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Mastering the Art of Asking Powerful Questions

The views expressed are those of the author and do not necessarily reflect the views of ASPA as an organization.

By April Townsend
May 9, 2022

Have you ever seen a manager struggling with a problem who is determined to find the solution on their own? Perhaps you’ve even been that person. This is particularly common with new managers who may be reluctant to reach out to others for help. Instead, they rely on their own experiences for the answer. As you watch them struggle, you keep thinking, “Sheesh! I wish they would ask me.”

Why Do We Avoid Questions?

Unfortunately, we often overlook a key component in developing successful managers—the ability to not only lead by telling, but to realize there is also great value in mastering how to lead by asking. Why is it that we avoid asking questions? Perhaps it’s because:

  • We don’t want to look like we don’t know the answer.
  • We’re too busy and asking questions takes too much time.
  • Our work environment discourages asking questions because it’s viewed as being confrontational.
  • We aren’t sure what questions to ask or how to ask them.

I’d like to dig deeper into that last point. Could it be that we don’t ask questions because we aren’t sure what questions to ask or how to ask them.  

Do Questions Matter?

Questions benefit both you and your team. The benefit for you is that powerful questions can reveal valuable information. They not only give you a better understanding of what’s happening in your organization, they provide a forum where you can gain greater empathy for what your team is experiencing.

In the book, Leading with Questions, Michael J. Marquardt points out that, “The desire to be appreciated is a fundamental principle of human nature, and listening is one of the highest forms of appreciation you can show another person.” By asking questions and then listening to the response, you have an opportunity to become a better problem solver because you have more information that helps you think differently about the issues you face.

Admittedly, asking good questions—let alone powerful ones—doesn’t happen overnight. Like anything else, it takes practice. Yet, I honestly can’t remember any course or training I’ve attended where the focus or title was, “How to Ask Questions.” And I don’t remember a single time when my annual performance appraisal included being evaluated or provided feedback on my question-asking skills. Instead, most of what I’ve learned is through observation and then practice.

Over time, I’ve seen how this one skill can support and even grow your leadership presence. Done correctly, mastering the skill of asking questions can help you surface ways to deal with unexpected challenges or pursue new opportunities or collaborations. But where to start?

It Starts with Reflection

One place to start is with yourself. Asking good questions requires a bit of self-reflection to make sure you’re not asking questions meant to reinforce your own expertise, thereby keeping you in control. To truly improve your questioning skills, do some deep reflection on how you can improve. As you do this, think about:

  • Are there any fears I may not be aware of that cause me to avoid asking questions?
  • How can I become comfortable with asking questions for which I don’t already know the answer?
  • Am I afraid that if I ask a question, I may not get the answer I want?
  • How can I support a work culture that respectfully asks questions?

Practicing Powerful Questions

The next step is to develop your leadership skillset through practicing the art of asking more powerful questions. By powerful, I mean questions that invite people to think more deeply about the issues or challenges they’re currently facing. By asking more focused questions, you’re likely to get more focused and meaningful answers.

When someone on your team asks what they should do, it may be tempting to jump in and offer a solution. Don’t do it. Instead, take a breath and think of a question that creates an opportunity for you to explore the possibilities together.

As you work to improve the questions you ask, it may help to compile a list of “go-to” questions you can keep handy. I offer the following examples to get you started:

  • Help me understand what you were thinking when you said…
  • What experiences have you had that brought you to this conclusion?
  • What possibilities come to mind?
  • Can you give me an example of what you mean?
  • What might happen if …?
  • What do you see as the advantages and disadvantages in this suggestion?
  • Let’s take this a little further. Could you say more about…?
  • From your perspective, what matters most?
  • What other options can you think of?
  • How do you feel about…?

Questions like these are designed to encourage the other person to stretch through thoughtful reflection. They can be used to surface and test assumptions and can lead to breakthrough thinking, allowing your team (and you) to see the situation from a different perspective. Finally, asking questions respectfully encourages a learning culture that can help you be a better leader while positioning your organization to respond to the challenges of the future.


Author: Dr. April Townsend worked in local government for over 30 years, holding a variety of executive leadership and management positions. She is currently a Scholar-in-Residence with the Utah Women and Leadership Project and owner of Townsend Consulting, LLC, providing leadership coaching and organizational consulting services. She can be reached at [email protected] Townsend.Consulting.  Twitter handle: @AprilT2014

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