The thing I would spend the most effort finding out is whether or not THEY are happy with their job. Do they have a career plan that starts with the position they are now holding? What plans do they have to build on their current situation? Or are they happy for now to be in a holding pattern until they make better plans?

Sharing with them that you think they are worthy of a better job, and that you miss them when they are away is an excellent idea. Who wouldn't want to hear that they are highly thought of and missed by their partner?

I have a question and answer exercise to suggest. Each of you takes one turn answering the following questions about the other:

1. Do you think my current job is a good match for me?

2. What sort of work do you think I would be good at?

3. How far up the ladder do you think I should rise, in the best of all worlds.

Take turns answering all three questions about each other. Only positive feedback or requests for clarification are allowed, not argumentation. In the best of circumstances, the person talking finishes his thoughts while the other person listens, and then they listen while the other person talks. The goal of the exercise is to allow both sides to express their opinions without arguing, and to allow both sides to listen and truly hear the thoughts of the other on this (or any) topic.