It's hard to guess from one child to another. I know DS7 is very sensitive to any criticism of his emotional responses. Also, given alternatives A & B he always picks C. There is some tricky line between someone to talk to and "the parent" that can be hard to navigate. The one questioning approach that I've found helpful is to ask future planning/creative questions like:
"If you could change anything about school, what would it be?"
or
"I was thinking of making this meal something we have on a regular basis, do you think it should be once a week, once a month or once a year."
