Opening the book…
If you assign someone a future they didn't choose, you get compliance and you pay for it later in quiet departures. Knowing what someone is actually building toward lets you hand them work that costs you nothing extra and means everything to them. It also tells you where your plan and their plan genuinely conflict, which is information you need before, not after, you commit.
Book thirty minutes with no agenda item but this question, and ask it plainly: what do you want to be able to do three years from now that you can't do today. Write the answer down where you'll see it again. Then say where your plans line up and where they don't, and don't pretend to an overlap that isn't there.
Someone in crisis or two weeks into the job has no useful answer yet — ask later. And in a genuine emergency, direction comes first and the conversation waits.