPEAKER_00: Raylene, Jorge, and there were like one or two others.
• 47:30
  SPEAKER_00: Jorge was managing a team of,
• 47:32
  SPEAKER_00: I think, 30 with maybe one manager underneath him for those 30 folks.
• 47:38
  SPEAKER_00: Raylene, I think, had no managers.
• 47:39
  SPEAKER_00: It was just like a very...
• 47:41
  SPEAKER_00: It was a very chaotic time as well.
• 47:43
  SPEAKER_00: But again,
• 47:43
  SPEAKER_00: kind of coming out of the Uber experience,
• 47:45
  SPEAKER_00: I was very, very familiar with chaos at that point.
• 47:48
  SPEAKER_00: But also the business was growing really, really fast.
• 47:51
  SPEAKER_00: And so I think really that period at Uber, though,
• 47:54
  SPEAKER_00: is when the cultural change around what is the role of manager,
• 47:58
  SPEAKER_00: I think, started to cement itself a little bit.
• 48:01
  SPEAKER_00: And kind of this role of manager,
• 48:02
  SPEAKER_00: not as a kind of a core doer or a decision maker,
• 48:06
  SPEAKER_00: but as a facilitator, really started to take hold.
• 48:09
  SPEAKER_00: And that was pretty fascinating to watch.
• 48:14
  SPEAKER_00: And one of the reasons why I wrote Staff Engineer,
• 48:16
  SPEAKER_00: which I think came out in 2021,
• 48:17
  SPEAKER_00: was actually collecting feedback for some of the staff engineers I'd worked with.
• 48:23
  SPEAKER_00: Because one of the ideas that I was really frustrated with at the time was this idea
• 48:28
  SPEAKER_00: that staff engineers principally got to work on interesting,
• 48:31
  SPEAKER_00: fun problems that they found personally rewarding,
• 48:34
  SPEAKER_00: which wasn't what I needed for my staff engineers at all.
• 48:37
  SPEAKER_00: I needed them to go work on the business problems and the scalability problems
• 48:41
  SPEAKER_00: that I,
• 48:42
  SPEAKER_00: as a leader,
• 48:43
  SPEAKER_00: and when I left Stripe,
• 48:44
  SPEAKER_00: I want to say my team was like 250, 260, something like that.
• 48:48
  SPEAKER_00: I had all these problems.
• 48:49
  SPEAKER_00: And so some of my very best engineers were like, I want like a more interesting problem.
• 48:54
  SPEAKER_00: And it's like,
• 48:55
  SPEAKER_00: I only have suffering to offer,
• 48:57
  SPEAKER_00: but this suffering is what's going to make the business succeed.
• 49:01
  SPEAKER_00: And so how do I refocus them?
• 49:03
  SPEAKER_00: And I think many of them at the time felt like that was a violation of the management contract.
• 49:09
  SPEAKER_00: Like my goal and my obligation was to give them interesting work they wanted.
• 49:13
  SPEAKER_02: Oh, interesting.
• 49:13
  SPEAKER_02: When we look back, just how it changed from like 10 years before.
• 49:17
  SPEAKER_00: Totally.
• 49:18
  SPEAKER_00: Right.
• 49:18
  SPEAKER_00: And so I think that was like a fascinating time to be in.
• 49:22
  SPEAKER_00: But I don't think that perspective was ever really right.
• 49:25
  SPEAKER_00: If you look at the people who are really senior at Stripe,
• 49:27
  SPEAKER_00: but also everywhere I've worked,
• 49:29
  SPEAKER_00: those folks were doing the really valuable work that the company needed.
• 49:33
  SPEAKER_00: You never saw that perspective like really take hold in the executive ranks.
• 49:37
  SPEAKER_00: But a lot of the folks coming in, um, Really had that belief.
• 49:41
  SPEAKER_00: And I'd say like without naming names,
• 49:43
  SPEAKER_00: certain companies that they came from had very strong versions of that where kind of
• 49:48
  SPEAKER_00: the obligation of the manager for senior hires was to give them fun work.
• 49:52
  SPEAKER_00: And I think the industry's really reverted on that one for sure.
• 49:55
  SPEAKER_02: Was this something to do with zero interest rates?
• 49:58
  SPEAKER_02: We often come back to this, which is so curious.
• 50:01
  SPEAKER_02: I wrote about this as well,
• 50:03
  SPEAKER_02: how an interest rate,
• 50:04
  SPEAKER_02: which feels so abstract and we sometimes hear about it,
• 50:07
  SPEAKER_02: how it probably impacted funding In tech for a very long time,
• 50:11
  SPEAKER_02: probably hiring startups,
• 50:13
  SPEAKER_02: startups that were funded that maybe didn't have a business model,
• 50:16
  SPEAKER_02: but they were still funded.
• 50:17
  SPEAKER_02: And ultimately, software engineering, archetypes, manager types, management decisions.
• 50:23
  SPEAKER_02: And then the music stopped sometime around 2022, where efficiency became more important.
• 50:28
  SPEAKER_02: And now we're kind of seeing this.
• 50:30
  SPEAKER_02: And now I think a lot of us are asking,
• 50:31
  SPEAKER_02: and I'm also asking myself the question like,
• 50:33
  SPEAKER_02: Everything that we did during that time,
• 50:36
  SPEAKER_00: was it right at the time?
• 50:37
  SPEAKER_00: Did you ever read,
• 50:38
  SPEAKER_00: I'm going to get his name wrong,
• 50:39
  SPEAKER_00: but I think it was like Ron John Roy's,
• 50:41
  SPEAKER_00: like, Zerp Explains Everything blog post from The Margins.
• 50:45
  SPEAKER_00: Yes, The Margins.
• 50:46
  SPEAKER_00: We'll also link that.
• 50:47
  SPEAKER_00: I love his writing, yes.
• 50:48
  SPEAKER_00: One of my colleagues at Digg,
• 50:49
  SPEAKER_00: who then I hired at Uber,
• 50:51
  SPEAKER_00: was John Durek,
• 50:52
  SPEAKER_00: who's the other writer on The Margins, along with, I think it's Ron John Roy.
• 50:57
  SPEAKER_00: So I read that piece.
• 50:59
  SPEAKER_00: And it really resonated, right?
• 51:02
  SPEAKER_00: I do think that Zurp has explained the entire like 2010s in terms
• 51:06
  SPEAKER_00: of how management styles changed,
• 51:08
  SPEAKER_00: salaries went up,
• 51:09
  SPEAKER_00: then competition for hiring became your ability to hire and close and retain became
• 51:14
  SPEAKER_00: the differentiator between these like successful companies.
• 51:17
  SPEAKER_00: The less successful because you simply couldn't retain great people.
• 51:21
  SPEAKER_00: And that like pulled kind of leverage back into the engineer's hands
• 51:25
  SPEAKER_00: and created like a very different environment.
• 51:27
  SPEAKER_00: And so part of the way companies were pitching themselves was like more relaxed,
• 51:31
  SPEAKER_00: more focused on you, more career development.
• 51:34
  SPEAKER_00: And I think in ways that I think were often like kind of self-defeating.
• 51:37
  SPEAKER_00: So I think there's this kind of like broad judgment of like the Google perk culture.
• 51:42
  SPEAKER_00: And I don't think any company that did incredibly well other than maybe Google
• 51:46
  SPEAKER_00: and Meta had that level of perk orientation.
• 51:50
  SPEAKER_00: But I do think ignoring the perks,
• 51:51
  SPEAKER_00: there are many other ways that companies try to focus on rewarding work,
• 51:55
  SPEAKER_00: interesting work.
• 51:56
  SPEAKER_00: You know, companies like, oh, engineers maybe shouldn't be on call.
• 51:59
  SPEAKER_00: That's right.
• 52:00
  SPEAKER_00: The second tier SREs to be on call.
• 52:03
  SPEAKER_00: Which was interesting because that was actually a place
• 52:05
  SPEAKER_00: where every single person I've worked with knows engineers being on call for
• 52:09
  SPEAKER_00: the work makes the software better.
• 52:11
  SPEAKER_00: And yet companies were still kind of like, oh,
• 52:14
  SPEAKER_00: maybe for the enjoyment of it,
• 52:17
  SPEAKER_00: we should let folks not be on call for the work they're doing
• 52:19
  SPEAKER_00: and instead page other people that aren't involved in the creation of the software.
• 52:24
  SPEAKER_00: And that orientation really reveals, I think, that the shift in priorities in those companies.
• 52:34
  SPEAKER_02: Managers were rewarded for having low attrition on the team,
• 52:38
  SPEAKER_02: meaning few people left, being able to hire on the team to fill headcount.
• 52:42
  SPEAKER_02: Because often there was a time, this might sound crazy, but filling headcount was difficult.
• 52:46
  SPEAKER_02: You were given, let's say you had a team of 30 as a director or senior engineering manager.
• 52:51
  SPEAKER_02: You had 10 headcount this year.
• 52:53
  SPEAKER_02: And if you couldn't fill that,
• 52:54
  SPEAKER_02: meaning you couldn't hire the right people,
• 52:56
  SPEAKER_02: and this was like, let's say senior and above.
• 52:58
  SPEAKER_02: So it was like, you couldn't just get new grass because that would be too easy.
• 53:01
  SPEAKER_02: Then it kind of counted a little against you.
• 53:04
  SPEAKER_02: Or if someone else will get that headcount,
• 53:06
  SPEAKER_02: which might help their promotion because it was kind of obvious
• 53:09
  SPEAKER_02: if you have 40 plus people,
• 53:10
  SPEAKER_02: you're now, you might be senior manager, that's your director title.
• 53:14
  SPEAKER_02: And so managers who did well in this environment became a bit of people pleaser.
• 53:19
  SPEAKER_02: And also they started to shield their engineers from the business, for example.
• 53:23
  SPEAKER_02: And I wonder if this shielding from the business has bitten back a lot of people
• 53:27
  SPEAKER_02: because now as engineers,
• 53:29
  SPEAKER_02: you're increasingly expected to be savvy about the business,
• 53:32
  SPEAKER_02: understand the business.
• 53:32
  SPEAKER_02: That's when you're going to be in demand.
• 53:34
  SPEAKER_02: And that's when in a startup or other places you get to hit the ground running.
• 53:37
  SPEAKER_02: And I still hear stories from people who worked at this big company,
• 53:41
  SPEAKER_02: let's say a big observability company, any of them.
• 53:44
  SPEAKER_02: And they want to start up, 7% startup.
• 53:45
  SPEAKER_02: And they say, it's terrible.
• 53:48
  SPEAKER_02: They're not letting me do things.
• 53:50
  SPEAKER_02: And I'm like, hang on, you're a 7% company.
• 53:53
  SPEAKER_02: How is it?
• 53:54
  SPEAKER_02: And you're an experienced person.
• 53:55
  SPEAKER_02: How is it that you're not asking, what does the business need to do?
• 53:58
  SPEAKER_02: Let's do it.
• 53:58
  SPEAKER_02: Boom.
• 53:59
  SPEAKER_02: And they've been socialized in a different place for a while.
• 54:02
  SPEAKER_00: Yeah, I think I think that is like a huge part of it in terms of the incentives.
• 54:07
  SPEAKER_00: I do think the orientation around the headcount filling team kind of management,
• 54:11
  SPEAKER_00: like the employee kind of survey results.
• 54:14
  SPEAKER_00: These are really valuable tools.
• 54:15
  SPEAKER_00: I get like a lot out of them.
• 54:18
  SPEAKER_00: But I remember spending a lot of time at these faster-growing companies analyzing
• 54:22
  SPEAKER_00: the quality of manager based on the survey results.
• 54:26
  SPEAKER_00: But survey results, you have to really interpret them.
• 54:29
  SPEAKER_00: High scores or low scores don't mean good or bad manager.
• 54:32
  SPEAKER_00: I think in general, I think I hate headcount conversations, right?
• 54:35
  SPEAKER_00: I think they're almost never the most interesting conversation.
• 55:00
  SPEAKER_00: But I think in a world where managers are not allowed to make technology decisions,
• 55:04
  SPEAKER_00: the only lever they have to actually execute faster is headcount for prioritization.
• 55:10
  SPEAKER_02: Oh, so are you saying that
• 55:13
  SPEAKER_02: At that time,
• 55:14
  SPEAKER_02: and during Zurb,
• 55:15
  SPEAKER_02: where managers were, the conventional wisdom was, do not make technical decisions.
• 55:19
  SPEAKER_02: This forced savvy and smart managers to put way more focus on
• 55:24
  SPEAKER_02: the non-technical side,
• 55:26
  SPEAKER_02: potentially under-investing in the technical things,
• 55:28
  SPEAKER_02: maybe just not making decisions that should have been done,
• 55:30
  SPEAKER_02: and over-indexing on the soft side,
• 55:32
  SPEAKER_02: or maybe shielding their team from the business,
• 55:35
  SPEAKER_02: or all these things, because they put their energy there.
• 55:37
  SPEAKER_00: Oh, 100%.
• 55:38
  SPEAKER_00: I think that's very true.
• 55:39
  SPEAKER_00: Like for most,
• 55:40
  SPEAKER_00: like what I tell my teams that I work with now is like the hiring is
• 55:43
  SPEAKER_00: the least interesting way to solve every problem.
• 55:46
  SPEAKER_00: Like we almost always should never talk about hiring.
• 55:49
  SPEAKER_00: But the corollary to that is like if you have open headcount and ask
• 55:52
  SPEAKER_00: for more headcount, we shouldn't talk about headcount either.
• 55:54
  SPEAKER_00: Because like what matters then is like the hiring throughput
• 55:57
  SPEAKER_00: and you actually like can't use more headcount anyway.
• 55:59
  SPEAKER_00: But yeah, I think we basically told managers they couldn't think about technology solutions.
• 56:04
  SPEAKER_00: And then what do they have?
• 56:04
  SPEAKER_00: They have like process solutions, they have scheduling or they have people.
• 56:08
  SPEAKER_00: And so I do think this was the natural consequence of the bifurcation
• 56:12
  SPEAKER_00: of these two roles, which isn't to say we shouldn't bifurcate at all.
• 56:16
  SPEAKER_00: But I do think we need effective leadership to have both or they over anchor on kind of hiring.
• 56:21
  SPEAKER_00: And that drives a lot of the bloated orgs we saw in the past.
• 56:24
  SPEAKER_02: Let's talk about careers, career development.
• 56:27
  SPEAKER_02: Let's start with individual contributors.
• 56:28
  SPEAKER_02: How do you think career opportunities have changed for software engineers working
• 56:36
  SPEAKER_02: at startups, mid-sized companies that you see?
• 56:38
  SPEAKER_02: Because we used to have a pretty clear career ladder, Eng1, Eng2, Senior Eng, Staff Eng.
• 56:44
  SPEAKER_02: It was clear on how you get promoted.
• 56:46
  SPEAKER_02: To start with,
• 56:46
  SPEAKER_02: you know,
• 56:46
  SPEAKER_02: AI tools are out,
• 56:48
  SPEAKER_02: you know, they're writing the code, which used to be like inch one and inch two.
• 56:51
  SPEAKER_02: They're now getting better at like architecture.
• 56:53
  SPEAKER_02: We're talking about loops.
• 56:54
  SPEAKER_02: Do we have a career ladder?
• 56:55
  SPEAKER_02: Should we have a career ladder?
• 56:57
  SPEAKER_02: If you are a manager at a company,
• 56:58
  SPEAKER_02: should you be worried about putting together a career ladder right now?
• 57:01
  SPEAKER_00: It's a good question, right?
• 57:02
  SPEAKER_00: And I do think the expectation is certainly from the teams
• 57:05
  SPEAKER_00: that we should have career ladders, right?
• 57:25
  SPEAKER_00: Maintenance work,
• 57:26
  SPEAKER_00: blue work,
• 57:27
  SPEAKER_00: gel work,
• 57:27
  SPEAKER_00: whatever you want to call it,
• 57:28
  SPEAKER_00: I think gets like underemphasized and flashy things that actually work
• 57:32
  SPEAKER_00: and get overemphasized.
• 57:33
  SPEAKER_00: I think that's definitely true.
• 57:36
  SPEAKER_00: So I'm still a believer in career laddering, right?
• 57:38
  SPEAKER_00: I think it's still valuable.
• 57:40
  SPEAKER_00: But what should be there, I think is like complicated.
• 57:42
  SPEAKER_00: And I think it's like much less clear about what should be it.
• 57:45
  SPEAKER_00: I think, I don't know which consultancy has been selling some of these career ladders.
• 57:49
  SPEAKER_00: We kind of small company by small company,
• 57:51
  SPEAKER_00: you see the exact same career ladder from some like kind of like I don't know,
• 57:55
  SPEAKER_00: like packet you can buy somewhere.
• 57:57
  SPEAKER_00: And so I think all of those are just really outdated,
• 58:00
  SPEAKER_00: but we don't have like the next version of it.
• 58:02
  SPEAKER_00: That said,
• 58:03
  SPEAKER_00: when I think about folks getting to like staff or principal these days,
• 58:07
  SPEAKER_00: like what I really care about is I've been thinking about doing like an add on
• 58:10
  SPEAKER_00: to staff engineer.
• 58:11
  SPEAKER_00: I'll get to it in like, I don't know, the next decade sometime.
• 58:14
  SPEAKER_00: But it's really about decision making and complicated situations.
• 58:18
  SPEAKER_00: And so first, this idea of navigating ambiguity.
• 58:22
  SPEAKER_00: And so at Stripe,
• 58:23
  SPEAKER_00: I remember working on this project where we wanted to go multi-region,
• 58:27
  SPEAKER_00: and I kept getting from the engineers trying to lead it.
• 58:29
  SPEAKER_00: Like, we need product to decide how cross-region replication works,
• 58:34
  SPEAKER_00: or what's the product behavior that we support if there is only the consistency
• 58:40
  SPEAKER_00: and availability, but no partitionability.
• 58:43
  SPEAKER_00: They wanted the product team to make these cap theorem trade-offs, which...
• 58:48
  SPEAKER_00: The product team can't possibly make their own trade-offs, right?
• 58:53
  SPEAKER_00: And what they were doing is they were finding a way to get stuck.
• 58:55
  SPEAKER_00: When instead,
• 58:56
  SPEAKER_00: what you need someone at the staff or principal level to do is to navigate
• 59:00
  SPEAKER_00: an ambiguity by making some trade-offs,
• 59:02
  SPEAKER_00: building conviction,
• 59:03
  SPEAKER_00: figuring out how to make a prototype that tests whether
• 59:06
  SPEAKER_00: the assumptions they've made are valuable and workable or not.
• 59:10
  SPEAKER_00: And so I think these ambiguous problems are still a really challenging one and to me
• 59:15
  SPEAKER_00: a strong marker even today.
• 59:17
  SPEAKER_00: Even with agents, you still have these complicated tradeoffs that you have to make.
• 59:21
  SPEAKER_00: And some of the tradeoffs,
• 59:22
  SPEAKER_00: to your point about kind of understanding the business earlier,
• 59:25
  SPEAKER_00: do come from not just understanding like how the technology works,
• 59:28
  SPEAKER_00: but the product implications.
• 59:30
  SPEAKER_00: And to understand product implications,
• 59:31
  SPEAKER_00: you have to understand what your users are actually trying to do.
• 59:34
  SPEAKER_00: You have to understand the unit economics of like the product that you're offering
• 59:37
  SPEAKER_00: and the cost to service it and to actually what you're charging.
• 59:40
  SPEAKER_00: And so increasingly,
• 59:41
  SPEAKER_00: I think you have to be quite broad to actually work these ambiguous problems.
• 59:46
  SPEAKER_00: But I do think decision making has always been where staff
• 59:49
  SPEAKER_00: and principal engineers have to make the impact.
• 59:52
  SPEAKER_00: And that hasn't changed at all.
• 59:53
  SPEAKER_00: I don't actually think agents are exceptionally good at making these tradeoffs.
• 59:56
  SPEAKER_00: I think the agents often don't even recognize the tradeoffs because they're not in
• 1:00:00
  SPEAKER_00: the context window.
• 1:00:01
  SPEAKER_00: Kind of subtle, implicit things that live kind of outside of the software.
• 1:00:06
  SPEAKER_02: What about Eng1, Eng2 careers?
• 1:00:09
  SPEAKER_02: I just had a senior engineer ask me saying, so,
• 1:00:11
  SPEAKER_02: you know, like,
• 1:00:12
  SPEAKER_02: AI clearly has gotten as good as an Eng1,
• 1:00:15
  SPEAKER_02: Eng2 writing code, because that's what we expected a lot of times from them.
• 1:00:19
  SPEAKER_02: And then this person was saying that,
• 1:00:20
  SPEAKER_02: well, at some point it'll come to senior, but it's not there right now.
• 1:00:23
  SPEAKER_02: But I still remember this one,
• 1:00:24
  SPEAKER_02: because obviously there's truth to it,
• 1:00:25
  SPEAKER_02: but I In your org,
• 1:00:28
  SPEAKER_02: how do you think of Eng1, Eng2,
• 1:00:30
  SPEAKER_02: new grad,
• 1:00:31
  SPEAKER_02: or people who are under a senior,
• 1:00:34
  SPEAKER_02: they don't yet have the battle scars or the expertise or the judgment
• 1:00:37
  SPEAKER_02: that you can fully trust them, both in terms of hiring, but also developing them?
• 1:00:41
  SPEAKER_00: So one of the things I try to stay away from is I call it artificial specificity.
• 1:00:45
  SPEAKER_00: And so what's the difference between an Eng1 and an Eng2?
• 1:00:49
  SPEAKER_00: And I think that's actually pretty hard to be super concrete about it.
• 1:00:52
  SPEAKER_00: I think a lot of companies successfully say the difference is three years of work experience.
• 1:00:57
  SPEAKER_00: And then you say, is that equitable?
• 1:00:59
  SPEAKER_00: And like, I don't know if there's any like super equitable way to evaluate NG1s versus NG2.
• 1:01:03
  SPEAKER_00: And again,
• 1:01:04
  SPEAKER_00: a really bad NG1 you can identify,
• 1:01:07
  SPEAKER_00: but the difference in like a really good NG1 and NG2 often is time and role in terms
• 1:01:11
  SPEAKER_00: of just like building more kind of context over time.
• 1:01:15
  SPEAKER_00: But it's not like it's not like super like they can do this or can't do this,
• 1:01:18
  SPEAKER_00: especially with,
• 1:01:19
  SPEAKER_00: you know,
• 1:01:20
  SPEAKER_00: the coding harnesses like they can do anything but actually deciding
• 1:01:24
  SPEAKER_00: whether they should be doing it increasingly, increasingly tricky.
• 1:01:28
  SPEAKER_00: And in the wrong situation, we're getting a lot of direction.
• 1:01:31
  SPEAKER_00: You can't even perceive their judgment in a lot of cases.
• 1:01:34
  SPEAKER_00: Right.
• 1:01:34
  SPEAKER_00: So I actually like hear less and less about some of these things
• 1:01:38
  SPEAKER_00: where I think just general things like time and level stuff like
• 1:01:42
  SPEAKER_00: that is probably good enough.
• 1:01:44
  SPEAKER_00: For a lot of these,
• 1:01:45
  SPEAKER_00: I do worry that getting incredibly detailed on these criteria is like a bit of
• 1:01:50
  SPEAKER_00: a like a fake victory where it's like, oh, it's made it really precise.
• 1:01:55
  SPEAKER_00: But often you've been in like calibration meetings where there are people who play
• 1:02:00
  SPEAKER_00: to the rubric.
• 1:02:01
  SPEAKER_00: I remember at one company I worked at, we had to get to like staff.
• 1:02:04
  SPEAKER_00: There was like a mentoring requirement.
• 1:02:06
  SPEAKER_00: And so we'd have people that literally went out and like would talk to someone and
• 1:02:10
  SPEAKER_00: then be like report them as like a mentee.
• 1:02:13
  SPEAKER_00: And they were like collecting mentees.
• 1:02:15
  SPEAKER_00: And then you talk to that person that I didn't know why I was talking to them.
• 1:02:18
  SPEAKER_00: They just talked to me once.
• 1:02:20
  SPEAKER_00: And so like this is where if you actually create like the you know,
• 1:02:23
  SPEAKER_00: like you get what you measure.
• 1:02:25
  SPEAKER_00: So I really think for promotions, there's always been a lot of judgment.
• 1:02:29
  SPEAKER_00: Whenever you try to remove the judgment,
• 1:02:31
  SPEAKER_00: I actually don't think you get good outcomes there either.
• 1:02:34
  SPEAKER_00: And so having the rubric to help guide people,
• 1:02:36
  SPEAKER_00: I think that's useful, but ultimately it's like pretty subjective.
• 1:02:40
  SPEAKER_00: And for a lot of these things,
• 1:02:41
  SPEAKER_00: I think it actually having kind of constraints is more interesting
• 1:02:45
  SPEAKER_00: than having really comprehensive rubrics that are used to make judgment.
• 1:02:49
  SPEAKER_00: So here's an example.
• 1:02:50
  SPEAKER_00: So something you did at Carta.
• 1:02:52
  SPEAKER_00: Well, at Carta, there's a lot of cost pressure.
• 1:02:54
  SPEAKER_00: Cost pressure, meaning that like to reduce costs of the, let's say, org or info or whatever.
• 1:02:58
  SPEAKER_00: To reduce or manage costs.
• 1:03:00
  SPEAKER_02: Yes.
• 1:03:00
  SPEAKER_00: Exactly.
• 1:03:01
  SPEAKER_00: And so I actually had like a ratio.
• 1:03:02
  SPEAKER_00: We can't have more than this number of staff engineers relative to the number.
• 1:03:08
  SPEAKER_00: And there just, you was not possible to exceed that ratio.
• 1:03:12
  SPEAKER_00: That was very annoying to a lot of folks, right?
• 1:03:15
  SPEAKER_00: But I think it actually is more honest where the industry was like 15 years ago.
• 1:03:20
  SPEAKER_00: 15 years ago, I think there wasn't a role past senior in most companies.
• 1:03:24
  SPEAKER_00: Like senior really was the ultimate role for almost every company.
• 1:03:28
  SPEAKER_00: And so, you know,
• 1:03:29
  SPEAKER_00: as people have gotten like further along in their careers and we have more people
• 1:03:32
  SPEAKER_00: with like 20,
• 1:03:33
  SPEAKER_00: 30, 40 years of software experience, they have opened up more of these levels.
• 1:03:37
  SPEAKER_00: But like a lot of these levels are like ultimately more like time and roll kind
• 1:03:42
  SPEAKER_00: of titles rather than like really like a definitive like I try not to worry quite
• 1:03:52
  SPEAKER_00: as much about the details.
• 1:03:54
  SPEAKER_00: And I do think having a hard block of one or one to eight or whatever it is,
• 1:04:00
  SPEAKER_00: is really helpful if what you're trying to do is manage costs.
• 1:04:04
  SPEAKER_00: Because when you're managing costs,
• 1:04:05
  SPEAKER_00: what you have to be honest about is that you're managing costs.
• 1:04:09
  SPEAKER_00: And so at Carta, that was kind of the situation we're in.
• 1:04:11
  SPEAKER_00: Now at Imprint, like we're not trying to manage costs.
• 1:04:14
  SPEAKER_00: We're trying to manage velocity and quality level.
• 1:04:16
  SPEAKER_00: And so we haven't thought about that at all.
• 1:04:19
  SPEAKER_00: But this is where I think part of leadership is knowing what you're doing.
• 1:04:23
  SPEAKER_00: Explaining how you're doing it and then letting people accept the consequences of that.
• 1:04:28
  SPEAKER_00: And so because of Carta, we were going to have like a fixed ratio.
• 1:04:31
  SPEAKER_00: That meant we had to start shifting hiring to be less senior.
• 1:04:35
  SPEAKER_00: So we could actually have more of a pipeline of folks coming in and filling those levels.
• 1:04:39
  SPEAKER_00: From that fix, a lot of things came from it, which worked really well.
• 1:04:43
  SPEAKER_00: But it wasn't if we had just tried to fix it without figuring out the other parts of
• 1:04:46
  SPEAKER_00: the hiring earlier in the funnel wouldn't have worked.
• 1:04:49
  SPEAKER_00: But I don't know,
• 1:04:50
  SPEAKER_00: I'm less of a believer in kind of like a perfect description of things that are true
• 1:04:56
  SPEAKER_00: than I was earlier in my career.
• 1:04:58
  SPEAKER_00: Just so many exceptions to everything.
• 1:05:00
  SPEAKER_02: The thing with like the rubrics and expectations,
• 1:05:02
  SPEAKER_02: like it used to be,
• 1:05:03
  SPEAKER_02: you know,
• 1:05:03
  SPEAKER_02: when both of us worked at Uber,
• 1:05:06
  SPEAKER_02: you later worked at Stripe,
• 1:05:07
  SPEAKER_02: it was pretty well understood what was expected of the role.
• 1:05:10
  SPEAKER_02: And, you know,
• 1:05:10
  SPEAKER_02: with the levels, like, yes,
• 1:05:11
  SPEAKER_02: I agree that I inch one inch to senior,
• 1:05:13
  SPEAKER_02: these can be murky, but there was a pretty clear expectation at some point.
• 1:05:16
  SPEAKER_02: For example, a senior You could trust them.
• 1:05:19
  SPEAKER_02: Typically,
• 1:05:20
  SPEAKER_02: I think the industry started to understand at some point for like closer to
• 1:05:23
  SPEAKER_02: a decade, a senior could trust them with a project.
• 1:05:25
  SPEAKER_02: If they had junior engineers, they would mentor them.
• 1:05:28
  SPEAKER_02: A staff, you could trust them to set the direction of a unit or multiple projects and so on.
• 1:05:33
  SPEAKER_02: And the NG1 and NG2, they could execute well, coding without too many issues, took feedback.
• 1:05:39
  SPEAKER_02: They were kind of like, almost like, they were like apprentice levels.
• 1:05:41
  SPEAKER_02: Like I think NG1 and NG2,
• 1:05:43
  SPEAKER_02: it wasn't a serious promotion in terms of, it was just, it wasn't a destination.
• 1:05:47
  SPEAKER_02: It was just, they're growing.
• 1:05:49
  SPEAKER_02: Some companies even had the expectation as Uber that you need to grow to a certain level.
• 1:05:52
  SPEAKER_02: But they were like, almost like apprentice, honestly.
• 1:05:54
  SPEAKER_02: Like they were just kind of getting to that, to have good judgment and all these things.
• 1:05:59
  SPEAKER_02: Now that...
• 1:06:01
  SPEAKER_02: We're all using AI harnesses a lot more, including for reviews.
• 1:06:05
  SPEAKER_02: Code reviews are slowly going away as well.
• 1:06:07
  SPEAKER_02: We're doing less of what we used to do,
• 1:06:09
  SPEAKER_02: which is coding and the very visible feedback between each other.
• 1:06:14
  SPEAKER_02: How would you define What's the role of a software engineer is?
• 1:06:18
  SPEAKER_02: Is it different from before?
• 1:06:20
  SPEAKER_02: Is it more ambitious?
• 1:06:22
  SPEAKER_02: How do you think about it?
• 1:06:23
  SPEAKER_02: Because it is changing.
• 1:06:24
  SPEAKER_02: I feel it's getting more ambitious somehow,
• 1:06:27
  SPEAKER_02: but I'm not sure I'm able to put my finger on exactly how,
• 1:06:31
  SPEAKER_02: especially from a CTO perspective.
• 1:06:32
  SPEAKER_02: And is this like the general role or is this like the level three?
• 1:06:35
  SPEAKER_02: No, this is the general software engineering role.
• 1:06:38
  SPEAKER_02: Because I feel each role has changed a lot.
• 1:06:41
  SPEAKER_02: Maybe the staff role,
• 1:06:42
  SPEAKER_02: the staff engineers never did too much writing code at like mid-sized and
• 1:06:46
  SPEAKER_02: above companies because they were busy making sure we're building the right thing.
• 1:06:49
  SPEAKER_02: So maybe it's hard to separate because now no one is writing too much code.
• 1:06:53
  SPEAKER_02: And even the smallest roles, they will have...
• 1:06:56
  SPEAKER_02: They will just need to decide, are we doing the right thing?
• 1:06:58
  SPEAKER_00: Am I doing it right?
• 1:06:59
  SPEAKER_00: First, I think we're still like early days in terms of where we're going.
• 1:07:03
  SPEAKER_00: And there's certainly people you're going to talk to.
• 1:07:04
  SPEAKER_00: They're like, hey, like the software teams of the future are five people for any size company.
• 1:07:10
  SPEAKER_00: And maybe that's true.
• 1:07:11
  SPEAKER_00: Maybe we'll get there at some point.
• 1:07:12
  SPEAKER_00: But we're definitely not there right now.
• 1:07:14
  SPEAKER_00: We're not there.
• 1:07:15
  SPEAKER_00: I don't know if we're going to get there soon,
• 1:07:17
  SPEAKER_00: but there certainly are companies that are,
• 1:07:19
  SPEAKER_00: you know,
• 1:07:19
  SPEAKER_00: have a small number of engineers spending just a staggering number of tokens
• 1:07:23
  SPEAKER_00: in productive whiz.
• 1:07:24
  SPEAKER_00: And that's like a pretty, a pretty cool thing to see.
• 1:07:27
  SPEAKER_00: Where is the role of software going?
• 1:07:30
  SPEAKER_00: I think we're going to find out.
• 1:07:31
  SPEAKER_00: And this is actually why it's such a fun time to be in the industry right now, right?
• 1:07:36
  SPEAKER_00: The most fun thing is like, I think our profession is changing.
• 1:07:40
  SPEAKER_00: In a much more extreme way than anything I've seen since I entered the industry.
• 1:07:44
  SPEAKER_00: And for me,
• 1:07:45
  SPEAKER_00: like someone who's always been very oriented around the outcomes of
• 1:07:49
  SPEAKER_00: the work I'm doing, it's just been like the most fun time I've had.
• 1:07:53
  SPEAKER_00: But I've also spoken to folks who got basically joy from,
• 1:07:56
  SPEAKER_00: you know, being in the zone, being in that flow state.
• 1:07:59
  SPEAKER_00: And they like have fallen out of love with software because what they loved was like
• 1:08:03
  SPEAKER_00: the actual art of doing it.
• 1:08:05
  SPEAKER_00: And for them, like,
• 1:08:06
  SPEAKER_00: you know,
• 1:08:07
  SPEAKER_00: a few folks, like one person I've spoken with recently, he actually, he's retiring.
• 1:08:11
  SPEAKER_00: It's like, I just don't enjoy writing software anymore.
• 1:08:15
  SPEAKER_00: And he's lost this flow state.
• 1:08:16
  SPEAKER_00: He's like, I'm more productive, but like, I just don't enjoy it.
• 1:08:20
  SPEAKER_00: And so I think the role is shifting, but I think it's shifting in a really interesting way.
• 1:08:24
  SPEAKER_00: And I, to me,
• 1:08:25
  SPEAKER_00: I have this kind of idea of software that the time
• 1:08:28
  SPEAKER_00: to actually implement is approaching zero.
• 1:08:31
  SPEAKER_00: These systems are still very slow in terms of like,
• 1:08:34
  SPEAKER_00: you know, okay, let's say you can instantly implement stuff.
• 1:08:37
  SPEAKER_00: You still have to make all these decisions.
• 1:08:39
  SPEAKER_00: It still doesn't work in all these ways.
• 1:08:41
  SPEAKER_00: It still is going to scale poorly in all these ways.
• 1:08:43
  SPEAKER_00: It's still going to break the user expectation.
• 1:08:45
  SPEAKER_00: It's still going to have like the wrong unit economics to actually be like
• 1:08:48
  SPEAKER_00: a profitable business.
• 1:08:49
  SPEAKER_00: And so I do think even if software were like literally free to write,
• 1:08:54
  SPEAKER_00: it's still really, really, really hard.
• 1:08:57
  SPEAKER_00: And so like today,
• 1:08:58
  SPEAKER_00: you'll see this,
• 1:08:59
  SPEAKER_00: like if software is free,
• 1:09:01
  SPEAKER_00: Then all of a sudden engineers are running ahead of the PRDs from product
• 1:09:05
  SPEAKER_00: and running ahead from the high fidelity mocks from design.
• 1:09:09
  SPEAKER_00: And that's creating a ton of issues for design teams trying to work
• 1:09:11
  SPEAKER_00: with this engineering led model and something we're still trying to figure out
• 1:09:14
  SPEAKER_00: at imprint totally honestly, right?
• 1:09:16
  SPEAKER_02: That also could create opportunities where like, well,
• 1:09:19
  SPEAKER_02: if an engineer also puts on a design hat or a business domain hat and now runs
• 1:09:25
  SPEAKER_02: an experiment full on.
• 1:09:28
  SPEAKER_02: And obviously now you get to like,
• 1:09:30
  SPEAKER_02: there's only so many experiments you can And so I wonder if...
• 1:09:56
  SPEAKER_02: If software is becoming faster,
• 1:09:57
  SPEAKER_02: like as engineers,
• 1:09:58
  SPEAKER_02: we will need to discover the constraints of the other parts of the business,
• 1:10:02
  SPEAKER_02: the domain,
• 1:10:03
  SPEAKER_02: the customers, the reality, like you say, unit economics,
• 1:10:09
  SPEAKER_00: how money can be made.
• 1:10:10
  SPEAKER_00: I think something I thought about a lot working at Carta.
• 1:10:13
  SPEAKER_00: So Carta is a low scale business,
• 1:10:16
  SPEAKER_00: by which I mean there's not like hundreds of thousands of requests per second coming
• 1:10:20
  SPEAKER_00: in.
• 1:10:20
  SPEAKER_00: There's no like Massive infrastructure problems there, but it's incredibly detailed business.
• 1:10:26
  SPEAKER_00: How cap tables work is really, really, really specific.
• 1:10:30
  SPEAKER_00: And it's very complicated.
• 1:10:31
  SPEAKER_00: And there are tons of exceptions.
• 1:10:34
  SPEAKER_00: And then doing accounting.
• 1:10:34
  SPEAKER_02: And it's important, right?
• 1:10:35
  SPEAKER_02: It's a little thing, but you need to get that right.
• 1:10:37
  SPEAKER_00: And the accuracy is really important from like an audibility perspective.
• 1:10:41
  SPEAKER_00: You're also working with law firms that have like a real strong point of view
• 1:10:44
  SPEAKER_00: of how everything should be done very particularly as well.
• 1:10:47
  SPEAKER_00: And you could be in a legal battle.
• 1:10:49
  SPEAKER_00: Between two founders who were arguing about how much equity was actually vested
• 1:10:53
  SPEAKER_00: or something like that.
• 1:10:55
  SPEAKER_00: Similarly,
• 1:10:55
  SPEAKER_00: the other businesses Carta went into,
• 1:10:57
  SPEAKER_00: like the fund administration, also incredibly detail-oriented.
• 1:11:01
  SPEAKER_00: And so there are a lot of businesses out there where
• 1:11:03
  SPEAKER_00: the domain context has always been the hard thing.
• 1:11:06
  SPEAKER_00: And it's not super clear to me if businesses where the domain context is really
• 1:11:10
  SPEAKER_00: the hard part have benefited that much yet from kind of all the AI tools.
• 1:11:16
  SPEAKER_00: It's still incredibly hard to do cap table management because of the details,
• 1:11:20
  SPEAKER_00: the laws,
• 1:11:21
  SPEAKER_00: the relationships with the law firms in terms of training like the paralegals there.
• 1:11:25
  SPEAKER_00: There's like all these little pieces that I think Domain,
• 1:11:28
  SPEAKER_00: like complex domain businesses still have like a lot of defensibility in this day
• 1:11:33
  SPEAKER_00: and age.
• 1:11:34
  SPEAKER_00: And I don't know if that's how that's going to change.
• 1:11:36
  SPEAKER_00: I think it will change.
• 1:11:37
  SPEAKER_00: Every two to three years, there's this kind of like the product engineers are the new king.
• 1:11:41
  SPEAKER_00: Product engineers are the new superhero.
• 1:11:43
  SPEAKER_00: Kind of like meme that comes around.
• 1:11:45
  SPEAKER_00: Now it's the AI engineer.
• 1:11:46
  SPEAKER_00: Now it's the AI engineer who really are like product engineers
• 1:11:48
  SPEAKER_00: that use like AI techniques, right?
• 1:11:50
  SPEAKER_00: And so the question is...
• 1:11:51
  SPEAKER_02: Which is pretty much every product engineering these days.
• 1:11:54
  SPEAKER_00: 100%, right?
• 1:11:54
  SPEAKER_00: So it's unclear.
• 1:11:55
  SPEAKER_00: I mean, I've never really quite understood what AI engineer means.
• 1:11:59
  SPEAKER_00: I think it means someone who uses harnesses and wants to get paid a lot
• 1:12:02
  SPEAKER_00: of compensation is I think what it means.
• 1:12:04
  SPEAKER_00: But it probably means something else too that I've just sort of missed the nuances on.
• 1:12:08
  SPEAKER_00: But like...
• 1:12:10
  SPEAKER_00: Can you actually get individuals to hold all this context in their head?
• 1:12:13
  SPEAKER_00: So even today,
• 1:12:14
  SPEAKER_00: you know,
• 1:12:15
  SPEAKER_00: people used to talk about like the front engineer who's actually a good designer or
• 1:12:18
  SPEAKER_00: the designer who could actually write production running code.
• 1:12:21
  SPEAKER_00: That person's always been rare.
• 1:12:22
  SPEAKER_00: And now a designer with like a little bit of taste can write production code, right?
• 1:12:27
  SPEAKER_00: And vice versa, a front engineer with a good design taste can do design.
• 1:12:32
  SPEAKER_00: Why aren't we seeing more of that yet?
• 1:12:33
  SPEAKER_02: And so I think that's like a Well,
• 1:12:36
  SPEAKER_02: it's a really good question because I was asking the same thing.
• 1:12:39
  SPEAKER_02: I saw some data from linear showing that PRs for designers and product managers are up.
• 1:12:45
  SPEAKER_02: And I was like, oh,
• 1:12:46
  SPEAKER_02: actually,
• 1:12:46
  SPEAKER_02: someone messaged this to me,
• 1:12:49
  SPEAKER_02: a fellow engineering manager said like,
• 1:12:51
  SPEAKER_02: hang on,
• 1:12:52
  SPEAKER_02: I've been asking around,
• 1:12:53
  SPEAKER_02: like, we should be seeing more designers push to production, right?
• 1:12:56
  SPEAKER_02: Or product managers.
• 1:12:57
  SPEAKER_02: Asked around 10 companies.
• 1:12:59
  SPEAKER_02: I asked around another 10, including the likes of linear, ramp, open AI.
• 1:13:03
  SPEAKER_02: I have yet to hear.
• 1:13:05
  SPEAKER_02: Except for like some exotic edge cases or like just one example
• 1:13:10
  SPEAKER_02: of designers pushing production code.
• 1:13:11
  SPEAKER_02: They will find bugs,
• 1:13:12
  SPEAKER_02: they will identify them,
• 1:13:14
  SPEAKER_02: but they will still get an engineer involved who confirms this approach works in
• 1:13:19
  SPEAKER_02: the code base, especially when we're talking about outside of prototyping.
• 1:13:22
  SPEAKER_02: They do prototype more.
• 1:13:24
  SPEAKER_02: But even if we're not there, I wonder if it's an accountability thing.
• 1:13:30
  SPEAKER_02: Even though I can change a light bulb,
• 1:13:33
  SPEAKER_02: I will still call the electrician when I need to do something a bit more on my house
• 1:13:37
  SPEAKER_02: because it's electricity, right?
• 1:13:39
  SPEAKER_02: And I can read the book.
• 1:13:41
  SPEAKER_02: I wonder if it's this or specialization.
• 1:13:43
  SPEAKER_00: I don't know.
• 1:13:44
  SPEAKER_00: You know,
• 1:13:44
  SPEAKER_00: one of the things I think a lot about is like there's one worldview right now,
• 1:13:48
  SPEAKER_00: which is like if you have a great design system and you've actually used
• 1:13:51
  SPEAKER_00: that design system, you don't need product designers anymore.
• 1:13:54
  SPEAKER_00: That's like a viewpoint that a few people have.
• 1:13:56
  SPEAKER_00: I haven't found that to be true, though, even with a good design system.
• 1:14:01
  SPEAKER_00: Understanding how all these different components fit together,
• 1:14:03
  SPEAKER_00: understanding the missing components in your design system,
• 1:14:06
  SPEAKER_00: figuring out when you have like tradeoffs across different screens,
• 1:14:09
  SPEAKER_00: how you manage those tradeoffs while presenting like the unified experience for
• 1:14:13
  SPEAKER_00: the user.
• 1:14:14
  SPEAKER_00: These are still really hard things to do.
• 1:14:16
  SPEAKER_00: And so, you know, I know attention is all you need is actually not about human attention at all.
• 1:14:22
  SPEAKER_00: But I do think there's some dimension where people are still constrained on attention.
• 1:14:26
  SPEAKER_00: Great designers and great product designers and great design system designers
• 1:14:30
  SPEAKER_00: as well are all so constrained on the details of what they're doing to do it well
• 1:14:36
  SPEAKER_00: that they just don't have a ton of time to also be branching out.
• 1:14:39
  SPEAKER_00: Does that inherently have to be true?
• 1:14:42
  SPEAKER_00: I don't think it's inherently has to be true.
• 1:14:44
  SPEAKER_00: And I do think...
• 1:14:45
  SPEAKER_00: In theory,
• 1:14:46
  SPEAKER_00: if you have a great design system and you have a ton of consistency and a ton
• 1:14:49
  SPEAKER_00: of linters in terms of like it has to be used this way,
• 1:14:52
  SPEAKER_00: all of a sudden your design system folks,
• 1:14:55
  SPEAKER_00: your product designers can be just looking at the exceptions much more aggressively.
• 1:14:58
  SPEAKER_00: That is where we're trying to get to at Imprint for what it's worth,
• 1:15:02
  SPEAKER_00: where the base case is just done by engineering.
• 1:15:05
  SPEAKER_00: Using the stock design system and product design is more working on
• 1:15:08
  SPEAKER_00: the really complicated kind of versions of it,
• 1:15:11
  SPEAKER_00: along with extending the design system of the design system folks.
• 1:15:14
  SPEAKER_00: It's not working that way yet, though.
• 1:15:15
  SPEAKER_00: Like, it's still it's still a little bit tricky.
• 1:15:18
  SPEAKER_00: But, you know,
• 1:15:19
  SPEAKER_00: as as like the folks deep in AI say, like,
• 1:15:21
  SPEAKER_00: I kind of do assume this is like a quote unquote skill issue and that we will get to
• 1:15:25
  SPEAKER_00: the other side of it.
• 1:15:26
  SPEAKER_00: But it's still a skill issue for us.
• 1:15:28
  SPEAKER_00: We're still figuring that out.
• 1:15:30
  SPEAKER_02: One thing related to this is you wrote revised rules of engineering management,
• 1:15:34
  SPEAKER_02: a really nice article, we'll link it in the show notes below.
• 1:15:36
  SPEAKER_02: And one of the rules that I want to highlight,
• 1:15:38
  SPEAKER_02: you say we wrote durable high ownership team,
• 1:15:40
  SPEAKER_02: I'm quoting you,
• 1:15:41
  SPEAKER_02: durable high ownership team, so domain contexts are even more important.
• 1:15:45
  SPEAKER_02: One of my biggest lessons at Uber was that persistent,
• 1:15:47
  SPEAKER_02: durable teams work magic by accumulating domain concepts,
• 1:15:50
  SPEAKER_02: building a sense of camaraderie,
• 1:15:52
  SPEAKER_02: and feeling increasingly a strong sense of ownership over an area as they continue
• 1:15:56
  SPEAKER_02: to work on it.
• 1:15:57
  SPEAKER_02: Now, this was from Uber,
• 1:15:58
  SPEAKER_02: like what,
• 1:15:58
  SPEAKER_02: like 2014,
• 1:15:59
  SPEAKER_02: 15, so like more than 10 years ago, and you're saying that you feel this is...
• 1:16:05
  SPEAKER_00: I think this is the only way to build skilled organizations.
• 1:16:08
  SPEAKER_00: And it's interesting, though,
• 1:16:09
  SPEAKER_00: I think this is this seems kind of like obvious,
• 1:16:11
  SPEAKER_00: but it's actually a bit of like a non-consensus take, if you will.
• 1:16:16
  SPEAKER_00: And so a lot of times you're at a company,
• 1:16:18
  SPEAKER_00: say there is 50 engineers and you have a really important project for a partner.
• 1:16:21
  SPEAKER_00: That project's late.
• 1:16:23
  SPEAKER_00: There's still the Mythical Man Month thing.
• 1:16:24
  SPEAKER_00: They're like, hey, we're moving 15 more people to work on this key project.
• 1:16:28
  SPEAKER_00: And, you know, the Mythical Man Month, I want to say was written in like 80, 84, 75.
• 1:16:32
  SPEAKER_00: 1975 and the second version 95.
• 1:16:36
  SPEAKER_00: And it's that that's a while ago.
• 1:16:38
  SPEAKER_00: And so more than 50 years, we know this doesn't work.
• 1:16:42
  SPEAKER_00: And so first,
• 1:16:43
  SPEAKER_00: like when people do things like this,
• 1:16:44
  SPEAKER_00: a lot of it's like optics and creating the perception of doing everything possible.
• 1:16:48
  SPEAKER_00: Yes.
• 1:16:48
  SPEAKER_00: So that when you miss it's not it's not your fault.
• 1:16:51
  SPEAKER_00: But actually,
• 1:16:52
  SPEAKER_00: not only does it not work,
• 1:16:53
  SPEAKER_00: it also destroys the thing that does work,
• 1:16:56
  SPEAKER_00: which is creating little pods that are able to own areas.
• 1:16:59
  SPEAKER_00: And so when I joined Stripe,
• 1:17:03
  SPEAKER_00: I took over kind of the team Jorge was leading at the time,
• 1:17:06
  SPEAKER_00: and he moved on to a different part of the company.
• 1:17:08
  SPEAKER_00: I think to lead Connect.
• 1:17:09
  SPEAKER_00: And so I had 30 people and one manager who was managing like four or five of them.
• 1:17:14
  SPEAKER_00: And then I was directly managing, say, like 23, 24 people.
• 1:17:18
  SPEAKER_00: The first thing I did was like, all right, what are some pods?
• 1:17:21
  SPEAKER_00: And figuring out like some areas I could put together who could own areas.
• 1:17:25
  SPEAKER_00: And then once I saw some progress,
• 1:17:27
  SPEAKER_00: I just stopped thinking about them entirely until something went really wrong.
• 1:17:31
  SPEAKER_00: So I could focus on the bigger priorities for me,
• 1:17:34
  SPEAKER_00: which is like the problems you couldn't solve.
• 1:17:35
  SPEAKER_00: This works so well.
• 1:17:37
  SPEAKER_00: And so at Uber, I did the same thing.
• 1:17:40
  SPEAKER_00: I came into Imprint, did the same thing as well.
• 1:17:42
  SPEAKER_00: Same at Com.
• 1:17:45
  SPEAKER_00: Carto was like a really well kind of scaled organization by the time I joined it.
• 1:17:48
  SPEAKER_00: So I didn't need to do the same thing there.
• 1:17:50
  SPEAKER_00: I think this just works incredibly well.
• 1:17:53
  SPEAKER_00: I think if you do this well,
• 1:17:55
  SPEAKER_00: that people actually do better work than you will from top-down dictation,
• 1:17:59
  SPEAKER_00: simply because they understand it really well.
• 1:18:01
  SPEAKER_00: And it gives you the ability to actually put your attention on the highest leverage
• 1:18:05
  SPEAKER_00: or most painful parts of the company.
• 1:18:07
  SPEAKER_00: And so, yeah, I think this is a strange non-consensus take, but it just works incredibly well.
• 1:18:13
  SPEAKER_00: But optically, it almost always looks wrong.
• 1:18:16
  SPEAKER_00: And that's like one of the reasons it's hard to do,
• 1:18:18
  SPEAKER_00: where you have like a partner launch and you're like,
• 1:18:20
  SPEAKER_00: hey, I'm not going to move these folks.
• 1:18:24
  SPEAKER_00: I'm going to let them stay on what they're doing.
• 1:18:25
  SPEAKER_00: It's really important.
• 1:18:27
  SPEAKER_00: Instead, the team that's on the critical path, we're going to work hard as hell together.
• 1:18:31
  SPEAKER_00: But like, We're going to burn to get through it.
• 1:18:35
  SPEAKER_00: We're not going to pull everyone over.
• 1:18:36
  SPEAKER_00: Because if you don't do that.
• 1:18:37
  SPEAKER_02: Or what you might have done in the past is,
• 1:18:40
  SPEAKER_02: especially in SERP, where it was, you had meetings, recruitment, all that.
• 1:18:44
  SPEAKER_02: You would say, like, for this team on a critical path, we removed them from all of the BS.
• 1:18:48
  SPEAKER_02: Totally.
• 1:18:48
  SPEAKER_02: The recruitment, the university trip.
• 1:18:50
  SPEAKER_02: You don't need to attend all hands and all these things.
• 1:18:53
  SPEAKER_02: So you can be, which actually, by the way, works so much better than adding people.
• 1:18:58
  SPEAKER_02: And also sometimes telling people like, look, this will be a two-week push.
• 1:19:01
  SPEAKER_02: Anyone who can commit to it, please do so, including putting extra hours.
• 1:19:06
  SPEAKER_02: And in return,
• 1:19:07
  SPEAKER_02: you can take time off afterwards or,
• 1:19:09
  SPEAKER_02: you know, like you create incentives and you just treat them as adults.
• 1:19:13
  SPEAKER_02: And you're saying like,
• 1:19:14
  SPEAKER_02: can you and oftentimes people will like I know in my life outside of work,
• 1:19:18
  SPEAKER_02: sometimes you are OK taking a thing for this one thing,
• 1:19:22
  SPEAKER_02: especially when you know that I will repay you in kind somehow.
• 1:19:26
  SPEAKER_00: And if you don't do that, the thing that happens is actually at a real growing company,
• 1:19:31
  SPEAKER_00: there's a crisis every day.
• 1:19:34
  SPEAKER_00: And that means if you rotate people to crises, there's a crisis for everyone every day.
• 1:19:40
  SPEAKER_00: And it creates this sense of devastation.
• 1:19:42
  SPEAKER_00: And so I remember talking with someone at Stripe one or two years in.
• 1:19:45
  SPEAKER_00: They were talking about this.
• 1:19:47
  SPEAKER_00: And he's like,
• 1:19:47
  SPEAKER_00: the way Stripe had run up to that point,
• 1:19:49
  SPEAKER_00: his metaphor was like people were on a wall trying to defend a castle.
• 1:19:53
  SPEAKER_00: And they were always running to the place where they're about
• 1:19:55
  SPEAKER_00: to get like overwhelmed,
• 1:19:56
  SPEAKER_00: but they just couldn't be everywhere because they were getting faster and faster
• 1:19:59
  SPEAKER_00: at running, but they still were not everywhere all at once.
• 1:20:03
  SPEAKER_00: And what we were trying to do was switch this metaphor was like we had many people
• 1:20:06
  SPEAKER_00: in many places.
• 1:20:07
  SPEAKER_00: And so the people working in one spot had to solve that spot,
• 1:20:11
  SPEAKER_00: but it meant they didn't have to be everywhere.
• 1:20:13
  SPEAKER_00: Those are kind of the two tradeoffs.
• 1:20:15
  SPEAKER_00: But to be a successfully scaling company that's growing quickly,
• 1:20:18
  SPEAKER_00: you do have to get to a mode where it's not the same people running everywhere
• 1:20:22
  SPEAKER_00: at once because those people just completely burn out over time.
• 1:20:26
  SPEAKER_00: And there's a certain point where they just can't manage the coverage anymore,
• 1:20:30
  SPEAKER_00: no matter how amazing they are.
• 1:20:32
  SPEAKER_00: Although I think the question with AI is, is that point much further than it was before?
• 1:20:37
  SPEAKER_00: But I'm not sure if it is.
• 1:20:38
  SPEAKER_00: I still think their attention runs out before their ability to write code does.
• 1:20:42
  SPEAKER_02: Also recently,
• 1:20:43
  SPEAKER_02: something that I was thinking about this with
• 1:20:45
  SPEAKER_02: the durable high ownership teams is just an example with Slack
• 1:20:49
  SPEAKER_02: on how you have Google,
• 1:20:51
  SPEAKER_02: Google Chat, you have Mattermost, you have Microsoft Teams and Slack.
• 1:20:56
  SPEAKER_02: Let's say these are four big
• 1:20:59
  SPEAKER_02: You can
• 1:21:04
  SPEAKER_02: also instruct an AI to copy Slack.
• 1:21:07
  SPEAKER_02: And here's the interesting thing.
• 1:21:08
  SPEAKER_02: If you do, the AI would copy Slack's UI or find open source things.
• 1:21:12
  SPEAKER_02: First of all,
• 1:21:13
  SPEAKER_02: there's a lot of decisions that have never been documented that are behind
• 1:21:15
  SPEAKER_02: the scenes that people at Slack will know and it takes years.
• 1:21:18
  SPEAKER_02: Which if you build it,
• 1:21:19
  SPEAKER_02: you'll figure it out if you're big enough from the concurrency,
• 1:21:21
  SPEAKER_02: deliverability, platforms, yada, yada, yada.
• 1:21:24
  SPEAKER_02: But taking that aside,
• 1:21:26
  SPEAKER_02: Slack launched Slack Agents,
• 1:21:28
  SPEAKER_02: which was a super sweet integration with coding agents that do the work inside
• 1:21:33
  SPEAKER_02: of Slack.
• 1:21:34
  SPEAKER_02: It just works beautifully.
• 1:21:35
  SPEAKER_02: It's been well thought out.
• 1:21:36
  SPEAKER_02: Clearly,
• 1:21:38
  SPEAKER_02: this is a team that has a domain context,
• 1:21:40
  SPEAKER_02: and they've clearly been working behind the scenes with Teams partners.
• 1:21:44
  SPEAKER_02: I'm kind of like, hang on, why has none of the other competitors launched it?
• 1:21:48
  SPEAKER_02: Why has Google Chat,
• 1:21:49
  SPEAKER_02: who have amazing people as well,
• 1:21:50
  SPEAKER_02: these are all people that have the domain,
• 1:21:52
  SPEAKER_02: and I think this is where I'm starting to...
• 1:21:54
  SPEAKER_02: This one example just started to realize there is probably value
• 1:21:57
  SPEAKER_02: in Slack having all these people who are working.
• 1:21:59
  SPEAKER_02: I'm sure we would be horrified of how many people work there.
• 1:22:02
  SPEAKER_02: I know it's from Uber.
• 1:22:03
  SPEAKER_02: Why does Uber have this many people?
• 1:22:05
  SPEAKER_02: But they're working on this,
• 1:22:06
  SPEAKER_02: but they're not only able to operate what they have,
• 1:22:09
  SPEAKER_02: But they keep reinventing what customers will want as the world changes.
• 1:22:14
  SPEAKER_02: The other companies seem to have not responded,
• 1:22:17
  SPEAKER_02: even though agents have been here for a while, they just haven't responded.
• 1:22:20
  SPEAKER_02: Slack has not only responded,
• 1:22:21
  SPEAKER_02: they did something that is objectively good, and now it's copyable.
• 1:22:26
  SPEAKER_02: How did you get there, right?
• 1:22:28
  SPEAKER_00: There's some paper about the size of the bureaucracy of managing the British empire
• 1:22:33
  SPEAKER_00: and the size of bureaucracy.
• 1:22:35
  SPEAKER_00: The number of bureaucrats kept growing even as the territory getting managed kept shrinking.
• 1:22:40
  SPEAKER_00: And there's sort of this inherent kind of thing where companies do just expand
• 1:22:44
  SPEAKER_00: and create bureaucracy and create more kind of overhead.
• 1:22:48
  SPEAKER_00: There's something there where sometimes companies have just kind of lost the plot
• 1:22:52
  SPEAKER_00: on their ability to actually move.
• 1:22:54
  SPEAKER_00: But like my assumption,
• 1:22:55
  SPEAKER_00: I think this is true for the Muse work for Meta,
• 1:22:58
  SPEAKER_00: my impression is that when really interesting good products come out,
• 1:23:01
  SPEAKER_00: there is one or two highly empowered people that are connected to the founder,
• 1:23:07
  SPEAKER_00: the CEO, the executive team that are pushing it through.
• 1:23:11
  SPEAKER_00: And that are able to make painful tradeoffs that are not well liked.
• 1:23:15
  SPEAKER_00: And those can be like legal versus like company tradeoffs.
• 1:23:18
  SPEAKER_00: Those can be product tradeoffs.
• 1:23:20
  SPEAKER_00: Those can be,
• 1:23:20
  SPEAKER_00: there are,
• 1:23:21
  SPEAKER_00: you know,
• 1:23:21
  SPEAKER_00: the sacred kind of elements of how things have to be done, not doing it that way.
• 1:23:26
  SPEAKER_00: And so like my guess is like for Slack,
• 1:23:29
  SPEAKER_00: there was some sponsor and look,
• 1:23:31
  SPEAKER_00: people hate overemphasizing executives,
• 1:23:34
  SPEAKER_00: but I do think executive sponsorship to actually empower folks
• 1:23:37
  SPEAKER_00: to do something difficult.
• 1:23:39
  SPEAKER_00: Imprint moved over to linear, you know, like three or four months ago from Jira.
• 1:23:42
  SPEAKER_00: We did it in like less than four weeks.
• 1:23:45
  SPEAKER_00: And there were basically zero people that thought it was a good idea when I decided to do it.
• 1:23:50
  SPEAKER_00: We still did it in less than four weeks.
• 1:23:51
  SPEAKER_00: And now people are really glad we did.
• 1:23:53
  SPEAKER_00: It solved a lot of problems we had about having centralized issue management so
• 1:23:57
  SPEAKER_00: the agents could actually know where tasks were,
• 1:24:00
  SPEAKER_00: pull them down, work them, actually do kind of task unification, et cetera.
• 1:24:04
  SPEAKER_00: We're having a really hard time managing workloads of tasks without that.
• 1:24:07
  SPEAKER_00: But there were like And maybe three people out of like 230 that thought it was
• 1:24:12
  SPEAKER_00: a good idea before I did it.
• 1:24:14
  SPEAKER_00: And that one I just, you know, pushed through.
• 1:24:16
  SPEAKER_00: And I think now people are like, oh, that was a good idea, but they just didn't think it was.
• 1:24:21
  SPEAKER_00: And sometimes you do have to have someone who's willing to take the risk.
• 1:24:25
  SPEAKER_00: And then,
• 1:24:26
  SPEAKER_00: you know,
• 1:24:26
  SPEAKER_00: the flip side is we then need to judge execs and other senior leaders on are
• 1:24:30
  SPEAKER_00: the risks they made us take good.
• 1:24:32
  SPEAKER_00: And so I think three months into the linear migration,
• 1:24:35
  SPEAKER_00: I think,
• 1:24:36
  SPEAKER_00: you know,
• 1:24:36
  SPEAKER_00: no one talks about Jira anymore, but certainly no one's upset about the change.
• 1:24:40
  SPEAKER_00: People are really glad with it.
• 1:24:42
  SPEAKER_00: But conversely,
• 1:24:42
  SPEAKER_00: if people had hated it,
• 1:24:44
  SPEAKER_00: like they should be like, you know, rallying to get me fired.
• 1:24:47
  SPEAKER_00: Right.
• 1:24:47
  SPEAKER_00: But I think a lot of times people don't get held accountable to this.
• 1:24:51
  SPEAKER_00: And so that's the flip side of that highly empowered executive sponsor
• 1:24:54
  SPEAKER_00: that does make these great products.
• 1:24:56
  SPEAKER_00: Sometimes we let them do incredibly boneheaded things and don't hold them to account.
• 1:25:01
  SPEAKER_02: Great segue to talking about executives.
• 1:25:03
  SPEAKER_02: You've been a CTO, which is a former executive.
• 1:25:07
  SPEAKER_02: Can you tell me what in your interpretation an executive is and what is
• 1:25:12
  SPEAKER_02: the career path today to get to that level from an engineer?
• 1:25:16
  SPEAKER_02: Like, okay, I like the idea of executive.
• 1:25:18
  SPEAKER_02: I like that to be able to make decisions,
• 1:25:20
  SPEAKER_02: including unpopular ones, helping people, helping companies.
• 1:25:24
  SPEAKER_02: What was the old path and what's the new path, if there's any?
• 1:25:28
  SPEAKER_00: So I think the old path,
• 1:25:29
  SPEAKER_00: your software engineer for some number of years, could be pretty short.
• 1:25:32
  SPEAKER_00: Then you get into management,
• 1:25:34
  SPEAKER_00: and then you climb through middle management, and then you get to the CTO role.
• 1:25:37
  SPEAKER_02: And middle management, end manager, senior end director.
• 1:25:40
  SPEAKER_02: Exactly.
• 1:25:41
  SPEAKER_02: And so I think there are a lot of
• 1:25:42
  SPEAKER_00: problems with that.
• 1:25:43
  SPEAKER_00: First, it means that often the people that were selected
• 1:25:46
  SPEAKER_00: for management initially weren't like the most focused on the technical pieces
• 1:25:49
  SPEAKER_00: the work because they're trying to get promoted to management.
• 1:25:51
  SPEAKER_00: And then the selection bias is really towards people that are able to operate well.
• 1:25:55
  SPEAKER_00: Which doesn't necessarily have a whole lot in common with technology side.
• 1:25:59
  SPEAKER_00: Often they happen to be really good technology,
• 1:26:01
  SPEAKER_00: but there wasn't like a strong kind of selection bias for it.
• 1:26:04
  SPEAKER_00: But you really do have to be a good bureaucrat to be an executive.
• 1:26:07
  SPEAKER_00: And this is like one of the interesting challenges where a lot
• 1:26:09
  SPEAKER_00: of my work is incentive management.
• 1:26:11
  SPEAKER_00: It's knowing,
• 1:26:11
  SPEAKER_00: hey, if we roll out this sort of performance review, here's how it's going to fail.
• 1:26:15
  SPEAKER_00: And so we just shouldn't do that.
• 1:26:16
  SPEAKER_00: We should do this other thing instead.
• 1:26:18
  SPEAKER_00: And so if you haven't done the reps of being like a bureaucrat,
• 1:26:21
  SPEAKER_00: you actually can't run a function because a lot of running a function is,
• 1:26:25
  SPEAKER_00: in fact, being a bureaucrat.
• 1:26:28
  SPEAKER_02: You learned to be a good bureaucrat.
• 1:26:30
  SPEAKER_00: I was a bureaucrat, right?
• 1:26:31
  SPEAKER_00: And so, I mean, out of necessity.
• 1:26:33
  SPEAKER_00: So at Uber, there weren't really like rubrics.
• 1:26:36
  SPEAKER_00: There wasn't like an interview.
• 1:26:37
  SPEAKER_00: We didn't have any structure how we interviewed when I was there.
• 1:26:40
  SPEAKER_00: So you had to make it all up yourself for your function.
• 1:26:44
  SPEAKER_00: And again,
• 1:26:44
  SPEAKER_00: we were doing tons of interviews and each time we didn't give an offer out,
• 1:26:47
  SPEAKER_00: I was like so pained because I was doing so many interviews.
• 1:26:50
  SPEAKER_00: So I had to figure that out.
• 1:26:51
  SPEAKER_00: And then at Stripe, Stripe was like a much more structurally cohesive company.
• 1:26:56
  SPEAKER_00: And so we did have like a lot of structured process.
• 1:26:58
  SPEAKER_00: And then I got to I worked on a lot of that and learned a lot there.
• 1:27:01
  SPEAKER_02: You got pulled into it.
• 1:27:02
  SPEAKER_02: You picked up the pace.
• 1:27:03
  SPEAKER_00: A hundred percent.
• 1:27:03
  SPEAKER_00: And a lot of the structure,
• 1:27:04
  SPEAKER_00: I thought,
• 1:27:05
  SPEAKER_00: wasn't working well at the point that I joined to kind of like work to try
• 1:27:08
  SPEAKER_00: to iterate and improve little pieces of it because we were growing pretty quickly.
• 1:27:12
  SPEAKER_00: And so really,
• 1:27:13
  SPEAKER_00: you know,
• 1:27:13
  SPEAKER_00: working these middle management jobs,
• 1:27:15
  SPEAKER_00: I think,
• 1:27:16
  SPEAKER_00: did educate me on how to be a good bureaucrat,
• 1:27:18
  SPEAKER_00: which is part of being an effective executive
• 1:27:20
  SPEAKER_00: because you can just allocate processes that work and avoid processes
• 1:27:25
  SPEAKER_00: that don't work.
• 1:27:26
  SPEAKER_00: Think about incentives that work and don't work, structure that does work and doesn't work.
• 1:27:29
  SPEAKER_00: You know,
• 1:27:30
  SPEAKER_00: the Jeffrey Reed scene like a state,
• 1:27:31
  SPEAKER_00: like you're not allowed to be in Silicon Valley if you haven't read seeing as like
• 1:27:35
  SPEAKER_00: a state.
• 1:27:35
  SPEAKER_00: But it's basically a book about how states see citizens and accomplishments and how
• 1:27:40
  SPEAKER_00: that shapes how policy works.
• 1:27:43
  SPEAKER_00: It's the same thing.
• 1:27:43
  SPEAKER_00: Like if you've never been a bureaucrat, you don't know how to see things as a bureaucrat.
• 1:27:47
  SPEAKER_00: But also like if you can only be a bureaucrat, you don't know how anything actually works.
• 1:27:52
  SPEAKER_00: You don't know how software actually gets made.
• 1:27:54
  SPEAKER_00: And so it's like very damaging to you.
• 1:27:57
  SPEAKER_02: Am I getting this right that you're saying to be a good engineering executive,
• 1:28:01
  SPEAKER_02: so VP engineering or CTO,
• 1:28:03
  SPEAKER_02: you want to be excellent at technology,
• 1:28:05
  SPEAKER_02: knowing how it works,
• 1:28:06
  SPEAKER_02: being hands-on if you need to be or just be hands-on and also be a good bureaucrat
• 1:28:10
  SPEAKER_02: where you can manage it and you want both.
• 1:28:12
  SPEAKER_02: And you're saying that if you go the middleman of this route,
• 1:28:15
  SPEAKER_02: oftentimes it might happen that you either never were a good technologist
• 1:28:19
  SPEAKER_02: or you stopped becoming that by the time you get up there.
• 1:28:21
  SPEAKER_02: So you're a great bureaucrat, but not technology.
• 1:28:24
  SPEAKER_02: But if you just go from like an engineer,
• 1:28:26
  SPEAKER_02: a great technologist straight up here,
• 1:28:27
  SPEAKER_02: let's say like you're a startup tomorrow,
• 1:28:29
  SPEAKER_02: congrats to your decision, you will not be a good bureaucrat.
• 1:28:32
  SPEAKER_00: I think that's exactly right.
• 1:28:34
  SPEAKER_00: And it's interesting where oftentimes I think line managers are better kind of And
• 1:28:39
  SPEAKER_00: so this is why I think being an executive is hard and why it's a hard career path is
• 1:28:42
  SPEAKER_00: that it was,
• 1:28:42
  SPEAKER_00: you know,
• 1:28:43
  SPEAKER_00: in the 2010s in particular, you had
• 1:28:44
  SPEAKER_00: to climb these like layers of middle management.
• 1:29:03
  SPEAKER_00: To learn this kind of bureaucratic component of it.
• 1:29:06
  SPEAKER_00: And that was the only way to get scale to actually understand that.
• 1:29:09
  SPEAKER_00: Now those layers are kind of gone.
• 1:29:11
  SPEAKER_00: But the interesting thing is like the other half of the job is now really emphasized
• 1:29:14
  SPEAKER_00: in terms of better decision making,
• 1:29:16
  SPEAKER_00: understanding the actual product,
• 1:29:17
  SPEAKER_00: understanding the actual business,
• 1:29:19
  SPEAKER_00: understanding how software shipped in a way where we kind of de-emphasize that.
• 1:29:22
  SPEAKER_00: So I think, you know, people are like, is it easier?
• 1:29:25
  SPEAKER_00: Is it harder?
• 1:29:25
  SPEAKER_00: I don't think it's like any easier or any harder.
• 1:29:28
  SPEAKER_00: It's a lot harder to become like a bureaucrat now,
• 1:29:31
  SPEAKER_00: which again, make negative connotations, right?
• 1:29:33
  SPEAKER_00: But this is like learning how to actually operate a function is really difficult work.
• 1:29:37
  SPEAKER_00: And as like a C-level,
• 1:29:39
  SPEAKER_00: like you'll often end up running three or four functions,
• 1:29:42
  SPEAKER_00: often one you don't know much about yourself.
• 1:29:44
  SPEAKER_00: So for example,
• 1:29:45
  SPEAKER_00: at Imprint,
• 1:29:45
  SPEAKER_00: I was running the customer operations team for,
• 1:29:48
  SPEAKER_00: you know, much of the last year, which is not something I am incredibly detailed on.
• 1:29:54
  SPEAKER_00: I have like some exposure to and had like an amazing leader in place.
• 1:29:59
  SPEAKER_00: But I've had to learn how to do that, and I've had to do that, you know, a number of times.
• 1:30:03
  SPEAKER_00: At Stripe,
• 1:30:04
  SPEAKER_00: I was managing support engineering,
• 1:30:05
  SPEAKER_00: which is not something I've done, personally myself.
• 1:30:08
  SPEAKER_00: I was running data engineering, which is not something I've personally done myself.
• 1:30:11
  SPEAKER_00: And so, you know, you learn how to run that way when you have to.
• 1:30:15
  SPEAKER_00: It's really hard to get the jobs to learn how to, like,
• 1:30:17
  SPEAKER_00: operate a function that way where you don't actually know the details of the work.
• 1:30:20
  SPEAKER_00: But you get to be a much better, more detail-oriented leader for longer.
• 1:30:23
  SPEAKER_00: And that's really where I think the best...
• 1:30:27
  SPEAKER_00: Future executives are our line managers,
• 1:30:29
  SPEAKER_00: because middle management has historically selected for totally different set
• 1:30:32
  SPEAKER_00: of skills.
• 1:30:33
  SPEAKER_00: How do you get both?
• 1:30:34
  SPEAKER_00: It's incredibly hard now, and it was always hard in different ways.
• 1:30:38
  SPEAKER_02: And what's your take on middle management?
• 1:30:40
  SPEAKER_02: Slowly dying?
• 1:30:41
  SPEAKER_02: Do you agree?
• 1:30:42
  SPEAKER_00: It's definitely a hard time to be a middle manager right now,
• 1:30:45
  SPEAKER_00: especially if you came up in the 2010s,
• 1:30:48
  SPEAKER_00: you were kind of selected and trained in this more of this empowerment model,
• 1:30:51
  SPEAKER_00: more of this like functional like bureaucracy model.
• 1:30:55
  SPEAKER_00: And now people are like, we don't want it and we don't need it.
• 1:30:57
  SPEAKER_00: And so you've kind of risen to this pinnacle,
• 1:30:59
  SPEAKER_00: but you can't get to the next step because of these other skills that are more kind
• 1:31:02
  SPEAKER_00: of in the details execution.
• 1:31:04
  SPEAKER_00: Really de-emphasized and kind of people have changed the rubric on you,
• 1:31:08
  SPEAKER_00: which is like super, super frustrating for folks who kind of get trapped by that.
• 1:31:11
  SPEAKER_00: That's definitely the challenge that folks are in now.
• 1:31:15
  SPEAKER_00: And I don't know how this wave of execs are going to happen,
• 1:31:19
  SPEAKER_00: but it's always been a hard role to get.
• 1:31:21
  SPEAKER_02: Well, and I do want to ask you,
• 1:31:23
  SPEAKER_02: two people asked me for advice and I'll share both of their stories
• 1:31:26
  SPEAKER_02: and you can decide if they're similar or different.
• 1:31:28
  SPEAKER_02: One is the head of engineering who has about Seven people reporting to them at
• 1:31:33
  SPEAKER_02: a company and was thinking,
• 1:31:36
  SPEAKER_02: I wonder about my future because I'm seeing about this middle management.
• 1:31:40
  SPEAKER_02: The other one was a story from another head of engineering
• 1:31:43
  SPEAKER_02: who has three EMs reporting to them and three ICs reporting to the VP
• 1:31:48
  SPEAKER_02: of engineering.
• 1:31:49
  SPEAKER_02: They've been shifting to AI transformation in the end department, also doing some other things.
• 1:31:55
  SPEAKER_02: The VP of Engineering is satisfied with their work, but they're under the VP of Engineering.
• 1:31:58
  SPEAKER_02: And this person also wondering, like, both people are wondering, am I in a bit of a career trap?
• 1:32:05
  SPEAKER_02: And they asked me to ask you, well, you have a lot of experience.
• 1:32:10
  SPEAKER_02: What tactics would you...
• 1:32:14
  SPEAKER_02: Yeah.
• 1:32:29
  SPEAKER_02: They had this path and it was pretty clear where they would go.
• 1:32:31
  SPEAKER_02: Next would be VP of Engineering for both of them.
• 1:32:33
  SPEAKER_02: But in the current company, clearly will not happen or unlikely.
• 1:32:38
  SPEAKER_00: It's a hard time in middle management, right?
• 1:32:40
  SPEAKER_00: There's a lot more competition for these roles.
• 1:32:43
  SPEAKER_00: And so I think what I found personally very rewarding is kind of getting back into
• 1:32:48
  SPEAKER_00: the details of writing software.
• 1:32:49
  SPEAKER_00: And so when I left Carta, my team was 250, maybe something like that.
• 1:32:54
  SPEAKER_00: When I joined Imprint, the team I was leading was, I think, 25.
• 1:32:57
  SPEAKER_00: And so for me, this is kind of like a unique moment to actually reskill.
• 1:33:01
  SPEAKER_00: Well, if you're in management,
• 1:33:02
  SPEAKER_00: I think right now,
• 1:33:03
  SPEAKER_00: either you have to get back into the details or the world is changing so radically
• 1:33:07
  SPEAKER_00: that the profession you know will not be valued in three years.
• 1:33:13
  SPEAKER_00: And I think you sort of have to decide, like, am I retiring now or am I reskilling?
• 1:33:18
  SPEAKER_00: And I thought about that, too.
• 1:33:19
  SPEAKER_00: Like, you know, I could just I could just be done.
• 1:33:23
  SPEAKER_00: Right.
• 1:33:23
  SPEAKER_00: Is this is this is what I want?
• 1:33:25
  SPEAKER_00: But it's not what I want.
• 1:33:26
  SPEAKER_00: Right.
• 1:33:26
  SPEAKER_00: I really want to still be participating.
• 1:33:29
  SPEAKER_00: And I really genuinely believe the way that we work has radically changed in the last year.
• 1:33:34
  SPEAKER_00: It hasn't changed everywhere.
• 1:33:36
  SPEAKER_00: There's like a long tail that's going to take a long time to catch up.
• 1:33:39
  SPEAKER_00: But in the places I work, it's changed a tremendous amount.
• 1:33:43
  SPEAKER_00: And for me personally, it's a lot more fun.
• 1:33:46
  SPEAKER_00: So first,
• 1:33:47
  SPEAKER_00: I think there has to be some like openness to like taking a backward step or
• 1:33:51
  SPEAKER_00: a lateral step.
• 1:33:52
  SPEAKER_00: Just what people want is very different and you have to be open to like getting
• 1:33:57
  SPEAKER_00: a different like look at it.
• 1:33:59
  SPEAKER_00: And so I think going back into like a line management position,
• 1:34:02
  SPEAKER_00: for example, is actually much more educational than a middle management.
• 1:34:06
  SPEAKER_00: The tools for line management and writing software are so good.
• 1:34:10
  SPEAKER_00: The tools for headcount planning or doing performance reviews are basically terrible, right?
• 1:34:15
  SPEAKER_00: Like all LLM applications for these things are not good.
• 1:34:19
  SPEAKER_00: So I do think you're missing a lot in middle management right now.
• 1:34:22
  SPEAKER_00: I would try to find my way out of it.
• 1:34:25
  SPEAKER_00: But thinking a little bit about some folks that I hired at Imprint,
• 1:34:28
  SPEAKER_00: one of them that comes to mind is Jasmine,
• 1:34:30
  SPEAKER_00: who I worked with at Carta,
• 1:34:32
  SPEAKER_00: came over and she was hired as a VP,
• 1:34:35
  SPEAKER_00: but she was a VP that was hiring or managing a team directly.
• 1:34:38
  SPEAKER_00: So she was a line manager?
• 1:34:39
  SPEAKER_00: She was a line manager,
• 1:34:40
  SPEAKER_00: a really experienced line manager,
• 1:34:42
  SPEAKER_00: was running engineering at Unlux some time ago,
• 1:34:45
  SPEAKER_00: and she came in to line manage and she's doing just a tremendous amount of software.
• 1:34:51
  SPEAKER_00: Which she would have never done at Carta because she could have never gotten time to do it.
• 1:34:55
  SPEAKER_00: And at Mux,
• 1:34:56
  SPEAKER_00: she was also like way too busy like running the function to actually be in
• 1:35:01
  SPEAKER_00: the details of writing.
• 1:35:02
  SPEAKER_00: Those people that are willing to actually go back and get their hands onto it are so valuable.
• 1:35:07
  SPEAKER_00: And if that is who you are,
• 1:35:08
  SPEAKER_00: you have to let people know
• 1:35:09
  SPEAKER_00: because otherwise people would think you would never take that opportunity.
• 1:35:12
  SPEAKER_00: But I would hire more people like this all day long.
• 1:35:14
  SPEAKER_02: You know,
• 1:35:15
  SPEAKER_02: we were talking about in the 2010s on the reserve,
• 1:35:19
  SPEAKER_02: how engineers got a little bit too used to like,
• 1:35:22
  SPEAKER_02: oh, yeah, my company and manager is here to do what I would like to do.
• 1:35:25
  SPEAKER_02: I would like to do platform.
• 1:35:27
  SPEAKER_02: No, no products are even if the business needs it.
• 1:35:29
  SPEAKER_02: It's just not for me.
• 1:35:30
  SPEAKER_02: You know, I'd rather quit.
• 1:35:32
  SPEAKER_02: And sometimes they quit.
• 1:35:34
  SPEAKER_02: I wonder if there's a little bit of this with management.
• 1:35:36
  SPEAKER_02: We're like, look, again,
• 1:35:37
  SPEAKER_02: I don't mean to imply too many things for these folks,
• 1:35:40
  SPEAKER_02: but generally, I have this path.
• 1:35:43
  SPEAKER_02: I thought I would be VP of engineering soon and I want to get there.
• 1:35:46
  SPEAKER_02: But is that what the industry wants?
• 1:35:48
  SPEAKER_02: Is that what the other companies want?
• 1:35:49
  SPEAKER_02: No, right now they want really good, let's say, line managers.
• 1:35:52
  SPEAKER_00: Yep.
• 1:35:53
  SPEAKER_02: And either similar to those engineers,
• 1:35:56
  SPEAKER_02: the best engineers I know, they kind of put their ego on the back.
• 1:35:58
  SPEAKER_02: And when the business said like,
• 1:35:59
  SPEAKER_02: look, we need product to build, they're like, look, I'm great at platform.
• 1:36:03
  SPEAKER_02: You know what?
• 1:36:04
  SPEAKER_02: Let me be the best product engineer I can be.
• 1:36:06
  SPEAKER_02: I felt with you as well that you,
• 1:36:08
  SPEAKER_02: you know, you have 250 people, I assume, you know, compensation, equity, status.
• 1:36:13
  SPEAKER_02: And you went down to lesser known startup with not as a well-known brand yet or at
• 1:36:19
  SPEAKER_02: the time, taking a lot smaller team, smaller responsibility.
• 1:36:23
  SPEAKER_02: You let the ego at the door, if you know what I mean.
• 1:36:26
  SPEAKER_02: And then you learn so much more.
• 1:36:28
  SPEAKER_00: I think in a lot of ways, it was just like a much better situation for me.
• 1:36:32
  SPEAKER_00: And so like there are a lot of pieces that weren't like kind of like this is a hit.
• 1:36:35
  SPEAKER_00: That's not really how I thought about it.
• 1:36:37
  SPEAKER_00: It was the perfect situation for me
• 1:36:39
  SPEAKER_00: because what I knew what I wanted was getting back into the details,
• 1:36:42
  SPEAKER_00: relearning how to do software in the current age.
• 1:36:45
  SPEAKER_00: That's I've always been someone who kind of got...
• 1:36:58
  SPEAKER_00: tricked into management, going back to the story, where they just needed a manager.
• 1:37:03
  SPEAKER_00: And so I said, yes,
• 1:37:04
  SPEAKER_02: you've been tricked ever since.
• 1:37:05
  SPEAKER_00: And then they made a director.
• 1:37:07
  SPEAKER_00: So it looked like they had a director and acquisition conversations.
• 1:37:10
  SPEAKER_00: So there was more palatable.
• 1:37:11
  SPEAKER_00: But I didn't know how to line manage, let around direct.
• 1:37:14
  SPEAKER_00: I just they kind of needed one on paper.
• 1:37:17
  SPEAKER_00: So, you know, very kind of them.
• 1:37:19
  SPEAKER_00: So for me, this has been kind of what I wanted.
• 1:37:22
  SPEAKER_00: And this has been like a unique opportunity.
• 1:37:25
  SPEAKER_00: But I think for a lot of folks,
• 1:37:26
  SPEAKER_00: there is this I've sensed the industry has betrayed them and
• 1:37:31
  SPEAKER_00: that they're owed something that they've worked for.
• 1:37:33
  SPEAKER_00: And the thing is, they're right.
• 1:37:35
  SPEAKER_00: They have worked incredibly hard, but the rules have changed.
• 1:37:39
  SPEAKER_00: And so I think that at certain moments,
• 1:37:41
  SPEAKER_00: the world looks very stable and our industry looks very stable.
• 1:37:45
  SPEAKER_00: And I think in the 2010s, we...
• 1:37:47
  SPEAKER_00: Forgot that our industry is actually very volatile.
• 1:37:50
  SPEAKER_00: Our industry has changed just a staggering amount in the last every decade.
• 1:37:55
  SPEAKER_00: Things are just radically different than they were in the decade before.
• 1:37:59
  SPEAKER_00: And we've sort of like lost sight of that.
• 1:38:01
  SPEAKER_00: And I think that people that kind of came up in the era of a lot
• 1:38:04
  SPEAKER_00: of stability don't remember that sometimes.
• 1:38:06
  SPEAKER_00: And so I do think we have to be willing to kind of take lateral moves.
• 1:38:09
  SPEAKER_00: We have to be willing to be a little bit humble.
• 1:38:12
  SPEAKER_00: But if doing the actual work Right.
• 1:38:31
  SPEAKER_02: What about the TLM role, tech lead manager?
• 1:38:33
  SPEAKER_02: This was a role that we declared dead.
• 1:38:36
  SPEAKER_02: You and me both declared dead as a dead end.
• 1:38:38
  SPEAKER_02: It is there,
• 1:38:39
  SPEAKER_02: but this was back in the tech leads who were given a very small team to manage
• 1:38:44
  SPEAKER_02: as well.
• 1:38:45
  SPEAKER_02: And we were clear in Zerp that it's just a career rut.
• 1:38:49
  SPEAKER_02: And if your experience is great, I think you also made it clear that it's a trap.
• 1:38:52
  SPEAKER_02: I think you have that article.
• 1:38:54
  SPEAKER_02: What do you think about this role now?
• 1:38:56
  SPEAKER_00: It's funny.
• 1:38:56
  SPEAKER_00: It's still a trap, but it's a highly demanded trap.
• 1:39:00
  SPEAKER_00: And so and I think in many cases, there's no way to actually there's no alternative.
• 1:39:04
  SPEAKER_00: So kind of it's less a trap than simply what's there.
• 1:39:07
  SPEAKER_00: And so I think in a lot of companies, management is getting flattens.
• 1:39:11
  SPEAKER_02: So we're starting to see like a director,
• 1:39:13
  SPEAKER_02: let's say, have a bunch of like tech tech leads and like.
• 1:39:16
  SPEAKER_02: I
• 1:39:19
  SPEAKER_00: think you're either seeing two models.
• 1:39:21
  SPEAKER_00: You're seeing that there are engine managers, but they're managing much larger scopes.
• 1:39:25
  SPEAKER_00: And so they're actually less hands-on individuals than they were before
• 1:39:29
  SPEAKER_00: because they're managing, say, 12, 13, 14 people before instead of four to eight.
• 1:39:35
  SPEAKER_00: And then we're also seeing kind of directors
• 1:39:36
  SPEAKER_00: within managing tech lead managers instead of managing kind of these line managers.
• 1:39:41
  SPEAKER_00: And different companies are trying different things.
• 1:39:42
  SPEAKER_00: But I think this is where I see the industry kind of asking for folks right now.
• 1:39:48
  SPEAKER_00: And I do say like some of the best folks we've hired at Imprint have been folks
• 1:39:52
  SPEAKER_00: that were in like more pure management roles that came in but really wanted
• 1:39:56
  SPEAKER_00: to be writing software and have just been doing an amazing job of kind of like doing
• 1:40:00
  SPEAKER_00: a blend of both.
• 1:40:01
  SPEAKER_00: It is hard to find those folks where it's almost like, Interview them to be a great EM.
• 1:40:06
  SPEAKER_00: And then like, do you just get frustrated if you're not writing more software?
• 1:40:11
  SPEAKER_00: It's really that person is kind of what you want.
• 1:40:13
  SPEAKER_00: But it's hard, you know, not how we've been interviewing them so far.
• 1:40:17
  SPEAKER_00: I think we've just found a few great folks.
• 1:40:19
  SPEAKER_00: But that is the role that we really want.
• 1:40:22
  SPEAKER_00: And again,
• 1:40:22
  SPEAKER_00: it kind of goes back to this thing where you want people who have the capability
• 1:40:24
  SPEAKER_00: to do the bureaucratic parts, but don't want to.
• 1:40:28
  SPEAKER_00: Like the capability, but not the desire.
• 1:40:30
  SPEAKER_00: Because those are really the folks that I see super effective these days.
• 1:40:33
  SPEAKER_00: They can use that when they need to,
• 1:40:35
  SPEAKER_00: but they default to actually writing software,
• 1:40:38
  SPEAKER_00: which is really where most of the value is.
• 1:40:40
  SPEAKER_02: As a closing topic, I wanted to ask you about How you write.
• 1:40:44
  SPEAKER_02: You've been such a perfect writer.
• 1:40:46
  SPEAKER_02: Still, I really enjoy your blog.
• 1:40:48
  SPEAKER_02: Whenever there's a new article, I check it out.
• 1:40:50
  SPEAKER_02: There's also, you can subscribe.
• 1:40:53
  SPEAKER_02: There's an email that I subscribe to and I actually get it in my inbox.
• 1:40:55
  SPEAKER_02: How you approach writing and what you think about AI.
• 1:40:59
  SPEAKER_02: And also,
• 1:40:59
  SPEAKER_02: what is your take on,
• 1:41:00
  SPEAKER_02: there's a lot of AI writing going on,
• 1:41:02
  SPEAKER_02: not just for social media on LinkedIn,
• 1:41:04
  SPEAKER_02: we know that,
• 1:41:04
  SPEAKER_02: but also for some authors who Before AI,
• 1:41:07
  SPEAKER_02: they didn't write with AI, but now they're starting to a little bit.
• 1:41:10
  SPEAKER_00: So I've been writing for about 20 years online in my blog,
• 1:41:14
  SPEAKER_00: and I founded Irrational Exuberance in 2007.
• 1:41:17
  SPEAKER_00: And then,
• 1:41:18
  SPEAKER_00: you know,
• 1:41:18
  SPEAKER_00: in next year,
• 1:41:20
  SPEAKER_00: I actually might have been like May or June or something when I started writing it.
• 1:41:24
  SPEAKER_00: So I'm getting close to this 20 year anniversary.
• 1:41:28
  SPEAKER_00: And when I first started writing,
• 1:41:30
  SPEAKER_00: I was simply trying to figure out how to network my way into a job, basically.
• 1:41:34
  SPEAKER_00: But I did a ton of tutorials, just like, here's how I did this.
• 1:41:37
  SPEAKER_00: And this was a different era.
• 1:41:39
  SPEAKER_00: Now, the sort of thing that you just ask, you know, an AI, like, how do I do X?
• 1:41:43
  SPEAKER_00: And it would write a great tutorial just for you, or maybe just do it for you directly, right?
• 1:41:48
  SPEAKER_00: Then as I started working at Uber,
• 1:41:49
  SPEAKER_00: I started writing a little bit more of like the things I've been learning
• 1:41:52
  SPEAKER_00: in hyperscale, right?
• 1:41:54
  SPEAKER_00: And then it really took off when I was writing at Stripe,
• 1:41:57
  SPEAKER_00: because I think Stripe was a place that both had a lot to learn,
• 1:42:00
  SPEAKER_00: but a real love of writing.
• 1:42:01
  SPEAKER_00: And that, to me, really energized my work.
• 1:42:04
  SPEAKER_00: And then wrote my first book,
• 1:42:06
  SPEAKER_00: kind of the culmination of the things I had written at Stripe,
• 1:42:09
  SPEAKER_00: An Elegant Puzzle, and then got a lot of momentum.
• 1:42:11
  SPEAKER_00: I think a total of four books.
• 1:42:14
  SPEAKER_00: Probably not writing another book for at least a decade, maybe not ever.
• 1:42:18
  SPEAKER_00: But I think it's just been it's been so transformational for me,
• 1:42:22
  SPEAKER_00: I think,
• 1:42:22
  SPEAKER_00: like so much of like when people know me, which is not that very often, really.
• 1:42:27
  SPEAKER_00: But like when people know me, it's exclusively from the books that I've written or the blog.
• 1:42:33
  SPEAKER_00: And I really do believe writing is like unique way that we
• 1:42:36
  SPEAKER_00: as individuals can actually change the shape of the industry.
• 1:42:39
  SPEAKER_00: And I think when you've done that, there's like little things that kind of pop up.
• 1:42:43
  SPEAKER_00: So for you, like the tri-modal kind of salary piece, right?
• 1:42:47
  SPEAKER_00: And that is first like a memorable name that helps.
• 1:42:50
  SPEAKER_00: But also like I think was like a really important observation that a lot
• 1:42:53
  SPEAKER_00: of people didn't understand.
• 1:42:55
  SPEAKER_00: I think you've changed a lot of people in how they approach compensation.
• 1:43:01
  SPEAKER_00: And then Patrick McKenzie has his work on negotiations.
• 1:43:05
  SPEAKER_00: So impactful, probably created so much wealth.
• 1:43:08
  SPEAKER_00: For people in the world.
• 1:43:09
  SPEAKER_00: I think so.
• 1:43:09
  SPEAKER_00: I think he might try to track how much he's created on it,
• 1:43:12
  SPEAKER_00: but I'm not sure if that's still true.
• 1:43:14
  SPEAKER_00: But for my books,
• 1:43:15
  SPEAKER_00: I really think I've changed the industry with,
• 1:43:18
  SPEAKER_00: I think,
• 1:43:19
  SPEAKER_00: Staff Engineer,
• 1:43:20
  SPEAKER_00: I think notably,
• 1:43:21
  SPEAKER_00: I think like the Staff Plus kind of concept,
• 1:43:24
  SPEAKER_00: that book created Staff Plus as like a concept, right?
• 1:43:28
  SPEAKER_00: And there's other things that I think are like less like quotable, but have mattered.
• 1:43:32
  SPEAKER_00: And there's just like,
• 1:43:33
  SPEAKER_00: there's nothing I could have done in my work in any company that could have impacted
• 1:43:36
  SPEAKER_00: the industry in this way.
• 1:43:38
  SPEAKER_02: This many people and so positively or I remember both the Elegant Puzzle and Sapinger.
• 1:43:44
  SPEAKER_02: I read it and I took a lot of guidance from it.
• 1:43:46
  SPEAKER_00: And that's just so powerful.
• 1:43:47
  SPEAKER_00: And then I think about writing with AI and I've spent tens of thousands of hours
• 1:43:53
  SPEAKER_00: over 20 years creating this, writing this stuff.
• 1:43:57
  SPEAKER_00: I'm not like super craft oriented in my writing,
• 1:44:00
  SPEAKER_00: by which I mean I'm really trying to get ideas out more than I'm trying
• 1:44:02
  SPEAKER_00: to write like the best blog posts that I've never been I think what I like
• 1:44:07
  SPEAKER_00: about your writing is there are very punchy ideas.
• 1:44:08
  SPEAKER_00: It's not about the writing, per se.
• 1:44:10
  SPEAKER_00: I would say you're a decent writer.
• 1:44:22
  SPEAKER_02: I don't like it because it's enjoyable to read.
• 1:44:25
  SPEAKER_02: The idea comes and is there, and it makes me thinking.
• 1:44:29
  SPEAKER_02: And I'm not thinking because of how you presented it.
• 1:44:31
  SPEAKER_02: And again, the presentation is fine, but the idea is what brings me home.
• 1:44:35
  SPEAKER_00: Yeah, it's pretty minimal writing.
• 1:44:37
  SPEAKER_02: And some of your articles are short.
• 1:44:40
  SPEAKER_02: It's not even about the length.
• 1:44:41
  SPEAKER_02: I'm way more wordy in my writing than you are, which you will know.
• 1:44:44
  SPEAKER_02: But it's just my...
• 1:44:46
  SPEAKER_02: But in yours, it doesn't have to be like what I like about yours.
• 1:44:49
  SPEAKER_02: You don't waste a breath in your writing when there's not much.
• 1:44:54
  SPEAKER_00: And that's complete.
• 1:44:56
  SPEAKER_00: And then I think about that,
• 1:44:58
  SPEAKER_00: all the stuff I put together,
• 1:44:59
  SPEAKER_00: all of the things I've tried to change people's minds on.
• 1:45:03
  SPEAKER_00: And to me, like writing with AI would just be like throwing that away.
• 1:45:06
  SPEAKER_00: And so I think,
• 1:45:07
  SPEAKER_00: you know, I've never done a newsletter trying to collect a huge number of folks.
• 1:45:12
  SPEAKER_00: It's more if you want to read what I'm writing, this is what it is.
• 1:45:15
  SPEAKER_00: It's not my business like it is for you.
• 1:45:18
  SPEAKER_00: But still,
• 1:45:19
  SPEAKER_00: I've gathered some number of folks,
• 1:45:21
  SPEAKER_00: and I think they read what I write, and that's really powerful.
• 1:45:24
  SPEAKER_00: And I know...
• 1:45:26
  SPEAKER_00: I know if I write something,
• 1:45:27
  SPEAKER_00: like often there'll be hundreds of companies talking about the idea there in
• 1:45:32
  SPEAKER_00: the next week.
• 1:45:33
  SPEAKER_00: And that's just such like a privileged spot to be in.
• 1:45:36
  SPEAKER_00: If I just wrote slop, I would just throw it away.
• 1:45:41
  SPEAKER_00: I can never get it back.
• 1:45:42
  SPEAKER_00: Like I'll never spend another 20 years doing this, right?
• 1:45:45
  SPEAKER_00: And so when I think about the advantages I have that I've kind of carefully built
• 1:45:51
  SPEAKER_00: over like two decades, why would I throw that away?
• 1:45:54
  SPEAKER_00: And so if I don't have something to say, I just don't say something.
• 1:45:57
  SPEAKER_00: I'm not trying to manufacture content or something like that.
• 1:45:59
  SPEAKER_00: I think it would be such like a devastating moment to me to throw that all away for nothing.
• 1:46:04
  SPEAKER_00: Like if I was throwing it away for something, I could maybe get there.
• 1:46:07
  SPEAKER_00: But I think it would just be like an uncompensated loss if I were to write.
• 1:46:11
  SPEAKER_00: Yeah, well, I feel that, to me, writing is how I think.
• 1:46:26
  SPEAKER_02: And when I write the drafts,
• 1:46:27
  SPEAKER_02: I often like a lot of my social media activity,
• 1:46:30
  SPEAKER_02: actually,
• 1:46:30
  SPEAKER_02: and I never talked about this before,
• 1:46:32
  SPEAKER_02: but sometimes people ask me, what is your social media strategy?
• 1:46:35
  SPEAKER_02: I have a large number of followers, which is just a byproduct of doing things consistently.
• 1:46:39
  SPEAKER_02: And in my case, honestly, it's researching and thinking about like, I almost do.
• 1:46:43
  SPEAKER_02: Full-time or close to full-time thinking about stuff that's happening in
• 1:46:46
  SPEAKER_02: the industry and that I'm talking with engineers.
• 1:46:49
  SPEAKER_02: Usually what happens is I start writing a draft about something and I have this idea.
• 1:46:53
  SPEAKER_02: I put it in a tweet,
• 1:46:55
  SPEAKER_02: just like in another window and I keep writing it and I lay Look back,
• 1:46:58
  SPEAKER_02: it's now got traction because I guess it was an interesting idea.
• 1:47:03
  SPEAKER_02: Sometimes it's controversial.
• 1:47:06
  SPEAKER_02: Sometimes I actually test them up.
• 1:47:07
  SPEAKER_02: I'm not quite sure.
• 1:47:08
  SPEAKER_02: I'll just put it out there.
• 1:47:09
  SPEAKER_02: I call these a little bit like brain farts,
• 1:47:11
  SPEAKER_02: which is not entirely true because I am thinking about things,
• 1:47:13
  SPEAKER_02: but I don't really care about them.
• 1:47:14
  SPEAKER_02: And I'm actually more interested in the conversation.
• 1:47:17
  SPEAKER_02: So sometimes it then distracts me when I go back, but it then makes my ideas form.
• 1:47:23
  SPEAKER_02: And a lot of my ideas are about observation.
• 1:47:26
  SPEAKER_02: Is this happening?
• 1:47:27
  SPEAKER_02: Are you seeing this?
• 1:47:28
  SPEAKER_02: Which just generates conversation.
• 1:47:30
  SPEAKER_02: And to me, that is the right.
• 1:47:33
  SPEAKER_02: And what I found with AI,
• 1:47:35
  SPEAKER_02: there was a time where it was popular to feed all your writing and have a bot
• 1:47:39
  SPEAKER_02: that you can talk to.
• 1:47:39
  SPEAKER_02: And some people wrote a pragmatic engine and bot, which I didn't like the idea to use.
• 1:47:43
  SPEAKER_02: But anyway, I still tried it out.
• 1:47:45
  SPEAKER_02: And it was almost hilarious because, for example, My opinions change all the time.
• 1:47:50
  SPEAKER_02: My views change.
• 1:47:51
  SPEAKER_02: And it will kind of spit back something that I said, you know, like years back.
• 1:47:54
  SPEAKER_02: And I know that we talked about TLM.
• 1:47:58
  SPEAKER_02: If you had a Will Larson bot, it would say TLM is a trap.
• 1:48:01
  SPEAKER_02: And now we're talking about like, well, actually, there's way more to it.
• 1:48:05
  SPEAKER_02: I tell people like, don't put your thing.
• 1:48:07
  SPEAKER_02: And whenever I see someone write on LinkedIn,
• 1:48:09
  SPEAKER_02: especially a fellow professional or they message me,
• 1:48:11
  SPEAKER_02: I'm They often comment with their real voice.
• 1:48:13
  SPEAKER_02: And I'm like, why don't you just write that imperfect?
• 1:48:16
  SPEAKER_02: That's you.
• 1:48:17
  SPEAKER_02: I like the you.
• 1:48:19
  SPEAKER_02: And I don't like the sterile thing.
• 1:48:21
  SPEAKER_02: And I also don't like how with AI,
• 1:48:24
  SPEAKER_02: it's got the same voice for millions of people using it,
• 1:48:27
  SPEAKER_02: whereas millions of people talking have millions of different voices.
• 1:48:30
  SPEAKER_00: So this connects to something I think is really related to this,
• 1:48:33
  SPEAKER_00: which I think is a lot of people believe to be successful,
• 1:48:37
  SPEAKER_00: they need to be writing content.
• 1:48:39
  SPEAKER_00: But they don't really want to be writing content.
• 1:48:41
  SPEAKER_00: And so they're like, I really hate writing content.
• 1:48:43
  SPEAKER_00: But to get my promoted, to get my next job, I need to be writing content.
• 1:48:47
  SPEAKER_00: Like, how do I do that?
• 1:48:48
  SPEAKER_00: And it's like, obviously AI, right?
• 1:48:50
  SPEAKER_00: And I think something I've been trying to push back on folks on for a while,
• 1:48:54
  SPEAKER_00: I wrote,
• 1:48:55
  SPEAKER_00: I forget the exact name, but how to be a tech influencer or something like that.
• 1:48:59
  SPEAKER_02: We're going to link that.
• 1:49:01
  SPEAKER_02: That post, it's such a, not catchy, but almost a click-baity name.
• 1:49:06
  SPEAKER_02: It is the single best post about how to be influential in tech.
• 1:49:10
  SPEAKER_02: I will link it.
• 1:49:11
  SPEAKER_02: It's one of my favorite articles I forward to so many people.
• 1:49:14
  SPEAKER_00: So by the way, thank you for writing that.
• 1:49:16
  SPEAKER_00: Of course.
• 1:49:17
  SPEAKER_00: And the reason I wrote it was like these people were like,
• 1:49:19
  SPEAKER_00: oh, I need to write 200 things, 300 things.
• 1:49:21
  SPEAKER_00: I need to write every week.
• 1:49:23
  SPEAKER_00: I need to do this.
• 1:49:23
  SPEAKER_00: And it's like, well,
• 1:49:24
  SPEAKER_00: if your goal is to be visible,
• 1:49:27
  SPEAKER_00: what you need to do is write one thing that gets traction.
• 1:49:29
  SPEAKER_00: Spend a lot of time on it.
• 1:49:30
  SPEAKER_00: Test it.
• 1:49:31
  SPEAKER_00: Figure that out.
• 1:49:32
  SPEAKER_00: You don't actually need to write a ton of stuff.
• 1:49:34
  SPEAKER_00: There's almost no value in writing a ton of stuff unless you are running a business
• 1:49:38
  SPEAKER_00: that is based on a subscription.
• 1:49:40
  SPEAKER_00: If you're just trying to get your ideas out,
• 1:49:42
  SPEAKER_00: if you're just trying to be a little bit more visible,
• 1:49:45
  SPEAKER_00: if you're trying to show proof of your ability to write cogently,
• 1:49:48
  SPEAKER_00: you can write like two things.
• 1:49:49
  SPEAKER_00: You can write three things.
• 1:49:50
  SPEAKER_00: You can write one thing every two years.
• 1:49:53
  SPEAKER_00: And you don't have to write a lot.
• 1:49:55
  SPEAKER_00: I think about Tanya O'Reilly,
• 1:49:56
  SPEAKER_00: who has not written a lot on her blog,
• 1:49:59
  SPEAKER_00: but when she writes something, it says something really interesting, right?
• 1:50:02
  SPEAKER_00: And so she's not like a volume writer, but she's been able to have really impactful pieces.
• 1:50:07
  SPEAKER_00: I think No Glue is like the most obvious one that has really been transformative.
• 1:50:12
  SPEAKER_00: And so I think even for people that do write a lot,
• 1:50:14
  SPEAKER_00: people don't remember the vast majority of what they write.
• 1:50:17
  SPEAKER_00: There's like a few pieces that stick out.
• 1:50:19
  SPEAKER_00: So I really think that if people reoriented around the real goal,
• 1:50:24
  SPEAKER_00: which is maybe to have some visibility,
• 1:50:26
  SPEAKER_00: one or two good things matter so much more than volume.
• 1:50:30
  SPEAKER_00: And so I wish people would Stop creating volume if they don't actually,
• 1:50:35
  SPEAKER_00: I think it doesn't serve their goals.
• 1:50:37
  SPEAKER_00: And in fact,
• 1:50:37
  SPEAKER_00: like I've seen some candidates that have interviewed,
• 1:50:40
  SPEAKER_00: you know,
• 1:50:40
  SPEAKER_00: over the last year where they have just like AI slop content and like a huge volume
• 1:50:46
  SPEAKER_00: of it.
• 1:50:46
  SPEAKER_00: And I don't know,
• 1:50:47
  SPEAKER_00: I'm pretty conflicted on those candidates because it's like,
• 1:50:49
  SPEAKER_00: hey, people weren't reading it.
• 1:50:51
  SPEAKER_00: You keep doing it.
• 1:50:52
  SPEAKER_00: And it's sort of like, Why are you continuing to do something that doesn't serve any purpose?
• 1:50:57
  SPEAKER_00: Because no one's responding to it.
• 1:50:59
  SPEAKER_00: So it just feels like people who are running a recipe but aren't tasting the product.
• 1:51:05
  SPEAKER_00: It's cargo culting, right?
• 1:51:06
  SPEAKER_00: They don't actually know why they're doing it.
• 1:51:08
  SPEAKER_00: And so to me,
• 1:51:09
  SPEAKER_00: it actually implies poor judgment rather than showing a sign of,
• 1:51:13
  SPEAKER_00: oh, this is an ambitious person trying hard.
• 1:51:16
  SPEAKER_02: Yeah.
• 1:51:16
  SPEAKER_02: And as a closing, what's a book that you would recommend or books that you enjoyed reading?
• 1:51:22
  SPEAKER_00: Certainly,
• 1:51:22
  SPEAKER_00: I think I would recommend kind of my books to anyone who enjoys spending money
• 1:51:27
  SPEAKER_00: on things.
• 1:51:28
  SPEAKER_00: Your books are all excellent, really.
• 1:51:30
  SPEAKER_00: Thank you.
• 1:51:30
  SPEAKER_00: And certainly,
• 1:51:31
  SPEAKER_00: I think Crafting Engineering Strategy came out last year
• 1:51:34
  SPEAKER_00: and I think it's I read it based on your recommendation.
• 1:51:36
  SPEAKER_00: I think it's honestly the book that kind of formed my view about management and kind
• 1:51:40
  SPEAKER_00: of operating in companies.
• 1:51:41
  SPEAKER_00: I think that it's not really about operating companies,
• 1:51:43
  SPEAKER_00: but it's like a mental model you can use.
• 1:51:59
  SPEAKER_00: That book, I think, is incredibly, incredibly helpful.
• 1:52:02
  SPEAKER_00: But really, like, any book that forces you to have, like, a different perspective on something.
• 1:52:07
  SPEAKER_00: And so I spent, you know, a decent enough time thinking about typing a couple years ago.
• 1:52:11
  SPEAKER_00: Like, not typing, like,
• 1:52:12
  SPEAKER_00: on a keyboard,
• 1:52:13
  SPEAKER_00: but how to have, like,
• 1:52:14
  SPEAKER_00: better type systems, which is not that relevant to my work on a day-to-day basis.
• 1:52:19
  SPEAKER_00: And then there's another great book whose name I'm losing on TLA Plus and using that.
• 1:52:23
  SPEAKER_00: Is that Hillel Wayne?
• 1:52:24
  SPEAKER_00: Yeah, exactly.
• 1:52:25
  SPEAKER_00: Yeah, he was on the podcast.
• 1:52:26
  SPEAKER_00: Yeah, he has the famous TLA Plus.
• 1:52:28
  SPEAKER_00: Fantastic book.
• 1:52:30
  SPEAKER_00: And look,
• 1:52:30
  SPEAKER_00: I'm not using a lot of TLA Plus on a day-to-day basis,
• 1:52:33
  SPEAKER_00: but I think just the ideas there are incredibly powerful in terms of using languages
• 1:52:37
  SPEAKER_00: to Increase the verification or verifiability of your software,
• 1:52:41
  SPEAKER_00: which is one of the biggest challenges of our time, right?
• 1:52:43
  SPEAKER_00: If all of our software is getting written by someone else,
• 1:52:46
  SPEAKER_00: which is an agent, making verification cheap is really critical.
• 1:52:50
  SPEAKER_00: And even if TLA Plus is not the tool for that in many cases,
• 1:52:54
  SPEAKER_00: thinking about that problem,
• 1:52:55
  SPEAKER_00: and this is the same reason why typing is really interesting,
• 1:52:57
  SPEAKER_00: really, really valuable.
• 1:52:58
  SPEAKER_00: And so I think right now those are some useful ones.
• 1:53:02
  SPEAKER_02: Thank you.
• 1:53:02
  SPEAKER_02: Will, it was awesome to have you and finally have this super nice conversation.
• 1:53:07
  SPEAKER_00: Likewise, thank you for having me.
• 1:53:08
  SPEAKER_01: I've known Will for so many years, and it was great to sit down in person.
• 1:53:11
  SPEAKER_01: And we did it at a time when there's a lot of change happening
• 1:53:14
  SPEAKER_01: with traditional best practices when it comes both to engineering management as well
• 1:53:18
  SPEAKER_01: as engineering career progression.
• 1:53:20
  SPEAKER_01: One really interesting topic was how farm managers used to bend backwards
• 1:53:24
  SPEAKER_01: to find interesting projects for their engineers.
• 1:53:26
  SPEAKER_01: Will recalled how at Stripe, some of his best engineers asked him for more interesting problems.
• 1:53:31
  SPEAKER_01: Back then,
• 1:53:32
  SPEAKER_01: he already pushed back saying that the only thing he has is suffering to offer,
• 1:53:36
  SPEAKER_01: meaning not particularly glamorous problems,
• 1:53:38
  SPEAKER_01: but that suffering is what's going to make the business succeed.
• 1:53:42
  SPEAKER_01: But back in the 2010s and the early 2020s,
• 1:53:45
  SPEAKER_01: lots of engineers saw this approach And yet today, it's kind of a default.
• 1:53:51
  SPEAKER_01: For career stability and promotions,
• 1:53:53
  SPEAKER_01: as an engineer,
• 1:53:54
  SPEAKER_01: especially the senior plus levels,
• 1:53:56
  SPEAKER_01: you will want to help the business solve their most pressing problems.
• 1:53:59
  SPEAKER_01: And this includes having empathy for those problems.
• 1:54:02
  SPEAKER_01: I also found it eye-opening how Will thinks about what it takes to be a great CTO.
• 1:54:06
  SPEAKER_01: He thinks of it as unique to be two things.
• 1:54:08
  SPEAKER_01: One, a great standout technologist who knows what to build and how to build,
• 1:54:13
  SPEAKER_01: as well as a bureaucrat who can run a whole function,
• 1:54:15
  SPEAKER_01: including a function you might not be an expert on, like product or design.
• 1:54:19
  SPEAKER_01: In the 2010s,
• 1:54:20
  SPEAKER_01: lots of managers learned mostly about the bureaucracy part,
• 1:54:23
  SPEAKER_01: and by the time they became CTOs, they lost the technology side.
• 1:54:28
  SPEAKER_01: Today, with smaller teams and less mental management,
• 1:54:30
  SPEAKER_01: many CTOs will be technologists first,
• 1:54:32
  SPEAKER_01: which Will thinks it might be better overall, and I have to agree with it.
• 1:54:36
  SPEAKER_01: Finally,
• 1:54:36
  SPEAKER_01: I appreciated Will's advice to middle managers,
• 1:54:38
  SPEAKER_01: middle managers being engineering managers who have teams that other managers report
• 1:54:42
  SPEAKER_01: to them.
• 1:54:42
  SPEAKER_01: Will did not beat around the bush.
• 1:54:44
  SPEAKER_01: Yes, today, it's a hard time to be in middle management.
• 1:54:47
  SPEAKER_01: The two paths to seize looking forward are either you go back to being closer to
• 1:54:51
  SPEAKER_01: where soft Will himself took it backwards when he left
• 1:54:53
  SPEAKER_01: the 250-person engineering team at Carta to have a 25-person team at Imprint.
• 1:54:58
  SPEAKER_01: But he did it consciously to learn how to build with AI changing the engineering profession.
• 1:55:14
  SPEAKER_01: I do find it inspiring that Will not only talks about the importance of learning
• 1:55:17
  SPEAKER_01: the new rules of software engineering, but also walks the walk.
• 1:55:21
  SPEAKER_01: Do check out the show notes on related to Pragmatic Engineer deep dives
• 1:55:23
  SPEAKER_01: on zero interest rates and engineering and EM careers.
• 1:55:26
  SPEAKER_01: If you've enjoyed the podcast,
• 1:55:27
  SPEAKER_01: do subscribe in your favorite podcast player,
• 1:55:29
  SPEAKER_01: and a special thank you if you also leave a rating on the show.
• 1:55:31
  SPEAKER_01: Thanks, and I'll see you in the next one.