I really don’t know, to be honest! Somewhere in my milieu, I picked up lots of different tricks for asking leading questions, absorbing them from different examples.
I do think that you can boil them down into two parts:
- The assumption. This is a stricture that you impose on the players, and it forms the groundwork for the question you’re about to ask. Your assumption has to be substantial, or else the question won’t spark inspiration or drive the story forward. However, your assumption can’t be so substantial that it strips major agency away from the player. Learning where the line is definitely requires experience, and it won’t be the same for everyone; I like to start a bit on the small side and then lean into players progressively more.
- The question. It’s the gap of knowledge that you’re asking the player to fill in. There’s the assumption, and then there’s this unknown space they answer with a question. It should be big enough that the player is getting meaningful input, but it can’t be too big, or it’ll be overwhelming. Here, I like to err on the side of big, and if they look like they’re getting stuck, I’ll rephrase the question to be more specific.
Don’t forget that you can totally reword the question or try again if it’s not working out the way you first phrased it, so it’s okay if you’re not 100% certain that you’re doing it right. Try, experiment, you’ll get it right in time. Make mistakes, get messy, etc.
Sometimes, the question has a preface which acts as an assumption. “You recognize Iceshatter from your past. What was the ambition you remember her always chasing?” Even then, notice how there’s also an assumption baked into the question? The question itself presumes that she has an ambition that she used to chase with some degree of seriousness.
I guess for me, the key is cultivating that attitude of presumption, which requires a certain willingness to benignly impose your will on the story in a small way which still lets players steer it in their own direction. I think understanding just how much players are able to push the story in their own direction is helpful here. Sure, you’re telling them something that you presume, but they’re also telling you something that’s true about this character.
And remind them during play that they can always veto something. You’re also free to ask “would that make sense?” if you’re not sure.