Curiosity: The Power of Thoughtful Questions

Excerpted with permission from, CHANGE-friendly LEADERSHIP: How to Transform Good Intentions into Great Performance” by  Dr. Rodger Dean Duncan


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Egyptian novelist Naguib Mahfouz said it best: “You can tell whether a man is clever by his answers. You can tell whether a man is wise by his questions.”

Decades of diagnostic work—survey research, interviews, etc.—have taught me a lot about the value of thoughtful questions. I can distill it into two salient points. First, you must ask the right questions. Well of course, you say. That’s obvious. Yes, but the second point may not be quite so obvious: You must carefully avoid asking the wrong questions. Why? Because asking the wrong questions will still get you data, and then you’ll chase the wrong rabbits.

Asking the wrong questions is a dangerous and common mistake. It can result in massive reports and beautiful PowerPoint presentations that take unwitting detours to conclusions that shouldn’t be reached and decisions that shouldn’t be made.

In some ways, we live in the age of the reluctant thinker. Original thinking is not always rewarded. Despite a lot of lip service about the value (and necessity) of strategic change, many corporate cultures cling tenaciously to the status quo. People who question “the way things have always been done” risk being branded as mavericks or even troublemakers rather than as innovators.

Smart organizations use systems thinking to find simple and cost-effective solutions to a wide range of performance issues. They sort through the loops and links. They ask the right questions. They avoid asking the wrong questions. They diagnose before they prescribe.

In our “just do it” society, thinking is often viewed as unproductive. When economic times get tough, training budgets are often among the first to be slashed. Good training involves good questions and good answers, which lead to good thinking, which leads to productive people. But many short-sighted managers don’t have the big picture. So they cut the training and development, then wonder why their people seem stuck in the old ruts. It’s sort of like “I don’t have time to stop and get gas because I’m too busy driving!” Asking thoughtful questions—which can be strengthened with good training and development—is a core competency that pays huge dividends.

Let’s consider six dividends of Think-friendly questions.

(1) Think-friendly questions stimulate exploration (and even serendipity). When we get stuck in a particular pattern of thinking, it’s often because we keep asking ourselves the same questions. Change the question and you’re more likely to come up with a more practical answer.

Seventy years ago, Edwin Land was walking along the beach with his young daughter. He stopped to snap a few photos with his Brownie camera. Impatient for the results, his little girl asked an intriguing question: “Daddy, why can’t we see the pictures right now?” It was a problem in search of a solution, and from that innocent question came the development of the Polaroid Land camera and the ability to see a completed photograph only seconds after it was taken. The development of the Post-it Note was an example of a solution in search of a problem. The sticky-but-not- too-sticky adhesive concocted in a 3M lab was just the answer to the question “How can we make a bookmark that will stick to the page but won’t tear the paper when we move it somewhere else?”

(2) Think-friendly questions lead to valuable information. Change-friendly people tend to be questioning detectives. Remember Columbo, the television cop who always solved the crime by asking (in his famously offhand manner) just one more question? We should be more like Columbo, asking that extra question to probe and clarify until we’re sure we understand what we need to know or do.

Good journalists, good detectives, good thinkers focus on five Ws and an H—Who, What When, Where, Why, and How. They ask questions that march them down the path to the information or understanding they seek. They know that not everyone volunteers information, so they ask. They know that some people speak in generalities, so they ask for specifics. They know that assumptions can be faulty, so they question assumptions—beginning with their own. They know that effects have many disguises, so they dig for root causes. They know that words and phrases can mean different things to different people, so they seek clarity and common ground.

Even in this age of Internet search engines and other means of instant information, we can never know everything. And even when we do find answers, we only generate more questions. For generations, scientists struggled with the question “How can we prolong life?” Today we have the technology to keep people alive long after their bodies cease to function on their own. So now one of the questions has become “Should we prolong life?”

(3) Think-friendly questions help us gain control. Just like there’s bad cholesterol and good cholesterol, there’s bad control and good control. The bad kind of control has to do with manipulation of others or smothering their initiative. The good kind of control has to do with managing situations and, especially, managing ourselves.

We can help manage our own physical vitality by asking the right kind of questions of our doctors, dentists, pharmacists, and other health care providers. We can manage our own financial health by asking the right questions of our brokers, accountants, attorneys, insurance people, and financial planners. We can manage our own home maintenance by asking the right questions of the plumber, the electrician, the landscaper, and the guy at the hardware store.

Change-friendly people tend to be good conversationalists. And the best conversationalists are usually people who ask good questions. They don’t interrogate, they simply ask meaningful questions that other people are willing to answer. People who seem to do best in job interviews are those who come prepared with questions of their own. People who are really good at engaging the heads, hearts, and hopes of others tend to ask questions that evoke that engagement.

Good questions, coupled with genuine listening, enable us to be in control without appearing to be controlling, to be assertive without being aggressive.

Although effective communication usually has a spontaneous feel to it, a bit of planning is often in order. Lewis Carroll’s book Alice in Wonderland offers some pertinent lessons. You may recall the ex- change between Alice and the Cheshire Cat about the importance of setting goals. Consider this passage in which Alice asks the Cheshire Cat for advice on which direction to go.

“Would you tell me, please, which way I ought to go from here?”

“That depends a good deal on where you want to go,” said the Cat.

“I don’t much care where—” said Alice.

“Then it doesn’t matter which way you go,” said the Cat. “—so long as I get somewhere,” Alice added as an explanation.

“Oh, you’re sure to do that,” said the Cat, “if you only walk long enough.”

It really takes no effort to get somewhere. Just do nothing, and you’re there. If you want to get somewhere meaningful, however, you must know where you want to go. Then you need to make plans on how to get there. Think-friendly questions can help provide a good roadmap.

(4) Think-friendly questions stir people to open up. Ask routine questions and you’ll likely get routine, minimalist responses.

“How was your day?


“Was the traffic any better?”

“About the same.”

“Did your presentation go okay?”

“Pretty much.”

I practice my questioning habits with my young grandchildren.

Why? Because they’re among my all-time favorite people and because their answers usually lead to delightful, self-revealing conversations. The questions that jump-start these great dialogues are designed to provoke thought and are not conducive to routine answers. One of them doesn’t even end with a question mark.

“What was the funniest thing that happened to you today?”

“What part of today would you like to happen again tomorrow?”

“Tell me how that spelling bee can help you in other school subjects.”

“What important thing have you learned since we last talked?” “How can you help me be smarter?”

“In what ways were you a good friend today?”

“Who are the characters in the book you’re reading? What do you like about them?”

Of course I delight in the innocent questions of my grandchildren, too. Questions like:

“What color is thunder?”

“Do cows get bored? Do they care?”

“Does the Fairy Princess know she’s not real?”

“How old is dirt?”

“Who came before God?”

There’s really nothing complicated about thought-provoking questions. They simply require thought—your thought in asking them, and the respondent’s thought in answering them. And they are appropriate in any venue.

Rather than ask a client to tell me generally what’s going on in his company, I may ask “What kind of day-to-day business situation has the power to keep you awake at night?” Or “If you could wave a magic wand over your business, what would you change? Why?” Or, “Whose leadership style do you most admire? How is your own style different or similar?”

While good questions can stir others to open up, it’s our own genuine listening that helps persuade them to stay open with us.

A comic once said that authentic communication is 50% sincerity, and then you just fake the rest of it. That line may get a chuckle, but it’s a dangerous practice. Genuine listening is
much, much more than eye contact and an occasional “uh-huh.” Genuine listening involves connecting heart to heart and working to understand the other person’s viewpoint even if you don’t agree with it. Good questions can pave the way.

(5) Think-friendly questions influence people to persuade them- selves. A secret to persuasion is to encourage or enable people to come up with their own solutions to problems. Said another way, we can persuade others by helping them persuade themselves.

It’s a fact of human nature that many people have more confidence in what they say than in what you say. When people come up with their own answers and when they say something in their own voice, they’re much more likely to take ownership of the idea.

The best coaches I know—athletic coaches, speech coaches, mu- sic coaches, business coaches—invest most of their time and effort in asking pertinent questions that result in focused feedback.

For example, let’s say a speech coach is helping a business executive prepare for an important presentation to employees. Rather than simply prescribe a step-by-step approach to drafting and rehearsing the presentation, the coach is likely to ask a series of targeted, Think- friendly questions:

“Specifically who are your audience members?”

“Based on the feedback you receive, what seems to be their view of your own work performance? What is your credibility with them?”

“In what ways can you help your people ‘catch the vi-sion’ of the organization’s possibilities?”

“How can you genuinely differentiate your business from your competitors?”

“What kind of data will meet the information needs of your audience, and how can you package the data in a fresh, compelling way?”

“How can you show your audience the linkage be- tween the company’s success and their own personal best interests?”

“How can your presentation come across as a friend- to-friend chat on subjects of mutual interest rather than as a hollow pronouncement from the big guy in the corner office?”

These are pertinent questions, and the answers have a lot more influence when they come from the person being coached.

(6) Think-friendly questions foster self-coaching. Self-coaching requires the willingness to seek honest feedback from others and the discipline to translate that feedback into deliberate improvement. Unfortunately, many people have fallen into the “been there, done that” rut. They forget that self-criticism—when it’s honest and balanced—is a critical ingredient in personal improvement.

Change-friendly people tend to ask themselves questions like these:

“What went well yesterday that’s worth repeating to- day? How can I make it happen?”

“How can I prepare for this meeting so my participation will add real value?”

“This interesting solution doesn’t quite fit the problem. Can it be applied to another problem?” (Remember the Post-it Notes.)

“What things are my colleagues genuinely interested in? What questions are most likely to trigger an interesting conversation?”

“What specific activities—right now—are most likely to advance me toward my goal?” (Yard by yard it’s hard, but inch by inch it’s a cinch.)

“What have I learned from a recent mistake or missed opportunity? How can I put that learning to good use?”

Remember to ask questions from the perspective of the “learn-er” rather than as a “judger.” Acting as a judger can influence us to look for blame rather than solutions. In the learner mode, you use questions to probe the dilemma gently, without bias. Learners tend to ask open-ended, information-gathering questions. If you find yourself in the judger
mode, you can change the character of your inquiry by using your mental “switching lane” and asking learner questions. For example, instead of thinking “Why is this person such a jerk?” you can “switch lanes” and ask “What is this person looking for?” or “What is this person really concerned about?” Learner questions, posed in a Think-friendly way, help create a safe environment that influences people to explore their own motivations honestly and openly.

Think-friendly questions are not complicated. In fact, they’re deceptively simple. And using smart questions to make yourself even smarter is a practice that’s—well, it’s as old as dirt.

Don’t miss out!  To request your free CHANGE-friendly LEADERSHIP” book simply click HERE to provide Dr. Duncan with your mailing address. 

Rodger Dean Duncan


Dr. Rodger Dean Duncan is an award-winning and bestselling author, consultant, executive coach, and trainer who is widely known for his work in organizational performance and leadership.
He’s founder of Duncan Worldwide, a consulting practice with clients ranging from cabinet officers in two White House administrations to senior leaders at corporations in more than a dozen industries. In addition to teaching at three major universities, Duncan served in senior positions at two Fortune 100 companies. His work has been featured in major media including The Washington Post, Fast Company, Inc., and PBS. He has keynoted conferences in many industries, and he writes a regular column for, a platform that reaches 75 million readers each month.


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