[stephengillie]

1. Who is the most difficult person here to work with, and why? (Who should I watch out for - do they have a bad temper or goto management every disagreement?)

2. What's the biggest technical thorn in the company's side? (This is almost always something basic - like convincing management to buy more storage, or getting everyone to migrate to the newest version of something, or an underperforming vendor with a long contract.)

Both of these tell you about the company, and also about the person's perspective from their role and expected duration.

[benburleson]

I would never honestly answer #1. In my head I know my honest answer today, but out of context I would never attempt to explain the history with a candidate. If the candidate joins the team, then what? Are some offices so impersonal that this doesn't become an issue?