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Whoever Asks the Questions Leads the Conversation

Questions Part: 1

By Rick Aman
on

The best strategy starts with the right questions. – Warren Berger

One of the most overlooked insights in leadership is this: the person who asks the questions sets the direction of the conversation. I’ve seen it in boardrooms, retreats, and executive sessions, those who lead with well-placed questions shape the tone, direction, and depth of the dialogue. They determine whether we end up solving the right problem or just refining a familiar answer. Peter Drucker cautioned us long ago: “The most dangerous thing is the right answer to the wrong question.” It’s a trap many boards and leadership teams fall into without realizing it. We get busy solving, analyzing, presenting when in truth, we haven’t paused to ask whether we’re still solving the right thing. In times of uncertainty, the temptation is to speed up.

Strategy doesn’t begin with speed; it begins with clarity. And clarity often comes from slowing down long enough to ask the right question at the right time. A classic example comes from Arthur Levine and Scott Van Pelt’s book, The Great Upheaval (2021) which highlights how the railroad industry missed a pivotal shift in the 1920s. As airplanes became a viable mode of transportation, rail leaders focused on improving train schedules, believing they were in the railroad business. The better question would have been: “If we’re in the transportation business, what alternatives might redefine the future?” It wasn’t a failure of intelligence; it was a failure to ask the right question.

The Questions That Shape Direction

Strategic leaders don’t begin with answers, they begin with curiosity. They pause before planning. They ask questions that reveal what’s underneath the surface: Is this still our purpose? What will matter most to our community in five years? What are we assuming that may no longer be true? What is our preferred future?

Chris Voss, the former FBI hostage negotiator, famously built his communication framework on asking well-timed, open-ended questions. He writes in Never Split the Difference (2016) that great questions disarm tension and guide the conversation without force. It’s not about dominance; it’s about direction. This approach translates powerfully to educational leadership. When a president asks, “How are we measuring mission fulfillment?” it shifts the board’s attention from activity to impact. When a trustee asks, “What future are we unintentionally creating by holding onto this?” the room begins to think differently. That’s leadership, not because it gives an answer, but because it reframes the entire conversation.

This kind of inquiry isn’t soft. It’s strategic. As the Harvard Business Review notes, Relearning the Art of Asking Questions, Gregersen (2018) questioning is “a powerful tool for unlocking value in organizations.” Strategic leaders don’t just provide answers, they frame the questions that surface new ideas, challenge assumptions, and open doors to innovation. This is true especially when it breaks past organizational inertia and unlocks critical thinking. Yet, in education, where tradition is often cherished, we tend to rush toward metrics before considering meaning.

The Trust-Building Power of Inquiry

Evy Poumpouras, former Secret Service agent and author of Becoming Bulletproof (2020), argues that great questions don’t just seek information, they build trust. They demonstrate presence. They signal care. In fact, research from the Journal of Personality and Social Psychology It Doesn't Hurt to Ask: Question‑Asking Increases Liking, Huang (2017) found that people who ask more questions especially follow-up questions, are perceived as more trustworthy and likable.

In governance and executive leadership, this matters. I’ve seen presidents who invite their boards into the future, not just the past, create greater alignment. I’ve watched trustees ask forward-looking questions like, “What does success look like three years from now?” and completely shift the dynamic from oversight to co-ownership.

Too often, we default to what’s easy to measure, enrollment numbers, budget variances, retention rates. These are important, but they’re trailing indicators. Better questions ask what’s ahead, not just what’s behind. And better questions build the space where truth and innovation can emerge.

Try This Social Interaction Experiment

On your next flight, try a simple experiment. Start a conversation with your seatmate but only ask questions. Don’t offer information about yourself unless asked. What happens is revealing. Some people will talk for the entire flight without ever asking you a single thing. Others might pause, reflect, and eventually reciprocate. It’s a small test, but it mirrors what happens in our leadership teams and boardrooms every day.

We’ve all been in meetings where one or two voices dominate the space, sharing personal insights, circling the same points, or speaking at length without moving the conversation forward. While these individuals may appear confident or knowledgeable, they often aren’t guiding the discussion. They’re filling the room, not framing the direction. In fact, they can become a barrier to meaningful progress.

Here’s the truth: being the loudest voice in the room isn’t the same as leading the conversation. The person who shapes the conversation is usually the one asking the most thoughtful, well-timed questions; the one who listens, distills, and then helps the group focus on what really matters. Dominating airtime may create the illusion of control, but it rarely creates clarity. More often, it causes fatigue, confusion, or silent disengagement from others at the table. It can be annoying, unproductive, and at worst, a distraction from the real work.

The remedy? You can only manage yourself so: Be a thoughtful asker of questions.

 Ask to clarify. Ask to refocus. Ask to reframe. For example:

These kinds of questions don’t just add value; they elevate the conversation. They invite others in. They build space for collaboration, not just commentary. And they help reset the dynamic when a discussion starts drifting or spiraling. The leadership lesson is simple: ask more, talk less, and guide with purpose. In today’s noisy environment, clarity is a competitive advantage and questions are how we get there.

From Conversation to Culture

Questions do more than guide discussion, they signal culture. If your boardroom always asks, “What’s the risk?” before asking, “What’s the opportunity?” that says something. If your leadership team defaults to, “How did we do last quarter?” rather than, “What do our students need next year?” that says something, too.

In his book A More Beautiful Question, Berger (2014) writes that innovative companies are built on inquiry. They cultivate a culture of questions that challenge conventional thinking and invite deeper reflection. The same applies to higher education and not for profit organizations, especially in this era of rapid change.  Strategy, innovation, transformation don’t begin with answers. They begin with the courage to ask something different. What are you really solving for and is it still the right problem? Before the metrics, before the motion, pause and ask: Are we asking the right question?

Summary

In leadership, the person asking the questions often shapes the future. This article unpacks how well-timed, strategic questions clarify purpose, build trust, and shift conversations toward what matters most. Drawing from voices like Drucker, Voss, Poumpouras, and Berger, it challenges leaders to slow down, think deeper, and lead with inquiry. In times of complexity, the right question isn’t just smart, it’s transformational.

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At Aman and Associates, we believe that the best strategies begin with the right questions. We partner with boards, CEOs, and leadership teams to strengthen decision-making through inquiry-driven dialogue that aligns vision with action. If you're ready to elevate your conversations, refocus your leadership, and build a culture of clarity, we’ll help you ask the questions that lead to lasting impact.

Rick Aman, PhD
http://www.amanarts.com/articles
rick@rickaman.com

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