When you reflect on this question you remember vacations, or family holiday feasts, or a great date night, or a home-cooked meal that you’re really proud of. And of course you remember the food itself. Jerk chicken with that red sauce all over the rice. Mom’s caramel stickybuns on Christmas morning. Homemade pizza that you just knocked out of the park. With this question you get all the most important relationships in life, delicious food, you put everyone in a good mood, and it doesn’t have to take more than 30 seconds to answer. For a meeting starter, dang! That’s a quadruple threat.
Continue reading What was the best meal you’ve had so far this year?
All posts by Carlo
What’s the best thing that happened today?
Austin Kleon writes beautifully about how to live a creative life. Austin encourages creators to keep a daily log book or journal that answers this exact question. In his words:
“If you ask yourself ‘What’s the best thing that happened today?’ it actually forces a certain kind of cheerful retrospection that pulls up from the recent past things to write about that you wouldn’t otherwise think about. If you ask yourself, ‘What happened today?’ it’s very likely that you’re going to remember the worst thing because you’ve had to deal with it – you’ve had to rush somewhere or somebody said something mean to you – that’s what you’re going to remember. But if you ask what the best thing is, it’s going to be some particular slant of light, or some wonderful expression somebody had, or some particularly delicious salad.” Continue reading What’s the best thing that happened today?
What do you remember about when each of us kids was born?
I don’t have any kids yet. At my age, my dad already had 2. When I stop to think about that it doesn’t take me long to start wondering, “Holy shnikeys, what the heck was pops thinking around that time?” (He’d had this wild high school and young adult life so for it to change so dramatically as he started a family…it just makes me wonder.) I’ve got a phone call coming up with my parents later today. I’m gonna ask him. I’ll let you know what the response is.
Continue reading What do you remember about when each of us kids was born?
Who at school is most likely to be arrested? A standup comedian? A millionaire?
Arrested. Haha. That’s what caught my eye about this series of questions. It’s edgy enough perhaps to get a response! You know? Throw ’em a curveball! Follow up with these other career categories and if it goes well, try out: “What future would your friends say is most likely for you?” Continue reading Who at school is most likely to be arrested? A standup comedian? A millionaire?
If you could skip any assignment this week, what would you skip? Why?
There are plenty of reasons why your kid might want to skip an assignment. The subject is frustrating because it’s confusing. It’s a partner assignment and he doesn’t work well with his partner. Maybe it’s just not that interesting a subject to him. Ask and find out! Continue reading If you could skip any assignment this week, what would you skip? Why?
What’s the one argument that your parents had that you try very hard to avoid with me?
I’m not a huge believer in the idea that men turn into their fathers and women turn into their mothers and that my marriage is destined to reenact my parent’s and my wife’s parent’s marriages. But I’m not NOT a believer in that either. Let’s just put it that way. Haha! There’s a grain of truth to it all. There is an influence – even if it’s in the opposite direction. Honestly, asking this question on the front end can save you and your partner hours of arguments because you’ll start to see the patterns earlier. “Oh yeah… his parents fought all the time about money. Part of his reaction is coming from that.” Or “Oh yeah… her dad wouldn’t eat healthier post-heart attack even though her mom tried so hard. Part of her reaction is coming from that.” It’s helpful. I promise. Continue reading What’s the one argument that your parents had that you try very hard to avoid with me?
If you could change anything about the way you were raised, what would it be?
In the Stony Brook study from which this question comes, this is classified as one of the deeper level questions. Nobody’s family is perfect but this prompt asks you to reflect very intentionally about what could have (or sometimes SHOULD have) been different. This is a good conversation to have with a close friend because it can remind us that ALL families have their shortcomings. There’s no need to feel ashamed about parts of your own family. You can look back on your experience with a bit more perspective and a bit more compassion.
Continue reading If you could change anything about the way you were raised, what would it be?
If a time machine could drop you right in front of us as kids, what year would you want to appear and what would you say to us?
There are so many different directions to go with this. I’m imagining what my answers would be. I might time warp to 1996 when my sister and I were entering middle school (which are always weird, difficult years for kids). I’d tell myself to look out for her and not to be a punk. I really regret how I treated people, my sister included, during middle school. Or I might time warp to a 1999 family road trip in our dodge caravan and tell us all to soak it in, really love it and pay attention even if all we’re doing is eating at a Denny’s off the freeway and playing the claw machine game with the 50 cents we BEGGED my parents for. Ask this question. Sometimes questions involving time machines are, in fact, already time machines themselves. Continue reading If a time machine could drop you right in front of us as kids, what year would you want to appear and what would you say to us?
What are the most difficult and most rewarding things about growing older?
It’s not easy. Growing older. I recently read the deeply affecting memoir When Breath Becomes Air by a Stanford neurosurgeon who died of cancer in his 30’s. The memoir includes a quote by C.S. Lewis that points out, “Bereavement is not the truncation of married love but one of its regular phases – like the honeymoon. What we want is to live our marriage well and faithfully through that phase too.” Dang C.S. Lewis. Drop the mic. This type of hard, unflinching wisdom is so valuable because it helps us see life’s joys more clearly and prepare for its pains more intentionally. C.S. Lewis isn’t the only one with that wisdom. I bet your grandparents have it. Ask them.
Continue reading What are the most difficult and most rewarding things about growing older?
What’s the last picture you took on your phone?
This is actually more personal a question than it might seem at first. Like it or not, our phones contain more and more details about us with every passing day. So only use this if the date is going well. If it is, this question is playful and can help you both let your guards down. Continue reading What’s the last picture you took on your phone?
What 20% of customers are giving us 80% of our sales? (And are we treating them differently?)
This is Pareto’s Principle. 80-20. Very often 80% of your outputs come from 20% of your inputs. For a non-profit, 80% of all money raised comes from 20% of donors. For a coach, 80% of scoring comes from just 20% of your players. Or for a business (as this question suggests), 80% of sales come from 20% of your total customer base. These are your champions. They love you and your product. Dig down and identify who they are and make sure to treat them differently than you treat everybody else! Continue reading What 20% of customers are giving us 80% of our sales? (And are we treating them differently?)
Can you tell me about the team I’ll be working most closely with?
From Monday to Friday, you’re going to spend more waking hours interacting with these people than you’ll spend with your friends, significant other, kids, dog… It pays to know what the team is like. How many people? How long have they been with the company? Gender mix? What does collaboration usually look like on the team? Do they spend time with each other outside of work? These are important data points on your job search. Continue reading Can you tell me about the team I’ll be working most closely with?
What book do you think everyone on the team should read?
This question does darn near everything. You find out if the person reads regularly (it’s my strong bias that they SHOULD). You learn a bit about his personality. You get to check if he really gets the company ethos and the culture. You can start to gauge whether or not he’d mix well with the existing team. And you get a book recommendation out of it whether or not you hire the person or not! Win^5 Continue reading What book do you think everyone on the team should read?
Who was the best teacher you ever had in school (at any level)?
Where would we be without great teachers? It’s not just the math, literature, or science. It’s what they’ve taught us about confidence, pushing ourselves, compassion, and a hundred other things. Great teachers teach us the things that change our lives forever (which is exactly why this question is so good to kick off a meeting and learn more about the people on your team). Continue reading Who was the best teacher you ever had in school (at any level)?
If I get exactly what I want (a certain outcome, object, or even person) what will I make that mean about myself?
This is an important question. And an unusual one. I want to do it justice… So the thing about being human is that we make EVERYTHING mean something. Every event contributes to a story that we tell about ourselves and the world. Having trouble finding a job? Must mean all my skills are useless and outdated. Get invited to a new-ish friend’s wedding? Must mean I made a good impression at our last get-together. Stop reading a book half way through? Must mean I’m a quitter and always will be a quitter. We do this with everything. We can’t help it. It’s just human nature to make narratives. Sometimes the stories are more “true” and sometimes less. But that’s not the point. The point is that they’re A-L-L stories. Knowing this will help you understand why you want the things you want. Here’s an example from my life: I want to rebuild the back deck that is falling apart at the small house my wife and I just bought. If I learn how and can do it, it will mean that I’m man enough, that I’ll be able to take care of my family, that I’m well-rounded as a person. That’s the story I’ll tell myself about that outcome. Telling it will be as alluring as ever but I’ll at least know I made it all up. It’s all stories. And the real power lies in this: Change the story and you’ll change your life. It’s a constant challenge but whenever you are able, you might as well tell a story that’s compassionate with yourself and with the world.
What three events most shaped your life? Why?
This is a wide open question. And a deep one! I wouldn’t recommend opening with this. But if you’ve already asked a few other questions from the “Ask Your Parent” list, give this one a go. You’ll gain some serious wisdom and your parent will feel valued in a way that is just impossible for a greeting card or random birthday gift to achieve. (And if you’re thinking that asking these kinds of questions is weird and touchy-feely and that you have plenty of time with your parents, let the hilarious Tim Urban over at WaitButWhy change your calculus.) Continue reading What three events most shaped your life? Why?
Grandma was asking about Youtube. What would be a good, funny Youtube video we could send her so she can see how it works?
(Online technology) + (Asking your teenager for help) = (Recipe for a good interaction)
Plus you can always expand the conversation by asking your teenager where he found the videos he’s recommending, what he thinks grandma will say, and if he has any video recommendations that YOU might like. Continue reading Grandma was asking about Youtube. What would be a good, funny Youtube video we could send her so she can see how it works?
If one of your classmates could be the teacher for the day who would you want it to be? Why?
This question gets a good conversation going about who your kid respects and likes in her class. It can also easily turn into a discussion about her interests as well as how she feels about the real teacher. (One pro tip: Try adding the requirement that your kid can’t pick a best friend as the teacher.) Continue reading If one of your classmates could be the teacher for the day who would you want it to be? Why?
Can you give me a mock session of how you would discuss sex education with our kid?
(Almost posted this one to the “Ask Your Date” category. Haha. That would’ve been a mistake!) If you and your partner haven’t completely ruled out starting a family, this question is a good one to work through. Marriages are all about being on the same page. Finances, faith, work, and of course how to raise a family. This question gets right to the heart of parenting styles, strictness, and family values. And it gives you an opportunity to practice “the talk.” (I don’t have kids yet but I feel like I’m going to need a lot of practice.) Continue reading Can you give me a mock session of how you would discuss sex education with our kid?
In the past year, what have you felt most grateful for in life?
In good years and in bad, there are always things to be grateful for. Talking about them makes the year seem better, no matter what kind of year it’s been. And reflecting on this question provides us with a much needed pause – a bit of space to take in what’s happened in the recent past and to feel thankful. It’s what meditation advocate and teacher Tara Brach would call a “sacred pause.” Go ahead. Ask this question and hit pause for yourself and a friend. Continue reading In the past year, what have you felt most grateful for in life?