I always thought it was easier to ask senior managers and senior technical staff questions, because they had so much experience. But especially with managers, much of their experience is about judgement calls and the way they make decisions. So, I'd ask about that. But from some questions I've received recently, I'm in the minority of enjoying interviewing senior staff. Here are examples of questions I've asked in the past:
- Give me an example of a time you had to choose between two alternatives you didn't like. What did you do? (I'm looking for someone to say they didn't limit themselves to two options. Or if they did, I'm looking for how they made the decision.)
- Has there been a time you felt your ethics were challenged by something your management wanted you to do? What happened? (Anyone who's been in a senior position or has been working at mid- and upper-management levels for any amount of time has been in a position like this. I want to see them admit it, and say what they did.)
- Have you ever been in a position to provide feedback to an employee who wasn't working out? What did you do?
- Have you ever had to fire someone? What were the circumstances? What did you do?
- Have you been in a position to coach or mentor someone? What did you do? When do you choose to take on coaching or mentoring? (These questions work for managers and senior technical people alike.)
Asking senior people behavior-description questions provides you a way to have a conversation about real experiences, and to see if the circumstances around those experiences are relevant to your context.