The art of asking leading questions


Playing with The Gauntlet has taught me that asking good leading questions is often make or break for a game. Asking correct questions can set the game for a success and asking bad or too little questions makes the game plain normal.

How do you ask proper leading questions?
Where do you draw inspiration for them?


From watching Rich, I realized that the best leading questions, especially during character creation, are like interview questions. I try to frame it in my head like that: what would be of interest to an audience, what might surprise them? I’ve listened to interviewer on podcasts and the like trying to pay attention to that. Paul F. Tompkins on the Spontaneanation podcast starts each episode with a guest interview. They’re great and I recommend listening to those segments.


Honestly this is the hardest part of GMing. I don’t think there’s a way to cheat this process.

The most generic, milquetoast answer is: If you’re doing pbta rely on your principles and agenda and do what the scene demands.

In reality it’s just the same answer to how to be an interesting conversationalist. /shrug

just gotta rely on playing a lot, reading a lot, watching a lot of movies, and probably being more aggressive with scene framing.


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:

  1. 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.
  2. 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.


Another resource that helped me think about leading questions. Those dumb wirters’ books on character and characterization. I hate Orson Scott Card, but before I realized what a terrible person he was, I read his Characters & Viewpoint book which gave me lots of ideas for questions about characters. There are lots of books like that and they often provide shopping lists of characterization questions. Since those are the most important kinds of leading questions for me, those proved useful.


Small addendum to my previous: PbtA games often include a bunch of leading questions in the character creation process, specifically that bit where you’re establishing bonds between characters. Check those out, mull them over, ask yourself how they work, dissect them, see how they constrain but give freedom.


With class-based games I like to think about the class and what their role is in the world.

Cleric: Have you ever married two people or given last rites or named a baby?

If there is something the character is good at, ask about who taught them how to do that. RPG’s need more relationships between student and teachers because so few games demand character learn from teachers. If they are good at something, they’ve probably failed a bunch in order to get that good. Ask about those failures and how they dealt with that, ask about their greatest success.

If they aren’t sure, drop it and move on. Let them marinate on them. Sometimes I’ll ask a question, drop it and the person will e-mail me a week later or mention that they’ve been thinking about it in-between games and suddenly the answer came to them.

I’ve found that the secret of asking good questions is to listen very carefully to what folks are saying.


Do not ask question that can be answered by Yes/No for a start. And push some information into the Question.

  • What did you lose last time you went here? (implies the character been there and lost something)

As the other, listen to what have already been brought around the table.

Also, you can ask questions with bias, like a word that could have several meaning. Let the door open for the answerer to input anything he wants.


I usually look to the genre presumptions as both guides and contrasts. If a character is playing into a genre trope, I’ll ask what makes the character different from the baseline version. Sometimes I’ll load the question too: “What makes your wizard different from those other magic-users? Why are you The Wizard, as opposed to just another magician?”

When I’m in my elements of choice (like weird fantasy, modern urban fantasy, or superhero stuff), I will pull from the genre media to paint comparisons and contrasts with the questions if I can. "This person sounds a lot like a Mercy Thompson kind of conflicted werewolf to me. What parts of being a werewolf do they enjoy, in spit of themselves? What parts of their human lives actually disturb them more than being a werewolf does?


Yeah, I think this is very important; yes/no answers end the question, other answers can suggest further lines of thought. The classic “Five W’s and an H” work well here: “What did you…”, “When did you…”, “Where did you…”, “Who did you…”, “Why did you…”, and “How did you…”.


I don’t know if they qualify as “leading” questions, but my approach is pretty basic: I cultivate curiosity about the PCs and the world, and ask questions based on my curiosity. At the outset that means asking surface questions about PC appearance and belongings (“How are you dressed?” “What does your sword look like?”), which lead to background details (“When was the last time you took a bath?” “Who made your sword?”), and later relationship/emotional stuff (“How do you feel about Olaf after he said you smell terrible?” “Who was the last person you killed with that sword, and how did you feel about it?”

Invariably, simple questions lead to bigger or deeper questions, and the answers provide plenty of fodder for reincorporation. I guess it boils down to a GM principle along the lines of, “Be curious about the characters and their world.”


That! A good leading question should lead to other questions.

Also, as I’m a lazy GM, when I ask question, I tend to ask the player to help me build the world. “You got to Greenmile village. Last time you went there, a new shop was starting. What was it? Is it still there? …”


Late to the party, but wanted to jump in with a random recommendation - playing Spyfall (the board game) honestly really helped me hone this skill. Because you have to figure out how to ask questions that are the right “size” - ie big enough to allow the other player to give an answer that provides plausible deniability, but specific enough force them to provide useful information.

Agree with everything else said above, but also wanted to add - another other type of leading question I like is forcing players to make a choice to give additional color to previous decisions they’ve made, like, if they’ve designed a character that’s just generically family-focused, I might ask, “What’s more important to your character - being a good wife or being a good mother?” Then the followup “Why?” is just a gimme :slight_smile:

Another conversational hack that I use in my daily life as well as GMing, is the all purpose “What do you mean?” as well as “Can you give me an example?” after a player makes any broad or abstract statement. Those are more open-ended than leading, but I’ve found them SUPER useful for getting more conversational “threads” you can then pull on for more specific lines of inquiry.