I think this really depends on your style.
My first meeting is the set-up for the entire relationship of the project.
Let's assume, for some reason, I am already on the project, but we haven't had a meeting yet. (It happens).
This is how I start.
1) Why this show?
2) How do you feel about the cast? Do you have any concerns?
3) How has the design process gone? What have you lost or had to adjust?
4) How are your interactions going with the theater? Producer? GM?
5) What do you want this final project to "be"? (Look like, make the audience feel, what is this event?)
6) What do you want from me? What do you like in past successful stage management relationships? What do you hate?
7) How do you like rehearsal to be?
Good cop or bad cop?
9) I outline my "typical" style, how I can adjust, and what my process is like, and what I want/expect from the,.
I start in territory he feels comfortable talking to, and the turn it back on me.
But, this works for my style.
If you aren't comfortable engaging a director in artistic conversation . . . then maybe don't start there.