I like collecting good questions. Here are some.
What is your favorite compliment of all the compliments you’ve ever received?
It’s too easy to hoard hurtful insults, so as an antidote, we can try to collect compliments instead.
What are you looking forward to right now?
The question “seems to center the conversation on hope.” It’s a good way to find things to celebrate and move toward in our lives. If you use this icebreaker, push beyond the obvious — of course we’re all looking forward to the pandemic ending, so seek specifics about what your icebreakee most looks forward to when that happens.
What would you write on a gigantic billboard?
This too shall pass? Is it necessary? Don’t lose the kid in you?
What random stranger from your life do you think about or (even talk about) regularly?
Indeed; we are all someone else’s random stranger, are we not?
What famous masterpiece painting or sculpture would you like to own?
Also questions about your little-kid career dream, and the famous person you’d most like to have lunch with.
If you went into the witness protection plan what identify would you like to assume?
And more: What food would you recommend to visitors to your home town? and If you could only be one of these things, which one would you choose: rich, smart or beautiful? and If you decided to run away, where would you go?
What is a boring fact about yourself?
Can be used students in part to “help mitigate privilege inherent in ‘what is one interesting fact about you’ or ‘what did you do over the summer’” sorts of questions. Asking about boringness is more of an equalizer. Besides: “This gets kids talking, which is fun — real mundane stuff like ‘my favorite sandwich is club’ or ‘I prefer dogs to cats’ ends up being a nice way to make connections — and can be sometimes surprising, actually.” Coming up with a suitably boring fact may be more of a creative challenge than coming up with an interesting one.
Which book did you read in college or high school that was actually interesting enough that you still think or talk about it sometimes?
This has the advantage of not only interesting talk about whatever nonfiction and fiction books the folks in the conversation mention, but, it also leads to talk about favorite teachers and classes, the merits and demerits of assigned reading (and formal education, in general), post-formal education reading habits, reading recommendations, what makes a book or work of art memorable, etc.
Without using the title of your job, tell me what you do.
My favorite interview question.
What’s the most expensive habit you’ve started as an adult that you now wish you could break?
What was fun about asking this question was that it also lends itself to a lot of easy follow-ups. When did you start that habit? Any fond memories you can share?
Describe something that’s made you smile today.
You get a huge range of responses. Everyone smiles along with the stories, and you get a short glimpse of the personal story behind each response.
What was the first R-rated movie you saw? How old were you?
This question creates many different points of possible discussions: the movie itself, your parent’s parenting philosophy, and the rating system in general.
What’s something new you’ve learned about yourself in the last three months?
This question offers a gentle way to zoom out from what’s happening in the moment and reflect.
Have you been pleasantly surprised by anything recently?
A good time to ask that question, even of yourself.
What material are you most like? (E.g., plastic, porcelain, dirt, silk, stone etc.)
The interesting thing about this question is that it forces you to really focus on one or two or maybe three major qualities of yourself. And the more you think about it, the more other dimensions might come into play, leading to answers like blue porcelain or 20,000 year old granite or sparkling water …. We’re all so complex, but this provides a fun and challenging exercise.
If you weren’t doing your current job, what would your dream job be?
My dream job? A local guide who takes interesting people on long Himalayan treks!
What thing from nature are you? (Excluding animals. )
There are so many interesting responses. Including: stone at the bottom of a river; a smoldering ember; a geyser; a vine; moss; an unattached leaf. Or dirt — dirt can take on many different qualities under different situations, and it’s the stuff from which plants grow, so there is an element of creativity to it.
What would you do if I gave you a billion dollars?
Can get a better sense of the nature of the folks’ ambitions — and to prod them to think at a bigger scale. Good answers maybe rare.
Imagine you could devote a year to researching someone’s biography. Who would your subject be?
I think my answer would be Christopher Alexander.
Of the places you have lived or spent significant time, which one had the most pleasing view out the front door/main window/etc for you and why?
This question can make us remember a lot of views.
Tell me about a time when you changed your mind.
Or: Tell us your name; where you are from; about your family structure growing up; about your family structure now. Encourages people to share personal information without feeling invasive.
If you’re going to win the lottery, would you rather win $10 million, or $100 million?
Most people look cross-eyed and ask, ‘Is that a trick question??’ $10 million may make you comfortable without ruining your life, while $100 million might ensure that you couldn’t really trust new people you meet, and guarantee a stream of financial requests that could be overwhelming. More interestingly, the question leads to conversations about what people really care about if money is not an issue.
What is your earliest memory?
It’s so simple, yet it can work with not only with someone you just met, but someone you’ve known for ages.
Tell me something about yourself that I could never tell from looking at you.
This rather simple one is useful because it leaves the option of going deep, but the person answering really has control over how exposed they want to be.
If you could only use three condiments for the rest of your life, what would they be?
While it may sound silly at first, it’s actually a subtle test of creativity, among other things. It’s interesting to see what people think they can use across so many things, and where their preferences lie.
Here is another great questions resource.
altLearners 