Brutal truth from @Lethain
“If you're in [middle] management (…) you sort of have to decide, am I retiring now or am I re-skilling?”
He did just this: step down from leading a large team (250 ppl) to be hands-on with a small team (25 ppl), ship code & re-learn the new “rules”
Gergely Orosz
@GergelyOrosz
The Pragmatic Engineer @Pragmatic_Eng
Why a 3x CTO went back to a 25-person team. From Will Larson @Lethain, Imprint CTO and 4x book author.
"It's a hard time in middle management, right? There's a lot more competition for these roles. What I found personally very rewarding is getting back into the details of
"It's a hard time in middle management, right? There's a lot more competition for these roles. What I found personally very rewarding is getting back into the details of
1:09 PM UTC · Oct 24, 2026 · 77.3K Views
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Gergely Orosz
@GergelyOrosz
He told me he shipped more PRs ina year than in his previous 10+ year exec career combined.
That’s how much the game is changing.
Forget becoming a CTO (as an ext hire) if you’ve not been also shipping code to prod, with AI. It would mean your might be a good buerocrat not a good technologist any more, and this “new gen” of execs need to be great technologists
That’s how much the game is changing.
Forget becoming a CTO (as an ext hire) if you’ve not been also shipping code to prod, with AI. It would mean your might be a good buerocrat not a good technologist any more, and this “new gen” of execs need to be great technologists
1:12 PM UTC · Oct 24, 2026 · 7.7K Views
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