A few days back, I poked a little fun at some of the weird questions that can pop up during the interview process.  This week, I'd like to turn you on to a really insightful article over at Mashable Business by Jayne Mattson,  a senior vice president at career management firm Keystone Associates.  Below are a few that have come up for me from both sides of the interview table.
What qualities of your last boss did you admire, and what qualities did you dislike?
Mattson is right in her assessment on this one.  It is a tightrope of a question, but it can be pretty revealing.  We recently had a candidate flame out on this one, revealing a pattern of pushing blame off on "the man" and not taking personal responsibility for early communication problems with his boss.  Be ready for this one, striking a thoughtful critique, yet positive tone.
How would you handle telling an employee his position is being eliminated after working for the company for 25 years, knowing they would be emotional?
This is also a great barometer question into the very soul of a candidate, even if they aren't being considered for a management position.  I can't really tell you what the "right" answer is here, but am always a little wary of the cold, "it's just business" line.  Sure, we're in business, and the primary survival goal of a business is to make money, but businesses are made up of people, and a little humanity goes a long way toward having successful career.  Give some thought to this one.
As you look at your previous companies, can you describe in detail which company culture did you excel in the most and why?
This is a great culture fit question, as Mattson points out.  We've often asked a variant of this question.  After settling whether or not you have the chops for the job, the next most important thing an interviewer wants to know is whether or not you're going to fit in with the rest of the folks. I think Mattson nailed most of these.  Whether you're the interviewer or the interviewee, check out the article.  It will sharpen your saw.