Job security (both in their current job but also how easy it is to find another job)? How they found their job (word of mouth, networking, headhunter etc)? Leading employers in their field? Career path options (ie will you still be growing and learning for a while or will it fizzle out and you'll be fighting grads for your job)? What makes them get out of bed every morning to do that job (best bits, motivators)? What kind of personality does it suit? What leads to career suicide? (links to the q above, eg for me being clock watched makes me stabby, so any job where punctuality is crucial isn't for me) What would they look for if they were hiring someone to do their job?
What aspect of their job do they find the most challenging? How did they get their job? Opportunities for advancement/extended training/etc.? Know this is a tricky one based on how well you know the person you're asking, but if you can find out what the going pay rate is for the job you're considering, it will help you when you're going in for the interview. Dress code
Sorry, probably should have explained - it will allow them to get into the flow of what they do so will help to pull up some of the answers to the questions you already have, but un-selfconsciously. If you take notes, that will mean you can also then ask questions that occurred to you during the first bit.
Best of luck figuring out what's best for you to get back to, too.
I gave up a career after DD2 to stay at home for a couple of years, with the view I would then retrain once the youngest is in school.
I am now at the stage where I am seriously considering the options so that I can be sure of the career choice before I invest fees and everything else into it. My heart says teaching, and I am getting experience in schools, but I want to rule out other service / caring type careers.
Friends of friends are willing to give up their time to talk to me about what it is really like, doing what they do. I want to make the most of their valuable time, and start to find out much as possible from these willing strangers!
I have loads of questions Already - what do you enjoy, what is frustrating, employment prospects now, and maybe in a few years time, how satisfying it is, key skills, flexible working options.....