A tiny language tip for you when leading a conversation.
Instead of asking “are you sure?”, instead ask “how sure are you?”.
The former asks for a “yes/no” answer and may create defensiveness.
The latter, delivered in an open and curious way, invites and encourages a thoughtful and open response, as well as (I have found) often bringing out some thoughts around the topic that the person being asked the question had not as yet recognised in themselves.
PS bonus tip for changing the language of questions. Instead of “anything else?” (again a “y/n” question that basically invites a “no” answer), instead, ask “what else?”