Ask, Listen, Lead—The Power of Humble Inquiry

You’re in a leadership meeting, reviewing a critical initiative. A team member brings up a challenge—something that’s slowing down execution.

They lay it out, expecting a conversation. But before the discussion unfolds, someone jumps in with a quick fix:

“Just bring in IT.”

“Sounds like a process issue—let’s put a template in place.”

“I see the problem—just do X.”

And just like that, the conversation moves on.

The leader thinks they’ve helped. They’ve offered a solution, checked a box, and kept things moving. But in doing so, they may have shut down the deeper conversation that needed to happen.

Maybe the real issue wasn’t the process, but misalignment across teams. Maybe it wasn’t a tech problem, but an unclear priority. But now, we’ll never know—because the discussion ended before it even started.

I have to admit, I’ve been guilty of this myself—jumping straight into “solution mode” as soon as I see an issue surface. Over the years, I’ve improved, but I still find it challenging to resist the impulse to offer an immediate fix. Yet experience has taught me that the best, most sustainable solutions rarely come from quick answers. Instead, they emerge from asking honest questions with a genuine intent to understand different perspectives. When I manage to pause, ask questions, and genuinely listen to the answers, the outcomes are consistently stronger.

Edgar Schein, one of the most influential thinkers on organizational culture, saw this dynamic play out time and time again. Leaders thought they were listening, but they weren’t. They were responding. Evaluating. Fixing. But they weren’t actually understanding.

As he studied what made teams thrive, he developed a simple but transformative concept: Humble Inquiry.

He defined it as “the art of drawing someone out by asking questions to which you do not already know the answer, thereby building a relationship based on curiosity and interest in the other person.”

In other words, leadership isn’t about having the right answers. It’s about creating an environment where the right answers can surface.

I have to admit, I’ve been guilty of this myself—jumping straight into “solution mode” as soon as I see an issue surface. Over the years, I’ve improved, but I still find it challenging to resist the impulse to offer an immediate fix. Yet experience has taught me that the best, most sustainable solutions rarely come from quick answers. Instead, they emerge from asking honest questions with a genuine intent to understand different perspectives. When I manage to pause and practice this type of humble inquiry, the outcomes are consistently stronger.

The Impact of Humble Inquiry

In his decades of research, Edgar Schein saw time and again how leaders who practiced Humble Inquiry changed the culture of their organizations.

When leaders truly listen and ask with curiosity, three powerful shifts happen:

• Hidden obstacles come to light. A missed deadline isn’t just about time management. It could be due to conflicting priorities or a fear of making the wrong call.

• Trust deepens. When people feel safe to share what’s really going on, communication improves at every level.

• Execution accelerates. No more wasted cycles trying to decode what leadership really wants—teams can move forward with clarity and confidence.

Practicing Humble Inquiry: Listening and Asking with Purpose

Schein believed that listening and questioning weren’t separate skills. They worked together. Leaders who mastered Humble Inquiry didn’t just nod along and offer advice—they created space for deeper thinking.

Here’s how to apply it:

1. Listen Deeply

• Be fully present. No multitasking. No half-listening. Give your full attention.

• Resist the urge to fix. Instead of jumping in with solutions, stay curious. Ask another question.

• Embrace silence. If there’s a pause, let it sit. The best insights often come after a moment of reflection.

2. Ask Better Questions

• Start with curiosity. Ask questions you don’t already know the answer to.

• Go deeper. Follow up with, “What’s the biggest challenge you’re facing?”

• Encourage reflection. “What did you learn from this experience?”

• Avoid leading questions. Don’t steer them toward your preferred answer—let them arrive at their own.

A culture of execution isn’t built on top-down directives. It happens in the way we engage with our teams, the questions we ask, and the space we create for ideas to emerge.

Schein’s lesson is clear: leaders supercharge execution culture by listening—really listening—and asking the kinds of questions that help their teams think for themselves.

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This post is an excerpt from my upcoming book, a practical handbook for executing strategy from an operator’s point of view. Drawing on decades of real-world experience, it’s designed to help leaders turn strategy into action through clear, actionable steps. Stay tuned for more insights and updates as we get closer to launch!