How to Become a Phenomenal Questioner

I recently experienced the powerful impact of a masterful questioner.

He asked questions at appropriate times. Each question was insightful and thought provoking. Each prompted deeper discussion. And all led to greater trust.

You could see the impact in real time. As he asked questions, people would look up at the ceiling thoughtfully for a moment and say, “Hmmm, great question.” Then they would respond in ways that showed they were gaining deeper insights as they spoke.

“You are such a phenomenal questioner,” I said as we debriefed the meetings afterwards.

Why do phenomenal questions matter? Questions have the power to get us past the façade of ego, insecurity and quick fixes. They locate common ground and foster common understanding. Good questions prompt people to reveal who they really are, what they really think and what’s really going on below the surface.


When were you last complimented on how well you ask questions? Can you think of a time in the past year when someone said to you, “You are a phenomenal questioner” or “Thank you for the way that you ask questions”?

In his book, How to Win Friends and Influence People, Dale Carnegie wrote that a person can become a superstar questioner by applying practical ideas. For example, the book begins with nine practical principles. Principle number four is to “Become genuinely interested in other people,” which is a mindset shift from our own affairs to the concerns of others. And principle number seven is to “Be a good listener. Encourage others to talk about themselves.” This simple concept is one of effort and will. Imagine entering your everyday interactions with the intention to “encourage others to talk about themselves.”

Taking those principles further, think about what it would take to get you to the point where people say, “Your questions are amazing. I love how they bring people greater understanding.”

Ready to elevate your questioning ability? Here are six key points I’ve discovered from my work coaching leaders on powerful questioning strategies:

  1. Expand to broader context. Most people lose sight of the forest for the trees. That’s why Six Sigma quality and process methodology recommends “5 Whys” in the Analyze phase of its method. By repeatedly asking “why” (like my two-year old daughter), you can peel away layers of symptoms, leading you to root causes or driving factors.
  2. Provoke new thinking. Good questions don’t have obvious answers. They make people scratch their heads and wonder. The Greek philosopher Socrates’ most enduring contribution is perhaps his form of asking questions to stimulate critical thinking. Questions should prompt people to pause and say, “Hmmm, that’s a great question.” I remember interviewing several candidates to be the Controller of our company. The one we selected was the one that made us uncomfortable with her questions. We wanted someone who would make us think.
  3. Incorporate research and past conversations. Great questioners remember what’s been said or previously discovered. Questions should reference what’s already known for understanding of context and to avoid restating the obvious. This requires memory and sometimes documentation.
  4. Guide without leading. Provoking critical thinking is not about asking leading questions like, “Well, wouldn’t it be a good idea to go on a diet?” Rather, it’s asking questions that lead people to new insights like, “What’s holding you back from being your healthiest self?” A couple of years ago I wrote this article on the difference between leading and guiding questions.
  5. Make them safe. Human beings unknowingly cause others to hide their true selves. We judge, fix, reprimand, shame, interrupt and just don’t pay attention. Questions can very quickly make people feel unheard, interrogated or over-exposed. On the other hand, questions can help people feel encouraged and inspired. Much of that stems from your purpose—is it to empower someone or is it to manipulate them? More about that in another article I wrote on how to maximize emotional safety in a relationship.
  6. Go beyond the surface. Most people have resigned themselves to living and working with mediocre listeners. We assume that no one really actually cares about how we’re feeling or what’s really going on with us. People around us are too busy, too rushed. David Brooks wrote an excellent op-ed in the New York Times on the difference between a transactional and a relational interaction. He said that our goal should be to get to a place where, “nothing is held back…when two or more people are totally immersed in their situation, when deep calls to deep, when they are offering up themselves and embracing the other in some total, unselfconscious way.”

It’s an amazing thing that human beings can interact at this deeper level of connection. It’s rare, though, that we transcend our to-do lists, politics and cover-ups to really know and be known. When we do it creates an understanding and appreciation that’s much needed at work and in the world today.

Are you willing to become a phenomenal questioner?



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