The rarest thing anyone ever did for my thinking was to stop talking and start asking questions.
When someone asks you a question they genuinely don’t know the answer to, hold on to them for dear life. Then learn to do it for others around you.
By Danny Kenny
“What do you want?” might be one of the hardest questions for humans to answer.
Not at the drive-thru or cafe — if you’re in line in front of me, you better have your order locked and loaded or I’ll be speaking to your parents, who I know raised you better.
My performance coach, Lauren, is constantly asking me various versions of “What do you want?” She fires short, seemingly simple questions from the hip, leaving me confused before I eventually ramble and stumble into something I didn’t even know I thought.
Lauren doesn’t know the answers when she asks “What does success look like?” or “What are you hoping for here?” Only I know that, somewhere inside. But she knows the questions create space. First, for me to think. And second, to decide what I want to do with these (often new) thoughts.
Count the people in your life who have ever asked you a question they genuinely did not know the answer to. If it’s a quiz with a right answer they were subtly and secretly steering you toward, that’s lawyering, and your friends typically don’t appreciate that (a lesson I learned the hard way). That means no “do you think...?” or “have you considered...?” That’s advice disguised as a question. A real question means someone didn’t know the answer and valued your perspective enough to look for your answer and be changed by it.
Those people are rare. Most of us can count them on one hand. Some of us can’t even do that.
Psychologist and MIT professor Edgar Schein called it Humble Inquiry: “the fine art of drawing someone out, of asking questions to which you do not already know the answer, of building a relationship based on curiosity and interest in the other person.” The coaching world has prized it forever, and it’s why many great leaders have adopted the mindset of “manager as coach.” It fosters genuine curiosity: You ask questions because you really want to hear someone else’s thoughts, not steer them to predetermined conclusions. Fortunately, this skill can be learned, and its impact spans the professional and personal realms.
Want to go deeper on asking great questions? Check out this Big Think Class featuring Angie McArthur, Natalie Nixon, Jonah Berger and more.
In many ways, the world isn’t built for it. We tend to reward the fast take, the strong opinion, the reply that wins the thread. Curiosity, in contrast, is slow. To ask a real question, you have to stop being the center of attention and cede the floor to someone else. Lauren just did it all day, as if it were obvious, but it was also a skill she worked to perfect. And because this is a skill, it means we can break it down into parts, and the parts can be practiced. Here are three to start with:
1. The best questions are short and sweet
Most of us, when we try to ask a good question, make it longer. We add context. We supply half the answer inside the question so the other person knows where we’re going. We say, “I’m wondering if maybe part of what’s happening here is that you feel like the team doesn’t fully—” and by the time we arrive at the question, we’ve removed curiosity and the person in front of us has visibly aged. Get to the point faster.
Lauren’s questions were almost rudely short. “What are you hoping I’ll say?” “And then what?” “What would you tell me?” “What’s changed?” A short question leaves the whole space open and hands the other person openness to fill. Long questions narrow the aperture piece by piece, often railroading someone toward the conclusion you want them to reach. Brevity refuses to play such games.
2. Ask the question. Then stop talking.
The first time Lauren asked me something hard, she asked it and then said nothing. Five seconds. Ten. That is an eternity. I could feel the silence like a physical pressure. She just waited. So I started blabbing to save us both, and eventually, my real answer surfaced. I was as surprised as anyone to discover it.
I exploit this tactic in my work standing in front of a workshop audience because people hate silence. Oh, they despise it. And in a 1:1 setting, that permission (and it is permission) is important because even if the answer is rushed, allowing someone to continue until they find the golden nugget underneath is a gift. When you don’t interrupt, you signal this is a space for you to explore, to find your own answers. Please, continue.
This is the part almost everyone gets wrong, and it’s why most “good questions” die. You can ask the perfect question, but if you rush to fill the pause, you let the other person off the hook with their first, most shallow answer. Depth requires time. The answer worth having is usually the second or third, and it only arrives if you tolerate the quiet. One of Lauren’s best skills (and something common across the best facilitators, coaches, and friends I encounter) is a refusal to save anyone from silence.
3. Ask what, not why
I used to think why? was the deep question. It has the shape of insight. But it tends to trigger defensiveness (it’s a weird thing of the human brain) sending the other person hunting for a justification. Why did you do that? is rarely a fun question to face. Lauren almost never asks me why, because if I’m asked why, my brain is clever enough to come up with an excuse or a reason that sounds good but tends not to be the true reason. “I bought it because it was on a once-in-a-lifetime sale” was really “it’s pretty, and I wanted it.” We don’t have clean access to the inner workings of our own motives.
In contrast, what questions are open enough to surface unexamined assumptions. “What made that feel true at the time?” “What do you want to do next?” What questions provide space and permission to examine the thinking underneath the hood, which is the only kind that ever changes anything.
If you’re skeptical of coaching (and you should be a little skeptical), remember all I’m asking you to buy here is the idea that a good question moves someone further than good advice. People are best persuaded by their own arguments, not yours. Telling someone what to do, how to be, or who to be does not work in the long run.
The clinical foundation of this in psychology is motivational interviewing. What predicts whether someone changes isn’t how good your argument was. It’s the balance of what they say out loud. Push people into voicing their reasons against change, and they dig in harder. It’s called “sustain talk,” and it’s one of the better predictors that someone stays put exactly in the same situation. Good questions tilt the balance the other way, toward the person building their own case for change, and meta-analyses of the method find that balance is what tracks with what people actually do.
There’s a sideways benefit too. Alison Wood Brooks and her colleagues at Harvard find that people who ask more questions, especially follow-ups, are better liked and learn more, and that almost all of us badly under-ask. There is a difference between being interesting and being interested. People tend to favor those around them who are interested. Questions are your vehicle to that particular destination.
Two final things worth holding onto here.
Number one. When you find someone who asks you the real questions and lets silence sit, be they a coach, a friend, a boss, whoever it is... hold on to them. They are rarer than you think.
Number two. You can be this person. It is the most undervalued thing you can offer the people you lead and the people you love. They don’t need your answers. They are rarely asking for your take and your best impression of Stephen A Smith. Giving the people in your life the space to hear themselves think and the patience to let them choose what happens next is a gift. It costs you nothing but a willingness to ask and then shut up. Most people never pay that price.
Who in your life asks you short questions and gives you the space to answer? And if the answer is no one, how could you become that person for the people you lead and the ones you go home to?
Danny Kenny is a behavioral scientist, a writer, and an Associate VP at InspireCorps, where he designs leadership programs and coaches executives at the intersection of performance, meaning, and wisdom. You can find Danny on LinkedIn, Substack, and his website.
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🤔 great read & thanks . Have you tried the " we have two ears , one mouth, do twice as much listening vs talking" approach? Listening teaches people you are interested. If they become more in you , it becomes a win win situation
This made me laugh: "They are rarely asking for your take and your best impression of Stephen A Smith."