The issue isn’t awkwardness—it’s a lack of curiosity
Thoughts on the value, challenge, and craft of asking questions
Hey folks
Somebody on Reddit asked how to come up with questions to help them feel less awkward in social settings. It was a good instinct to turn to questions for help. And the question itself struck me as both important and urgent.
It’s not just that questions help you connect with people, they also help you get hired, sell products, find love, teach, lead, stay relevant in the job market, challenge authority, and make people feel seen. Questions really are the closest thing you’ll find to a bona fide silver bullet.
In this post, I'm going to show you why it’s imperative you keep asking questions. I'll consider why coming up with questions in the first place is so hard (spoiler: it's a skill that is being bred out of you). And I'll end with a simple but versatile way to have questions coming out of your ears.
Why questions matter
Questions create opportunities. Say you own a pizza shop. A guy walks in, takes a look at your pepperonis sizzling under the lamps and asks, “Do you do smaller slices?” If you say no, he'll bounce and you’ll sell nothing. But if you ask him why he wants a smaller slice, he might say, “I'm looking to buy ten pizzas for my brother's party, but I wanna try it first and I'm not hungry enough for a whole slice.” Giving answers kills opportunities. Asking questions creates them.
Questions spark love. They are the symbolic starting points (“Will you?”) of all your dates and marriages (“I will!”). And think about it, who would you rather go on a second date with—the girl who injects herself into every story? Or the one who puts you centre stage and asks about your clothes, your boots, and your motorcycle?
Questions cure loneliness. When me and my wife first became working travellers, it was like lockdown with better scenery. To escape it, we came up with a plan to interview locals about their businesses—asking them questions like “How has your city been misunderstood?” and “How did you learn the art of XYZ?” Within two weeks, we'd been put up in a five-star resort, given a private tour of the oldest church in the Americas, and were invited to live with a mezcal producer and his little black cat Tomás. We had only asked questions, we hadn't said a word—demonstrating what Dale Carnegie meant when he wrote, “You can make more friends in two months by becoming interested in other people than you can in two years by trying to get other people interested in you.”
What else can questions do? They can help you coach and be coached. They're the crux of all therapies. They can help you invent insulin and Polaroid cameras (true stories). They can help you start essays too 😉
Questions are egalitarian. You don't need to be in authority to ask questions. In fact, by asking questions, you can direct conversations without anybody realising. When you ask questions, you give other people licence to do the same, and before you know it, you've changed the culture into a questioning nirvana.
Perhaps the most pressing reason to be good with questions is to stay ahead of the job curve. Every few years, the World Economic Forum studies 800 million employees and employers across the world. Their 2023 Future of Jobs Report shows that a quarter of today's jobs will be disrupted in the next five years—and “Governments, businesses, and workers need to foster a culture of lifelong learning.”
What are the most valuable skills employers say you’ll need in order to thrive in this brave new world of work? It ain't physical skills. It ain’t leadership. It ain’t reading or writing or mathematics. It ain't even environmental stewardship, AI, or big data.
The skills you need today, by a big and growing margin, are:
Analytical thinking
Creative thinking
Resilience, flexibility and agility
Motivation and self-awareness
Curiosity and lifelong learning
I can’t think of a more reliable route to fostering those skills than getting curious and asking questions. How is your industry changing? Should you diversify more or focus on specialising in one area? Should you be thinking more in terms of finding a job or creating one?
Pablo Picasso once said that computers are useless because they only give you answers. I used to think he was being facetious, but as usual, that guy was way ahead of his time. If you’re gonna be hot property in your industry, if you’re gonna be an influential leader or parent, if you’re gonna find the right relationships and make sure that they keep growing, then you’ve gotta reclaim questioning as a part of who you are.
Why questioning is hard
I say “reclaim” because questioning is a skill that you’re losing as you age. You lose it first through schooling, then you lose it through modelling powerful people, and finally you lose it through your creeping conservatism.
Schools don't set out to do this, but it’s true they often educate you out of your curiosity. The chart below shows the frequency of the three main learning skills: reading, writing, and asking questions. When you’re young, your mind’s like a sponge. You’re asking questions at an exponential rate. Then, from age three or four, something strange happens: whilst reading and writing continue to rise, questioning plummets all the way to teenagehood.
And if you're thinking, “Well if kids can read and write, maybe they don't need to ask questions to thrive in school,” then consider this next chart. Loss of questioning maps neatly onto student withdrawal. As questioning perishes, so does engagement.
What about the world outside of school? Is adulthood any more welcoming to questioners? Generally it’s not. To question is to not know. And not knowing often carries a heavy social cost.
It means that asking questions is most risky for people in authority, so that the more power and influence you gain, the more of your freedom to question you lose.
If the influential people you look up to aren't asking questions, then you’re going to assume that's normal. You’re not gonna learn how to be comfortable not knowing, and you’re not gonna learn how to prepare for what's to come.
Finally, it's just damn scary asking some questions—especially the important ones. Why don't you know more of your neighbours? What talent do you have that you're not using? What's the commitment you've made that you no longer believe in? What would you do if you weren't afraid?
In spite of the challenges, you need to ask questions. And you need to ask lots of them. But how?
How to ask questions
The biographer of the 20th century novelist E. M. Forster said of him, “To speak with Forster was to be seduced by an inverse charisma, a sense of being listened to with such intensity that you had to be your most honest, sharpest, and best self.” [The emphasis is mine]
I love that quote. It describes a man who brings people alive with his questions. He asks questions because he cares. About your life. Your ideas. About the mystery of you.
And I don’t think he was faking it. People would have cottoned on to that. His questioning must have stemmed from a deep and sincere curiosity.
In that quote, we get a clue that becoming a better questioner is really just a matter of adjusting your mindset. It's about forgetting yourself. And recognising that other people are the biggest source of fascination you have.
If you feel awkward, or worried you won't know what to say to someone, it's probably because you haven't spent time thinking about them in enough breadth or depth.
The fear you feel beneath your awkwardness is a signal that you need to prepare. And if you prepare, not only will it chill you out, it’ll give you a list of life-affirming, conversation-sparking questions you can carry around in your pocket.
Here's a simple exercise for coming up with questions. In her best-selling book, Feel the Fear and Do It Anyway, Susan Jeffers offers nine areas that apparently make up a rich and complete life.
What’s cool is—whoever you’re due to speak to, you can look at Jeffers’ grid and think of questions you'd like to ask them.
Who never fails to make them laugh?
What activities help them make the most of their alone time?
When will they know they’ve “made it”?
Where could people find them at a party?
Why are certain qualities in their partner important to them?
Once you've practised asking your friends how they came to have the jobs they have, once you’ve practised asking your manager what their favourite memory is, it gets easier. You'll probably find that your relationships get stronger. And you’ll wonder how you ever got tongue-tied in the first place.
Asking questions is not so much a skill itself as an outcome of a particular perspective you can choose. If you choose to see other people as intrinsically interesting unsolvable mysteries—if you can make other people the hero of your story—then everything else flows from there. Questions. Confidence. Real connection. And you can leave a trail of inverse charisma in your wake.
The world is getting more complex and we’re getting bombarded with more information all the time. In this environment, the value of answers goes down. What's valuable now is knowing what to do with all that complexity and knowledge. If questions and answers were two stocks on the market, I know which one I'd be investing in. And I think the question of how to ask questions is precisely the right question to ask.
Thanks for reading, see you next time.
Harrison
“Our new civic and professional life is all about doubt. About questioning the status quo, questioning marketing or political claims, and most of all questioning what’s next.” – Seth Godin
More resources on how to come up with questions:
The Right Question Institute (community)
A More Beautiful Question (book)
Over years, this is the single most important metric I use to evaluate people where I want to further social relationships with. There are people who are exceptionally gifted at story telling but very poor at asking questions to know more about me. I tend to withdraw from them over time. I feel like they use the social moments just as a stage, to project themselves, Whereas there are others who are genuinely curious and ask questions that show that they actually listened. Those are the relationships I like to cultivate more.
The “inverse charisma” frame is really helpful, especially given the rising interest among gen z in “rizz”. Reframing questions that was is valuable. Also couldnt agree more with questions opening possibilities— I like to think of it as expanding the surface area for possible intersections between the other person and you on things you actually care about/could learn/teach each other etc. Enjoyed reading this one!