Hiring lessons from year one

The first five hires at any company set the culture more than any values doc will. I learned this the expensive way.

What went wrong

I hired for skill and ignored fit. Twice. Both people were technically excellent and left within six months because the pace and ambiguity of an early-stage team wasn’t what they signed up for.

What I do differently now

1. Reference calls before the offer, not after. Ask “what would you change about working with them?” — the hesitation in the answer tells you more than the words.
2. A paid trial project for anyone joining in the first ten hires. Two days of real work, paid, no exceptions.
3. Write the job’s first 90 days down before posting the role. If I can’t describe the first quarter concretely, I’m not ready to hire for it.

The checklist

• Can they operate with 60% of the information they’d want?
• Have they built something from zero to one before, in any context?
• Do they ask better questions than I do about the problem?

Hiring lessons compound. The bar you set for hire #5 becomes the bar hire #50 measures themselves against.