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Good Leaders Ask Better Questions

by Ryan Cornell-d’Echert

“Once you have learned how to ask questions – relevant and appropriate and substantial questions – you have learned how to learn, and no one can keep you from learning whatever you want or need to know.”  

-Neil Postman and Charles Weingartner

From an organizational perspective, conflict isn’t always at the end of a rifle. Sometimes conflict comes from unmet expectations. On multiple occasions throughout my career, my colleagues and I rigorously prepared and presented a deliverable for our boss, only for the boss to say, “This isn’t what I wanted. This isn’t even close to what I wanted!” 

How could we have done better, how can we prevent this in the future? To build strong relationships between leaders and followers, we need to communicate effectively. We need to ask the right questions. As leaders, we need to be clear about our expectations. As followers, we need to ask for clarification if we don’t know what those expectations are. If we don’t communicate effectively and don’t manage expectations, we can create conflict or drain the energy out of organizations

It is important for leaders, especially as they become more senior and more influential, to choose their words carefully. Teams will get confused, frustrated, or burned out by a boss who cannot distinguish rhetorical questions from real guidance and direction. Whenever senior leaders ask a question, that question creates work. Sometimes that work diverts time and effort from existing (and more important) priorities. A particularly dangerous phrase for leaders is “I wonder.”

Imagine the commanding general visits a unit’s motor pool to assess the readiness of their maintenance program. The general and their entourage walk past a series of tactical vehicles. At one point, the general says, “I wonder how many of our trucks are green and how many are tan.”  Then–days later, someone presents the chief of staff with an elaborate cost estimate for a contract to repaint every vehicle in the division. The staff spent considerable time and effort researching and producing something the boss never actually wanted or requested.

The Power of Leaders’ Questions

One of my best commanders was extremely observant and self-aware. He recognized the weight of his words – and he knew his staff opened their books and took notes whenever he spoke. He knew the potential for those “I wonder” statements to send his team into a tailspin or a wild goose chase. Therefore, he was more precise with his language. He knew words have meaning. He would say, “I would like to know if we can do X. Hey S3, please look into that,” leaving no doubt about his intent. Occasionally, he would say, “I am interested to know more about Y.” Upon noticing everyone taking notes, he would add, “Nobody needs to do anything right now. Just think about it.” As a leader, the next time you tell your team “I wonder…” or “It might be nice if…,” stop and listen to yourself. Is that something you seriously want your team to do? How much time and energy will it take for them to find the answer? How many other projects and priorities will stall because you sent your team on an “accidental science project”? As a leader, can you withhold those questions that, if answered, have no effect on the decisions you need to make? Given the volume of data in large organizations, leaders should discern which details are worth not knowing. Leaders should understand their team’s existing workload, and trust those who require specific details already possess them. What are we doing to release time back to the team?

What if you ask great questions, but your boss is not as observant or self-aware, not as precise with his or her language, or doesn’t distinguish between ideation and ‘foot stomps’? What if your boss’s questions are unrelated or seem irrelevant? Before your meetings and engagements end, I recommend having someone (if not you) recap what you believe all the expectations, due-outs, and “homework” to be. This helps ensure shared understanding and reduces the potential for sending people on accidental science projects. Some leader questions are simply to indulge a random curiosity. Some questions will help drive a decision. Both leaders and followers need to know the difference.

Thinking Critically: Asking Better Questions

Army doctrine defines critical thinking as a deliberate process of thinking to improve our thinking – or, thinking about thinking while we’re thinking. Personally, I define critical thinking as having a good “BS filter” that goes beyond mere skepticism. When critical thinkers take their thinking apart and examine it, they assess the quality of their thinking using the nine intellectual standards of clarity, accuracy, precision, relevance, depth, breadth, logic, significance, and fairness. Each standard must be clearly understood for critical thinking to occur, but clarity is the gateway to the other intellectual standards. If the questions we are trying to answer, the information we are using, or the assumptions we are making are unclear, we can’t move forward. Clarity does not provide comprehension, but it makes comprehension possible. 

Below are some example questions for each of the intellectual standards – these are the kind of questions to ask if we’re trying to think more critically.

  • Clarity: Could you illustrate what you mean?
  • Accuracy: How could we verify or test that?
  • Precision: Could you be more specific?
  • Relevance: How does that relate to the problem?
  • Depth: What are some of the difficulties we need to deal with?
  • Breadth: Do we need to consider another point of view?
  • Logic: Does what you say follow from the evidence?
  • Significance: Which of these facts are most important?
  • Fairness: Am I taking into account the thinking of others?

We can test the quality of our thinking using the nine intellectual standards, but we can

demonstrate the quality of our thinking by the quality of the questions we ask. 

Leading by Asking Questions

When I was an instructor, if a student asked a well-considered, thought-provoking question, it suggested that the student was thinking critically. When a student only ever asked a question like, “Will this be on the test?” it suggested he or she was thinking at a lower level. This paradigm is not limited to the classroom. In an operational and organizational context, a rich exchange of questions can help sharpen us and even reveal gaps or flaws in our planning and processes. 

I prefer leading by asking questions. I don’t necessarily withhold information, but if I always supply my people with all the answers, then I become the “answer man” and my team will always be utterly dependent on me. I challenge my subordinates to try answering their own questions first, and I try to include them in my decision-making whenever I can. When one of my subordinates comes to me with a question or problem, my first reaction is not typically  to fix their problem for them. Instead, here are some of the questions I might respond with:

What does the regulation say?

What would you like to be able to do that you can’t right now?

If you were in charge, what would you do first?

What else do you need to accomplish this?

Why do you believe these conditions exist? How did we get here?

What have you already tried?

What assumptions did you make?

What choices do you have?

What do you think?

I have found asking questions and involving team members, regardless of rank, creates more buy-in and helps team members go from compliance to commitment. When we lead by asking questions, our people will feel like they matter because we create an environment that encourages them to think. An exchange of questions gives our teammates a voice and a vote, ensuring everyone is heard. People feel a sense of pride and ownership in the team when they are included, we accomplish greater things in teams. My teammates have experience that I don’t, and they’ll see things I might miss. That’s why I like to include them, by asking better questions. 

Major (Promotable) Ryan Cornell-d’Echert is currently the J1 and Multinational Force and Observers (MFO) Desk Officer for the U.S. Military Observer Group (USMOG) in Washington, DC. He recently spoke in a podcast covering the same topic as this article. He is the author of Surprises are for Birthdays, Facilitating Leader Professional Development in Your Unit, You and Your NCO, The Brigade S4 Survival Guide, Genuine Leadership, and How to Enable as an Enabler.