Jason M. Lemkin gives practical interview advice for hiring VPs (especially VPs of Sales). He favors simple, direct “Columbo” questions that probe whether a candidate can bring high-quality teammates with them (e.g., naming who they'd recruit like “Bob, Diane”) and warns that candidates who only promise to hire recruiters—not bring their own experienced people—are poor VP hires.
Especially VP of Sales. But any vp, you have to bring in good folks. You have to bring in good folks. And when I'm interviewing any VP candidates, engineering, marketing, but especially sales, there's a few trick Columbo questions I ask. I never ask tough questions. I always ask simple questions. Layups. But I ask, okay, who are you going to bring with you if you join this startup? Bob, Diane. Great. Okay. What are their backgrounds? Are you sure they're going to come with them? Go talk to Bob and Diane. It's okay if she's going to bring Bob and Diane with her. They've known each other for years. They're already grooming them to come. It's okay to go talk to them. If you hear a VP of Sales, or really any VP candidate say, I don't know anyone, but I'm going to hire a bunch of recruiters. That's not a vp. It's not a vp and this is a mistake again and again.
