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This is a really great thread and really resonated with my personal journey, although at a smaller scale. I’ve transitioned within a large enterprise from leading a deep & broad engineering team with about 50 people to a vertically integrated ops/technology team with about 800 people.

The “work” is challenging, but the communications is much harder than I expected. It’s difficult to actually say anything at all because nobody will perceive what you say the same way, and then the telephone game with amplify whatever insecurities or worries that folks have.

The hard part about flipping from “move fast and break things” to more order is knowing when the right time is to transition. The other hard part is that the official “communications” functions live in a different vertical, and getting them involved often makes things worse. So we get stuck getting engineers and interns to communicate with people.



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