What single behaviour or attitude is most likely to upset your boss?

When is your boss most pleased with direct reports? What do they say or do during the course of carrying out assignments or in meetings that earns his approval?

What are your boss's demons? What work issue do you think keeps him up at night pacing the floor?

What do you think your manager's career objectives are? What capstone position is he aiming for? What does he need to accomplish to achieve these objectives?

What drives your manager? What non-career motivators push her? Is she after power, money, fame, security, knowledge, innovation, etc?

What trait or attitude that you possess makes you think you are well-suited to work for this particular boss?

What trait or attitudes makes you think you are ill-suited?

If your boss were a famous movie star, political, or other celebrity, who would he be? What particular traits does he share in common with this well-known individual?