They were a mission-driven team with big goals: providing safe, affordable housing for vulnerable communities. But despite their dedication, every day felt like triage—reacting to problems rather than solving them.

The executive director sat in yet another crisis meeting, listening as her team ran through the same list of recurring issues: delayed approvals, funding gaps, growing waitlists. The tension in the room was palpable.

Then, someone asked a question that shifted everything:
“Why do we keep putting out fires? What’s fueling them in the first place?”

It was the kind of question that cuts through the noise and forces a deeper reckoning. Suddenly, the conversation wasn’t about fixing today’s issue—it was about rethinking the entire approach. 

The team started mapping out patterns, uncovering root causes, and asking harder, more strategic questions.

In the months that followed, they didn’t just adjust policies; they reimagined their entire approach. Their work became more proactive, more systemic, and, ultimately, more impactful.

Here’s the truth: the questions we ask determine the results we get.

Yet, in the rush to get things done, we often skip over the most important ones—the questions that challenge our assumptions, open up new possibilities, and lead to lasting change.

This piece is about the power of asking better questions. Whether you’re leading a team, rethinking strategy, or tackling tough challenges, your ability to ask intentional, transformative questions can make the difference between incremental progress and real, systemic impact.

The Power of Better Questions

The questions you ask as a leader shape everything—how your team thinks, how they solve problems, and ultimately, the results you achieve.

Better questions lead to deeper understanding, fresh perspectives, and more innovative solutions.

But here’s what happens when we don’t ask the right questions:

• We solve surface-level problems without addressing root causes.
• Teams spin their wheels, burning out without making real progress.
• Assumptions go unchallenged, leading to missed opportunities.

This is where the Strategic Inquiry Framework comes in. It’s a simple yet powerful tool to help leaders ask better questions and drive transformational change.

By focusing on three types of inquiry—Reflective, Probing, and Visionary—you can ensure that your strategy is grounded in insight, driven by curiosity, and aligned with long-term goals.

Reflective Inquiry: Learning from the Past

Reflective Inquiry is about pausing to look back and learn from what’s gone before. It’s the foundation of continuous growth because it helps your team understand not just what happened but why—and how those insights can shape future decisions.

The Wrong Question:

“What went wrong?”

The Better Question:

“What factors contributed to our challenges, and how can we apply what we’ve learned moving forward?”

The first question is about blame; the second is about growth.

Consider a nonprofit struggling with donor retention. Leadership keeps asking, “How can we get more funding?”—but the real breakthrough comes when they ask, “Why do donors stop giving in the first place?”

That shift leads them to discover that donors feel disconnected after their first gift. The solution wasn’t just more outreach—it was reimagining the donor experience entirely.

Reflective Inquiry also builds accountability. It creates space for honest conversations where teams can own their mistakes, celebrate their wins, and grow together. This isn’t just about fixing what’s broken—it’s about understanding what has worked and replicating it.

For leaders in the social impact space, Reflective Inquiry is essential. We work in dynamic environments where change is constant and resources are limited. By taking time to reflect, you uncover insights that strengthen your strategies and make your team more resilient.

Probing Inquiry: Challenging the Present

Probing Inquiry is about questioning the here and now—digging beneath the surface to challenge assumptions and break free from the status quo.

The Wrong Question:

“Why are we facing these challenges?”

The Better Question:

“What assumptions are driving our current practices, and how might those assumptions be holding us back?”

Take a youth mentoring program that notices disparities in student success rates. The team initially asks, “How can we improve engagement?”—but a better question is, “Who is thriving in our program, and who isn’t? And why?”

That shift leads them to recognize that the program design unintentionally favors students with strong home support, prompting them to build new structures for those who need additional scaffolding.

Probing Inquiry sparks creativity and drives innovation. It encourages teams to break out of old patterns and think beyond the obvious.

This isn’t about questioning for the sake of it—it’s about getting to the heart of what’s really standing in the way of progress.

Social sector leaders, in particular, need to embrace Probing Inquiry. The challenges we’re tackling—systemic inequities, resource gaps, shifting community needs—require fresh thinking.

Visionary Inquiry: Envisioning the Future

Visionary Inquiry is about looking forward and aligning your team’s actions with your long-term goals. It’s where you connect your daily work with the bigger picture, ensuring that every step you take moves you closer to your mission.

The Wrong Question:

“What are our goals for the next year?”

The Better Question:

“If we were truly bold, what could we change at a systemic level?”

A climate justice organization is setting its five-year goals. Instead of asking, “What should we aim for?”—they push themselves with, “If we were truly bold, what could we change at a systemic level?”

That question shifts their focus from awareness campaigns to coalition-building that drives policy change.

Visionary Inquiry provides clarity and alignment. It helps teams stay grounded in their purpose while adapting to changing circumstances.

For social impact leaders, Visionary Inquiry is critical. Our goals aren’t just ambitious—they’re transformative. Staying focused on the big picture is essential to creating meaningful, systemic change.

Bringing It All Together: Implementing the Strategic Inquiry Framework

To fully harness the power of the Strategic Inquiry Framework, integrate these practices into your organization’s daily work:

• Start with Reflection: Before launching new initiatives, take time to reflect on past experiences. Identify key lessons to inform your approach.
• Challenge Assumptions: Use probing questions to uncover hidden barriers and push your team to think beyond the obvious.
• Align with Your Vision: Regularly revisit your long-term goals and ensure your strategies align with them.

When you combine these three types of inquiry, you create a culture of intentionality, accountability, and growth. This isn’t just about solving problems—it’s about building a foundation for sustained, transformative impact.

Closing: Shaping the Future Through Better Questions

The questions you ask as a leader define your organization’s journey.

→ Reflective Inquiry helps you learn from the past.
→ Probing Inquiry uncovers hidden challenges.
→ Visionary Inquiry ensures you stay focused on the future.

Together, these practices form the blueprint for transformational leadership.

Asking better questions isn’t just about gathering information—it’s about reshaping the way we think, act, and lead.

So ask yourself:

Are you asking the right questions?

Because the future of your organization—and the impact you want to create—depends on it.