I think it's important to be on the same boat money-wise, while also expecting similar things for the near (or not-so-near) future.

Questions: * Do they have any loans that need to be payed? If yes, how would this affect future decisions to stay in the company? * Are they thinking about wanting to do something they haven't been able to do before (traveling for long, living abroad)? * How much do they need the stability of a regular job?