Asking questions is a great way to get to the bottom of things. It is one reason that three year-olds master “why?”– keep asking and you’ll slowly unravel deeper and deeper explanations for events. Or you’ll drive your parents crazy– really it’s win/win for the tykes.
Answering questions is a great technique for deepening characterization. PCs and major villains benefit the most from these techniques, but asking yourself a question or two about even the smallest NPC can lead to less stereotyped bit characters. As a depth technique, you should know something about your character first– though some questions can be a good place to start digging into a character.
Where can you find good questions?
Many RPGs build a list of questions right into the rulebook. I first remember encountering “20 Questions” in the Shadowrun RPG. Some are generic and could apply to any game– why does your character do dangerous things instead of sitting in an office? Others are more specific: Where were you on the Night of Rage?
Like all lists of questions, you shouldn’t go through and answer them all in order. Instead, skim the questions until you hit one that makes you excited, or until you find a question where the standard answer doesn’t make sense. (For example, if you’re playing D&D, skip over the question “why are you adventuring?” unless you flash on an exciting reason as you read the question. If your subconscious shouts “To rescue my little sister from kobolds”, then the question’s a good one for you. If you shrug and think, “That’s just how the game works,” move along to the next question.)
Questions don’t just lurk in game books– many rulebooks omit such questions altogether, while questions lurk everywhere. Writers also try to develop characters– many books for writers are loaded with good questions to spark character development. Heather’s 365 questions for writers and roleplayers turned into a book  of prompts, questions, and writing exercises. Other fun prompts include online quizzes (try taking them from your character’s perspective), party game questions (like Say Anything  or Scruples), or even personality tests. (Bognar the barbiarian in an INTJ!)
Working Questions into your Game
There are a lot of ways to ask character deepening questions. Some are cleverly disguised, some are bold, and some just look like homework. Here are several approaches for introducing questions into your group.
Often players will straggle into the game session over time, rather than all showing up at 6:32 precisely. For all that we joke about players rambling about their characters, we joke because it’s true. Any kind of question can wind up explaining more about the character to the GM– and often such questions lead to new trains of thought even for the player. This also can work well during a dinner break, where you want to keep people thinking about the game, but not rolling dice with greasy fingers.
“I really liked the way Sir Jacob threw himself in front of the dragon last game, but I was sure Jacob hated his little sister. Why did you do leap in the way?” OR “You couldn’t hit the sorceress last week at all. How does your character explain missing last week– her combat skill, his reluctance to hit her, or something else?”
Conversation with NPCs
The world is filled with people impressed by the PCs, interested in their obvious wealth, or running a scheme of some sort. Innkeepers, con men, blind dates, and star struck admirers all want to know more about the PC. Pick a question and ask it in character. This can lead to very interesting discussions where the player comes up with two different answers at once– the real answer, and a bland answer for the crowd. As they explain their answer, be sure to ask them if they need to make a deception roll…
“Were you scared when that minotaur roared at you?”, (from an idolizing kid) “Do you ever think about your parents anymore?”, or “Hey, why is your tabard blue? I thought your favorite color was green.”
Ask Action Questions
Sometimes the question being asked doesn’t need to be answered in words at all. If the question is “Who would you die to protect?”, that sounds like a good adventure prompt, not tea time question and answer. Similarly, if a character is horribly racist, maybe it’s time to put them in a room with a troll where the solution to the problem requires negotiation instead of swords and guns. This can be a great way to put the characters under pressure and reveal quite a bit. It can also be a chance for the character to engage with the question and change, if the player is looking for an opportunity.
If you’re looking for a good way to keep players thinking about their characters, consider asking everyone a question about their character a couple of days before the session. It makes a good exercise and a nice way to start thinking about the character again after a break.
If you’re playing a few players short, consider running a session of flashbacks instead. Depending on the amount of guiding that you’re comfortable with, you can ask very leading questions “Was it cold outside the night Fransesca kissed her first man?” or “On your seventh birthday you took revenge against the neighborhood bully. How did it go?”. Introduce something in the current adventure to prompt the associations: drugged interrogations work, but so does watching a pickpocketing child get caught, or bumping into a kissing couple in the shadowy corner of the tavern. The association doesn’t have to be perfect, though the inspiring event might shape the flashbacks. White Wolf style preludes often follow this pattern.
Choosing Questions that Enhance the World
In you’re looking to convey the world in a specific way, the questions you ask can really enhance the feeling. Instead of asking about what a character did on his seventh birthday, ask what they did on St. Phillbert’s Day when they were seven. Or ask how their character’s family was affected by the Invasion of Rats in 422. This can be a good way of establishing common threads– and subtly getting the Rat Invasion of 422 out of that paragraph at the end of the setting chapter and into the game.
What has worked for you?
Are there any questions that you always ask the players– or that you always ask yourself when creating a character? Do you have good ways to work questions into the game, or have questions that make for great discussion? Would getting a question about your family’s response to the rat invasion of 422 be something you’d look forward to as a player? Would you prefer to have the question asked at the table or between sessions? Please share your favorite character revealing questions and strategies.