• What is a great conversation? They are the ones that leave us feeling smarter or more curious, with a sense that we have discovered something, understood something about another person, or have been challenged.
• There are 3 design principles that lead to great conversations: humility, critical thinking, and sympathetic listening.
• Critical thinking is the celebrated cornerstone of liberalism, but next time you’re in a challenging and rewarding conversation, try to engage sympathetic listening too. Understanding why another intelligent person holds ideas that are at odds with your own is often more enlightening than merely hunting for logic errors.

EMILY CHAMLEE-WRIGHT: So think about the last conversation you had where you thought, golly, that was such a great conversation. What did it feel like? Why did it seem like a really great conversation? And the chances are good that it was a kind of conversation that left you feeling smarter. It was the kind of conversation where you felt like you discovered something new, that it left you deeply curious about something else. It might have been a conversation that challenged you in all the right ways. That's a truly great conversation. It's one where we genuinely learn something or we come to a deeper understanding about why someone else holds a particular point of view. Right? That deeper understanding and that learning is what we're after with great conversations.

And so one of the things I'm interested in is what are the design principles of a great conversation. What are the essential elements that make a conversation truly a great conversation? And humility would be one basic design principle that we should all start from. Now with humility, I don't just mean deference to expertise, right, that you are so much smarter at that thing so I'm going to have humility with respect to you on that thing because you know more about it than I do. Now maybe that's true, right? But that's not the kind of humility I'm talking about, because that's a sort of humility that could come to an end, right? I could learn as much about that particular topic, and therefore with that kind of thinking I would say I can set aside my humility.

The kind of humility I'm talking about is the kind that you can't set aside. Because the world is an incredibly complicated place. None of us can ever have the full lock on truth. We can only see the world from a particular vantage point. And that means that our knowledge is going to have special insight because of our vantage point, but it's also going to be limited because of our vantage point. And so that limited knowledge that we can have about the world means that we must enter into any conversation with a deep sense of humility, because I need you to help me fill in my knowledge gaps. Right? And you need me. And that's the cool thing about conversation, is that it is mutual in the sense that both of us look at the same world from different vantage points, and that means that we each have something to offer the other. And that's true whether one person is the expert or not. Right? We have the opportunity to gain in our knowledge, to learn from anyone. With this way of thinking about humility, anyone can be your teacher, whether it's your professor, or whether it's an elementary school student who's lived on the planet in different circumstances than you lived on the planet. That elementary school student can teach you something that you can only get by talking with them. That's that deeper level of humility.

Some of the other key design elements of a great conversation would be, for example, critical thinking and sympathetic listening. There's a lot that gets said about critical thinking; it's that ability and eagerness to identify gaps in logic or shortfalls in evidence-based argumentation. It is the cornerstone of what it means to have a liberal education, is to engage in that kind of critical thinking. Now less often discussed and surely less often celebrated is what I call sympathetic listening. And I use the word sympathetic in the way that Adam Smith used the word sympathetic, which is: Am I really understanding from that other person's point of view? That commitment to understanding the argument from the other person's perspective.

Now, what sympathy in this case means is not that I feel what they feel. It's that I'm willing to set aside, even if it's just temporarily, that hunt for the slightest misstep in logic or reasoning. Setting that aside for a moment so that I can listen really carefully to what my conversation partner is saying, so I can understand from their perspective what their intellectual project is or why it is that they are looking at the same world I'm looking at but coming to a very, very different conclusion. I should assume that that person that I'm having that conversation with is intelligent and is exercising reason, so when I enter into the conversational space with that good faith that they're exercising reason, then what that means is that I need to set aside for a moment my hunt for the slightest misstep in logic so that I can really hear why it is that this smart person came to a different conclusion than I came to.