Ask a real question

Some questions are statements in disguise: "Don't you think you should have left earlier?" The speaker hears advice, not curiosity.

A real question is one you do not know the answer to. "What was the hardest part?" or "What happened next?" invites the person to say more, in their own direction.

Open questions — what, how, tell me about — tend to open a conversation. Yes-or-no questions tend to close it. Neither is wrong, but if you want to understand someone, reach for the open kind.