Be Curious: The Leadership Art of Good Questions

“What’s your latest obsession?”

Dr. Denis Pym, Organizational Behavior Professor at the London Business School, told us eager MBA candidates what a great question this was for engaging conversations.

“I’ve come to hate cocktail parties, donors and academics standing around drinking plonk white wine, eating Jarlsberg, and talking about banalities. This question gets you away from the dreadful ‘What do you do?’ If people quibble about the word ‘obsession,’ I move on, because talking with dispassionate people is painfully boring. But this question sparks some really interesting conversations. You get to know people.”

Denis was a bit eccentric, to say the least. He expounded on “the transformation of labour in the post-industrial economy,” lived on a Kent farm, and told us how he asked corporations to pay him for his consulting in sheep. But he was onto something. Get people to talk about what they are passionately interested in, and you’ll be amazed at how you’ll connect with them.

For five years I conducted a leadership workshop for mid-level leaders at an international oil company. The workshop was called training, but its real purpose was to engage these managers in solving problems facing the corporation. This group of leaders touched many people and they were often purposefully disengaged from change because their job was to make daily work happen. They sometimes felt change happened to them, but for change to happen they had to lead it.

One idea I shared with these leaders was that leadership is about asking good questions. Management is about getting today’s work done; leadership is about change. The key accountability of a leader is to attract followers. Yes, vision is important, because who would follow you if they didn’t have a clear picture of the future? But the act of following is a choice.

People choose to follow because you make them feel part of something. People are more likely to feel part of something if they are talking, not you. How do you get people to talk? Ask them a question.

I’m not suggesting the standard managerial question: “Have you considered the impact on this quarter’s contribution margin?” In pursuit of accountability, some managers ask progressively more detailed questions to test the thoroughness of the work. Sometimes they play “Gotcha” with subordinates to avoid slipshod thinking. Some managers get far too much enjoyment from this kind of question.

Nor am I talking about the “I’m so smart” question: “Clearly you have built upon the work of Dr. Deming in this customer feedback system, but have you considered the work of Argyris and Schon on double-loop learning to avoid coloring feedback by the means used to collect it?”

Nor am I talking about the “I’m the executive and you’re not” question: “Do you mean to tell me. . . ?”

No, I’m talking about questions that truly engage, that open a real dialogue from which you learn something. These are questions born of genuine curiosity about what the other person has to say.

First, some questioning basics:

  • Open-ended questions begin with What, How, When, Where, and Tell me about. They let the answerer talk.
  • Closed-ended questions begin with Do, Did, Will, Have, Is, Should. These questions can be answered yes or no or with very short responses. They are used to clarify and summarize. When overused the dialogue feels like an interrogation.

I think everyone knows this distinction conceptually, but sometimes I find myself asking closed-ended questions unintentionally. The result is somewhat like the Saturday Night Live sketch with the late Chris Farley interviewing Paul McCartney:

“Do you remember when you were in the Beatles?”

“Yes, I do.”

(long uncomfortable pause)

“That was awesome!”

Clearly, if we want people to talk, we need to ask an open-ended question. “Tell me about your job. What are the critical elements?”  “What’s working well today?”

In their 1985 book, A Passion for Excellence, Tom Peters and Nancy Austin introduced the phrase MBWA (Management by Walking Around). Even they called it a “blinding flash of the obvious.” The premise was that leaders should get out of their offices, and talk to customers, suppliers and their people. Good managers have always done this. It seems everyone knows it’s a good idea, but in these days of the email-instant-messaging-social-media-tsunami, it seems to be tougher to do.

When you are walking around, what questions you ask depends on why you are asking.

Some types of leadership questions include:

  • “Getting to know you” questions: They demonstrate that you are interested in others as people. “Where do you come from?” “How long have you worked here?” “Tell me a little about yourself.” “What do you do outside of work?”
  • Questions about the work: “What’s going on today?” “What’s working?” “What do you wish worked better?”
  • Questions to find success stories: “What are you most proud of?” “What around here do you want to make sure we don’t change?”
  • Questions to surface work problems or risks: “What’s getting in the way of your work?” “When do you say ‘I can’t believe we do it this way’?”   “What keeps you awake at night?” “How do you ensure we make safe decisions?” “How do you know?”

When making a change, you might use questions to test understanding of why we are changing, or check on progress, or surface problems or things that are getting in the way.

Ask easy questions first, slightly harder questions next, and save the hardest for last. The hardest kind of question, and the one with the biggest payoff, is the open-ended question that calls upon the answerer to:

  • Speculate about something that is unknown or uncertain. “What level of quality errors do you think would cause a customer to leave?” “What kinds of features would delight a customer to such a degree that she would call all her friends to recommend us?”
  • Compare two or more unlike things. “How do the problems we are having with delivery compare to something that frustrates you on vacation?” “What is the customer value of our medical device product compared with XYZ pharmaceutical?”
  • Evaluate the impact of an action or decision over multiple time horizons or groups of people. “What is the difference between the way our suppliers look at this product versus the customer, our people, and the regulators?” “If we looked at this change over ten years or fifty years, would that make any difference in how we look at it now?”

Use high payoff questions sparingly because they take time and thought both to ask and to answer. But use them occasionally. They can take the discussion to a very different level. You will know they are working by the sound of teeth-sucking inhale (“Ooeesh”) or nasal-vocal exhaling (“Hmmmnn”) followed by “That’s a gooooood question. . . .”

There is another requirement in the leadership art of good questions. You have to want to know the answer. What are you genuinely curious about? Ask those questions.

You can’t fake curiosity. Memorizing a list of questions that you don’t care about will show you to be a caricature of a superficial boss and not someone who genuinely connects with and attracts followers.

And, of course, you have to listen to the answer and remember it. We’ve all been in the active listening courses that teach us how to nod, make eye contact, vocally tune in (Uh-huh”) and summarize (“So if I hear what you’re saying. . .”) But if you’re not truly interested and just focused on the behaviors, you come off as phony. So the leadership art of good questions starts with asking ourselves some questions:

  • “What am I curious about?” “What do I want to know, learn, verify, or think about?”
  • “Why would anyone follow me?” What’s in it for them?”
  • “What would surprise me about myself as a leader? About this work, or this change? About those with whom I need to connect to make this happen?”

D.J. DePree was the founder of Herman Miller, the furniture makers of the Eames chair and the awesome Aeron desk chair. His son, the late Max DePree, shared one of his father’s stories in his book Leadership is an Art.

In 1927, the Herman Miller millwright, an excellent mechanic and a long-term employee, died unexpectedly. Mr. DePree visited the widow and was surprised to learn that the man was a sculptor and a poet. The pastor read some of the millwright’s poetry at the funeral and it was very beautiful, unexpectedly moving.

In his book, Max DePree asks the questions, “Was this man a millwright who happened to write poetry, or a poet who happened to work as a millwright in a furniture factory? How would I know the answer?”

I urge you to think about this question: If the millwright was one of my followers, how would I have really known him? What questions would I ask?


Alan Culler
Alan Culler
Alan Cay Culler is a writer of stories and songs, his fourth career (aspiring actor, speakers agent, change consultant, storyteller.) He retired after thirty-seven years as a leadership and change consultant. Alan was an executive coach, a leadership team facilitator, trainer, and project manager for innovation and improvement initiatives. Alan’s point of view: "Business is all about people, customers, staff, suppliers, and the community - pay disciplined attention to these people and rewards follow; ignore them and success will not last." Alan is “a seeker of wisdom from unusual places.” He is currently completing three books: Wisdom from Unusual Places, Is Consulting Wisdom an Oxymoron?, and Change Leader? Who me?. Alan earned a BA in Theatre from Centre College, an MBA from the London Business School, and a post-graduate certificate in Organization Development from Columbia University. Alan also builds cigar box guitars and wood sculptures, hikes, travels with his wife Billie, and gets as much grandchildren playtime as he can.

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  1. Fantastic post brother Alan

    I loved reading this “This group of leaders touched many people and they were often purposefully disengaged from change because their job was to make daily work happen. They sometimes felt change happened to them, but for change to happen they had to lead it.”

    How true and what questions the leader asks may determine if followers are willing to follow. Your suggestions of questions is superbly explained. To follow is a choice and your questions make the choice sweet and attractive.
    This post is for all leaders.