# Middle managers may need to return to hands-on engineering

Markdown copy of https://realalpha.app/s/middle-managers-may-need-to-return-to-hands-on-engineering/ 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: 1:33:30 to 1:39:27 of the episode (6 min), playing on https://realalpha.app/s/middle-managers-may-need-to-return-to-hands-on-engineering/; the episode from there: https://realalpha.app/v/Prl858_AovM/?t=5610

## Quote

> “either you have to **get back into the details** or the world is changing so radically that the profession you know will not be valued in three years.”
> — [Will Larson](https://realalpha.app/people/will-larson/) at [1:33:56](https://realalpha.app/v/Prl858_AovM/?t=5636) · The Pragmatic Engineer

## Takeaways

1. Management roles may lose value as expectations change.
2. Line management can offer more learning than middle management.
3. Be open to a lateral move and hands-on work.

## About this segment

Will Larson says managers can reskill by moving closer to software delivery, even if that means taking a lateral step. His own move to lead a smaller team gave him room to relearn how to build with AI.

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.

[1:33:37](https://realalpha.app/v/Prl858_AovM/?t=5617) It's a hard time in middle management, right? There's a lot more competition for these roles. And so I think what I found personally very rewarding is kind of getting back into the details of writing software. And so when I left Carta, my team was 250, maybe something like that. When I joined Imprint, the team I was leading was, I think, 25. And so for me, this is kind of like a unique moment to actually re-skill. Well, if you're in management, I think right now, either you have to get back into the details or the world is changing so radically that the profession you know will not be valued in three years.

[1:34:12](https://realalpha.app/v/Prl858_AovM/?t=5652) And I think you sort of have to decide, like, am I retiring now or am I re-skilling? And I thought about that, too. Like, you know, I could just I could just be done. Right. Is this is this is what I want. But it's not what I want. Right. I really want to still be participating. And I really genuinely believe the way that we work has radically changed in the last year. It hasn't changed everywhere.

[1:34:35](https://realalpha.app/v/Prl858_AovM/?t=5675) There is like a long tail that's going to take a long time to catch up. But in the places I work, it's changed a tremendous amount. And for me, personally, it's a lot more fun. So first, I think there has to be some like openness to like taking a backward step or a lateral step. Just what people want is very different. And you have to be open to like, getting a different like look at it. And so I think going back into like a line management position, for example, is actually much more educational than a middle management. The tools for line management and writing software are so good. The tools for headcount planning or doing performance reviews are basically terrible, right? Like all LLM applications for these things are not good.

[1:35:17](https://realalpha.app/v/Prl858_AovM/?t=5717) So I do think you're missing a lot in middle management right now. I would try to find my way out of it. But thinking a little bit about some folks that I hired at Imprint, one of them that comes to mind is Jasmine, who I worked with at Carta, came over and she was hired as a VP, but she was a VP that was hiring or managing a team directly. So she was a line manager? She was a line manager, a really experienced line manager, was running engineering at Mux some time ago, and she came in to line manage.

[1:35:46](https://realalpha.app/v/Prl858_AovM/?t=5746) And she's doing just a tremendous amount of software, which she would have never done at Carta because she could have never gotten time to do it. And at Mux, she was also like way too busy, like running the function to actually be in the details of writing. Those people that are willing to actually go back and get their hands on to it are so valuable. and if that is who you are, you have to let people know because otherwise people would think you would never take that opportunity but I would hire more people like this all day long.

[1:36:13](https://realalpha.app/v/Prl858_AovM/?t=5773) You know what we're talking about in the 2010s on the reserve how engineers got a little bit too used to like, oh yeah, my company and manager is here to do what I would like to do. I would like to do platform. No, no products are, even if the business needs it, just not for me. You know, I'd rather quit and sometimes they quit. I wonder if there's a little bit of this with management where like, look, again i don't mean to imply too many things for these folks but generally similar i have been i have this path i i thought i would be vp of engineering soon and i i want to get there but is that what the industry wants is that what the other companies want no right now they want really good let's say line managers yep and either similar to those engineers the best engineers i know they kind of put their ego on the back and when the business said like look

[1:36:59](https://realalpha.app/v/Prl858_AovM/?t=5819) Win. a product to build. They're like, look, I'm great at platform. You know what? Let me be the best product engineer I can be. I felt with you as well that you, you know, you had 250 people, I assume, you know, compensation, equity, status. And you went down to lesser known startup with not as a well-known brand yet, or at the time, taking a lot smaller teams, smaller responsibility. You let the ego at the door, if you know what I mean. And then you learned so much more.

[1:37:26](https://realalpha.app/v/Prl858_AovM/?t=5846) Yeah, I think in a lot of ways, it was just like a much better situation for me. And so like there are a lot of pieces that weren't like kind of, oh, like, this is a hit. That's not really how I thought about it. It was the perfect situation for me because what I knew what I wanted was getting back into the details, relearning how to do software in the current age. That's what I believe is going to be the unlock to kind of the longevity of my career.

[1:37:50](https://realalpha.app/v/Prl858_AovM/?t=5870) also though it's just like much more fun and so like to me it's just like much more energizing and i i've always been someone who kind of got tricked into management going back to the story where they just needed a manager and so i i said yes you've been tricked ever since um and then they made a director so it looked like they had a director and acquisition conversations so they that was more palatable but i didn't know how to line manage letter and direct i just they kind of needed one on paper. So, you know, very kind of them, though. So for me, this has been kind of what I wanted. And this has been like a unique opportunity. But I think for a lot of folks, there is this sense the industry has betrayed them, and that they're owed something that they've worked for. And the thing is, like, they're right, like, they have worked incredibly hard,

[1:38:36](https://realalpha.app/v/Prl858_AovM/?t=5916) but the rules have changed. And so I think that at certain moments, the world looks very stable. and our industry looks very stable. And I think in the 2010s, we forgot that our industry is actually very volatile. Our industry has changed just a staggering amount in the last every decade. Things are just radically different than they were in the decade before. And we've sort of like lost sight of that. And I think that people that kind of came up in the era of a lot of stability don't remember that sometimes. And so I do think we have to be willing to kind of take lateral moves.

[1:39:08](https://realalpha.app/v/Prl858_AovM/?t=5948) We have to be willing to be a little bit humble. But if doing the actual work, that's like the thing that matters to the company is humility, then we've sort of like lost track of what we're doing here because we really do just get paid to do things that are valuable to the companies, right?