The Art of Asking Better Questions

How the right question at the right moment can transform everything.

Last month, I was facilitating a strategic planning session for a nonprofit struggling with declining volunteer engagement. Two hours in, we were stuck in the familiar territory of "we need more volunteers" and "people just aren't as committed anymore." The energy in the room was flat, and I could feel us circling the same tired assumptions.

Then I tried something different. Instead of asking "How do we get more volunteers?" I asked, "What would have to be true for someone to feel so connected to this work that they couldn't imagine doing anything else?"

The silence that followed wasn't empty—it was full of possibility. Slowly, stories began emerging. Maria talked about the volunteer who stayed late every week because the community garden reminded her of her grandmother's farm. James shared how their literacy program volunteer had started bringing her own children because she wanted them to understand the joy of helping others learn.

Within an hour, we'd shifted from recruitment strategies to relationship strategies. The question had revealed what was already working and illuminated a path forward that honored both the organization's needs and the volunteers' deeper motivations.

This is the power of better questions. They don't just gather information—they shift the entire frame of what's possible.

The Questions That Change Everything

In my work with organizations, I've noticed that breakthrough moments often arrive disguised as questions. Not the surface-level queries we're used to ("What's our budget?" "When's the deadline?"), but the deeper ones that invite us to examine our assumptions and imagine new realities.

Better questions share certain qualities:

They assume abundance rather than scarcity. Instead of "What's wrong that we need to fix?" try "What's working that we can build on?"

They invite stories, not just data. "What's been your experience with..." opens different doors than "What are the metrics for..."

They create space for emergence. "What wants to happen here?" allows for possibilities we haven't yet imagined.

They honor complexity. "What are all the ways this could be true?" acknowledges that most challenges have multiple valid perspectives.

The Ripple Effect of Inquiry

When we ask better questions, we don't just get better answers—we create better conditions for thinking, connecting, and innovating together. Questions shape the quality of our conversations, and conversations shape the quality of our relationships, and relationships shape the quality of our work.

The nonprofit that started with "How do we get more volunteers?" ended up creating a community engagement model that tripled participation within six months. But more importantly, they discovered something they didn't know they were looking for: a deeper understanding of what draws people to meaningful work and how to create more opportunities for that kind of connection.

That's the thing about better questions—they often lead us to better problems worth solving.

Your Turn

This week, I invite you to experiment with the questions you're asking. Before your next team meeting, strategy session, or even casual conversation about a challenge you're facing, pause and consider: What question would open up the most interesting possibilities here?

Sometimes the spark that ignites transformation is as simple as curiosity, courageously applied.

What questions are you ready to ask?