Thanks for the good wishes. Here is a list of questions I have developed for the next session (in no particular order):

When are you planning to retire? (I'd put his age around 60 - I don't want him to quit me before I quit him)
What goes through your mind when I tell you that I was betrayed and then abandoned by my previous T?
What would make you consider terminating me?
What was your previous career? (He got his PhD in 1989, so he was doing something else before that)
How often do you take time off?
Have you ever called the police on a client? Without them knowing beforehand?
Do you have a good professional support network? (not that he'll say no) How do you use it? (I just want to have a brief conversation about how it works -- I think it's important that T has one and uses it)

Appreciate your comments / suggestions / additions for session #2 with T#9.