Some questions that I’ve found to be very effective in one-on-ones:
If we could improve in any way, how would we do it?
What’s the No. 1 problem with our organization? Why?
What’s not fun about working here?
Who is really kicking ass in the company? Who do you admire?
If you were me, what changes would you make?
What don’t you like about the product?
What’s the biggest opportunity that we’re missing out on?
What are we not doing that we should be doing?
Are you happy working here?