Late last year I had been doing some informal research on asking good questions, with a very little bit of the very little free time I had. For some reason, I had come to the conclusion that I wanted to be a better question asker - I want to be more like my friends who are good at getting other people to talk about themselves. I think it probably had something to do with the whole introvert's manifesto I wrote. Anyway.
Here's a few I've come up with. They range from the theoretical, to the comical, to the deep, but I've found all of them to work well in one situation or another, at some point. (I've included my personal answers to the questions below each, in parens - now that I've shared mine, I expect to be recompensed accordingly.)
Would you rather be able to fly or be invisible? This question is a personality thing, and I can usually guess with 75%+ accuracy what a person is going to say before I ask it. (Flying would be pretty awesome, but I'm still going with invisible on this one.)
The two things: What are the two things about X? This one is situational. You can use it about someone's line of work, for instance - what are the two things about advertising? 1. Get their attention. 2. Overwhelm them with charm. You can apply it to whatever the topic of conversation at hand is, really. Its like a game. (The two things about me: 1) Where am I going? 2) Why am I in this hand-basket?)
Similarly: What's the best and worst thing about X? I learned this one from a friend who asked me what the best and worst part of my day had been. Situational, like the last one. (The best thing about my work is the client. The worst part is trying to get time with them.)
How much would you sell a kidney for? Assume you will not be told what it will be used for, if anything. Pretty self explanatory. ($750k, but that's my minimum, I'd start out asking twice that)
The "or's": Cats or dogs? Creamy or crunchy? Mac or PC? Sugar or salt? Superman or Batman? White or wheat? Paper or plastic? Tent or hotel? Pirates or ninjas? etc. Simple enough here. The last one is kind of an important one, clearly. The nice thing here is that you can elaborate any of them into more extended discussion. (dogs, creamy, PC - but only cause I'm a poor working man, salt, Batman, wheat, paper, tent, and...wouldn't you like to know.)
Related: Ok, so bird flu or SARS or whatever wipes out the human population (like gone) leaving practically the entire rest of the ecosystem intact. Bears and primates battle for dominion over dry land. Who wins? I can't take credit for this one but I still love it. Rules include: 1) No peaceful solution. 2) No write-in candidates. 3) We left all our toys behind. (Bears.)
What are you reading right now? This one works better with people who read. Unlike the first one, above, I usually can't predict with great certainty what the answer will be, which is fun. I can, however, usually determine who will be able to answer this one well. (A Prayer for Owen Meany, Blink, and The Problem of Pain.)
Where were you on 9/11? I would never bring this one up but its an interesting one if the subject is already on the table. (Trying to get out of a frenetic downtown Pittsburgh while the 3rd plane flew over us.)
What are you passionate about? Good one, but not for a lead in. Comes out later. (War relief work in Africa. Social theory & the Tech generation. Also, writing.)
What scares you? This is one of my very favorite if you can get people to be honest with the answer(s). (2 things: Being sedentary and out of shape. Not making a positive difference for the world before I die. That's really it, I have a healthy fear of pretty much nothing else.)
Do you think we're alone in the cosmos? Can only use this one on the especially bright, otherwise it sounds like a joke. (No - but I don't think we'll ever get the real answer in this life.)
What would you hope your tombstone would say? Can be sentimental but is often interesting. ("Died gallantly.")
What do you think happens to you when you die? This is my favorite one to use with people with whom I'm unfamiliar on their spiritual leanings. Has started some really great conversations. (You go to heaven, or hell. Forever.)
Would you rather be fabulously rich and of average intelligence or vice versa? I like this one because then I get to speculate how honest the person really was about going with fabulous intelligence. (Intelligence.)
Related: Do you think your above average (in any category, and if so, which ones)? (Yes. At being accident-prone.)
What's your favorite color and list three adjectives why. Remember adjectives are descriptive words, not nouns or phrases. I like this one because its a bit of a trick. Once they answer it you explain to them that the adjectives are really things they think about themselves. Not to be used everywhere, better in crowds where you're comfortable. (Blue. Relaxed. Flexible. Incredibly sexy.)
What would you attempt to do if you knew you could not fail? Another one I get surprisingly wide responses to. (Start my own business, run for office, write the next great American novel, and go talk to that rather incredible girl across the bar.)
There's quite a few more I've come up with, but for brevity's sake I won't go into too much detail: Who would you spend a day with if they could spend one with anyone? (My sister Margy, right now - this one changes from time to time though.) What one thing would you want with you if you were stuck on a desert island? (A satellite phone.) What's your favorite type of art, and why? (Late American Painters. Because.) How would you choose to die, if you could? (Blaze of glory.) What could you not live without? (Internet, running shoes, and avocados.) What are your pet peeves? (Lines, also traffic. Lazy grammar. Ignorance.) What do you think you're best at? (Driving. Doing nothing.)
But here's one of my favorite new ones I came up with:
You die. You show up in heaven, and St. Pete tells you that "the way things work up here is this: you get to pick one day from your life and re-live it, over and over again." What day do you pick? (Still trying to decide on this one.)
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"If I find in myself a desire which no experience in this world can satisfy, the most probable explanation is that I was made for another world."