Each player rolls twice for their class. Of course you may add tables for backgrounds, traits etc. I made the questions simultaneously generic and somewhat evocative to the best of my abilities, as I believe this works best when they are made for the campaign itself to set mood.
Some questions assume social class as well. My reading of the starting money roll compared to the equipment list is that it suggests PCs as minor nobles, rural gentry, petty bourgeois and similar depending on how the campaign setting is presented (faux-medieval, faux-Renaissance etc.) The Thief is reasonable to assume as peasantry and the starting money as their latest big score. It also assumes domain game as an objective (and Fighters can start the domain game from level one, so there’s that.)
Fighter (d20)
- Why did you join the war?
- Your greatest defeat?
- Who taught you fighting?
- Why do you want a stronghold?
- Do you enjoy killing? Why (not)?
- A monster you would like to slay?
- Do you enjoy song and wine? Why (not)?
- How did you feel the first-time wearing plate?
- When did you throw yourself to protect another with a shield?
- Do you take pride on your ability?
- What are your feelings towards those who can’t fight?
- What creature you dream of using as mount?
- What excites you more, treasure or conquering enemies?
- Why do you abhor violence despite your class?
- Who was the first person you maimed?
- Are you fascinated by magic?
- Civilization or barbarity?
- Does a true warrior need to know poetry?
- Which hours do you prefer training? Why?
- How did you learn the importance of retreat?
Thief (d20)
- Talk about the last time you stole from a child.
- Are you interested in the local thieves’ guild? Why (not)?
- How does stolen food taste like?
- Who did you share your loot with one time?
- How did your former partner betray you?
- Do you see your job as more legitimate than others?
- Why did you backstab them? Who even were they?
- Does your family know?
- Who taught you how to speak cant?
- How did you come across your starting money?
- Why do you deserve to run crime in town?
- Why wouldn’t you steal from a fellow adventurer?
- Who are the easiest targets?
- Why heist the dungeon instead of a house?
- Is the law watching you?
- When do you feel free?
- Why did you start stealing?
- Would you employ poison?
- Will only the grave retire you from the great game?
- Why do you trust your companions instead of other thieves?
Magic-User (d20)
- How did you get your spell?
- Any creature you would like to study?
- When did you fumble a spell?
- Who taught you calligraphy?
- Do you dream of visiting other dimensions?
- Why do you study?
- Would you kill an innocent for their spell book? Why (not)?
- Which monster would you enjoy as your servant?
- Why a lonely tower?
- Why do you dress funny?
- Who paid for your studies?
- How is your spell book?
- How did you learn so many languages?
- Why do you want an apprentice eventually?
- Why do you want to meet a dragon?
- Do you believe love interferes with the craft? Are you celibate?
- Do you feel unsuited for dungeoneering?
- Do you look much at the stars?
- Do you avoid using magic?
- What do you feel about Clerics?
Cleric (d20)
- How did you ended up joining the clergy?
- What was your first encounter with the undead?
- Who couldn’t you save?
- Do the heathens deserve death?
- Do you think dungeoneering is a holy quest? Or do you just believe your mission is meaningful and a god seems to favor you for it?
- Do you trust your companions regardless of belief?
- Do you look down on Thieves?
- Would you ever hold a blade if it meant to save someone or vanquish evil?
- Would you prefer to just proselytize instead of fighting?
- What did you leave behind to be a Cleric?
- Did you family force you to join the clergy? Why?
- How does it feel when you channel divine power to turn undead?
- Where and how do you prefer praying?
- Who have you killed for their sins?
- Who have you screamed at on the streets for their ways?
- Which doubt you hold within?
- Are Magic Users to be trusted?
- When did you fell to temptation?
- Do you dream of your dead body being turned into relics?
- How do you imagine your future temple to look like?
Roll to Doubt 