Reading through this, I kept coming back to the problem of setting and situation: players need something to care about, to grab onto as you put it, in order to make something so specific as a flag. In my own group, setting flags is a problem because as a group, we’re fairly impervious to setting until we’re actually playing and engaging with the setting, but by then it’s far too late for the GM to develop setting based on players’ flags.
I feel like the GM counterpart to flags is situation, but it’s asymmetrical in a way that makes it not work as well as flags do: the GM can only set one situation, and it has to suit all the players or it doesn’t do the flagging work it needs to do. Which is why game pitches are a thing: “here are a bunch of ideas I have for what play could be about; which engage you?”
I think there has to be some kind of stair-step way to get both situation and flags working together. Some way of the GM creating a Session 1 (not zero) that gets the activity going and the players’ characters contacting things they can develop opinions about, which would then be turned into flags. Lots of video games that are sandboxy give you an initial “tutorial dungeon” or “main quest” that you can otherwise ignore, but that gives you something to grab onto.
My preference for Burning Wheel is for players to have honed character concepts with cracking Beliefs, but I find myself better understanding how the book needed to say that you only need 1 Belief to start. As a GM excited to run BW, that seems like thin gruel for me to work with, but that fits with the need to kick the game into gear with something and then let the players develop cares about the game during play.
Play to find out what the players find interesting?
To bring the ramble to a close, thanks for giving me food for thought. Next time I run a game that thrives on flags, if the players are at all unsure of their flags, I’m going to let them leave them blank or mostly blank, and come with a strong set of very short rails for session 1 to launch them into the world and get them bouncing off things that they can develop a care for.
I see that happen in more traditional games all the time—who doesn’t see D&D players fixate on certain NPCs or factions or places that the DM didn’t plan to be relevant at all? Well, if I run a flag-ful game as if it has none for a short bit, and let those attachments develop, then flags are already right there in the mechanics to reward that interest!