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Will Larson

CTO, Imprint

Led engineering at Stripe, Uber, Calm and Carta; author of Staff Engineer and The Engineering Executive's Primer.

Real Alpha has cut 7 moments of Will Larson (CTO, Imprint) talking, from an interview on The Pragmatic Engineer published Oct 21, 2026.

What Will Larson said

  1. The Pragmatic Engineer ·

    The revised rules of engineering management with Will Larson

    7 moments · 36 min

    1. 19:39

      Digg launched a rewrite without load testing or rollback capacity Pro pick

      “we made the decision to launch on Cassandra. And there's like a joke at the time”
      at 20:11
    2. 50:47

      ZIRP pushed managers toward hiring and people-focused work Pro pick

      “salaries went up, then competition for hiring became your ability to hire and close and retain became the differentiator”
      at 52:00
    3. 1:33:30

      Middle managers may need to return to hands-on engineering Pro pick

      “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.”
      at 1:33:56
    4. 1:16:22

      Durable teams let leaders focus on the problems only they can solve

      “The first thing I did was like, all right, what are some pods? And figuring out like some areas I could put together who could own areas.”
      at 1:18:10
    5. 1:26:01

      A CTO needs both technical judgment and bureaucratic experience

      “If you've never been a bureaucrat, you don't know how to see things as a bureaucrat.”
      at 1:28:36
    6. 57:21

      Staff engineers are distinguished by how they resolve ambiguity

      “what you need like someone at the staff or principal level to do is to navigate an ambiguity by making some trade-offs”
      at 59:49
    7. 10:19

      Central server approvals created a black market at Yahoo

      “And so on my team, there was like one engineer that had 30 servers from a prior canceled project he never gave back.”
      at 11:53

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