# A CTO needs both technical judgment and bureaucratic experience

Markdown copy of https://realalpha.app/s/a-cto-needs-both-technical-judgment-and-bureaucratic/ on Real Alpha, the best minutes from long interviews with the people building AI. Cite and link the page, not this copy.

- Speaker: [Will Larson](https://realalpha.app/people/will-larson/) · Will Larson is CTO of Imprint and author on engineering leadership. · Led engineering at Stripe, Uber, Calm and Carta; author of Staff Engineer and The Engineering Executive's Primer.
- Host: [Gergely Orosz](https://realalpha.app/people/gergely-orosz/) · Host, The Pragmatic Engineer · Spent four years at Uber heading mobile, web and backend teams; shipped part of its payments system.
- Show: The Pragmatic Engineer
- Episode: [The revised rules of engineering management with Will Larson](https://realalpha.app/v/Prl858_AovM/), Oct 21, 2026
- Moment: 1:26:01 to 1:31:36 of the episode (6 min), playing on https://realalpha.app/s/a-cto-needs-both-technical-judgment-and-bureaucratic/; the episode from there: https://realalpha.app/v/Prl858_AovM/?t=5161

## Quote

> “If you've **never been a bureaucrat**, you don't know how to see things as a bureaucrat.”
> — [Will Larson](https://realalpha.app/people/will-larson/) at [1:28:36](https://realalpha.app/v/Prl858_AovM/?t=5316) · The Pragmatic Engineer

## Takeaways

1. Executives need to understand software delivery and org operations.
2. Middle-management reps teach process, incentive, and structure design.
3. Line managers may retain stronger product and technical judgment.

## About this segment

Will Larson says executive work requires technical judgment and practice designing processes, incentives, and structures. He argues middle management can build the latter while eroding the former.

From “The revised rules of engineering management with Will Larson”, Oct 21, 2026. [Watch the full episode](https://realalpha.app/v/Prl858_AovM/)

## Transcript

Transcribed by machine (Whisper) from the episode’s audio, so a word may be off here and there.

[1:26:08](https://realalpha.app/v/Prl858_AovM/?t=5168) executive is and how what is the career path today to get to that level from an engineer like okay like i like the executive executive i like that to have be able to make decisions including unpopular ones helping people helping companies what was the old path and what's the new path if there's any? So I think the old path, your software engineer for some number of years, could be pretty short. Then you get into management, and then you climb through middle management, and then you get to the CTO role. Middle management, end manager, senior end director. Exactly. And so I think there are a lot of problems with that. First, it means that often the people that were selected for management initially weren't like the most focused on the technical pieces of the work because they're trying to get promoted to management. And then

[1:26:51](https://realalpha.app/v/Prl858_AovM/?t=5211) the selection bias is really towards people that are able to operate well, which doesn't necessarily have a whole lot in common with the technology side. Often they happen to be really good technology, but there wasn't like a strong kind of selection bias for it. But you really do have to be a good bureaucrat to be an executive. And this is like one of the interesting challenges where a lot of my work is incentive management. It's knowing, hey, if we roll out this sort of performance review, here's how it's going to fail. And so we just shouldn't do that. We should do this other thing instead. And so if you haven't done the reps of being like a bureaucrat, you actually like can't run a function because a lot of running a function is, in fact, being a bureaucrat.

[1:27:26](https://realalpha.app/v/Prl858_AovM/?t=5246) You learned to be a good bureaucrat. I was a bureaucrat, right? And so, I mean, out of necessity. So at Uber, there weren't like really like rubrics. There wasn't like an interview. We didn't have any structure how we interviewed when I was there. So you had to make it all up yourself for your function. And again, we were doing tons of interviews and each time we didn't give an offer out, I was like so pained because I was doing so many interviews. So I had to figure that out. And then at Stripe, Stripe was like a much more structurally cohesive company. And so we did have like a lot of structured process. And then I got to work on a lot of that and learned a lot there. You kind of got pulled into it. You picked all the pace. A hundred percent. And a lot of the structure I thought wasn't working well at the

[1:28:05](https://realalpha.app/v/Prl858_AovM/?t=5285) point that I joined to kind of like work to try to iterate and improve little pieces of it because we were, you know, growing, growing pretty quickly. And so really, you know, working these middle management jobs, I think, did educate me on how to be a good bureaucrat, which is part of being an effective executive, because you can just allocate processes that work and avoid processes that don't work. Think about incentives that work and don't work, structure that does work and doesn't work. You know, the Jeffrey Reed scene like a state, like you're not allowed to be in Silicon Valley if you haven't read seeing as like a state, but it's basically a book about how states see citizens and accomplishments and how that shapes how policy works. It's the same thing.

[1:28:42](https://realalpha.app/v/Prl858_AovM/?t=5322) If you've never been a bureaucrat, you don't know how to see things as a bureaucrat. But also, if you can only be a bureaucrat, you don't know how anything actually works. You don't know how software actually gets made. And so it's very damaging to you. Am I getting this right, that you're saying to be a good... engineering executive so vp engineering or cto you want to be excellent at technology knowing how it works being hands-on if you need to be or just be hands-on and also be a good bureaucrat where you can manage it and you want both and you're saying that if you go the middle management route oftentimes it might happen that you either never were a good technologist or you stop becoming that by the time you get up there so you're a great bureaucrat but not technology but if you just go

[1:29:24](https://realalpha.app/v/Prl858_AovM/?t=5364) from like an engineer great technologist straight up here let's say like you're a startup tomorrow congrats here to CTO, you will not be a good bureaucrat. I think that's exactly right. And it's interesting where oftentimes I think line managers are better kind of instinctual executives than kind of middle managers because they're used to working in the detail. So they can make better calls for the team or the company.

[1:29:45](https://realalpha.app/v/Prl858_AovM/?t=5385) Their judgment's just better on all these like non-bureaucratic dimensions of the job, but then their judgment's terrible on kind of the bureaucratic dimensions of the job. And so this is why I think being an executive is hard and why it's a hard career path is that it was, you know, in the 2010s in particular, you had to climb these like layers of middle management to learn this kind of bureaucratic component of it. And that was the only way to get scale to actually understand that. Now those layers are kind of gone. But the interesting thing is like the other half of the job is now really emphasized in terms of better decision making, understanding the actual product, understanding the actual business, understanding how software shipped in a way where we kind of de-emphasize that. So I think, you know, people are like, is it easier?

[1:30:23](https://realalpha.app/v/Prl858_AovM/?t=5423) Is it harder? I don't think it's like any easier or any harder. It was, it's all harder to become like a bureaucrat now, which again, like negative connotations, right? But this is like learning how to actually operate a function is really difficult work. And as like a C-level, like you'll often end up running three or four functions, often when you don't know much about yourself. So for example, at Imprint, I was running the customer operations team for, you know, much of the last year, which is not something i am incredibly detailed on i have like some exposure to and had like an amazing leader in place but i've had to learn how to do that and i've had to do that you know a number of times um at at stripe i was managing support engineering which is not something i've done personally myself i was running data engineering which is not something i've

[1:31:09](https://realalpha.app/v/Prl858_AovM/?t=5469) personally done myself and so you know you learn how to run that way when you have to it's really hard to get the jobs to learn how to like operate a function that way where you don't actually know the details of the work. But you get to be a much better, more detail-oriented leader for longer. And that's really where I think the best future executives are, are line managers, because middle management has historically selected for a totally different set of skills.