Chapter 9. Bootstrapping Culture

When you are in the role of senior engineering leader, part of your job is to set the culture of your function. A common failing of first-time CTOs is to underestimate the importance of being clear and thoughtful about the culture of the engineering team. Whether you are growing a new team or reforming an existing team, neglecting the team culture is a sure-fire way to make your job harder. As the team grows and evolves, it’s important to attend to your culture as you would attend to any other important piece of infrastructure that you rely on.

At Rent the Runway, I had the opportunity to set up many of the cultural elements of the engineering team. Because the team was still running on the classic, unstructured “scrappy startup” model when I joined, I was able to introduce many cultural structures and practices to both the team and its members. This process was a great learning experience for me.

For many people who are attracted to startup culture, the ideas of “structure” and “process” are seen as pointless at best and harmful at worst. I have seen surveys of startup teams in which the idea of introducing structure evoked such reactions as “slow” and “innovation-crushing.” These respondents believed structure is the reason large companies move slowly, foster bureaucracy, and are generally boring places for bright people to work.

When talking about structure with skeptics, I try to reframe the discussion. Instead of talking about structure, I ...

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