Ask the potential hire about a time something went wrong in a past campaign and how they responded. It's a common interview question, but helps reveal how the staffer would handle the challenges facing an upstart organization. Every campaign is going to make mistakes; what matters is how you respond.

Let's say you're working a congressional race and you mail out thousands of invitations to a town hall event with the incorrect address. Are you willing to drive to the address you put on the mailer and wait there all day until they agree to rent you the building for that night? That's the kind of pivot required early on in a campaign.