There is a moment every leader hits, that quiet realization that being helpful might actually be holding others back.

It happened to me one afternoon during a team meeting. My colleagues were asking for approvals, directions, clarifications. “Should we do A or B?” “What do you think of this idea?” “How would you handle this situation?” Twenty questions in an hour, all directed at me. I left the room proud at first. They needed me. I was the problem-solver, the go-to person. That had to mean I was doing something right.

But later that night, while reviewing our progress reports, it struck me: I wasn’t building a team of problem-solvers. I was building a team of order-takers. They were not thinking independently, they were waiting for instructions. Every time I answered a question, I was reinforcing dependence. Every solution I handed out was a subtle message: your judgment isn’t enough; mine is better.

That’s when I decided to stop answering, and start asking.

The change was deceptively simple. Every time someone came to me with a question, I would respond with one of my own.

“What do you think we should do?”
“If this were your project, what would you choose?”
“What’s your instinct saying?”

The first week was awkward. My team looked irritated, even confused. They wanted clarity, not more questions. “Just tell us the right answer,” one of them said, half-jokingly. But I held my ground.

By the third week, something subtle but powerful began to happen. People came to me less often, not because they didn’t care, but because they had started trusting their own reasoning. The quality of their questions changed too. They weren’t seeking permission anymore; they were testing hypotheses. Instead of “Should we do this?” they were saying, “Here’s what I’m thinking, can we test it?”

That shift from dependence to ownership, changed the energy of our entire organization.

Many leaders fall into the same trap I did. We think we are being supportive when we jump in with solutions. It feels good to be needed. It feels efficient to have the answers ready. But over time, it quietly creates a culture of dependence.

Every time you answer a question that your team could answer themselves, you make them weaker. Every time you make the final call without discussion, you steal their chance to build judgment.

It’s the same problem teachers face in classrooms. When a student struggles with a question, the instinct is to step in quickly, to rescue, to explain. But when teachers supply answers too soon, they interrupt the very process that builds understanding. As John Dewey wrote, “We do not learn from experience… we learn from reflecting on experience.”

Questions create that reflection. Answers end it.

From Classroom to Boardroom

This philosophy applies equally to schools and to organizations. In classrooms, the teacher who says, “What do you think?” teaches reasoning, not repetition. In boardrooms, the leader who says, “Convince me,” teaches accountability, not compliance.

Great leadership, in any setting, isn’t about how many answers you give. It’s about how many thinkers you grow.

Albert Einstein once said, “I have no special talent. I am only passionately curious.” Imagine if every school principal, every teacher, every manager led from that same place of curiosity. Instead of enforcing direction, they would be cultivating discovery.

When principals stop dictating and start listening, teachers become innovators. When teachers stop instructing and start questioning, students become creators. And when students grow up learning this way, they don’t wait for someone else to tell them what to do, they figure it out.

Of course, leading this way isn’t easy. It takes courage to resist the urge to control. It’s much safer to be the one with the answers than the one asking the hard questions.

When you let go of control, there’s uncertainty. People make mistakes. They take risks that don’t always work. But that’s the point.

If you want people, whether adults or children, to think for themselves, you have to give them room to fail. That’s where real learning happens.

Maria Montessori said, “Never help a child with a task at which he feels he can succeed.” The same is true for teams. When leaders rush in to fix, they rob people of growth. But when they wait, when they let others wrestle with the problem, they give them something far greater than answers: they give them agency.

When I began this experiment, I didn’t realize how far-reaching it would be. My team didn’t just become more independent; they became more confident. Meetings grew shorter, but decisions became sharper. People started leading projects on their own initiative. Creativity spiked.

The best part? They began doing it with others. I started hearing the same language I used, “What do you think?”, in their own conversations. The habit of asking had spread.

In schools, I have seen the same phenomenon with peer learning. When teachers encourage students to question one another, not just listen passively, both sides learn more deeply. Programs like ALfA (Accelerating Learning for All) use this principle beautifully, children learn by teaching each other, by explaining, by reflecting out loud. They don’t wait for authority; they engage in inquiry. That’s how curiosity becomes a habit.

Why Asking Matters More Than Ever

We live in a world obsessed with speed, certainty, and instant answers. AI gives us information in seconds. But what it can’t give us, what leadership and education must protect, is the ability to think.

Critical thinking, creativity, and collaboration don’t come from having all the right answers. They come from having the right questions, and the patience to explore them.

As Warren Berger wrote in A More Beautiful Question, “Knowing the answers will help you in school. Knowing how to question will help you in life.”

So, whether you are leading a classroom, a company, or a country, the job is not to be the smartest person in the room. The job is to make everyone else smarter.

Every leader should ask themselves:

Am I building dependency or developing judgment?
Am I giving clarity or cultivating curiosity?
Am I answering too much, and asking too little?

Because the real measure of leadership is not how many decisions you make, but how many people you enable to make their own.

The leader who answers every question creates dependency. The leader who redirects questions creates thinkers. And thinkers, confident, self-aware, independent, are the foundation of every thriving community, classroom, and organization.

The best leaders I have met are not the ones with the thickest binders or the most detailed plans. They are the ones who can look at a challenge and say, “I don’t know yet, but let’s figure it out.”

They build flexibility into their systems. They trust people to innovate. They make thinking a shared act, not a solitary one.

Because leadership, at its core, is not about having the right answers. It’s about creating the right conditions for discovery.