I've had this happen hundreds of times in immersive play:We're so into this conversation with this NPC! There are veiled threats and hints of opportunity! We said some charming and clever things! We told some strategic lies! This NPC seems like someone we might befriend! Or kill! We're loving this!
Ten minutes later:Is he gonna tell us anything useful or not? Did we get anything useful already? What was it? Is there something we're missing? Is there something else we should try? Should we trust this NPC? Plan to kill them? How do we know? We hate this.
There's an obvious solution to the less fun part: get certainty from the game system. Engage a procedure that forces a die or the GM to tell you, "Here! Look! This! This is the important thing, and here's how it is, and now you have to respond to that!"
A fine solution. But not a universal solution. In my experience, although a good game procedure often avoids the no-fun part, it also often discourages the super-fun part. Because why work and struggle and strive to master the fiction from within the fiction if you can push a game button to move forward? I'm not saying a useful dice procedure discourages roleplaying -- but I do think it changes the roleplaying. And I'm loathe to lose the no-rules version.
So! Here's my thought of the moment. The problem in freeform challenges is ambiguity. Can we provide in-fiction tools to remove that?
For example: what if player characters (or one player character per party) can read minds just the right amount? Like, maybe they can spot lies. So now you roleplay a conversation where you try to get the NPC to provide answers to telling questions. The effort is entirely in-character, but the feedback is no longer as ambiguous.
What do you think? Any other ideas for giving players concrete info without an extra-fictional procedure providing that?
I had another idea where players could propose a theory and then probe for things to confirm/deny, or account for what they've already seen to confirm/deny. So there'd be a game procedure -- "propose a theory!" -- but it would be more of a way to organize the conversation than to inject stuff into it from without. Inspired by @2097
's success with Petitioner/Granter, which I quite like, but I want a tool that's less vulnerable to being forgotten or superseded by existing habits.
I also thought about "formal rule as back-up only", where you hope that roleplay will get you there, but if the ambiguity is too frustrating, you can fall back on some Read a Person-type thing that'd say, "Here's one actionable answer. You now have the option to be done."