PC: Volk, cleric of the Silent Gull of Seven Eyes.
Situation: Volk and party are residing in Trondheim, raiding the megadungeon a few days to the east. So far all is standard D&D.
I need to know what Volk is unhappy, desperate, sorrowful, or otherwise dissatisfied with in his life. If I already know, great: just have to let all the other players see it. If that's been shown in game already, great, I can skip to #2. But let's presume we just started at the dungeon and these guys don't have personality other than race/class/alignment and whatever dialog has been uttered so far.
You can also just use random tables for this part and consider it part of chaacter generation. Simpler, less customization.
(I'll be addressing the character when I'm talking to the player for simplicity. GM text in bold, player text in italics.)
So Volk, what's wrong with you? Or are things going pretty well for you right now?
I dunno man I just showed up.
This is the likely case, and we'll proceed therefrom; however, for the sake of thoroughness, you have basically 3 situations at this point:
1. I dunno
2. Oh, I know! [and it's suitable]
3. Oh, I know [and it's not suitable]
1. I dunno. In this case, you start asking questions and making suggestions. You don't have to get a firm answer yet. If this is the very start of the game, maybe see how the PC responds to events that invite judgment or decision or self-revelation: invitations to religious services, witnessing crime or cruelty, invitations to go on a date or hang out or help with a project, NPCs who ask as part of friendly chatter what hobbies you have, where you're from, hostile NPCs that interrogate you.
Really, you should be able to tell (if you don't know already) from the player's reaction if they're even interested in this sort of thing. Maybe coming up with fictional stuff is stressful for them.
So here's what you do, if you ask, and keep getting I dunnos, offer suggestions. You can have a list; you can come up with ideas in the moment; you especially can ask the other players to come up with something.
If the player still doesn't engage, they're just the wrong audience, sorry. They will just be a supporting cast member, and that's fine.
2. Oh, I know [and it's suitable]. Great. Go with it.
3. Oh, I know [and it's not suitable]. Look, it's your game. You do the work. If someone's great idea is going to seriously harsh your mellow for real and you're not just being a control freak, say, hmm, I don't think that's a good fit with this campaign. Can you think of something else? Etc. Repeat until (1) or (2) obtains.
Back to the example at hand. Our player hasn't thought about it. That's fine. Question time.
Is Volk the really devout and evangelical type?
Oh yeah. Really annoying about it.
This is the kind of stuff you want to see. Now you think, what would make this sort of person unhappy?
Do you think maybe he's been trying to convert these pagans to the worship of the Septuply Blessed Gull and been having no luck and is really bummed out about it?
I'm trying to isolate a source of deep dissatisfaction. If the player doesn't like it, we can counter propose, get the other players in on it and such, but for sanity's sake:
Totally. Nobody can stand him here.
Now we are ready to show the PCs dissatisfaction. I'll frame a scene in which we can see his efforts to evangelize, the reaction of the villagers, and the PCs reaction to that in turn.
So you guys get back to town, get washed up, whatever. Volk, how do you usually try to evangelize the people here?
Oh, he just finishes his meal and gets up on the table and starts preaching. Extremely sincerely. Like, Know ye not that the wind against thy faces cometh from the downy underwings of the Wondrous Gull of the Seven Oceans, that kind of stuff.
So that happens. Everyone's kind of turning away from you, laughing at you, or being extremely annoyed. This one huge guy with a mullet just locks eyes with you and keeps banging his cup against the table. When you finish your spiel, the innkeep comes over and says, alright, let me have it. He holds out his hand—y'all have some kind of arranges where you can preach for a silver a night. Do you give it to him?
I don't have a silver…
Then what do you do?
I don't have it, sorry, but I'm good for it—
I'm adding it to your tab. He heads off, and people are looking at you only to laugh. How does Volk react? This bums him out right? It's not supposed to be this way.
I think he goes to his room and self flagellates, making squawking apologies to his god.
Wonderful. I'm seeing his back and the blood pouring down and soaking into the cracks in the floor.
Yes, fairly tediously described, but I wanted to convey the sense of what actually goes on when using a technique like this. While this particular example was just made up, I've seen many similar scenes where, at the end, I've got chills from how good the interaction between the players and the fiction is. It can be like watching a really great TV show with your friends that you are making up in the spot.
Now, I'm not going to go into the rest of the 10 agenda items because it would be a big pain. But if anyone requests an example for a particular one, I might be persuaded to do so.