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The Art of the Question

Writer: Calvin Webb III
Calvin Webb III
Sep 1
2 min read

Strong leadership does not require having every answer. It often begins with asking better questions, listening carefully, and remaining genuinely curious about others.



By Calvin Webb III, CPA, CIA, CFE


I recently read Edgar Schein’s Humble Inquiry. Schein describes humble inquiry as asking questions “to which you do not already know the answer” and building relationships through curiosity and genuine interest in another person (p. 2).


I was struck by how simple that idea sounds and how difficult it can be to practice. In business and consulting, regardless of industry, we often feel pressure to enter a conversation already knowing the answers to most, if not all, of the questions that might be asked. Leaders may feel expected to have every answer or risk appearing uncertain and losing authority.


Schein observes that our practical, problem-solving culture tends to value knowing and telling more than asking (p. 10). But is that really the best way for leaders to approach their work and the complex relationships within it?


I believe the answer is a firm no.


As consultants, we can be tempted to offer advice and recommendations readily. After all, organizations often bring us in to do exactly that. Yet one of the primary drivers of strong client relationships is not simply the advice we provide. It is also the questions we ask, the care with which we listen, and the relationships we build.


Schein, himself a former consultant, writes, “I learned early in my consulting that getting the questioning right was more important than giving recommendations or advice” (p. 4).


Although he directs this observation toward consultants, it is equally important for leaders at every level of an organization. In The Truth About Leadership, James Kouzes and Barry Posner report that people often describe the leaders they admire as making them feel listened to, understood, capable, important, and challenged to do more (p. 69).


I imagine those leaders were skilled at practicing humble inquiry. They understood that leadership is not demonstrated solely by having the answers. It is also demonstrated through curiosity, thoughtful questions, and a genuine willingness to listen.


Questions for Reflection on Leadership


To close, I would like to ask a few questions that may be helpful in your leadership journey:


  1. Do you seek to understand before telling others what you think?

  2. Would the people around you describe you as a good listener? Would you be willing to ask them directly?

  3. How well do you value your colleagues as people rather than viewing them primarily as direct reports, peers, or supervisors? Why did you answer that way?

  4. What steps can you take now to improve how you listen, ask questions, and build relationships with your colleagues?

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