The job of recruiting is an art, not a science. And like all arts, it's hard to teach or even talk about.
When you're interviewing candidates for a job at your startup, it's easy to feel like you're on a roller-coaster.
For one thing, the stakes are high: you need this person to work out, and working out means more than just doing the job well.
A single hire can change your whole company's trajectory.
You also feel like you've got limited time and limited information to make a big decision. And the candidate is in an equally difficult position: taking a job at a startup means signing up to take a risk, and most people want to minimize their risks.
You're both trying to figure out whether the other party is trustworthy over the long term; how smart they are; how much they know about your business, and whether they'll be able to learn what they don't already know; and whether their values will fit with yours.
There is no formula for making this kind of decision, but here are some guidelines I've found useful:
Risk
What risks did you take, and where did they lead you?