Build Your Own Apocalypse

I was literally hours away from running APOCALYPSE WORLD this summer when the group that would have played it flew apart. That was tough. I'd already invested a lot of time in preparing for that game - such as you can, in a game where you are expressly forbidden from preparing specific material for the first session - and all of that evaporated in a puff of changing schedules.

Well, why not make my loss your gain?

One of the few concrete things I could do to get ready for that first session that never happened was to write up a list of questions that I could ask the players during the first session, to get things rolling and begin collaborative worldbuilding during play. I think some of them are pretty good, and maybe they'll be useful to you if you're running your own Apocalypse World game or something similar.

• What does your living space look like?
• What small, personal object do you have in your living space that no one else knows about?
• What's the tallest object in the area?
• What does the sky look like today?
• What do you see when you open your mind to the Maelstrom?
• Who is the first person you see?
• Is there anyone you're close with? Anyone you love?
• Do you have any living family?
• Is there anyone out there that scares you or creeps you out?
• Is there anyone you hate or would like to hurt? Anyone you'd kill if you got the chance?
• What's the ugliest place in the area? The creepiest? The most dangerous?
• Where do you go to be alone?
• Do you have a secret place known only to you?
• Do you have many lovers? Anyone special? Anyone you want more from? Who turned you down?
• Who are you sleeping with now?
• Who's got your back when the shit hits the fan?
• Who do you trust to always tell you the truth, even if it hurts? Who lies to you for shits 'n' giggles?
• When was the first time you killed someone? Who? Did people look at you differently afterward? Are they scared of you?
• What's your group got going for it? You don't have everything, but you have a few things you need and you can barter for others.
• Who's the biggest wheel in the area?
• Who's willing to do anything to get in the game?
• Does your group have any rules or taboos? 
• Who is the smartest or wisest person in the area?
• There's a place you have to go sometimes that's really dangerous and scary. You never want to go there, but you always have to. Where? Why?
• Does your group have any weird superstitions?
• Who was the last person to die? How?
• What do people say about you when they think you're not listening?
• What's the most beautiful or amazing thing in the area?
• What does it smell like here?
• Was there anyone in your life that made you genuinely feel loved? Who turned their back on you when you needed them?
• One of these motherfuckers stole something from you. What was it and what are you gonna do when you find out?
• Who taught you every important thing you know? What happened to them?
• Are there any families - with children - in your group? Have you ever thought you'd like to have kids?
• Is there someone you won't let yourself be alone with any more? Who and why?
• Where is the safest place in the area?
• What do you wear on your body - or mark yourself with - as personal style?
• What happens to those who don't follow the rules?
• Tell me a secret.

A lot of the questions are meant to tease out details about the characters, especially pieces of their inner life and / or telling details about themselves. Some are meant to establish parts of the setting, of course, including other characters who could be part of the game, friends, enemies, lovers.

Of course I wouldn't actually ask each character all of those questions, although some would probably get repeated. Asking them of the other characters would likely get the other players thinking about that question for themselves, however, and that's the important thing.