"You have enough money you live the rest of your life in idle luxury. You could just go to the beach and never come back. If I had your money, that's what I wou

"You have enough money you live the rest of your life in idle luxury. You could just go to the beach and never come back. If I had your money, that's what I would do. Why the heck are you still working?" A wordy, trying-to-be-cute way of saying "What motivates you to keep working?" or "Why do you keep working instead of retiring?" which is a pretty good question. "Will you share slides from the last board meeting?" A bit presumptuous maybe, but not quite into the realm of arrogance. I would verbally summarize the slides. "Where do you see yourself in 5 years?" Nothing arrogant about this one; a CEO should have a 5-year plan at least. Although this particular way of asking it has been used verbatim enough times since I first heard it in the 80s, that it now shuts down my mind immediately due to its blandly mind-numbing cliché quality. Which doesn't speak to the candidate's amazing creativity. Don't ask it this way if you're sitting with a Gen-Xer probably. "When I leave here in 2-3 years, will it be because of the people, or because I haven't gotten a raise and/or promotion?" I mean, you tell me. Are you more "I have a terrible personality and poor social skills" or are you more "I get childishly petulant when I don't get promotions and raises I think I deserve?" Both these things are within your control... and so is your exit from the company for that matter. If you were mature enough to take responsibility that is. Terrible question, don't ever say this. It conveys four negative things about you, all of which I would assume are true. "What keeps you up at night?" The question is again trying to be all folksy and cute bygoshdarn bygolly, but at its heart it's a pretty good question. In other words right now what's your biggest obstacle / thing you're worried about / thing that's giving you a pain. At work mind you... not your personal life!