How to Ask Better Questions

The less I talk, the better the discussion.

This conviction sits at the center of how I aim to lead, facilitate conversations, run meetings, and create developmental space for others. Over time, I have learned that leadership presence is not measured by how much we say, but by the quality of space we create. Questions—well-timed and well-formed—do exactly that. They create room for participation, invite ownership, and unlock insight that no single leader could generate alone.

And yet, this raises an important tension. If questions are so powerful, why do so many conversations still feel flat, performative, or unproductive? Why do meetings stall, feedback sessions fall short, and dialogue feel shallow—even when leaders are asking questions?

The answer is simple but uncomfortable: not all questions are created equal. And even well-intended leaders can unintentionally undermine the power of questions by asking them poorly, asking them defensively, or asking them without genuine curiosity.

So, what does it actually look like to lead through questions? How powerful is this approach in practice? And how can leaders learn to ask better questions—questions that deepen thinking, elevate others, and meaningfully shape outcomes?

Let’s explore the power of questions and nine practical ways leaders can use them more effectively to have a greater impact.

Questions, Like Leadership, Are Inherently Selfless

At their best, questions come from a place of genuine curiosity. And genuine curiosity is fundamentally selfless.

Curious leaders care about people. We see them as complex, capable, and worthy of dignity and respect. We recognize that most people want to be known, understood, and valued. Thus, we use questions as a way of honoring that desire. We seek to understand others’ experiences, motivations, challenges, and aspirations. We work to make their efforts meaningful, their environments healthy, and their contributions matter.

Take note—this posture is not transactional. Curiosity should not be used as a tactic or leverage point. It should be employed because people matter.

Brendon Burchard captures this challenge well in The Motivation Manifesto when he writes:

“Too many have forgotten the charge that our ancestors left us: to direct our energy, knowledge, and talent toward making a difference. What are we all fighting for if not to improve one another’s lives?”

Curious leaders want things—and people—to be better. We care more about arriving at the right answer rather than being the one who provides it. We are willing to ask, listen, and wrestle with complexity rather than rush to premature conclusions. We look for problems that need attention and roll up our sleeves to address them alongside others.

However, before learning how to ask better questions, leaders must first confront a qualifying issue: our intent.

Intentional leaders seek to understand before they seek to be understood. We seek to love before we leverage. We care before we compel.

So, it’s worth asking ourselves a few hard questions first:

Am I actually a curious leader?
What am I curious about—and what am I noticeably not curious about?
Where are the boundaries of my curiosity, and why do they exist?
What do those boundaries reveal about my assumptions, gaps, and intentions as a leader?

Only then can we fully appreciate how asking better questions can elevate our leadership impact.

The Value of Leaders Asking Questions

When leaders leverage questions well, they create value across a wide range of contexts. Thoughtful questions can generate:

An invitation to participate. A leader who admits, “I don’t know,” is not signaling weakness or incompetence. More often, they are creating space for others to step forward. Questions distribute leadership, inviting others to contribute insight, experience, and ownership.
Ownership and pride. Asking questions gives people the opportunity to demonstrate competence and mastery. It affirms their expertise and activates intrinsic motivation. People take pride in what they help shape.
Diverse thinking. Questions open doors to multiple perspectives. They interrupt groupthink and broaden the solution space, which almost always results in better, more robust outcomes.
Growth and development. Questions stretch people. They invite reflection, challenge assumptions, and push individuals beyond their comfort zones. Leaders can use questions to inspire learning rather than simply transmit answers.
Clarity of thought and direction. Well-crafted questions can clarify both problems and solutions. They help surface root causes, align understanding, define next steps, and establish ownership. Leaders are responsible for clarity—and questions are one of the most effective tools to achieve it.

When we realize the depth and breadth of the value that questions create, it’s easy to see what is lost when leaders fail—or refuse—to ask them.

So, what does a more curious, intentional approach look like in practice? Below are nine simple, actionable ways leaders can begin asking better questions right now.

Nine Ways to Ask Better Questions

1. Ask a real question. Many “questions” are actually advice, lectures, or conclusions disguised with a question mark. Phrases like “Have you thought about…” or “Don’t you think we should…” are not questions—they’re directives. Start by asking something you genuinely do not already know or are seeking to explore with others.

2. Ask one question at a time. Avoid multi-part or rapid-fire questioning. One thoughtful question invites depth; many questions at once overwhelm. Slow the conversation down and allow space for meaningful engagement.

3. Ask a simple, focused question. Narrowing the scope of a question—by time, behavior, or context—makes it easier for others to respond and results in more actionable insight. Broad questions like “What feedback do you have for me?” can leave people paralyzed. A simpler, more focused one, such as “what are one or two things about my behavior as your boss that has made your ability to do your job harder in the last month?” makes a response more manageable, the discussion more concrete, and prevents anyone giving the dreaded deer-in-the-headlights look.

4. Get to the point. Long preambles and excessive context often complicate the question and dilute its impact. Ask the question plainly and trust others to engage without needing a lecture first. (Hint: it’s ok if they do want more context and respond back with questions of their own.)

5. Use what instead of why or how questions. Why questions can feel accusatory; how can prematurely rush to tactics or solution generation. What questions invite exploration without judgment and help surface intent, assumptions, and context. Consider these two questions: “what factors drove the team to take this approach?” and “why did you all do it this way?” Both essentially ask the same question. The latter, however, comes off more judgmental than curious.

6. Embrace silence. Silence feels uncomfortable—but it can be productive. Give people time to think. Ask the question, then be quiet (or, put more professionally: resist the urge to fill the space). Insight often emerges after the pause.

7. Actually listen to the response. Great questions are only a means to an end, which are: deeper understanding, better dialog, and thoughtful engagement. Use non-verbal cues to show engagement, but ensure they reflect genuine listening rather than performance. Use head nods, raised eyebrows to show interest, and even leaning into the person as they speak to mark your interest and engagement.

8. Acknowledge what you hear. It’s helpful to paraphrase to confirm understanding and engagement (“to make sure I’m understanding you correctly, what I hear is…”). But even simple acknowledgements—“I hear you” and “that makes sense”—go a long way. They validate the speaker, create psychological safety, and deepen the conversation.

9. Keep the game of catch going. Think of dialogue as a game of catch. You throw the ball with a question; they throw the ball back to you through their response. Instead of immediately reclaiming the ball with advice or explanation, consider throwing it back with another question. A game of catch is much more interesting and fun when the ball is regularly passed back-and-forth between people; it’s not so fun when one person monopolizes the ball. Two powerful prompts to throw the ball back are: “Say more about that,” and “What else are you thinking?”

Final Thoughts

Questions are powerful. They generate deeper thinking, richer dialogue, and clearer understanding. They work in meetings, one-on-ones, informal conversations, and structured development sessions alike.

But questions are only the vehicle, not the destination.

The goal is not to become a leader who asks clever questions for the sake of being clever. This is not even about us. The goal is to create better thinking, richer conversation, deeper understanding, real belonging, and ultimately, greater impact.

That journey begins with curiosity. It continues with intentional practice. And it is sustained by leaders who are willing to listen more than they speak.

So, here’s the challenge: Where can you talk less and ask one better question today? Think about your next meeting, your next one-on-one, or your next difficult conversation.

Ask it. Sit with the silence. Listen carefully.

And then throw the ball back.