So this question is categorized in the “Ask A New Hire” category but it was actually introduced to me by my friend Vicky who is the volunteer coordinator for a faith-based humanitarian organization. She asks the question like this when interviewing potential long-term international volunteers:
“Author James Baldwin, writes ‘The questions which one asks oneself begin, at last, to illuminate the world.’ Please share two questions that you have wrestled with during the last couple years, one that is personal in terms of your own life and issues and the other that is more global and/or about contemporary issues.”
Most good questions are good because they direct you very intentionally to a particular subject. But this question, on the other hand, is great because of how it OPENS up space and holds it open for the interviewee. Potential volunteers have used this question as an opportunity to wear their hearts on their sleeves, to speak passionately about what keeps them up at night, and to bring up personal details they want to share about their family backgrounds, religious views, even sexual orientation. These are important things to know. And you won’t know them unless you ask some questions that open up space! Continue reading What are two questions that you’ve wrestled with during the last couple years?→
I don’t mean hungry in the sense of driven or ambitious or desirous of some outcome. I mean physically in need of calories and uncomfortable because of it. When have you been hungriest? Literally. For me, a few moments come to mind immediately. Once after working an extra long closing shift at Baskin & Robbins (my first job ever), I was exceptionally hungry and stopped at McDonald’s on my way home and it was GLORIOUS. Glorious twenty times — one for each nugget. Another time, in high school after a summer water polo tournament, my team stopped at a diner before the long ride home. Food took about an hour to hit our tables and I was ravenous and angry by the time it came. Another time, in Haiti right after the 2010 earthquake I’d spent the entire day unloading and coordinating the receiving end of eight, 40-foot shipping containers. By the early evening I was very weak and shuffling back to my tent when my friend Gena (who has called Haiti her home for about 20 years now) took me by the arm and sat me in front of a steak(!) from her native Ireland that she’d been saving in the freezer. These are my moments of intense hunger. But they’re few and far between. And I remember them almost as much for the happy, food-filled endings as I do for the hunger pains themselves. It’s a TERRIBLE thing to be hungry. Truly horrible. I think it’s important for us, the well-fed, to remember that hunger is a daily reality for many. Continue reading When in your life have you been the most intensely hungry?→
And what were you doing? This is a really good meeting-starter, especially if there’s a bit of an age-range in the room. That Y2K new year’s eve is far back enough now that some of your teammates will have been at home with kids, others will have been out partying, and others will have been children at home themselves. And everyone remembers Y2K! So this is an easy one to answer! Continue reading Where were you on December 31, 1999?→
The organization could be a religious community, of course, but let’s also include any non-profit or for-profit, political party, university, research institution, etc… Any entity that isn’t you or your family — the money really has to leave your bank account and your control. In some communities, not tithing has immediate repercussions. But in most circles today (mine included), tithing that 10% is hardly an expectation. Sometimes, though, I wonder how all our communities would be different if tithing WERE an obligation. Continue reading If you had to tithe 10% of your income to an organization, who would receive your money?→
“No he’s cool.” “It’s alright, she’s with me.” Dang, it feels so good to have someone vouch for you! In my first year of college I showed up at a costume party hosted by Benny – one of my water polo teammates. He was an upperclassman and it was the first time I’d ventured socially onto “North Campus” where the Juniors and Seniors lived. An hour earlier, I was in my dorm room and couldn’t come up with a costume idea so I decided to use the materials I had at hand. Over the course of 2 months I’d polished off a lot of gatorade after practices and games. For some reason, I’d saved all the empty plastic bottles. I duct taped 3 dozen or so 32oz gatorade bottles all over myself to become “the human thirst quencher” and went rattling off awkwardly to the costume party. I eventually found the right room and cautiously stepped inside. Immediately, a guy and a girl I’d never met before screamed, “Hah!!” “Who the hell is this kid?” Other people looked over at me and I started regretting the gatorade bottles when, just at that moment, Bennie poked his head around a corner and said, “No he’s cool. Come on in!” And just like that, I was welcome. When has someone vouched for you? Continue reading When has someone vouched for you?→
I know we’re not “supposed to,” but people gotta brag sometimes, man! We just do! It’s hard-wired at some level. That’s what makes this an awesome question to ask your significant other. It gives your partner the opportunity to boast and it’s an easy way for you to celebrate something together (even if it’s not a major life accomplishment). Everyone wants to be celebrated and admired! And what’s funny is that it feels psychologically similar to be celebrated and admired for not snoozing the alarm once this week as it does to be celebrated for landing a huge promotion at work. So celebrate the small stuff! Continue reading What are you proudest of about this week?→
Answering this question brings up warm-fuzzy feelings about grandparents, it reveals cultural/ethnic details, it often leads to funny family stories, and it doesn’t take long to answer. Another PERFECT meeting starter question! Ask your team next time! Continue reading What do/did you call your grandparents?→
It can be from any holiday or occasion! And it can be from any age range. Everyone’s got a costume they remember and love! Just a few years ago, I was stumped for Halloween costumes and was supposed to be at a party in an hour. I ended up turning a Costco milk jug into a Guy Fawkes/”V For Vendetta” mask. I was really proud of it! Still am.
My brother gave me this question. It’s a good one! I do have to say, however, that feeling like an adult has come in waves. I mean that one day I’ll feel very much like a bona-fide adult and then the very next day I’ll feel like a little kid that’s just masquerading around in an adult costume. Nonetheless, I think the VERY first time I felt like an adult (no matter how briefly) was when I took home my first paycheck from the ice cream store Baskin&Robbins. I was 15 years old and I remember my mom taking me home from the BR. My paycheck in hand, I thought over and over to myself, “I’m part of the workforce now. I’m part of the workforce.” Never mind that I had no idea how to even deposit my check! (I told you, adulthood comes in waves.) Continue reading What was the first accomplishment that made you think, “Yes! I’m an adult now!” ?→
Fantastic question. More often than not, we find ourselves wearing the “consumer” hat and being defined by our consumer habits. So it’s a special thing this day and age to produce something in the world, whether it’s an app side-hustle, a home D.I.Y. project, or a pie from scratch. What a person has created lately tells a lot about them. This question is quick but still revealing (in a good way). Give it a shot to kick off your next team meeting. Continue reading What’s something that you’ve made that you’re the most proud of?→
My older sister has given me some exceptionally thoughtful gifts over the years. But the VERY first one I ever remember getting from her made me so mad. At Christmas, my parents allowed us to choose just one gift to open early on Christmas Eve. I remember being perhaps 8 years old. My sister and I weren’t in the habit of giving gifts to each other at that early age. But underneath the tree, there it was: a small wrapped box from “Jamie” – my sister. I was so intrigued that I chose to open the gift from her early. I was so excited. I remember tearing open the wrapping paper and looking down at… a “fun-size” box of raisins. I was so pissed because 1) I didn’t even like raisins and 2) I had completely WASTED my early gift pick. But bitter memories aside, this is a really fun question to ask your sister or brother. Continue reading What’s the very first present you remember getting from me?→
To turn young kids into problem solvers, they just need exposure to lots of situations where they can practice solving actual problems. Thankfully, these kinds of situations arise constantly between younger kids. When you see such a situation unfold, always remember to ask kids, “how might YOU solve that problem?”.
“I have no more white paint!” “And how might you solve that problem?” “Um… I could ask Ms. Julie for more.”
“Scott won’t share glue with me!” “And how might you solve that problem?” “Uhh, I could ask him to share with me.”
“I spilled my water!” “And how might you solve that problem?” “I could clean it with some paper towel.”
If a kid says, “I have no more white paint!” and your reaction is automatically “Oh… Sorry! I’ll get more white paint for you,” then you are fixing things for him before he’s had a chance (or the need) to think critically for himself about next steps. Make kids own the next steps and you’ll be setting them up for a lifetime of creative problem-solving! Continue reading And how might you solve that problem?→
You know the genre of superhero movie in which the protagonist starts out as a normal person and then only gradually discovers that she is descended from a long line of superhero badasses with special powers? I feel like every parent, at some point in parenthood, is the main character in exactly this kind of movie. Find out what the low points were for mom and/or dad. And find out how they stuck it out to raise you so damn well. It will give you ideas if you’re a parent yourself or at the very least it will give you a new appreciation of your own folks. Good parents truly are heroes. Continue reading Can you tell me about one particularly low moment you had while raising me? How did you get through it?→
Okay, if I’m being honest, the very last time that an advertisement really worked on me it was 9 days ago when the series of McDonald’s ads that played during NBC’s coverage of the Rio Olympics convinced me to eat some chicken nuggets. I loved nuggets as a kid and boy do I ever still love them now. Crispy fried golden perfection! The ads kept talking about how the new nugget formula (err I mean recipe) was better and more natural and free of artificial preservatives. And the ads hearkened back to childhood and made me remember family road trips and midnight snacks with my dad. I don’t delude myself into thinking that McDonald’s promotes healthy living or, as a company, is an ecological net-positive. But I acknowledge that a handful of my happy childhood memories involve the chain and I WANTED to feel good about eating the “new” nuggets. So I bought them for lunch on a Saturday and you know what? I enjoyed all 14. It’s important to recognize when advertising works on you. And it’s important to reflect on WHY it does when it does. You consume more deliberately this way. Continue reading When was the last time that an advertisement really worked on you?→
This is a really great question from a friend of a friend named Dan. He came across it at a house his parents rented in Portland, Maine. Here’s Dan to explain what about this question caught his eye:
“This was especially interesting to my wife and me because my college friends call me Uncle Dan… I am a year older than the rest of them because I spent a year as an exchange student after high school. I am old, sometimes cranky, sometimes wise. I feel older than my 31 years. My wife 26: carefree, playful, irresponsible. Her answer is 16 years old. Mine is 38.”
Here’s how you know when to ask this question: If you find that you and your significant other are getting worked up and are on the verge of arguing about something that is a) not that contentious, b) not that consequential, c) not that complicated, or d) all of the above, then probably you’re hungry. Eat something and the peaceable answer will present itself! (Or you’ll just forget what you were getting all riled up about in the first place.) Continue reading How about we eat something first?→
(This one’s a bit heady, so stick with me.) Many situations have close analogies. For example, I’ve never cooked pheasant but I have cooked turkey and chicken so I can probably guess a bit about what cooking pheasant is like. Or I’ve never lost the Superbowl but I have lost athletic events that I cared deeply about (in high school and college) so I can probably guess how Superbowl losers must feel. On the other hand, many situations simply do not have close analogies. Here’s the one that got me thinking about this question: I barely remember a time that I didn’t know how to swim. So I can’t imagine what it would be like for someone who can’t swim to be on a boat, or at the beach, or on a pool deck. I literally CAN’T imagine it because there are no close analogies for what that reality is like. You could say, “It’s like being afraid of heights.” Except it’s not. Because I could look over the ledge of a parking garage and it would make me feel uncomfortable, but I wouldn’t die after 40 seconds (which is the average amount of time a person can struggle on the surface of the water before submerging). A closer analogy would be walking around in daily life as a normal person except there are areas of your environment that are quicksand and you just know you have to avoid those places. Or pockets of blue poison gas that will kill you after 40 seconds. But that’s fantasy. I’ve never even seen quicksand. That’s why I can’t imagine what a non-swimmer’s experience of water is like. There are many other circumstances with no close analogies. Pregnancy. If you’ve never been pregnant, there is NOTHING in your experience that you can draw on to give you an idea of what pregnancy is like. (“Oh it’s like eating a really huge meal for 9 months! Oh birthing is like passing a kidney stone, I bet. I would guess that, nutritionally, pregnancy is like when tape worms were eating all the food I was eating.” Look! You sound batshit crazy just trying to come up with approximations.) Not knowing how to swim, being pregnant, being a different race than the one I am… To me, these things have no close analogies. What about for you? What circumstances have no close analogies? When you go through this thought exercise, you emerge with more humility, more willingness to dialog, and a changed posture that makes you more likely to learn from others. Continue reading What circumstances or situations can you think of that have no close analogies?→
Dave Grohl has a profanity laced quote that I really appreciate. It’s a long quote but it boils down to these first two sentences. “I don’t believe in guilty pleasures. If you fucking like something, like it.” (Here’s the quote in full. I point you to it so as not to increase the F’bomb count here on WBQ by 10x in a single post.) I think he’s right on. So I’m working on really owning the things that I like even if there’s something about them that embarrasses me. This question, “What’s your guilty pleasure?” has mostly lost its edge because we live in hipster times, and throwback culture, and the term “guilty pleasure” is commonplace. So if someone says, “Oh jeez, well I’m so embarrassed but… I like listening to Backstreet Boys on cassette,” it doesn’t automatically strike me as a huge confession. Liking Backstreet Boys on cassette probably makes you the coolest person in more than a handful of circles. When people hear “What’s your guilty pleasure,” I think the meaning has shifted enough that we are actually answering the unrelated question: “What is quirky-endearing about you?” Quirky/endearing is not guilt inducing. For me, as a liberal arts English major, when among other English majors I’ve often left The Fountainhead off of my favorite books list. In that circle, The Fountainhead is taboo as all getout. Ayn Rand is universally trashed. Admitting that I loved it at first read and still re-read it now makes me worry that people won’t take me (or what I write) seriously. It makes me worry about not being accepted. I feel guilty of having done something wrong. That’s a guilty pleasure. Guilt. But I’m working on it… Continue reading What’s something that you’re genuinely embarrassed to admit is a guilty pleasure?→
Maybe I’m not the only one. All growing up I thought that having a successful career would depend heavily on things like intelligence, talent, ambition, likeability, know-how… It’s a long list. Those things matter, certainly. But in adult life I continue to be amazed at how distinguishing a characteristic it truly is to simply DO WHAT YOU SAY YOU’RE GOING TO DO. You could take away so many of the other traits and skillsets and 5 Things Every Good Leader blah blah Bob Loblaw and have remaining ONLY great follow-through and you’d do fine. It’s with that assertion in mind that I ask this question about when you’ve delivered in your life. We should cultivate and celebrate follow-through moments more than we do. Big moments, small ones, all of them. Continue reading When you look back at all the times in your life that you said you’d do something and you delivered, which of those “follow-through moments” makes you proudest?→
What about a butterfly? What about a hummingbird? If I’m being honest, and if we were talking about an all-expenses paid surf trip vacation to somewhere amazing like Hawaii or Indonesia or Australia, I could do a fly for sure. And I could do a butterfly if it were small and maybe just one flat color like beige or something. If it was a really intricate, colorful butterfly… I don’t know. I think I might struggle. And a hummingbird, hell no. Something about this question made me uncomfortable. It might have been the cruelty, or observing my own calculations, or feeling petty. I don’t know what exactly. But just for the discomfort alone, it’s worth including here. Continue reading For an all-expenses-paid, one-week vacation anywhere in the world, would you be willing to tear the wings off a fly?→
What if we cared about new questions like we care about new phones?
