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Biggest mistake I've seen in company culture: being generic.
At Gainsight, we were pretty well known for our quirky culture. And that was why it worked.
I've watched so many founders define their company culture based on what other hot companies (SpaceX, Palantir, Stripe, etc.) have. I'm sure some asked ChatGPT to do it for them...
Here's an alternate recipe:
* Why: To me, the best cultures start with a founder defining why the culture is personally important to them. Cultures are intimately tied in the early days to the people who created them. Why did you want to create a company? For me, this showed up in the idea that I always wanted to be in an environment where people treated each other as humans above anything else. This turned into our mission statement "human-first business."
* Who: Who are the early people that you think represent what's unique about your company? What drives them? What do they value? Who didn't succeed and what was different about them? This might help you capture the essence. As an example, one of our early teammates, Dan Steinman, was always there for others with no expectation of anything in return.
* What: What words capture the essence of your cultural vision in a way that they would make no sense in any other company? What terms are so special and unique to what you do? The weirder the better. Our values - including "Childlike Joy" (bring the kid in you to work every day) and "Stay Thirsty, My Friends" (find your inner drive - also clearly a copyright violation off of the Dos Equis commercial!) were strange selections that only fit Gainsight.
* When: My personal opinion is canonizing these should be done early, but not too early. We captured most of this 1-3 years in. You need enough reps of hiring people that you have some patterns. Repeat founders might have more of a sense in the beginning, though.
* How: For our final 2 of 5 values, we brought our tiny team together and had folks brainstorm words to capture the spirit of our culture. I ultimately made the calls (including overruling on one item), but sometimes the ideas help.
Ben Horowitz said it well - "Culture is not a set of beliefs. It's a set of actions." Generic beliefs are the enemy of a culture of action.
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