How do you become a master conversationalist?

I was sitting in a sushi restaurant in L.A. with my friend who asked me if I had heard about The New York Times Article 36 questions.


I hadn’t, so he pulled it up on his phone. It’s a list of questions you ask people that promises to set the stage for the two of you to fall in love. After going through the questions with my friend for fun, I could see why. They were deep, intimate questions that would either uncover responses that helped you really get to know the other person, or you would hide away from having to reveal these personal details of your life.


So when two people are willing to be open and vulnerable with each other, that’s when the seed of a connection begins to blossom.


But instead of asking people deep, personal questions (which can feel invasive), we resort to looking outside and making a comment about the weather. It’s oddly comforting, annoying to people I know who hate small talk for this very reason, and yet seems to make it even harder to have a ‘real’ connection with someone else as the weather keeps it all safe and on the surface.


So how can we apply the depth of 36 questions, without the potential of feeling like you’re trying to pry someone open like a stubborn oyster within the first 5 minutes of meeting them? We all know that person who bombards us with a serious, philosophical question right after meeting for the first time and we find ourselves wondering how fast we can get away.


Because being a ‘master conversationalist’ is really The Art of Getting to Know Someone. And like most things we talk about, those are the easiest words to string together and yet the most difficult to put into practice. But today I want to give you the first step in how to master this ‘art’.


Back in the summer of 2009, I decided to live in a UCLA frat house in order to do an internship at a production company in LA. The day I arrived, I found out I had a roommate to share our teeny tiny room with, but she was nowhere to be found.


The next morning, I found her on the couch in our room. She was huddled over her computer, glasses on, looking nerdy yet adorable at the same time. We had a short conversation–nothing special. Then I went off to start my day.


When I came back to our room later on for lunch, she suddenly stormed into the room, upset. I looked at her and asked: “What’s wrong?”


She plopped down on the couch and started crying. She had just been fired.


And it was awful news for her. She didn’t know how she was going to afford to live. She’d have to go and find another job. And she never saw it coming.


I told her to tell me what happened and I just listened to her. Offered her some of my strawberries. Couldn’t think of anything comforting to say other than, Damn. That really does suck.


But something happened in that moment, where I was listening to her, a complete stranger. And she was opening up her heart to me, who was a stranger to her. We spent the rest of the day together at the pool, cracking each other up, and looking at each other as if we had just fallen in love. Her friend asked us how long we’d been best friends for. We had just met that day.


Compare that to the other night when I was out here in San Francisco at Bourbon and Branch, the dusty library slash speakeasy. A friend of my fiance’s had just ended his relationship with his long-time girlfriend over the weekend. Every time it came up, another guy who was with us just said: “You’re better off. Just don’t worry about it. Don’t think about it.” And even when my friend and I had a moment alone where he started talking, the moment the other guy came back he was dead silent.


So what is going on here?


You see that one approach to connecting with someone else is to listen to and empathize with them. (If this sounds like Vague Advice from Hell don’t worry — I’ll clarify exactly what it means in a moment.)


Then you have another approach that’s on the opposite end of the spectrum. Not willing to listen at all, and subtly telling a person that their feelings aren’t valid. There couldn’t be a faster way to prevent a connection and conversation from flourishing.


But what does ‘listening and empathizing’ really mean?


Because the first image that comes to mind is the sugary sweet asking someone else questions until they can’t stand it anymore. The second though is usually, “Duh! Listening!” (yet this is extremely rare) and the third is: Empathy. Come on. We’ve heard it all before!


But the reality is that listening and empathy are skills that anyone who wants to have a meaningful life can learn, and they are vital skills indeed. Daniel Goleman, a preeminent psychologist who’s written tons of books on emotional and social intelligence says it much better than I do: “Vitality arises from sheer human contact, especially from loving connections. This makes the people we care about most an elixir of sorts, an ever-renewing source of energy. The neural exchange between a grandparent and a toddler, between lovers or a satisfied couple, or among good friends, has palpable virtues…the practical lesson for us all comes down to, Nourish your social connections.


Let’s break the beginnings of these skills down in a real, practical way that you can apply the second you’re done reading this


LISTENING: Truly listening to someone else means that all the scripts, stories, routines, and words you’re trying to say–whether it’s to show you’re interesting, get attention, or impress someone else–you let go of in favor of what is happening in the conversation at that moment.


It means that if you’re dying to talk about what happened to you last weekend in Vegas, but the group is talking about where they want to go for dinner that night, it doesn’t do you any good to force the conversation to go in the direction that you want it to. You might say to yourself instead: I’ll get a chance to talk about that later. And even if you don’t, so what! There’s plenty of conversations to be had in the future.


LISTENING also means taking in what someone has just told you, and instead of asking them another question, you say: “So it sounds like what you’re trying to say is ‘X’…” or “That reminds me of ‘Y’…” ‘Y’ being a similar experience you had, or even a story or information you came across that describes what the person is talking about.


So LISTENING is not: having an agenda, competing for attention, waiting to speak, or asking a million questions. [And if you find yourself doing those things, I’d dig into it: why?]


It’s: Being present → asking questions that will help you learn about the other person → and reflecting back to them what they said and using that to keep the conversation going.


And what is ‘empathizing’?


EMPATHIZING means that instead of judging what someone is saying or experiencing, you don’t try to come up with anything clever to say or sweep their emotions under the rug. You encourage them to talk about it, and ask questions that reflect you’re trying to understand them as best as you can.


You might say things like:


“Wow, that must have been so challenging to do ‘X’…how did you get through it?”

“What was the hardest part about making that decision?”

“I’m curious — why do you think about ‘Y’ that way? I’d love to hear your perspective.”

“To be honest, I’m not sure what to say. But I know that must’ve been difficult/challenging/hard/etc”


You see that these questions are not designed to get certain answers. They’re designed so that you can understand how someone else thinks, understand how they’re feeling (and feel with them), and find a way to help them. They’re open-ended, and show that you’re thinking about what the other person said in a three-dimensional…four-dimensional….five-dimensional…however many dimensional ways! You’re not just taking what they say at face value, but digging deeper into it by being curious, yet not invasive.


Because I could give you scripts and routines to memorize for every conversation that you’re in, but I imagine you’ve experienced more than once the feeling that you’re trying to ‘fit in’ what you want to say in every conversation and when you do say it, it comes out feeling forced and not like ‘you’.


But if you have a framework for how to think about any conversation you’re in–whether it’s with a friend, co-worker, date, or boss–then you worry less and less about what to say and find it’s much easier to be spontaneous and creative in the moment.


What to Do Today


In your next conversation, apply just ONE of the frameworks we talked about today. So you might focus on putting aside your agenda and making it a point to reflect back to someone what they’ve said to you. Or, you might be dealing with a tougher conversation and apply how you can empathize with them by improving your understanding of where they’re coming from by asking a certain question, or even admitting you’re not sure how to respond.


Then, let me know how it goes. What was the best part, and the hardest part about applying it for you?


Talk soon!




PS: I really am curious to hear how this goes, because I’m interested in understanding what parts of conversation challenge people, and where they want to improve. Can’t wait to hear from you!

[ztl_optin slug=”confidence”]

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