Observations on excellent conversationalists

Why are some people so compelling to talk to? And why are some conversations as exciting as a growing rock?

Rocks rock. Watching them grow does not. (Photo: Geology.com)

On Monday mornings, I call an Uber to take me to Newark airport. I get on a plane to wherever my client happens to be located (nowadays, it’s in Atlanta). When I get back to the hotel after a long day, I sit at the bar and order dinner before retreating back to my room. Just a few years ago, this would probably have meant meeting and chatting with at least three people: my cab driver, my seatmate on the plane, and the bartender. Today, this means an extra hour (or two) spent on my phone.

I recently started paying attention to how my phone affected me, and I discovered that it was affecting my ability to hold good conversations. By becoming the new default, my phone has reduced the number of times I have to randomly interact with strangers and practice conversing with them. As a result, when I am forced to chat with someone face-to-face, whether it’s at a work event, an acquaintance, or a friend of a friend, I’ve found myself looking for the first “out.” It might be, “Excuse me, I need to get another drink,” or “Pardon me, I need to use the restroom (and never return, thanks).”

In an effort to relearn the art of conversation, I’ve started paying more attention to the people I meet who are able to control and sustain the conversation. The funny thing about conversations is that it really only takes one talented person to keep it going. I’ve compiled a list of some of these observations with suggestions on how we can apply them to our own conversations.

They are active listeners — and show it

Everybody loves when others listen to them, but few people will admit it. And while everybody listens too, few are particularly good at it. One communication technique I’ve seen several successful individuals use is called active listening, which involves repeating and rephrasing what the other person just said.

Perhaps I’d just shared that I went through a tough week at work; instead of responding with their own soliloquy lamenting their boss and co-workers, engaging conversationalists acknowledge what I said. They might say something like, “I’m sorry to hear that this last week was particularly challenging for you. I know what that feels like. Is next week looking tough too?”

Moreover, they also ask the right questions, and actually want to know the answer. Whenever I meet up with this one friend of mine, I always feel like we didn’t have enough time. I recently started to pay more attention to what caused this, and I’ve realized that it has to do with her ability to ask insightful questions. She doesn’t just respond with “That’s interesting” or “Cool” whenever I share a story. She’ll pause, consider what I just said, and ask an meaningful question.

There’s some science behind this: we love talking about ourselves. Talking about ourselves activates the same areas of the brain as eating good food and having sex, which explains why it’s inherently pleasurable. It’s not surprising, then, that we love people who will listen to us talk about ourselves.

I’ve also found that the most effective questions are open-ended personal ones. Instead of stopping at, “How was your week?” (of which the only acceptable answer is “Good”), they might slowly build up to, “What interesting things happened to you this week?” Other ways to start an open-ended question might be, “How are you thinking about…?”, “Why did you…?”, or “What’s it like to…?”

They’re positive and enthusiastic — not just about themselves, but about you too

I have a friend whom we often tease for some of his verbal crutches, which include: “Iiiiiinteresting!,” “Reeeeeally?,” and “Iiiiiincredible!” And while we probably won’t stop teasing him anytime soon, I think we can all learn a bit from him. Excellent conversationalists show not only interest, but also genuine enthusiasm and excitement.

It’s typically easy to be enthusiastic about yourself and the things you work on; it’s much more difficult to communicate the same towards others. By showing us that they are eager to learn more about what we are telling them, they make it easier for us to open up. They put us at ease. More importantly, they make us feel like they won’t judge us if we slip up and say something stupid.

Moreover, when great conversationalists share something, they actually sound like they want to share it. When they answer questions, the best ones don’t make it seem like they feel compelled by societal expectations to talk to you, but like it is their honor to share that moment with you. They also give non-verbal cues; they look you in the eye, nod as you speak, laugh at your (bad) jokes, and don’t feel the need to insert themselves and their experiences in the conversation immediately.

I’ve also noticed that the best conversations are those that don’t involve rants and negativity. Some particularly refreshing conversations I’ve had with strangers lately included one on how to select food from a menu and some celebrities who’ve lived near me. We have more things in common with strangers than political environment, pop culture, and, god forbid, the weather.

It’s worth mentioning that while we often think of enthusiasm as being overly energetic and eager, sometimes it can also manifest itself as concern and empathy. It’s not always appropriate to say “Iiiiiincredible!”


They ask for advice — and (literally) take note of it

A few years ago, I met up for lunch with an acquaintance who wanted to catch up and get my advice on something. I had not been looking forward to this conversation in particular because this individual had a reputation that preceded him. As soon as we sat down, he took out a small pocket-sized notebook and began jotting down notes about the things I said. Suddenly, I felt like I wanted to help him more because he was taking what I said seriously.

You don’t need to document every conversation in extensive detail in order to become an engaging conversationalist. Taking out your phone and saving a restaurant recommendation on Google Maps or bookmarking a website can be just as effective.

Again, there’s some more science behind this: research from Wharton professor Adam Grant shows that helping others is one of the best ways to succeed.

And if you really want to take it to the next level…

They follow up — and continue the conversation

“Great meeting you last night. Hope we can stay in touch.”

Yeah. Right. Of course you do.

Instead of writing these generic messages (of which I’m especially guilty), I’ve resolved to follow up about something relevant to what we discussed. Perhaps I send along a link to an article I referenced, or ask for one that they mentioned in passing. Perhaps a few weeks later, after trying a bar that they praised heavily, I drop them a quick note to thank them for it and let them know how much I enjoyed it.

One other question I’ve started asking as a follow up is whether they have any book recommendations. Everyone has at least one, and it shows that you trust their judgment.

I’m not especially good at doing this yet, but I’ve found that continuing the conversation is much more memorable than those where you exchange pleasantries and move on.

Ultimately, excellent conversationalists are able to make us feel important and special. They recognize a conversation as an opportunity to enjoy a human connection and to get to know somebody’s unique experience and world view. A conversation does not always need a purpose; we don’t need to speak to others in order to get something in return. Sometimes, exchanging a few stories and parting ways forever is worthy enough of a cause.

Did you enjoy this guide? This is my third piece for a new publication called Advo, which is a field guide to adulting (aka everything our parents were supposed to teach us but didn’t, perhaps for good reason…). For more articles like this, subscribe to our monthly newsletter below:

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