Thomas Shey
Legend
Yes, this is undeniably a thing we (by which I mean, we DMs who like to use this sort of action resolution process) have to contend with. A lot of players are going to be coming to the table with baggage related to being asked for specificity. It’s a bit of a leap of faith for them to try playing this way, and we need to be willing to show some patience and empathy to them in turn. It also helps if we run damn good games, cause at the end of the day that’s what’s going to sell someone on our GMing.
Its also one of those things you're more likely to have luck if the person has just absorbed it from the gestalt than if they've had it done personally; depending on the frequency and extent of the latter you may never be able to entirely get them beyond that.