You can certainly convince them to ask for details, but I'm not sure whether that makes them any good at knowing when exactly to ask vs just asking some percentage of the time regardless.
That is, does it actually know when it doesn't know, or are you just making it less confident overall, so it asks questions with no actual insight? Convincing a model to roleplay as someone who doesn't know things vs teaching a model to have insight into when it does and doesn't need clarification seems like a tough one.
You can certainly convince them to ask for details, but I'm not sure whether that makes them any good at knowing when exactly to ask vs just asking some percentage of the time regardless.
That is, does it actually know when it doesn't know, or are you just making it less confident overall, so it asks questions with no actual insight? Convincing a model to roleplay as someone who doesn't know things vs teaching a model to have insight into when it does and doesn't need clarification seems like a tough one.