I was talking with a colleague about the search for an academic dean, and about participating in the interview process with candidates. I confided that–while I found it helpful to see if the candidates seemed collegial, and to tease out what their relationship with EM at their current institution was like–I really had no sense of how to measure one candidate against another on the things that make a dean a dean.

My assumption is that our search firm only sent us the candidates with some level of gravitas. That the major research universities they mostly come from did a good job of vetting their research and contributions to the field during the tenure review process. And I assume our search committee members from the academic side of the house brought forth good experience in vetting the candidates’ resumes and cover letters, and that the people in the college will be able to apply a rigorous discernment process during their time in the room with them.

So what could I ask the finalists that might elicit a make-or-break response? I have no idea.

Having been on the receiving end of interview questions several times in my career, I often sensed people interviewing me had the same challenge. Any candidate who goes through the typical higher education hiring process (where everyone gets to cross examine the candidates) knows that the questions can range from the profound to the ridiculous to the sublime; knows they can be broad, narrow, or they can cut to the heart of the problem in an instant; is aware they can focus on 30,000 foot strategy or daily operations and processes; and that they can be driven by genuine institutional concerns or narrow and sometimes petty ax-grinding.

For your VP EM candidates, it’s often worse, because Enrollment positions carry very broad institutional responsibility, but a much narrower operating scope. When you’re interviewing for the dean of liberal arts, for instance, there are always other deans who can weigh in, and there are lots of faculty members who know how a professional approaches a discipline. But how many people on your campus know enough about Enrollment Management to sort the wheat from the chaff?

There are a lot of perfunctory questions you and your colleagues want to ask your candidates for Chief Enrollment Officer. You don’t need any help with that.

However, there are a few critical questions you should ask, and one you must ask. The response to that one question is what separates real EM practitioners who have been in the whitewater and those who have watched from the river banks.

Anyone can ask the question.

Figuring out if your candidate answers them correctly is the hard part.