The Art of Asking Better Questions
Observation, openness, and making space for wonder
As an adult human, I love to watch children ask questions. “Why do the planets stay in orbit?” “How do pencils get their lead?” “Who made you the boss?” I’ve found that they’re overwhelmingly more observant than most adults — thinking to question the nature of things we mostly take for granted. As a builder of design teams, this is what I look for in designers, researchers, and writers. The art of questioning what-is and why should be at the heart of all we do; you can’t build the world if you assume you understand it.
And so, a few thoughts on the art of asking questions — applicable in work and in life:
What’s a great question anyway?
Great questions do two things: they seek a truth and they open the door for more questions. Seeking truth is the art of understanding, not to be confused with locating an irrefutable fact about the universe. Some truths will be objective and agreed upon, like the amount of mass in a kilogram. Other truths will be subjective: personal experience and history, for example. The one rule is that a truth-seeking question be open to the truth described by the answering party. A question is no good if you’ve already decided the answer yourself — the key to the second factor, opening the door for more questions.
Great questions come from open, observant minds
If a man spent his whole life looking at the ground, he’d only ever ask about the things around his feet. If that same man looked all around, he could ask about infinitely more simply by virtue of observing more. Observation is question-fuel for you can only ask about the things you’re able to grasp, even marginally.
Sometimes I worry that observation is a dying art. We consume more content than ever, scrolling and scrolling through feeds and, to be sure, valuable exposure happens here — I’ve never been to Japan, but I certainly have many questions about it based on content I’ve consumed. Strong observation, however, requires a certain stillness and focus, the kind that enables you to sit at a city intersection and observe the shape of the road, the pattern of the lights, the types of people and their motions and their sounds, the birds that perch on the wires overhead. Observation, done really well, is a highly engaging endeavor in which many questions should arise as you unpack and zoom in on what you see and hear and smell, etc.
Observation does not require agreement, in fact, it shouldn’t involve judgement at all.
This task also requires an open mind, not just an observant one. Open minds are necessarily questioning minds — they don’t cloud their vision with assumptions and beliefs about the world. Note, this doesn’t mean you can’t have assumptions and beliefs, we all do. I challenge you to be open to seeing beyond them — observation does not require agreement, in fact, it shouldn’t involve judgement at all.
Great questions require great listening
Please raise your hand if you’ve been in an important conversation listening to… your own thoughts on what to say next. ✋Awesome, now that we’ve got that out of the way, I hope we can all agree this is just about the worst thing one can do in a conversation. Not only do you miss a point of valuable connection with another person, you’ve missed out on the kind of active listening that builds both trust and, you guessed it, more questions.
This is a good time to distinguish listening from hearing. Hearing is simply the action of sensing sound. Listening is hearing sound, acknowledging it, and absorbing it consciously. You respond to hearing a sound by jumping when a firework goes off or turning down the car radio when it’s too loud. We’ve got a richer set of actions to take when listening because our brains are engaged, what is heard is interacting with what we know and feel and that, my friends, is how you get questions.
As a side note, listening (not hearing) has the capacity to help change you — a desired outcome of great questions, but that’s for another set of musings.
Allow yourself to experience wonder
I have a vivid memory of wonder as a child — standing at the foot of an enormous kinetic sculpture at the Boston Museum of Science. It was composed of thin, metallic wires and spheres suspended from the ceiling and was making visible the forces of motion that govern how objects move through space. That’s some crazy sh*t for an eight year old, to realize that all-the-things in the universe run on tracks defined by physics. It was a syrupy, overwhelming, and addictive feeling. Questions came furiously, Does this apply to everything? Are there little invisible train tracks everywhere? Am I on one right now? How’d they get all those wires up there? What the hell does this have to do with MATH?
Wonder
Noun: A feeling of surprise mingled with admiration, caused by something beautiful, unexpected, unfamiliar, or inexplicable
Verb: To desire or be curious to know something
Sometimes I like to think of wonder as the echo produced by questions — as if so many of them have surfaced at once that none at all come to mind in the moment. It’s intensely satisfying and, to those who note it, can sustain a line of questions that take work and life in new directions. When I talk to people about wonder I mostly hear recounted stories of the extraordinary — solar eclipses, smashed world records, the birth of child. It’s easy to ask questions about situations that truly stop us in our tracks and I hope you always do.
However, I’ll wager that the best question-askers among us actively invite wonder to the mundane. It’s the effect of being open and observant at the right place and time for you and it could be anywhere; watching a baseball game, tide pooling, or doing some minor home plumbing (who hasn’t stood in wonder that their duct tape job hasn’t blown out the dishwasher yet? Professionals are worth every cent). Wonder can be found almost anywhere if you look closely enough. You’ve got to notice and keep noticing things, you’ve got to pull back the curtains, follow what you don’t know and I promise you’ll not only be asking better questions, but finding the satisfaction in how many more are left to ask.
