Challenge him with forward thinking. Use questions that allow him to project without taking ownership.
Like: If you designed a school, what would the day be like?
What would the perfect math lesson look like?
Or such. Also, don't probe backwards or try to fix what he tells you. Very useful to just listen and commiserate without judging. Have a separate conversation if needed at a different that starts with gaining his permission. "would you like to talk about how we might chnage your current situation with school?"
Guard your reactions, he may be sensitive to your reactions.
I've had luck with my DS7 this way when he is reticent about issues. But he is a talker who enjoys an audience, so I have one less hurdle to deal with.
