The Art Of Asking Great Questions For Leaders

“Asking great questions is not easy. This is because it is not just a matter of learning some ‘talking by numbers’
techniques. Techniques are important. But they work best when underpinned by deeply held values and are
reinforced by hours of confidence-building practice.

Great questions involve an intense awareness of the language you use. This does not come naturally to everyone. When asking great questions, your language will have a purity and brevity that your everyday conversation does not normally have or need. Each word will count. There are some paradoxes here.

For example, beginners typically try too hard and in doing so they make asking great questions far more difficult than it needs to be. Less is more in this work, but to get  to that point you have to understand which words and interventions count, and which simply get in the way.

For both of us, a useful guide came from observing our  kids, children are great at both listening and asking questions. As adults we start believing that listening is not communication and that solving problems is more effective than asking questions.

On listening we are often focus on our personal impressions, interpretations, perspectives and opinions of who and what we are listening to. We are often unable to empty ‘the cup of our being’ in order to refill it with the speaker’s.

As a result our questions focus on the techniques, steps or formulas that will deliver results. This means we often miss the intent, the bigger picture or the meaning of it all… The good news is, we already know how to both ask great questions and how to listen well.

Think about the quality of your listening. Imagine a child’s complete focus on your every word as you tell him a story, and think about the questions children ask: “What does it mean to be free? Why are people poor? How expensive is a tree?”

We have the capacity to ask deep and insightful questions. We have the capacity for deep, empathic listening. It is available to us right now, not tomorrow, not after practice time, not after attending class. We haven’t forgotten; we simply rarely use this innate resource. And we need to be reminded of that interpersonal skill.

We can regain our ability to really talk and to really listen. It is all about our willingness to notice. The inner work of leadership that Case-in-Point requires is only possible when we decide to listen more fully and deeply. Besides breakthrough dialogue, this brings us to the bigger question of how to be in the world—not so much in our classes, but everywhere.

It is all about answering the question: who am I? For this reason the answer to how (to listen, debrief, ask questions in a Case-in-Point session) is actually who: Who am I and who will I decide to be? How will I be myself and how will I show up to meet the challenge of this session I am teaching? Will I have the courage to be myself in a world that tries constantly to make me someone else?”

– Adriano Pianesi & Jill Hufnagel

(extract from “Teachable Moments of Leadership. Case-in-Point resources for daring leadership educators”)