All posts by Carlo

Can you tell me about how you did this?

If a kid has created something (on paper, in play-doh, in any medium at all…) here’s one question that you should NOT ask:

“What is it? It looks like a dinosaur.”

Focusing on “What is it?” boxes out tons of creative options. A 4-year old might have been trying to draw a bronto or she might have been putting down colors that she liked together. She might have been making a T-Rex in play-doh or she might have been focused on balancing the chunks on top of each other. But you won’t find out the real creative motivations if you focus only on “What is it?” Or even worse, you might “help” turn the play-doh into the T-Rex of YOUR imagination when the project HAD BEEN about balance. Instead of asking “What is it?” try using “Can you tell me about how you did this?” It leaves all creative directions open. Continue reading Can you tell me about how you did this?

 

How would you describe this new feature if you stripped away all the marketing hype jargon?

The surf company Billabong currently sells a pair of swim trunks for $150. No joke. Check it out at this link. But if the link goes dead at some point in the future, I’ve grabbed a screenshot and put it here below.

Ridiculous_board_shorts

How the heck can you justify a $150 price tag for something that costs a third of that amount under normal circumstances? Well, you do it by saying things like: “the pinnacle of boardshort design” and “Platinum X Airlite fabric.”

Marketers get paid to make everyday things sound like technological breakthroughs. They get paid for that because what they do often inspires consumers to cough up more cash for certain products. They cast a VERY convincing spell (and not just for surfing apparel, obviously). But the spell is easy enough to break. Just ask, how would I describe this new feature in normal English? Here’s a translation for the $150 swim trunks:

“micro perforations” = “the fabric is kinda bumpy in a way you won’t notice”

“Mirco Repel coats fabric to eliminate saturation” = “Scotchgard”

“Laser cut drain holes” = “a hole in the pocket to let water out”

This works for anything that has been given a thick glossy coat of marketing jargon. Breaking the spell will save you money and make you feel happier about the things you already own. Continue reading How would you describe this new feature if you stripped away all the marketing hype jargon?

 

What part of your job would you say is the source of most of your work-related frustrations or stress?

In Chip and Dan Heath’s mind-bogglingly useful (and entertaining) book “Decisive: How to Make Better Choices in Life and Work,” they talk about the importance of reality-testing your assumptions. In the context of a job search this means that you shouldn’t just assume that a new field or new position will be all roses. You should ask “disconfirming questions” that will help you see beyond your own personal bias. This particular question is not in the Heath brothers’ book, but it would count as a “disconfirming question.” Found out what vexes a person about her work and you’ll put yourself in a position to make a work decision that’s based more firmly in reality. Continue reading What part of your job would you say is the source of most of your work-related frustrations or stress?

 

What is a characteristic you like about yourself that you rarely acknowledge?

Beautiful question, this one. You want to be acknowledged. In some ways, maybe most of all you want to be acknowledged by yourself. This question invites one moment to do exactly that. Asking it is a gift. So go ahead and give it. (And if your friend is reluctant to answer, ask again. We often aren’t used to answering this kind of question…) Continue reading What is a characteristic you like about yourself that you rarely acknowledge?

 

How are you crazy?

Do you know how I’m crazy? It’s 3:48am and I’m writing about the questions I like for a made-up blog. Dang, I gotta get to bed.

This is a good question though. Ask your friends. Maybe they’re lactose intolerant but eat ice cream all the time anyway. Maybe sometimes (just to check for mind readers) they scream suddenly in their imagination just to see if anyone nearby gets startled.

Always remember: you can’t trust “normal” people. Continue reading How are you crazy?

 

What did you want most in the entire world when you were 5? And 25?

There’s not a real “point” to this compare and contrast. I just think it’s an interesting thought exercise.

When I was five years old I so badly wanted the ninja G.I. Joe action figure that had a sword that he could hold in his hand or carry in the sheath on his back. I had dreams about it. Man, it was so cool.

When I was 25, more than anything else in the whole world I wanted to be in the same place already as my then girlfriend (now wife). At that point, the long-distance phase of our relationship had already gone on for 2.5 years and there was no end in sight. (All told, of the first 5 years we were “together,” 4.5 of them were long distance. These days when people ask “Wow – what’s your advice for people in long-distance relationships?” I say, “Don’t do it.” But if you absolutely have to, don’t EVER, EVER go beyond 2 years. If you hit the 2 year mark and you’re both still into it, someone needs to relocate. You don’t learn anything new after 2 years. It’s just painful.)

5 years old vs. 25 years old. It’s just interesting how we change. (You can try this same thought exercise at different intervals if you have the time. 10-20-30… Or 5, 15, 25, 35… Whatever you like.) Continue reading What did you want most in the entire world when you were 5? And 25?

 

What intangible quality is this ad selling? How would I get that quality without money?

Every single advertisement in every single medium (web, mobile, print, tv, radio…) is always selling two things at once. First, it’s selling the widget (a car, a laptop, a beer, a cosmetic surgery…) but second, and more importantly, it’s selling an intangible quality that you in your humanity want dearly.

Respect: It’s what people feel for people who drive Audi’s.

Creative and relevant: How could you NOT be when you’ve got the Macbook Helium now with zero ports. That’s right. No ports. You’ll never charge your laptop again. Because you can’t. Because we literally removed all the ports.

Beautiful and wanted: If you don’t feel like you’re ever good enough, it’s probably because you’ve never tried Cool Sculpting! (Seriously, though. WTF is cool sculpting? Those guys are on the radio non-stop these days…)

When an ad catches your attention, ask yourself what intangible behind the widget is being sold. Then ask yourself how you would earn that trait, not by buying it (cuz it doesn’t’ work that way), but by making it a part of your character. Respect: In the last 6 months, where could I have done better to keep my word? Creativity: What daily habit should I start to keep me writing consistently? Beauty: What practices will make me more comfortable and confident in my own skin?

Buying more stuff can make you a consumer. That is all that it can make you. Continue reading What intangible quality is this ad selling? How would I get that quality without money?

 

How can I help you?

I really like this question as a closer for informational interviews or other “networking” type meetings. Instead of making the entire conversation about the information, connections, and direction YOU need, flip the script a bit. How can you help this person who has just been answering all of your questions? In an informational interview especially, odds are you’re talking because you come from different but overlapping backgrounds and professional circles. So you just might be exactly the right person to make a useful introduction or point out a resource that could help move things forward substantially. Not only does this give you good karma, it also provides you a way to stay in touch with this new contact (for example, if you happen across an article 2 weeks later that’s related to the issue that needed your help, you can remember to send it along). Continue reading How can I help you?

 

“I wish I had someone with whom I could share…” How would you finish this sentence?

By now you’ve probably heard of the SUNY Stonybrook study that was featured in a 2015 New York Times article about the questions to ask in order to fall in love with anyone. (Many of the questions appear here on WBQ.) But what you may not know is that the study separated the deep questions into three tiers of increasing intimacy. Participants started with Level 1 and made their way up to Level 3. This question right here is straight out of Level 3. And I happen to think that it’s one of the deepest of all the Level 3 questions. The deepest of the deep! To answer this question you have to 1) talk about something that you never share with anyone, 2) admit that you actually have a desire to share this thing, and 3) concede that you currently don’t have anyone in your life with whom you are comfortable bringing this thing up. Daaaang! Now that is next level. It almost goes without saying, don’t open with this question. Gotta build your way there. Let us know how it goes! Continue reading “I wish I had someone with whom I could share…” How would you finish this sentence?

 

What do you think needs to be done to make things as right as possible?

My sister came across this question. You know where of all places? On a posted sign in the hallway of a public elementary school (part of the San Francisco Unified School District). It was one question in a series encouraging kids to use the principles of restorative justice as they solved problems and settled arguments within their own classrooms. Restorative justice is a framework that has played a prominent part in many arenas including the truth and reconciliation efforts in South Africa after apartheid. After conflict of all kinds, this is a powerful question to ask everyone involved. Continue reading What do you think needs to be done to make things as right as possible?

 

How would you improve our interview process?

This is one of Wharton professor Adam Grant’s go-to questions for finding and hiring trailblazers and unique talents. His words are best: “I find this question powerful for a couple of reasons. One, it’s an opportunity to see if they’re willing to speak up. Two, it’s a window into their thinking process. When they encounter something that they don’t like, do they have the instinct not only to raise why it may be broken but also suggest how it can be better? It’s a chance to learn about their tendency to share opinions that might be unpopular but beneficial. It gives you a little bit of perspective on their ability and inclination to improve their environment.” Continue reading How would you improve our interview process?

 

What word or term do I most often end up using to describe the people I like?

Okay, this question isn’t going to make sense unless I explain it. My wife and I were talking with two friends about one of their consistent (but never planned) evening activities: Googling stuff. Rachel said she enjoys learning about things and that she values curiosity. And right there at “curious,” Rachel’s husband, Adam, jumped in and said “You know, if Rachel is describing the characteristics of a person that she likes, nine times out of ten ‘curious’ will be in the list of qualities.” Rachel laughed and agreed. But it was, in a way, news to her. She hadn’t realized that she so often listed “curious” in her high praise for others. I found this super interesting and it kicked off a really intriguing conversation. In turn, Rachel said that Adam describes the people he likes as “the man.” As in “I’d hire Brian – he’s the man!” I immediately chimed in that my wife, Emily, when she’s heaping on praise, will often say that someone is “classy.” This means that they’re the type of person to do things the right way. You know, send a thank-you card or stick around to help clean up after a party. That kind of thing. And apparently when it comes to me, when I get going about someone I like, what often gets mentioned is that “He/she can eat!” This doesn’t necessarily mean that the person eats a lot (though it often does). It means that they enjoy the food, appreciate the details even of extremely simple/cheap recipes, and really get into the act of eating a meal together – storytelling, jokes, connecting in meaningful ways. I never really noticed that but it’s true. So ask your significant other what word/term you use most often to describe the people you like. You’ll learn something about what you instinctually appreciate in others. Continue reading What word or term do I most often end up using to describe the people I like?

 

Couldn’t we at least…?

“’Couldn’t we at least…?’ is the beginning of all progress.” This is what Dean James Ryan says in his 2016 commencement speech at the Harvard Graduate School of Education. The speech is called “Good Questions” and it’s well worth a full listen. The next time your team is stuck, either because consensus can’t be reached or because the solutions are not yet clear, start out with “Couldn’t we at least…?” and see where it takes you. As Dean Ryan wisely puts it: “This is the question to ask that will enable you to get unstuck, as they say. It’s what enables you to get past disagreement to some consensus, as in couldn’t we at least agree that we all care about the welfare of students, even if we disagree about strategy? It’s also a way to get started when you’re not entirely sure where you will finish, as in couldn’t we at least begin by making sure that all kids have the chance to come to school healthy and well-fed?” Continue reading Couldn’t we at least…?

 

What type of intelligence do you possess that could never be measured on a standardized test?

When researchers talk about types of intelligence, they will mention, for example, “logical mathematical” intelligence (characterized by aptitude with reasoning, numbers, and critical thinking) or “interpersonal” intelligence (characterized by sensitivity to other people’s moods, motivations, and feelings). There are many other “official” types of intelligence. But if you were to name and describe a type of specific intelligence that you possess, what would it be? I can tell you that my dad is a troubleshooting GENIUS. He can diagnose and then address the root issue in dang near anything: a sputtering engine, a crashing computer, an a/c unit on the fritz. My sister’s longtime boyfriend possesses “food deliciousness intelligence.” Haha. Seriously. He’s not a trained chef and I’ve never seen him cook from a recipe but he has the ability to understand what kinds of ingredients and what kinds of flavors will make something amazing. He can also taste a sauce in a restaurant and if he likes it, he’ll go back home and re-create it from what he tasted in the sauce. It’s crazy! And delicious! What kinds of intelligence surround you? Continue reading What type of intelligence do you possess that could never be measured on a standardized test?

 

What has surprised you most about ____ as your profession?

About teaching? About medicine? About computer programming. Whatever the profession, it’s always good at least to try and learn the things that people only know after they’ve gotten into the field. And if the person you’re meeting with starts off her answer with a negative surprise, make sure to also ask about what has been the most surprising positive thing. For example, a teacher friend of mine said that he was surprised that he has never once reused a lesson plan verbatim. The days and school years are much more varied than he thought they’d be. He loves that. I followed up by asking what has surprised him in a negative way about teaching. He said the sheer craziness of some parents has been astounding. Continue reading What has surprised you most about ____ as your profession?

 

Have you ever had a nickname?

There are family nicknames, sports team nicknames, nicknames from camp or school or work… And nickname origins often involve a personality trait/quirk or a slightly embarrassing story. Even a short answer to this question gives you tons of conversation starters. “When I played soccer, my teammates called me “Gumby.” Why Gumby? How old were you when you played soccer? What position did you play? Do you still play any soccer? Do you miss organized competition? Have you ever seen an actual episode of Gumby? Continue reading Have you ever had a nickname?

 

What are all the ways you can think of for finding out if the light turns off?

This is a favorite of my good friend and talented entrepreneur, Ari, who’s done his fair share of hiring. Here’s the setup: Say you work at a factory that makes refrigerators. Due to an assembly error, it’s suspected that the little light inside the fridge is not turning off as it should when the door is closed. But nobody knows for sure. What are all the ways you can think of for finding out if the light turns off? Ari says that 1-2 ideas is average. 3 is above average. And 4-6 is excellent. If what you need from your new hire is someone who can solve problems creatively and find a way forward even when plans A, B, and C all fail, then you want someone who can think of 4+ methods of checking if the light turns off. (Set your smartphone camera to record video and put it in the fridge. Test the front hinge/switch that is supposed to turn off the inside light. Cut a hole in the fridge door. Put a person small enough inside the fridge. Wait a minute with the door closed and then see if the bulb inside is hot as soon as you open the door. Etc…)

Continue reading What are all the ways you can think of for finding out if the light turns off?

 

What are the last 10 expenses/purchases you made that were over $50? What does this say about your values?

This is a slight modification from something I heard in a sermon. The original phrasing was: “Your checkbook tells you what your values are.” This might be a touch reductive, but there is a TON of truth to it. If you say you value something but none of your resources go towards supporting it, then what does that really mean? What do your resources actually support and promote in the world? Take a look at your checkbook (but also your credit card statements, automatic payments, Mint or other apps) and find your last 10 expenses over $50. (For the sake of the exercise, you can ignore things like regular groceries and utilities.) What do your expenses tell you about your values? Did a church get a part of your hard earned cash? Did a charity? Did restaurants get most of it? Did a used surfboard from Craigslist? Did you spend on a close friend for his birthday? Did you travel? (Feel free to tweak the parameters – look at the last 15 expenses or look at only the ones over $100.) Sometimes self-awareness involves no reflection at all – just a bit of time with your personal finances. Continue reading What are the last 10 expenses/purchases you made that were over $50? What does this say about your values?

 

If you had access at your fingertips to all the information in the world you’d need to learn any new skill or start any new hobby, what would you learn to do?

“I’d learn to watch cat videos,” said no one ever. So what the hell are we doing? Or more to the point, what the hell am I doing half the time on my pocket computer-phone?

“If you had access at your fingertips to all the information in the world you’d need…” This was a party-game hypothetical question to all people for all of human history until about 15 years ago. For many of us in the developed world, it’s now just reality. So what now? Let’s at least learn to play the ukulele. Or speak another language. Or learn to code. Something! Anything!!! Continue reading If you had access at your fingertips to all the information in the world you’d need to learn any new skill or start any new hobby, what would you learn to do?

 

If you had 10 years left to live, would you take this job?

This might be a touch too dramatic. But I still like the question. And they guy who’s been asking it built AirBnB so he’s definitely doing something right in terms of finding the right people to join his cause. If you had a team composed of even just 3 other people who all answered this question in the affirmative, can you IMAGINE the kind of work you’d get done every week?! Continue reading If you had 10 years left to live, would you take this job?