1. Why is this position open?
2. What are the biggest challenges or obstacles the person in this position will face?
3. Can you describe a typical day or week in the position?
4. What would a successful first year in the position look like?
5. How will the success of the person in this position be measured?
6. Thinking back to the person whom you’ve seen do this job best, what made their performance so outstanding?
7. How would you describe the culture here?
8. How would you describe your management style?
9. Are there reservations you have about my fit for the position? (This is a great way to give yourself the chance to tackle any doubts they might have about you—as well as for you to consider whether those doubts might be reasonable and point to a bad fit.)
10. When do you expect to make a hiring decision?
Here is the one question that I think should be asked at the end of each interview: When can I start? Admittedly, this is a hard question to ask and it takes a bit of confidence to be all exposed like this—after all, the answer may well be something the applicant does not want to hear. But if you consider the question as a way to simply check to see how you have done in the interview so far, it might help. The hiring manager will have to be honest with you as a result of this question. It is far better to know their objections while you are still there and can handle them.