The Benefits of Leaders Asking Powerful Questions



This is a guest post by Fred Halstead, founder and principal of Halstead Executive Coaching and author of Leadership Skills That Inspire Incredible Results*.


The Leadership Skill of Asking Questions

Powerful questions will help you learn both about the person you’re speaking with and the subject you’re discussing. You can find out how the person thinks and what is important to them, based upon what they say and don’t say. The more you continue to ask powerful questions, the more you will accomplish both. This confirms George Bernard Shaw’s point: “The problem with communication is the illusion that it has been accomplished.” So often we fall into a trap in which we believe we understand each other and grasp the concepts being explained, only to later find that it was almost as if we were speaking a different language to one another. Continual probing and on-target questions will help both you and the other person arrive at the best solution and learn more about each other and yourselves.



It seems obvious since we spent two chapters discussing the importance of listening, but when a question is asked, allow the other person the time to respond. You want to be sure that thought processing and critical thinking are at play. I had one client who felt that the reason the respondent didn’t answer immediately was that he or she didn’t have an answer. If you want a quick answer, there is a really low probability that you will gain a truly thoughtful answer. If your expectation from a thought-provoking question is a quick answer, you risk the other person being frustrated in a nonproductive way, with you and with themselves.

Powerful questions also satiate your sense of curiosity. When you are curious, you want to learn more and you will more naturally ask questions in ways that will maximize the other person’s thinking. When the right question does not come to mind or the person was not clear in what he or she said or was trying to say, you can always respond: “Tell me more about that.” This simple phrase will expand the other person’s thinking as they further verbalize their thoughts and your understanding of what they are saying. When one is not naturally curious, the desire to respect the other person by exploring their thinking provides a solid motivation to ask questions that bring out the person’s best thinking. Instead of saying, “Stay thirsty, my friend,” as Jonathan Goldsmith did in the Dos Equis ads, say to yourself, “Stay curious, my friend.” Lack of curiosity can be the foe of getting to the best result.



Powerful questions are perfect for discussing sensitive matters. Asking difficult, tough, or edgy questions can be hard for even the most veteran leaders, but those who want their colleagues and team members to succeed will of course need to ask some from time to time. As a coach, I ask those questions fairly often to bring out my client’s very best thinking. When the person is asked a tough question that reflects on them personally, you will find it interesting, maybe surprising, and rewarding to first ask for their permission to ask a difficult question.

The typical question is simply something like: “May I ask you a tough question about all of this?” (This is one example of when a yes/no question is wise.)leadership skills book cover

Tough or difficult questions are direct and go to the heart of personal accountability and, at the same time can inspire a higher level of performance. Examples of such questions include: “In retrospect, what could you have done differently to create the outcome we wanted?” or “What was an even better way for you to handle that?” These questions will help them reflect on their decisions and actions, and also on what they can do in the future to improve. A question such as, “What do you need to do to greatly improve this situation?” or “What specifically will you commit to do differently when this or a similar situation arises?” may feel too pointed at first, but it will lead to them being more reflective and thoughtful, help them avoid the same actions in the future, and to grow as a leader. These kinds of pointed questions also demonstrate that you care about them as a person and you care about their success—and they reflect clearly on who is responsible. They have no sense of “gotcha,” which tends to make it about you more than their responsibility.



Ask Questions that Touch the Core

One powerful way to inspire others is ask questions that touch the core of who a person is or who they want to be as a both a person and as a leader. Those types of questions tend to strengthen the foundation of who someone is or wants to be. They signal a respect for that person and a sense of keen interest in them. In giving that signal, what do you think their view of you as someone they want to follow will be? Some examples of such questions are: “In what ways did your actions reflect on who you want to be as a leader?,” “What should you change to create a better result next time?,” and “What do you think should be or are the consequences of what you did (or the consequences of what happened)?” The last question, of course, asks the person to say out loud what the consequences are for them and for the business. In some ways when they say it, it has a greater impact on them than if you do—especially when you affirm to them those are the consequences. In that situation, it might also be wise if they left an important consequence unsaid to ask: “What are some other consequences?” or “What about . . . ?” Another question to improve self-awareness and future performance is: “Taking a fresh look at this, which of your talents can you use to improve on what you did or said?”

Fred HalsteadPowerful questions also help remove distracting emotions or prevent traveling on rabbit trails from the conversation. The questions will often start with asking for a description of the forest—the broader view. This helps the other person get out of the woods and out of their own way. This is particularly the case when the other person is buried in the complexities and minutia of a certain situation. Some examples of questions to help someone extract their mind from the nonessential details and emotional reactions are:

  • As you look at the bigger picture, what are the key things in play here?
  • If you selected one or two things that are most important to accomplish, what would they be?
  • What really matters to you?
  • What really matters to the person or group most affected?
  • What will cause this effort to actually work?
  • What will motivate the players involved to take positive and productive action?
  • What makes a specific person or position critical in our company?
  • What do you think is at the heart of this issue?
  • Where should your focus be?
  • What are the things you can do that are most important for your success?
  • What are the benefits if you focus more on the most important things you just identified?



Powerful questions are the only ones that will get the conversation to where it should go, providing solutions and helping everyone involved move forward with increased vigor and excitement about the current task or project.


*Adapted and reprinted with permission from Career Press, an imprint of Red Sheel/Weiser.

For more information, see Leadership Skills That Inspire Incredible Results.


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