I recently had a conversation that felt like pulling teeth. And I would know– both my father and brother are dentists. It was one of the most awkward conversations I’ve had in a long time. Analyzing why the conversation was awkward and even painful has reminded me of something I (and millions of other people) discovered for myself a long time ago: conversation is art.

There are many different types of conversations. As a rabbi I’ve spent a considerable amount of time engaging in pastoral conversations. These conversations are different than say, supervisory conversations, or casual conversations with friends. And small talk is something completely different. But one thing all conversations have in common is that the conversing parties bring something to the table.

In a good conversation all participants want to contribute. They want to feel understood and they want to understand what others are sharing. There’s a generosity of spirit, a generosity of words, a generosity of silence, and a genuine curiosity at the center. There’s a desire to understand, to construct meaning, and to emerge changed, however slightly.

I guess there’s nothing like a bad conversation to make you think about what constitutes a good conversation. Since the bad conversation in question I’ve had dozens of good conversations, artful conversations. And for that, I am grateful.

The art of conversation