[devlopr]

Ask the CEO a question as a prize? Can I forefit my winnings?

Maybe it's me but I can't think of any question that would produce an answer of information I didn't know and actually want to know. From any CEO.

What would you ask Musk? Or your own CEO if you had the chance?

[joshspankit]

How about something like “How can I get from here to _____?”. Asking for the CEO’s perspective on moving up in your career.

They might not be good advice, or they might not have insight in to you as an employee (though I would challenge them to get that first as part of the question), but you just might uncover some unknown unknowns and open some doors.

[MR4D]

“What keeps you up at night”. The answers to that are usually pretty honest in my experience.

[acntr_employee]

I would ask, how he can sleep at night knowing that women earn significantly less than their male counterparts. Or how he would explain around 100% difference in salaries for the exact same job depending on the person.

[devlopr]

Asking that question after winning an employee game wouldn't give you much insight. He or she would say they are working towards some goal and ask you to join the committee on women's pay.

If you asked HR they will probably give you more of an honest answer. We are trying to pay people as little as possible.