How to have great conversations with strangers

Don’t get bored.
Don’t get bored.
Image: Reuters/Ruben Sprich
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Conversations with strangers can go one of two ways. Some are unyieldingly boring—an exchange of information in which neither side reveals more about themselves than could be gleaned from LinkedIn. But in some interactions there’s an alchemy at work, the meeting of two minds sparking a change in both during which something new—less tangible than gold, but nonetheless beautiful—is created.

The question is, how do you avoid the dull exchanges, which can be exhausting and depressing, especially if your work involves meeting a lot of people? And particularly when, to add a layer of confusion, boring conversations can masquerade as interesting: A whole load of information gets shared, yet they leave both interlocutors feeling dissatisfied, even hollow. How can we make the alchemy happen more reliably?

The recent Cannes Lions Festival of Creativity saw thousands of people gather on the French Riviera to discuss the future of the global advertising industry, with agencies, brands, and tech platforms hosting hundreds of talks, dinners, and side meetings. As an outsider attending for the first time, I found myself overwhelmed even before I arrived. How would I make sense of chatting to a mindfulness coach for breakfast, top executives at companies with expertise ranging from software to tobacco during the day, and then meeting academics for dinner? Attendance at plenty of conferences in the past warned me that a lack of vigilance could result in dozens of chats that, ultimately, blended into one.

During the planning phase, in a hailstorm of emails, press releases, and travel logistics, I decided to set an intention for the gathering: Don’t have boring conversations. The result was transformative.

Setting an intention is a practice that will be familiar to people who have engaged in mindfulness as a discipline. As an alternative to setting goals, it’s a way to inform one’s practice (in anything from yoga to sales) without limiting the idea of “success” to a single moment of specific achievement. Rather, success is framed as a process, something woven incrementally into the fabric of an activity or period of time. Earlier this year, my colleague Rosie Spinks wrote about the power of setting a New Year’s resolution that doesn’t involve a specific attainment (a certain level of weight loss, for example), but instead offers a lens with which to view all the choices we make. (Hers was “Do what feels good.”)

“Don’t have boring conversations” wasn’t a way to pick interlocutors, nor a means by which to judge them. It was a personal call to action. Conversations can easily become rote, especially in a setting like a conference where people want to discuss their industry. At a dinner with two psychology professors, the temptation was to ask about their research. But this information was already available: I could read the research itself. Instead I asked how their findings informed their parenting choices, because, as a new parent, I really wanted to know.  From there, the conversation touched on philosophy, the future of the species, and human-pet interactions.

Such intention-setting is powerful for introverts, and people who struggle with small talk, because it can take the attention off of oneself. In my example, the gentle pressure was not to be interesting, or even to think of good questions. It was simply to follow what I genuinely found interesting rather than any preconception of what might be thought so. For extroverts, it could open up more opportunities to listen, because however much we enjoy voicing our own opinions, we get more out of conversation by discovering what others truly think and feel.

Recognizing that a conversation is slipping onto a predictable track takes some attention, but we all have the power to notice it’s happening, and to change it. One strategy, suggested by research into the power of vulnerability, is to open up about oneself (for example, talking about your kids, or pets.) Another is to check your stereotypes: It’s easy to have a preconception about the kind of conversation you might have with a particular person because of what they look like, how they dress, or what their job title says. Those preconceptions can often be completely wrong.

The intention was useful while hosting a dinner where Colleen DeCourcy, co-president of agency Wieden+Kennedy, which won some of the festival’s most prestigious awards, talked with clarity and honesty about being a leader. Tasked with the job of interviewing her over dinner, I chose to ask questions about how she dealt with failure, rather than to expand on the secret to her success. On the plane home, it inspired a conversation with my neighbor Mike on the provenance of fabric (he was a curtain-maker; I was reading a book about 17th century merchants in Denmark.)

It also made me bolder. When asked publicly to cite one thing that had interested me about the conference as a whole, I could easily have said that diversity appeared to be a topic on everybody’s agenda. This was true, and good, but since it was on every agenda, it didn’t actually make for a very useful observation. Instead, I noted that climate change was surprisingly absent. Without an intention, I might have shied away from going out on a limb; with it, I felt a responsibility to avoid platitudes.

Conferences, work meetings, parties, and even idle chit-chat with strangers can be anxiety-provoking. Intentionally trying to avoid a boring conversation doesn’t only have the potential to make an interaction more exciting, it’s also a mark of respect to the person we’re talking to. Sharing personal information exhibits trust, and asking questions that go beyond acceptable conversational bullet points allows others to share, not just a professional version of themselves, but the self of internal conflict, confusion, passion, and transcendent thought that makes us who we are.