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The Power of a Really Good Question
As a mediator, thinking about questions is an ongoing practice. Coming up with that really good, powerful question in the moment is hard. More than once, I’ve left a session only to have that question pop into my mind later. Not that the questions I did ask were ineffective—the process usually moves forward. But I often wonder: What might have shifted if I’d asked that one Really Good Question? Could it have helped someone pause, listen more deeply, feel empathy, or see possibility sooner? Recently, during a conversation with a family friend, she asked me a question that I’m still thinking about. It was simple and centered on change: How would I feel if the issue I was struggling with suddenly went away? My immediate answer surprised me. It was honest—unfiltered—and revealed something I hadn’t allowed myself to consider. That’s the power of a Really Good Question: it opens a door inside us that we didn’t realize was shut. But for any of this to happen, we have to feel safe with the person asking. As a mediator, I work hard to build that trust—by explaining my role, staying impartial, and resisting the urge to offer solutions. With my friend, trust was already there. I asked her thoughtful questions; she asked me one that invited vulnerability in return. The other side of this is reflecting on how we respond to Really Good Questions. Do they trigger us? Do we answer quickly to avoid the truth? Do we feel challenged and become defensive? When someone we trust offers us the gift of their attention and curiosity, a good question can help us grow. It can deepen a relationship, shift a perspective, or reveal honesty we weren’t ready to name. We may not know what the Really Good Question is that we need—but we usually recognize it when we hear it. Who do you want to ask a Really Good Question? What is a Really Good Question you wish someone would ask you?
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Sunny Sassaman
Sharing experiences and insights of reflection and conflict management techniques. Archives
December 2025
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