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  • Writer's pictureJason R. Waller

How to Ask Truly Powerful Questions as a Leader (and Why It's Important)

Updated: Apr 30

To be an effective leader, you must develop the skill of asking powerful questions. Here's why — and how to do it.



The prominent psychiatrist Carl Jung once stated, "To ask the right question is already half the solution of a problem." As a CEO coach, I see that as leaders ascend the ranks of an organization, their questions become much more important than their answers.


As an individual contributor or junior manager, there's a lot of stock put into solutions and trying to figure out that answer. Success is equivalent to how much you do and how efficiently you do it. The leverage here is in your tools, your systems and processes. For more senior managers or executives, though, the dynamic starts to shift. They're less focused on their own output and start to define success as the output of their teams. The leverage here comes from the people who lead and deliver the outcomes.


As the definition of "success" changes, so too must the approach. How to get the most leverage out of people, people who are often leading others themselves? How to get the most relevant information in a noise of complexity? How to focus, motivate and empower others? A lot of this comes down to developing the skill of asking really powerful questions.


Powerful questions are the cornerstone of effectiveness in my profession of coaching. They're the currency that my clients and I trade in to develop deeper awareness and forward-meaning action. I know something about what makes good questions good and bad questions bad. And, although I do this full-time as my career, coaching is a core part of any effective leadership at scale. So, what's the recipe to make a question truly powerful? For that, I believe you need five key ingredients.



Powerful questions come from a genuine place


Often, I catch myself and others using questions as an argumentative tool to make a point. I call this weaponizing; they are statements masquerading as questions. Imagine asking questions like, "This isn't at all the right approach, what were you thinking?" or "Why in the world would you choose that option?" Even without the context or tone, you can imagine that these questions are intended to make a point, to convey an opinion. Powerful questions, on the other hand, come from a place of genuine curiosity and openness. There are no hidden statements behind them other than "I want to learn from you."


Powerful questions are open, not closed


A closed question is something that restricts the answers, usually a yes or no or a small subset of choices. "Are you making progress?" is a closed question. "Do you think we should go left or right?" is a closed question. This isn't to imply that closed questions are bad; in fact, they can be quite helpful to get clarity or encourage action. But really powerful questions are open, not closed. They begin with question words, especially the words "what," "why" and "how." These words invite a broader discussion, not a choice from a narrow set of possibilities.


Powerful questions are framed in a way that's encouraging


As a shortcut, I find that oftentimes the best word to start a powerful question off with is "what" instead of "why" or "how." Asking, "Why did you do this?" can prompt someone to be defensive and try to answer in a way that justifies their choice. Asking, "How did you do this?" can have a similar effect or result in a more analytical or superficial answer. In contrast, try reframing the question in a less confrontational way, such as, "What was important to you about doing this?" or "What were the steps you took?" Regardless, another way to frame a question in a more encouraging way is to simply share the context for the question.


Powerful questions focus on going deep instead of broad


As leaders, we must continue to develop a sense of priority and focus on what truly matters, reflecting that in our questions. Instead of asking questions to collect answers on a dozen different topics, ask questions that get you a dozen perspectives on the one most important topic. Try to reflect on what the most important thing is and then zoom in, not out. Focus on what more instead of what else.

Powerful questions are concise


Finally, powerful questions are concise; brief but potent. A short, sweet question is easier to understand, reflect on and respond to. There are two things to watch out for here: long questions and stacked questions. A powerful question should be short and fit comfortably into a simple sentence. If this isn't easy, pause to reflect on how to make your question shorter. But avoid trying to restate the question after the fact, which can just create confusion. Stacking questions one after the other makes it difficult to understand what the true question is. It's often better to ask a good question and stop short of adding the perfect question on top of it. Try to remember: Ask your question, then pause at the question mark.


Asking powerful questions is a skill — one that can be practiced and developed over time. Try noticing these five components of powerful questions as a structure for that practice. And, although this isn't part of building powerful questions, don't forget to truly listen to the reply. Think less of which question to ask next or what response to give, and try to stay present. Focus on understanding the answer. That is, after all, why we ask really powerful questions in the first place.




Originally published in Entrepreneur



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