Chinny Chukwudozie

What’s changed in “the unwritten rules” of engineering management since the 2010s, why are hands-on managers “back”, and what has it done to the engineer-to-CTO career path? With Will Larson (@Lethain). Timestamps: 00:00 Intro 08:20 Stories from Yahoo! 12:47 Digg’s v4 rewrite: the insider story 26:02 Will’s path to eng leadership 30:03 Uber, Stripe, Carta, and Calm 35:11 What does a CTO do? 38:09 Will’s role at Imprint 42:48 How engineering management has evolved 51:08 ZIRP’s impact on tech 57:21 Career ladders 1:01:03 Eng 1 vs Eng 2 1:06:58 How software engineering roles are changing 1:16:25 Revised rules of engineering leadership 1:21:57 The risks of becoming a bureaucrat as an EM 1:25:57 How to become a CTO? 1:31:33 Middle management vs. line management 1:41:36 Will’s writing 1:52:13 Book recommendations Brought to you by: • @turbopuffer – vector and full-text search built on object storage: fast, 10x cheaper, and extremely scalable. turbopuffer.com/v3 • @EntireHQ – Git hosting, rebuilt for the agentic era. Entire hosts your code in-region, and is up to 89x faster than any other competitor. entire.io/pragmatic • What if you only needed a single test to harden your system? Get a free introduction to property-based testing: through a live, online webinar hosted by Hillel Wayne, author of Logic for Programmers and Developer Educator at @AntithesisHQ. RSVP here: pages.antithesis.com/webinar… Two sage observations from Will on how engineering management changed: 1. ZIRP shaped engineering management practices in the 2010s, Will believes. As he put it: “Back then, your ability to hire and close and retain became the differentiator between successful companies. The less successful ones simply couldn’t retain great people. [This dynamic on hiring and retaining] pulled leverage back into the engineer’s hands and created a very different environment. So, companies were pitching themselves as a more relaxed environment, more focused on you, and offering more career development. And I think in ways that I think were often kind of self-defeating.” 2. Blunt message for middle managers: retire or re-skill. Will left a team of 250 at Carta to head up 25 tech people at Imprint. He purposely took a “step back” in his leadership career because he believes things are changing so radically that the engineering leadership profession that we know will not exist in three years. Amid all this, Will says that line management can be a lot more engaging for executives these days because the tools for line management and the tools for writing software are really good. Plus, the tech industry has always been volatile: during the 2010s most of us simply forgot about this!