Determine if they have a chip on their shoulder . Do they have something to prove? Where’s the hole they’re looking to fill? Ideally, you’d get someone with obvious talent/drive that is misunderstood by the world. Those types of people will run through walls to reconcile their internal view of themselves with external perception.
If you're the CEO of a fast-growing startup, the mistake you'll make in the next year that you'll regret most will probably be a hiring mistake. Possibly hiring someone established, which you'll feel you should do now you're getting big, and which VCs will strongly encourage.
The biggest difference in how I’m hiring the second time around:
Indexing heavily on people who really, really want to work at a high growth startup
If a candidate is deciding between us and a comfortable job at a big tech company, it’s already not a fit
regardless of what you think of this (hustle porn or roadmap to get ahead at work), I think more employers should adapt the practice of setting clear, non-negotiable expectations as part of the hiring process.