The “People I Mostly Admire” podcast’s recent episode “How to Have Great Conversations” is immensely inspiring, informative, wise and useful. Hosted by Steven D. Levitt, this episode’s guest Charles Duhigg shared his new book The Power of Habit.

The right conversation and the right moment can change everything.

Here’s points that I’d find insightful from the podcast.

three baskets of conversations

Not all conversations are created equal. We’re actually participating in one of three conversations: practical (What’s this really about?), emotional (How do we feel?), and social (Who are we?). Too often, when someone shares their feelings, our instinct might be to jump into problem-solving mode. This happens especially if we’re in a higher position of power.

[LEVITT]: So one of the most basic insights in the book — and it sounds totally obvious once you present it, but it’s something that I personally was completely oblivious to for the first 40 plus years of my life — is that the person you’re talking to can have various different goals from a conversation. You just alluded to it. You were talking to your wife and you wanted empathy. But for most of my life, I thought that the purpose of every meaningful conversation was to find a solution to a problem. But I was so wrong. I learned along the way, and I was reinforced by your book, that there are all sorts of things people want out of conversations, and one of the most fundamental aspects of being able to talk to people is recognizing that and figuring out what the point is of any given conversation.

Btw, empathy, especially from someone in authority, can be incredibly soothing.

The response for emotional conversation is hugely different from a problem solving one. In the former case, responding with empathy intentionally, or at least “pretending” to listen more and judge less can be fruitful in providing emotional support to others. It’s not about being insincere at all, and people won’t find it phoney.

ask deep questions

Deep questions are the ones that prompt introspection and self-reflection. Asking someone how they see themselves or how they think the world sees them can lead to intimate revelations. It’s about creating a scenario where people feel safe enough to open up.

[LEVITT]: Okay, so I have a permission giving example. I was at a conference with a set of incredibly high achieving people (…) Before dinner, one of the organizers pulls me aside and asks me if I could be responsible for facilitating the dinner conversation at my table. (…)

And when the eight of us sat down at the table, I didn’t want people to make their standard introduction. I wanted each of us to tell our life story with one simple rule: that you couldn’t show any modesty. And I even used the word permission. I said,

“I’m not only giving you permission to brag about how amazing you are. I’m insisting that you do it. I want you to tell your story in a way that breaks every social norm about restraint, about saying all the good things happened to you were because of luck. I want to hear the unfiltered version of your greatest hits.”

tricks

  • Reciprocity: when you share something personal, it often leads the other person to do the same.

    In general, reciprocity is a powerful social norm that governs human interactions. When one person shares something personal or intimate, it often creates a sense of obligation or willingness in the other person to share something of similar depth.

  • The looping technique: listening to what the other person is saying and then paraphrasing or summarizing their message back to them.

  • Positions: the moves would be slightly different depending on one’s relevant positions. For the empowered side, simply leading the intimacy of connection by initiating reciprocity, or giving permission of depth of talk would suffice. But for the other side, they might need to break the balance by stepping on the boundary–say, asking deep questions that touch the interest of the powered opposite to open up the conversation.

  • Habit loop:

    Every habit has three components. There’s a cue, which is a trigger for an automatic behavior.

    Good conversations are almost the same – they begin with a similar pattern – identify the cue and catch the opportunity is vital. Observe to actually see the person you’re speaking with, ask relevant and appropriate deep questions, listen, emphasize and reciprocate emotional connection in return:

    once you know how to diagnose the cues and the rewards in your life (or, in our case, what makes a good conversation), then you can start shaping these new behaviors that become more and more automatic.

In conclusion, great conversations are an art form that requires empathy, openness, and a bit of strategic thinking. We’re borned and trained over our lives that it’s almost a natural instinct. But a bit more systematic strategy goes a long way, isn’t it?