Good Generalist/Bad Generalist

How to be effective at a startup, without a specialty

There is an inherent insecurity that comes with being a “generalist” at a startup: you always wonder if a specialist will someday take your job.

You are, after all, someone without a speciality. Maybe you were a consultant, or you did a “management” rotation at a big company; maybe you got an MBA; you were almost certainly a liberal arts major. You are smart, capable, and hard-working. But you don’t have experience in any particular field, and your technical skill amounts to VLOOKUPs and/or the white lies you tell about Python and SQL.

I have been a generalist at Astranis for about four years now.

I started as a “finance” hire who spent half of his time recruiting and doing legal/regulatory work when Astranis was a 50-person Series A startup. Today, I am the Chief of Staff, and we’re a bit bigger than that:

Over those years, I’ve learned both from my personal experience and from watching the generalists I’ve hired either succeed or fail at Astranis.

Here’s what it takes to be a Good Generalist.

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Good generalists have concrete, specialized skills that can be brought to bear on a wide array of potential projects. Good generalists are effective communicators, rigorous systematizers, and know how to get shit done. Good generalists work quickly.

Bad generalists are wanna-be specialists. Bad generalists compensate for their lack of specialized skills by working slowly and tentatively. Bad generalists never get anything done, because they are afraid to be vulnerable and afraid to look incompetent.

Good generalists are fearless. Good generalists stare at a blank page, and get something — anything — written down with incredible haste. Good generalists aren’t afraid to share their shitty first drafts. In fact, good generalists excel at generating shitty first drafts, and make incredible, step-change improvements in quality with every cycle of revision.

Bad generalists are terrified of turning anything in. Bad generalists work in the shadows until they have generated a product that they “can stand behind,” which invariably look like well-polished turds. Bad generalists are timid when asking questions, and fail to get actionable feedback, causing their projects to stall at “good” without ever becoming “great.”

Good generalists can crush both the 80/20 of a project and the 20/80: they work fast to deliver high-quality products, and excel at finding things to improve in products that other people consider complete. You can throw a good generalist onto any team and expect their work product to improve. Good generalists love polishing as much as sculpting, and have incredible attention to detail.

Bad generalists use “80/20” as an excuse to do bad, incomplete work. Bad generalists give themselves passes when their final work product requires additional work before it is ready to be released into the world. Bad generalists rely on others to tell them what excellent work looks like, and begrudgingly slog through the hard parts of making products great.

Good generalists know more about “the rest of the company” than everyone else. Good generalists have asked deep questions to the rest of the company, and often know a startling amount about a startling number of topics — or at least immediately know who can help them when they get stumped. To a specialist, a good generalist is an incredible resource for getting context about what the rest of the organization is doing. Good generalists learn things that help the company.

Bad generalists live at the surface level, and never dive deep enough to understand how things really work. Bad generalists can parrot what they’ve been told, but never know deeper “whys” behind those superficial explanations. To a specialist, a bad generalist is useless because the generalist knows nothing more than what the specialist already knows. Bad generalists learn only those things which help themselves.

Good generalists actively and enthusiastically hire their own replacements — because it means that their time is freed up to learn something new. Bad generalists hold onto their LEGOs — because they want to luxuriate in the knowledge they’ve built up, and fear becoming a beginner again.

Bad generalists ask “what is everyone asking for?” Good generalists ask “what is nobody else doing?”

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Thanks for reading Silicon Valley Outsider! Here are a few past editions that you might like if you enjoyed this one:

• It’s okay to work hard.

• How to make startup life less painful

• How to find and crush a job as a startup Chief of Staff

If you want to join 600+ folks in getting an email from me each Monday, I’ll help you understand Silicon Valley using normal-human words.

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(NB: I stole this format from Ben Horowitz’s legendary post about product managers. Read it, if you haven’t already!)