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Tired of Small Talk? Here’s How to Turn Any Conversation into a Meaningful One

Talking to strangers doesn't have to be boring or stressful—boost your conversation skills with these simple tips.

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Conversation skillsPhoto: Shutterstock

Real talk

Bonnie Todd runs 250 food tours in Victoria, B.C., a year—a job that puts her in contact with hundreds of new people every week. Food-lovers come to her for an introduction to the local tastes and flavours. And a large part of what keeps her guests satisfied, and willing to recommend her business to others, is the personal connection she makes with them.

“I try to get past the small talk and general recommendations pretty quickly,” says the 42-year-old owner of Off the Eaten Track. “It’s all about finding common ground within the group, and trying to make it a unique experience. So I’m always asking questions. And when I find that spark of commonality, I dig into it.”

The practice is key to Todd’s approach because, unlike many tours, hers require people to sit together sharing food and drinks. When groups don’t gel, or never get past the “Where are you from?” stage, what should be a stimulating experience can turn into an awkward and draining couple of hours.

We’ve all been there: trapped in a superficial exchange that bounces aimlessly from one meaningless topic to the next. It can make you never want to step foot into another party again. But don’t despair: there are some tactics that can help you turn boring small talk into an energizing conversation.

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Put yourself out there

As a member of Second City’s Mainstage company, improv performer Natalie Metcalfe’s job is to keep a scene going—to create an exchange that’s compelling for both the people involved and for a live audience.

“In improv, it’s all about offers,” she says, referring to the act of bringing new information into the dialogue. Through these back-and-forths, the relationship between the characters is established and that kicks things off. “It’s the same thing in a regular conversation. You’re constantly making offers to see if you and the person you’re talking to can connect.”

An offer in real life can be as simple as complimenting someone on what they’re wearing, and asking them about it. You can try sharing something you recently learned, or an interest you’ve just developed, creating an opening for the other person to ask you a question. Or, you can describe a relatable problem you’re having—a noisy neighbour, a plant that’s not thriving, a question of etiquette—as a prompt for advice, or some cooperative troubleshooting.

One of Todd’s go-to approaches is to share a personal story of her own that relates to the other person’s experience. “If I find out someone has been to a place I’ve travelled, I’ll tell them an anecdote about what I did there, and ask them to share their own story.”

Of course, putting yourself out there can sometimes feel scary—even when you’re not on stage. But Misha Glouberman, who runs a course in Toronto called How to Talk to People About Things, says taking that leap pays off.  “A lot of the time in conversations, there’s something we’re interested in, but there’s a part of us that doesn’t want to take the risk of revealing it because we think it might be boring or inappropriate.” But the result of following those internal cues of fascination has the opposite effect, he says. “People like learning about other people’s interests. So be more open about yours, and a little more curious about theirs as well.”

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Be inquisitive and listen

Terry Gross, legendary interviewer and host of National Public Radio’s Fresh Air, once said that the only icebreaker you’ll ever need is, “Tell me about yourself.” Instead of asking a pointed question like “What do you do?”, this type of open question gives someone a chance to offer up a topic they might be more excited to discuss.

“Talking about yourself is really pleasurable. It activates the exact same hormone in your brain as sex,” says Celeste Headlee, the author of We Need to Talk: How to Have Conversations That Matter. “Another tip you can take from neuroscience is that if you start a conversation by allowing someone to feel good about themselves, then they’ll be more open to new ideas and new thoughts for the rest of the conversation.”

Of course, upping your curiosity quotient needs to be paired with actually paying attention to the answer. “Listening is hard for homo sapiens. It’s not something our species does easily,” says Headlee.

Indeed, people often start crafting their response before the person they’re talking to has finished speaking. Or they’ll get distracted, thinking about an email they forgot to answer. Since a great conversation is by definition a two-way street, these habits have the effect of ending one before it can even begin. Intentional listening, on the other hand, is a key to an empathetic, engaging dialogue.

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Use disagreement wisely

According to Headlee, one of the other things that gets in the way of a meaningful conversation is the all-too-human need to be right. “A really common mistake is the ‘well, actually’ response,” she says, referring to that deflating moment when a person lets their need to correct you about a small detail you’ve just mentioned get in the way of continuing a story. “Google has made this worse,” she adds. “You’ll say, I went to the hotel with the largest patio in the entire world, and while you’re still talking, the person is already on their phone looking to see if that’s actually true.”

But while trivial arguments can be an obstacle to a good conversation, Glouberman points out that differences of opinion can also help propel a chat into richer territory. “We assume that the world is just as we see it, that we see it directly,” he says. “But of course all of psychology and neuroscience tells us that’s not the case.”

A respectful disagreement, if the other party is open to it, is a great opportunity to enrich your view of the world by understanding someone else’s.

Next, find out how to politely exit any conversation.

Originally Published in Reader's Digest Canada