Will Larson on the new rules of engineering management: reskill or return to the line
The Pragmatic Engineer · rss · 2026-10-22
The Pragmatic Engineer interviews Will Larson, CTO of Imprint and author of several books on engineering leadership, on how the unwritten rules of engineering management have changed since the ZIRP-fueled 2010s.
Key points:
- Middle management is increasingly precarious; Larson recommends managers return to line management and re-skill technically, as he has done. The traditional path to engineering executive roles is shifting, and stepping back can sometimes be the best move forward.
- Inside account of Digg's v4 rewrite disaster: Digg was a top-10 global site until the 2010 rewrite. Root cause was Python memory leaks from devs unfamiliar with Python, but Larson argues Digg was doomed anyway — a Google algorithm change had already cost it 60-70% of traffic while Facebook ate its audience.
- At Yahoo, cofounder David Filo's requirement to personally approve every server purchase spawned a server black market among engineers, and since old servers never had to be returned, Yahoo ran large fleets of outdated, power-hungry machines.
- In the ZIRP era, hiring and retention were the differentiator, handing leverage to engineers; today Larson tells teams hiring is the least interesting way to solve any problem.
- 2010s-era wellbeing perks like exempting senior engineers from oncall reduced reliability, since teams never felt the pain of their own outages.
- AI is reshaping engineering roles and pulling technical decision-making back into leadership; Larson is hiring engineering managers at Imprint to rethink team workflows with agents.
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