The founder mistake I made twice before learning the actual lesson

I hired two early employees for potential rather than immediate need, reasoning we'd grow into needing them. Both times, the role I imagined they'd grow into never materialized on the timeline I'd guessed, and I was paying two salaries for work that didn't yet exist.

The actual lesson, learned the expensive way twice: hire for the problem sitting on your desk today, not the problem you expect in eight months. The eight-month problem, when it arrives, is never exactly the shape you predicted anyway, and a person hired for a guess rarely fits the reality that shows up.

Every hire now has to map to a task I could point to happening this week. It's a smaller, more boring hiring philosophy, and it's the one that's actually worked.

Related reading: The Complete Guide to Interviewing, Negotiating, and Surviving the Year After a Promotion and Why the salary-negotiation advice you've heard is backwards for most people.