Last week, I revisited a topic that’s easy to underestimate—but impossible to ignore once you experience its impact firsthand: the art of asking smarter questions.
Thanks to Arnaud Chevallier’s recent article in Harvard Business Review, I found myself reflecting not just on the questions I ask, but on what those questions unlock—for others, and for me as a leader.
In complex, fast-moving environments like EdTech and entrepreneurship, we often feel pressure to deliver quick answers. But in my experience, the most effective leaders don’t lead with answers—they lead with better questions.
In a recent meeting, my team and I were exploring options for a school district that had been denied funding for their Internet access. We found ourselves deep in the weeds of a single solution—focused, committed, and moving fast.
But before the conversation went any further, I asked:
“What problem are we trying to solve—and what would happen if we didn’t do anything?”
It was a clarifying moment.
That question paused the momentum—not because we lacked urgency, but because we needed clarity. What emerged was a more accurate understanding of the district’s real need. We uncovered assumptions, heard new perspectives, and ultimately reshaped our approach to better serve the school.
Sometimes, the smartest move isn’t to press forward.
Sometimes, it’s to pause—and ask why we’re moving at all.
Why Smart Questions Matter
Chevallier’s article outlines how thoughtful, well-structured questions can bring focus to ambiguity. I’ve seen this firsthand.
The best questions:
- Challenge assumptions without creating defensiveness.
- Invite others into the problem-solving process.
- Clarify what success looks like—and who defines it.
- Help us avoid solving the wrong problem really well.
For me, asking better questions is one of the clearest expressions of servant leadership. It’s not about steering the conversation toward my preferred outcome. It’s about helping others discover insight and direction for themselves.
A Leadership Habit Worth Practicing
At Funds For Learning, we often say intentional learning is a job requirement. But we can’t learn—individually or organizationally—without curiosity.
Better questions are where curiosity becomes leadership.
What if we practiced pausing more often to ask,
“What’s the real issue here?”
“What are we assuming?”
“What’s missing from the conversation?”
Those are the moments that shape culture. That build trust. That lead to decisions with depth, not just speed.
Read and Reflect
If you’re leading a team, launching something new, or simply trying to grow—this is a skill worth sharpening. I highly recommend Chevallier’s article.
But most of all, I encourage you to pause this week and consider:
What’s a smarter question I could be asking right now?
