“When you talk, you are only repeating what you already know. But if you listen, you may learn something new.”
— Dalai Lama
Have you ever witnessed a moment where a simple question—unasked—changed everything? Recently, a friend sent me an Instagram post about a spelling bee contestant who was asked to spell what sounded like “ledge.” The child confidently spelled it L-E-D-G-E, only to be told it was incorrect. My friend, like many viewers, felt outraged on the child’s behalf.
My reaction was different. As someone who has participated in and moderated spelling bees, I know contestants are encouraged to use every tool available—asking for definitions, language of origin, or hearing the word used in a sentence. I’m guessing that the word was “lech”, but without asking clarifying questions, the child never had the chance to distinguish between these homophones.
This small moment crystallized something I’ve been reflecting on deeply: how curiosity—particularly the practice of asking both clarifying and deepening questions in checking for understanding—transforms not just spelling competitions but our connections with each other, our communities, and ultimately our shared humanity.
Click on the video to see “bowery” and the power of checking for understanding
What I’m Recalling: Persistence in Seeking Understanding
For more than a decade, I served as a pronouncer at our regional Scripps-Howard spelling bee. One particular exchange stands out: a contestant and I spent nearly two full minutes going back and forth on the pronunciation of “Bowery.” What I was saying and what she was hearing seemed worlds apart, but through patient repetition and careful listening, we eventually found alignment (to the delight of both of us, as you can see at the end of this short video). That young speller went on to win the regional competition for two consecutive years.
This experience continues to influence how I intend to approach every conversation, personally and professionally. How often do we use the same words but attach different meanings? When a friend or neighbor says they feel “disconnected” from others in their community, do we know what connection would look like for them? When a family member or colleague suggests an idea that seems misaligned with our thinking, do we immediately disagree or pause to ensure we’ve truly understood their perspective?
The patience to check understanding—to ask “What do you mean by that?” rather than assuming—creates space for authentic connection in every realm of our lives, from our dinner tables to our community meetings to our philanthropic engagements. At its Greek root, philanthropy means “love of humanity,” and what better way to express that love by checking for understanding, and through genuine curiosity about one another?
What I’m Listening To: Discovering Sonder in a Connected World
Adam Grant’s WorkLife podcast recently introduced me to the concept of “sonder”—that profound moment when you suddenly realize everyone around you is living a life as rich and complex as your own. Sonder is the sudden, humbling awareness that you are not the center of the universe. Every person around you has their own web of experiences, emotions, and relationships that are just as intricate as yours.
This awareness transforms how we show up in our communities. When we approach our neighborhoods, local businesses, or community organizations with sonder in mind, we become genuinely curious about others’ experiences rather than filtering everything through our own perspective. It is the lived experience of others that provides a more accurate understanding of the communities that we seek to be a part of and serve. We ask, “What do you see that I might be missing?” rather than “Here’s what I think needs to happen.”
What I’m Reading: The Collective Power of Curious Minds
I recently read “The Big We: How Giving Circles Unlock Generosity, Strengthen Communities and Make Change.” At its heart, this book explores how curiosity builds community. When people come together—whether for neighborhood improvements, mutual aid, or philanthropy—they must engage in deep questioning, first with themselves and then with each other about values, needs, assumptions, and solutions. This collective curiosity creates powerful connections. The most vibrant communities aren’t those with the most resources, but those where people have developed the muscle of curiosity about each other’s lives and experiences.
“It may seem obvious, but in order to identify what issues concern people, we have to be curious and listen to them, which requires being there and at least some trust. In order to figure out what might address those concerns, we’ve got to engage, listen, talk, argue, strategize- all of which require being in relationships and deepening them.”
-Hali Lee
What I’m Watching: The Science of Better Questions
Charles Duhigg’s recent TED Talk, “The Science Behind Dramatically Better Conversations,” reinforces what I have experienced firsthand: that the quality of our questions determines the depth of our connections. Duhigg explains how specific types of questions activate different brain regions, creating conditions for meaningful exchange rather than surface-level interaction. His research-backed approach complements the intuitive wisdom many of us have discovered through experience- that genuine curiosity opens doorways to understanding that remain closed when we assume that we already know what others think or feel.
What I’m Learning: Curiosity is Compassion
Curiosity is not just an intellectual exercise but a muscle that represents compassion and deep care for others. Like any muscle, it must be exercised consistently to grow stronger. Research suggests that when we’re genuinely curious, our brains release dopamine, creating a natural high that motivates further exploration and turns curiosity into a self-sustaining cycle.
When we approach our communities with genuine curiosity, asking “why” repeatedly—why do people feel excluded? why does this issue persist? why might different perspectives exist?—our understanding deepens and our capacity to create meaningful change expands. The “five whys” approach helps us move beyond surface-level understanding to identify root causes. Each “why” builds greater understanding and more effective action.
Beyond the “whys”, curiosity can be exercised at this moment in time. On behalf of a client, I have been calling partners asking “What do you need?” In all cases, our partners shared their vulnerabilities and expressed deep gratitude for just being asked, and as a result, our relationships have deepened as we create a new understanding of our evolving partnership.
“Genuine curiosity is the beginning of empathy.”
-Brene Brown
I’ve begun collecting questions that open doors to deeper understanding:
“What do your values mean to you”?
“What experience shaped your perspective on this?”
“How has your thinking on this evolved over time?”
“What question do you wish that I would ask you right now?”
“What possibility do you see that might not be obvious to others?”
These questions invite people to move beyond positions to the experiences and values that inform them – often revealing unexpected common ground.
In a world that rewards quick answers and certainty, curiosity stands as a powerful alternative. It invites us to slow down and commit to deeper understanding, even when it takes time. As we move through this season of renewal, I invite you to bring a spirit of genuine curiosity to your relationships. What one question could you ask today that opens rather than closes a difficult conversation? Which relationship in your life might benefit most from more curious listening? What new connections await when we truly hear each other?