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What’s changed in “the unwritten rules” of engineering management since the 2010s, what drove the shift to today, and what has it done to the engineer-to-CTO career path? Today’s guest is one of the best people I know who can tackle these questions.

Will Larson is CTO of Imprint, was an engineering executive for 10+ years, and is the author of several popular books on engineering leadership, including ‘The Engineering Executive's Primer,’ ‘Staff Engineer, An Elegant Puzzle,’ and ‘Crafting Engineering Strategy.’ Previously, he was also CTO at Carta and Calm, and an engineering leader at Stripe and Uber.

In this episode, we explore how engineering leadership has evolved from management practices shaped in the long post-financial-crisis ZIRP era to the altered expectations of engineers and managers today.

Is middle management an increasingly precarious career path, and might managers need to reskill and return to hands-on technical work – or even consider retirement? Will makes the case, and we hear why the traditional path to engineering executive roles is changing, as well as why taking one step backward might sometimes be the best way forward.

We discuss Will's early career, and get his first-hand account of Digg's disastrous relaunch, his own path to CTO, and he tells us why career ladders still matter. We also explore how AI is changing engineering roles and bringing technical decision-making back to leadership.