Adam D I broadly agree with all that. But not all games are written that way. Like specifically with Encounters, there’s a push-your-luck element to it where any given failure might not sink the whole deal. So, you know, maybe go ahead and ask? Or ask for the big shit early?

There is a skill called Insight that I believe would actually be RAW-useful in lieu of negotiating between players. It is itself a gamble but the odds of it being harder than 14 are vanishingly small in my own mind at least. Unless you’re dealing with some squirrelly fucker going out of his/her way to be misleading (then it’s probably Insight vs Riddle).