The best interviewing: evaluate communication skills, introduce disruptions and observe the response, insist on explanations, and visualize this interview playing out once the candidate is hired. In other words, don’t play it safe, but instead embrace a little discomfort and uncertainty. Don’t be afraid to ask some regular questions, and then just throw out a curveball from time to time. Here are some possible curveballs from which to choose, some obviously with more “break” than others:

• Tell me about a recent system transition or migration that you were involved in. If the response becomes too technical, ask them to explain the budget, the stakeholders, the project plan, the politics, the mistakes, the lessons learned.
• What the heck is cloud computing anyway?
• Why did an employee tell me that the servers we have on campus are like cloud servers for him when he’s at home?
• What is an obsolete technology for you?
• What is your philosophy for on-prem versus off-prem?
• What types of questions do you ask a vendor when you’re evaluating their product?
• This SAMR model idea...is substitution such a bad thing?
• What are some good ways to negotiate with a vendor?
• What is your philosophy on password management and access control?
• What does the phrase, “Consumerization of IT” mean to you?
• Where do you go for professional development and growth?
• How do you inspire change among the entire faculty?
• What are your technical weaknesses?
• What’s the most annoying thing about technology?
• When is best to do group trainings versus 1:1 appointments versus drop in?
• Is it really possible (or worth it) to separate help desk support from academic technology support, at least from the eyes of faculty?
• Why is it so hard sometimes to train people on new technologies?