Larson urges middle managers to return to line management or reskill in AI

Will Larson describes the current career landscape for middle managers as difficult, noting that the bureaucratic skills selected for in the 2010s are less valued than technical execution skills in the AI era. He advises middle managers to either take a lateral or backward step into line management to re-engage with the details of writing software, or accept that their specific skill set may not be valued in three years. Larson argues that line managers are often better instinctual executives than middle managers because they remain close to the details, whereas middle managers often lose technical depth.

Larson illustrates this shift with his own career move. He left Carta, where he led a team of 250, to join Imprint as CTO leading a team of 25, specifically to reskill in AI-assisted development. In a year and a half at Imprint, he has completed over 500 pull requests, more than in his prior career combined. He highlights Jasmine, a former VP at Carta, who joined Imprint as a line manager and is now performing a significant amount of software work she would not have had time for in her previous role. Larson acknowledges that the industry has changed the rules, but maintains that returning to hands-on technical work is necessary for effectiveness.