Chapter 2. Your First 90 Days

The canonical book on starting a new role is Michael Watkins’s The First 90 Days. If you haven’t read it, you’ll certainly get something valuable out of it. I did. However, you may find that its advice skews somewhat generic. Yes, you should learn as much as possible. Yes, you should achieve alignment and negotiate for resources. Yes, you should build a team and partner with other organizations.

Those points are important, and this chapter focuses one layer deeper: on what you should do in your first 90 days as an Engineering executive. In this chapter, I’ll detail:

  • What you should prioritize learning

  • Why it’s important to limit the number of early changes you make

  • How to build trust and a support system

  • Understanding your organization’s health and processes

  • Learning how work (and hiring, in particular) is executed

  • Getting a grip on your technology when you have a limited amount of time to spend in your codebase

This chapter’s structure will help you craft your initial 90-day plan for your new role, ensuring that you focus on what’s most valuable rather than what happens to be screaming the loudest.

What to Learn First

Every role has a different set of priorities and different means for measuring them. What’s most important for a CTO starting at a Series A company, a pre-IPO company, and Google are going to vary a lot. That said, your discovery process—figuring out what is important—requires some structure, and I’d offer up these priorities as ...

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