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The Apocalypse World RPG has the following move:

When you read a person in a charged interaction, roll +sharp. On a 10+, hold 3. On a 7–9, hold 1. While you’re interacting with them, spend your hold to ask their player questions, 1 for 1:

  • is your character telling the truth?
  • what’s your character really feeling?
  • what does your character intend to do?
  • what does your character wish I’d do?
  • how could I get your character to ____?

One of my favourite things about hyper aware characters in other media is the scene where they strike up a conversation with someone and instantly know how to pull their strings, and I love these sorts of moves for how well they let anyone play that kind of character.

Every PbtA system I've played has a similar move, but each system uses its own set of questions; Urban Shadows includes questions like "Who's pulling your strings?" and "What's your beef with ___?", supporting its fraught political drama. Antagonists in Monster of the Week need to be investigated, so it allows the players to ask "Where did the creature go?" or "What is being concealed here?".

These questions are well-tuned to their systems, allowing enough wiggle-room for the answerer to provide an honest-enough-to-be-useful, but vague-enough-to-be-tense response. If I'm designing my own PbtA system, I'd obviously want to make sure I set a similarly good question list.

How can I make sure I've done that? What techniques can I use to make sure that an individual question is good? How do I know when I've got enough questions to keep the move useful, but not so many that it trivialises encounters?

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Let the specific genre of your game guide you

There’s some great advice in the other answers, but I’d add that one of the reasons for PBtA’s popularity and the number of games made with it is that it’s very good at providing an experience that fits a specific genre. A “generic” PBtA game wouldn’t really work because its moves wouldn’t tell you anything (and there are many parodies of what they might look like). All the power is in the detail. You recognise this in your question when talking about Urban Shadows’ focus on “fraught political drama”.

So I’d recommend you start by watching, reading, listening to and playing the kinds of stories that define your genre. (And if you don’t know what the genre is, pick the kinds of stories that you want to emulate and learn about it.) Make lots of notes, and include the kinds of questions they ask. Not just the ones the protagonists ask in dialogue, but those revealed by the things they say both during and after meeting someone.

For example, a PBtA version of family-friendly science fantasy would benefit from looking at Doctor Who. The Doctor frequently asks or otherwise works out that people they meet are scared of something, so “What are you afraid of?” would make a great question for such a game. They’re great at getting people to trust them almost immediately, so “How do I earn your trust?” is a good one that comes from the character’s actions rather than something they directly ask. They also manage to get villains to reveal their plans and motivations, either verbally or by observation, even when they are lying about their intentions, so “What do you really want?” or something like it would work. And they often find that aliens or old enemies are behind the actions of the humans they meet, so another one might be “Who are you working for?” By contrast, “What’s your greatest fear?” isn’t something the Doctor frequently uses against their opponents.

That’s just from one source, though, and most PBtA games benefit from drawing on a slightly wider pool of influences. For this theoretical family science fantasy game, you might also look at The Flash, where the characters spend a lot of time figuring out what they and their enemies need emotionally, so you might add a question like “What’s really making you feel this way?” or “What emotion is most clouding your judgment?” And there are plenty more you could look at.

Zoom out and look at the big picture of a typical story in your genre, too. Do protagonists try figuring out other characters - is it mostly antagonists? Do they ask about friends and allies? Are the people they’re asking about actually people, or are they monsters, ghosts, spirits etc? Are they interested in individuals or organisations?

This sort of analysis of the genre you’re going for will really help. Even if you’re not emulating existing media, you can think about the specific tone, mood and genre you’re creating, and about the information that characters might act on which will drive the kind of story you want to help players create. Once you have this starting point, test the questions (and all the other moves) out in play, and refine them as you go.

This will also help you pick the right number of questions: in the inspiration shows, do the characters ask a lot of questions or spend a lot of time figuring things out? Or do they go off half-cocked and then have to ask the right question to get back on track? Look at those circumstances and make sure there’s at least one that seems helpful in any given situation for your game’s genre. If a question isn’t picked during play, if it’s too hard to answer, or if the answers it provides don’t push the story in directions that serve the genre, it’s probably not right for your game.

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Playtesting

Iterative improvement beats out any other process for "getting it right", whenever different people are supposed to use something. Make your best effort, then test it out and see what works and what doesn't, what gets used and what doesn't, and where the game master and players feel restricted rather than assisted by your ideas and wordings.

Take that feedback, use it to cut, expand and improve your ideas further. Then playtest again, until you are satisfied with the feedback you receive. Then find new groups to playtest the refined product, until you feel reasonably confident that most groups will be able to read and understand your ideas, and both game masters and players feel empowered and assisted by the rules.

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Information doesn't just solve problems.

Or, stated in a less attention-grabby way, the kind of information that does solve problems isn't the kind of information you just get by making one move.

Read a Person and Read a Sitch will both upgrade over the course of an Apocalypse World campaign into moves that say "ask literally anything" and, heck, Open Your Brain starts out as a move that says "ask literally anything", but with slightly higher stakes and the MC can get cute with the answers.

As far as numbers go most hacks have it pretty well worked out. You've got your basic allotment of questions, 3 or less should almost always suffice, and once you've already tried to get information out of a situation it should have to change significantly before people get a second bite at the apple. Of the many concerns about information-gathering moves, "will people get too much or too powerful information" probably shouldn't be one of them.

Because even if you really do know the one truth that will save the world, there's an entire world already out there acting differently. What do you do to that world?

Setup and Resolution: The Path Information Built

So the important words in

One of my favourite things about hyper aware characters in other media is the scene where

are 'characters', 'media', and 'scene', because PbtA works its best when it's putting the certainty of rules and the uncertainty of chance into the compelling and dramatic points of whatever source media inspired it. So when you're looking for questions to ask to make your game pop, look at your inspirational media, look at all the points where presenting information is dramatic, and work based off of the questions behind that information. There'll be some collating into more generic questions and some flavoring those generic questions to express your desired themes, but it should start from looking at the dramatic informational moments that already exist.

When you're looking for how to distribute these questions among information-gathering moves, one thing you should consider is whether the information contributes more to the resolution of a scene or to the setup of a later scene. What's the difference?

A setup question gives you new things to do. Investigate a Mystery operates mostly as a setup move, opening up new scenes to put your characters in or new directions for a scene to go, when you e.g. follow the monster where it's gone or pry into the thing being hidden from you, things you wouldn't have been able to do at all without that information. Moves that let you ask setup questions often keep that number lower, sometimes even just one question with incomplete information on a partial success - still enough to get you to the next scene but not as well-informed as you might have been - and usually don't offer additional mechanical benefits.

A resolution question helps you do the things you were already doing. Read a Bad Situation is much more of a resolution move, in that if you look at the available questions you've pretty much got the generic blueprint of a scene set in a bad situation: get in, protect the vulnerable, confront the danger, get out. All of these should already come to mind when thinking about how a hunter acts in a bad situation, which is why moves that let you ask resolution questions are much more likely to give you multiple questions and attach mechanical benefits attached to the answers. Sure, there's the additional benefit that the Keeper just told you the best way in and out and probably doesn't have any golden opportunities waiting to drop on your head if you take them, but even if they just confirmed the plans you'd made already you're still better at doing those plans than you would have been if you never made the move at all.

A final thing to keep in mind when refining questions is that thing you're going to be doing all the time when you answer them.

GM Moves: The String Pulls Taut

In the same way that player-initiated questions are there to model the way your inspirational media presents information, GM moves are there to model the way your inspirational media introduces narrative tension. Now, a lot of them can just migrate around from game to game because some narrative twists are pretty universal: separate them, put someone in a spot, tell them the requirements or consequences and then ask, turn their move back on them. But all of your GM moves should reflect some narrative tension that could happen in your inspirational media, and at least a few of them should probably be specially tuned to that media's unique qualities in particular.

9 times out of 10, those player-initiated questions are going to be pointed at you, which means that everybody is looking at you to tell them what happens next, which means that when you give that answer you should also be making a GM move, adding in some narrative tension to keep spurring the action forward. So it's also useful, when refining those questions, to think about how answering them is going to pay forward into the GM moves you've already come up with -- or, perhaps, once you've refined some questions, they can point to GM moves you should be coming up with.

And hey, that turn their move back on them one is absolutely going to apply to some of those player-initiated questions too, so think about how it's going to feel for your players to have to answer for all those things they're usually asking.

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