Want to Be a More Effective Leader? Ask More Questions.

Questions can open up your capacity to embrace change and find better answers. Here’s how to become a better questioner.
Headshot of Amy Radin
Amy J. Radin
Expert Columnist
April 12, 2021
Updated: July 13, 2021
Headshot of Amy Radin
Amy J. Radin
Expert Columnist
April 12, 2021
Updated: July 13, 2021

I am the kind of person who is so inclined to ask questions that, in fact, I am certain during my corporate career that my propensity to want to know more was perceived at times as getting in the way of progress.

I volunteer as a mentor in the Chief Product Officer Accelerator, a training program run by Produx Labs CEO and founder Melissa Perri. As a mentor, I offer practical advice to help rising CPOs excel in their roles. It’s a great way to stay connected to the real problems that real innovators are having in a wide range of businesses and sectors and to also give back.

Following a recent meeting, one of the participants in the program reached out to me for help on how to ask questions. Their challenge was rooted in concerns that asking questions would make them either look incompetent or create conflict with colleagues.

I was really struck by this executive’s challenge. Reflecting upon our conversation led me (of course) to ask myself these questions:

  • Why are we afraid to ask questions?
     
  • How can leaders cultivate an environment where asking questions is encouraged?
     
  • What if we asked questions as readily as we like to provide answers?
     
  • How can asking better questions help us, especially to conquer today’s challenges?

Starting in our earliest school days, raising one’s hand with the answer is what gets rewarded and recognized. Asking questions? Those often get shifted to after class or even after school.

By the time we are adults and engaged in the world of work, we are well trained to find answers, a habit further reinforced by the focus on short-term thinking to get short-term results.

But great questions can open up our capacity to embrace change and better, perhaps less obvious, answers. They create the ability to:

  • Draw people in and open them up to sharing knowledge and ideas.
     
  • Affect people’s thinking and expand mindsets and willingness to question assumptions.
     
  • Create pathways to new insights, data and clues that lead us toward further questions that accelerate more meaningful progress.

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How to Ask Better Questions

Here are six tactics to become a better questioner. Not only will they lead you toward better answers, they will also signal to colleagues that you are listening and value their contributions.

  • Avoid yes or no questions. The world is not black and white and asking for a one-word answer can make others feel cut off. Or, if you must ask a yes or no question, plan to immediately follow up with a “how” or “why” question.
     
  • Frame questions as “how’s,” “why’s,” what’s” and “what if’s.” Such questions invite people to share their logic and rationale and offer the context and interesting details that help build understanding.
     
  • Avoid any variant of “What would you do...?” Asking people to project into the future is a set up for misleading answers. Much better to ask “What did you do when...?” and explore a time when the person solved a similar problem or had a similar experience and can share a real story about what they did, how and why.
     
  • Ask follow-up questions. So often the tendency is to go down a list of questions to which we think we want answers, without stopping to probe. Slow down. One of my favorite follow-ups is: “What you just shared is so interesting. Can you tell me more about what you were thinking or doing then?”
     
  • Gently poke at claims to be sure to get to the substance. “How did you figure that out?” or “How did you come to do that?” are great questions to move past surface replies that may or may not be well substantiated by data or facts.
     
  • Go beyond the usual suspects. Be thoughtful and push the boundaries on who to ask. Audience selection will lay the groundwork for quality learning, so aim for diversity of perspectives and tap into new audiences who may not be experts in your field but may bring valuable perspectives simply because they are not burdened with assumptions about how your business, sector or market has operated in the past.

In the current environment of constant change, unpredictability and uncertainty, asking questions is one of the best skills to strengthen for any leader intent on finding new directions and who sees challenging what they and others have long taken for granted as one of the elements of succeeding.

So what new questions are you asking?

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