The Unreasonable Effectiveness of Leading Questions

Posted at — Sep 30, 2021

Among all the skills a GM/facilitator needs, listening and asking questions are at the top of the list. Here I’ll focus on how to use leading questions — questions phrased to prompt a particular type of answer.

This article owes a great deal to The Gauntlet blog. Be sure to check out these posts.

Aside: Player Authorship

Some of these questions and techniques assume the players are comfortable authoring things outside their characters.

If you are playing Blades In The Dark or a similar game that assumes the “writer’s room” approach, you should facilitate their answers and coach them if needed. Let them know they are encouraged to answer. Be open to questions back from them. Keep talking till you find an answer together.

Some questions cross the line, and that is fine — as long as they are still satisfying for all parties to answer. Use your best judgment.

If you are playing a game where discovery is the focus and players are only responsible for their characters, you should restrict these questions to their senses, background, memories, and so on.

Keep in mind:

The Basics

Reasons to use Leading Questions

  1. To narrow the scope of the response. Including a “seed”, and showing what you’re looking for helps the responder come up with a good answer.
  2. To avoid players getting stuck. When faced with infinite possibilities and given nothing to grab on to, players often draw a blank.
  3. To get players invested. Some players get invested in things they create. Try to make them feel heard. Build on their responses.
  4. To deliver information. Sneaking exposition into concise questions is a good way to avoid boring info dumps.
  5. To be surprised! Players regularly come up with all sorts of ideas you never would have thought of. Reincorporating them adds depth to your games.

Properties of a good leading question

  1. It makes a significant assertion that provides context and/or primes the responder.
  2. It is open-ended. Avoid anything you can answer with “yes” or “no”.
  3. It leaves room for the responder to contribute a meaningful answer. Don’t ask questions where the answer doesn’t matter.

Consider these examples from Dread:

“What won’t you even try to do because you’re certain you will fail?”

“Which of the other characters do you feel you can trust with your secret, and why haven’t you told them yet?”

“What nickname has stuck with you since childhood despite your best efforts to erase it?”

Each of these establishes or asserts something about the character, and lets the player contribute concrete, meaningful details. They are specific, but not confining — open-ended, but well-defined.

Defer the answers if needed

Even if you ask a clear, specific question, it could be tough to answer. If the player needs time to answer, put the spotlight on another player, and come back to them later.

Listen and Reincorporate the Answers

When you ask a question and get an answer that anyone is particularly excited about, build on it. Either follow it up immediately, or write it down and reuse it later.

Examples: Blades in the Dark

When asking these, first pitch them to a specific player. For larger questions (origins, lair) ask the group. Try to avoid players feeling left out.

You don’t need to ask all of these, or all at once. You can also ask them during play.

Setting the Tone

Duskvol is an excellent setting, but your table still has to adapt it to their needs. In addition to CATS, discuss tone-setting questions as a group, such as:

“Are ghosts mostly hostile? Are encounters with them always scary?” This informs how often you should call for players to resist freezing or fleeing.

“How common are moments of kindness? Do people look out for each other, or is the city harsh and impersonal?”

“How public is the occult? Do cults and sects have a lot of secret power?”

Crew Creation

I prefer to do crew creation before character creation, so players have more context when they make characters. They can choose to lean into the crew type, or play against it and create drama. Both are good options.

Ask a few of these that seem interesting. No more than one per player.

Origins: “Who named the crew, and why was the name controversial?”

Reputation: “What do you routinely do that would alter your reputation if exposed?”

Lair: “For what nefarious purpose do locals come to your lair?”

Hunting Grounds: “What secondary use do your hunting grounds have for locals?”

Special Abilities / Upgrades: “Who in your Ghost Market distrusts your product but sells it anyway?”

Cohorts: “When did Leo refuse to follow an order because of their principles?”

Contacts: “When did you disappoint Lydra? Who did she lean on to fix your mess?”

Character Creation

Make characters as a group. It is fine to bring a concept to the session, but wait to fill out the details. That way you can riff off other players’ choices.

Again, ask what seems most interesting to you:

Background/Heritage: “You’re from a noble background? Why are you slumming it in this dingy lair with these scoundrels?”

Special Abilities: “Who taught you to be a ghost fighter? Which fight affected you the most?”

Special Items: “Why is your scary weapon so intimidating, and why did you pick that of all things?”

Vice: “So you have an obligation to your older sister. Why does she have mixed feelings about your help?”

Friends/Rivals: “Ah, Veleris the spy. Who have they given you intel on, and how did it cause blow back?”


Establish relationships between player characters. You don’t need to define every pairing. Each character should have a link with someone else in the crew.

Ask each player one question, such as:

Whisper, who asked you about a particular dark ritual? What did you tell them about it?”

Lurk, who did you have to cover for on the last score? What did it cost you?”

Hound, who looked after your companion while you were incapacitated? Do you feel you still owe them?”

Have the players work together to answer.

The Engagement Roll

Hard frame up to the point where the PC’s have an interesting, risky decision to make.


For example:

The PC’s are having a meeting at The Surly Tap to negotiate a truce with the Fog Hounds, who they have been warring with. They are starting in a controlled position, but I want to raise tensions.

GM: “You make your way inside the run down bar. It reeks of stale canal weed brew and gunpowder. The guards take your obvious weapons, and show you to the massive table with a crude map of Duskvol carved into it.”

“Margette Vale is at the head, with Bear and Goldie perched like gargoyles on either side. They have a confident air, and the guards are on edge. What tells you this is a trap?”

Jet: “Margette has that shit eating grin she gets when she is about to get revenge.”

Farai: “Bear never eats before a fight, and he ain’t touching that delicious smelling mushroom entrée.”

Tasi: “These tables are too conveniently placed. It’s a damn firing range, and we’re in the middle of it.”

For more examples refer to Paint the Scene by Jason Cordova.

Ask about the environment

Scenes need interesting environments. Conflict scenes especially so. Fighting in an open field is boring and should be avoided at all costs.

“The narrow street is filled with passersby on their mist-hour commute. Gas lamps burn softly, rain streaking their glass housings. What do you see in the refuse lining the streets that could be useful in a fight?”


Pay special attention to downtime. Pick interesting downtime activities to focus on. Set scenes for them, and use leading questions to liven the scenes up.

Acquire Asset: “Sure, you can find that, but they don’t accept coin. What do they ask you to pay with, and how do you exchange coin for it?”

Indulge Vice: “On the Black Lotus again I see. What do you see that reminds you of your mother when you trip?”

Recovery: “Sawbones treats your injury with the old ways. What about this treatment is strange or disgusting?”

Reduce Heat: “Alright, so you’re passing out food to the people whose homes you mostly destroyed. Who do you notice staring at you with murderous intent?”

Training: “What motivates you to endure this harsh training? Who trains you? Why?”

Long-Term projects often have enough juice on their own.

Extra Tips

Ask about their inner self

Reactions: “The demon skewers Leo with its tail and then rips it out. Looks like he has a few moments left. Are you going to chase down the demon, or let it escape and try to save Leo?”

Feelings: “Seems like you’re angry, is that right? When can we expect your revenge?”

Goals: “You wanted to find that demon, right? Are you going to work on that, or let it fester some more? What would Leo do if you were switched?”

Relationships: “Fordola is probably sinking into a pit of anger right now. Are you going to go see them, or wait it out?”

Beliefs: “I thought you were a revolutionary? Are you going to let those Bluecoats shake down that kid in broad daylight? On your turf?”

When making assumptions about a character’s inner state, you will often be wrong. Encourage the players to flip the question. If you ask why their characters are angry, they should be comfortable telling you “actually I’m not angry, just disappointed”. The question still got them to think about it

Ask about NPCs

If you know an NPC has a particular quality, and want to know how they express it, you can throw a leading question to the players.

“As you enter the penthouse Lyra is reveling in her new status as leader of the Red Sashes. What about her tells you she wants to be treated like a queen?”

Ask with NPCs

When you want to know something about a character and think it should be a scene, consider using an NPC to ask the PC’s.

The player characters are hassling Ela, their contact in the Dimmer Sisters to put wards on their lair.

Farai: “A few wards shouldn’t be that difficult. I saw you work on the corner shop. I bet I could even help. You could teach me!”

Ela: “You’re right, I could try. I doubt you would understand though, and you never call on me! Why should I bother to help someone who can barely keep in touch?”

Don’t overdo it!

Leading questions are a potent spice. Read the room, and pay attention to the flow of the game. Drop them in when you want to emphasize or explore something.


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