How to Become a Master at Talking to Strangers

July 7, 2021 15+ min read

This story appears in the July 2021 issue of Entrepreneur. Subscribe »

A couple of years ago, I started to talk to strangers.

That’s not to say I hadn’t talked to strangers before that, because I had. I’m the son and brother of highly social small-business owners, and I’m a journalist, so talking to strangers has been both a way of life and a livelihood for me. And yet, a few years ago I noticed I wasn’t doing it much anymore — if at all. Between balancing a demanding job and a really demanding small child, I was often tired, distracted, and overscheduled. The prospect of striking up conversations with random strangers in coffee shops, or bars, or on the bus started to feel daunting. Eventually, I just stopped doing it.

This was a coping strategy, of course. I was overwhelmed, so something had to go. And talking to strangers can, as it turns out, be taxing. Psychologists have found that just making small talk with a stranger can be cognitively demanding, tiring, and even stressful. That makes sense. You don’t know the person, you don’t know where the conversation is going, so you must pay closer attention than you would if you were talking to someone you know well. But psychologists have found that talking to a stranger actually boosts your mental performance — for that same reason: It’s a workout. I was saving myself a bit of effort, but I also noticed that my life was becoming less interesting, less surprising, maybe even a little lonely.

After my epiphany, I got to wondering: Why don’t we talk to strangers more, what happens when we do, and how can we get better at it? It turns out, many researchers are asking the same questions. I started flying around the world to meet them: psychologists, evolutionary scientists, historians, urban planners, entrepreneurs, sociologists, and — you guessed it — a ton of fascinating strangers I met along the way. They all taught me that talking to strangers can not only be fun but also enhance our sense of well-being, make us smarter, expand our social and professional networks, and even help us overcome some of our most intractable social problems. (I detail this all in my new book, The Power of Strangers: The Benefits of Connecting in a Suspicious World.)

And as I researched the book, I kept coming back to the implications talking to strangers could have for entrepreneurs. Because I come from a family of small-business owners — and for a while served as executive editor at this magazine — I have seen firsthand how beneficial it is for businesspeople to hone those social skills. I have also spoken to a lot of college professors who lament that their students struggle to make the sorts of serendipitous social connections that will serve them so well once they start their careers. And, like all of us, I’m coming out of a year spent in relative quarantine. I’m rusty on these skills and need to get used to the sorts of fun, fruitful, and, yes, sometimes difficult freewheeling social interactions we were deprived of for more than a year.

All of which is to say, I decided that I needed to become an expert at talking to strangers. How? I signed up for a class unlike anything I’d ever taken before and bought a plane ticket to London.

Image Credit: Nicolás Ortega

Our journey begins on a bright day in a small classroom at Regent’s University. I’m sitting on a chair, limp with jet lag, clutching my third cup of coffee. There are four other people there, too. They appear to be functioning at a higher level than I am, thankfully. We have come to this classroom to learn how to talk to strangers.

Our teacher is an energetic 20-something named Georgie Nightingall. She’s the founder of Trigger Conversations, an acclaimed London-based “human connection organization” that hosts social events and immersive workshops aimed at helping people have meaningful interactions with strangers. Since she founded it in 2016, Nightingall has done more than 100 events and many training sessions — with strangers, companies, communities, universities, and conferences, both in London and around the world.

Nightingall has learned that, for a lot of people, the hardest thing about talking to strangers is initiating the conversation: approaching someone, making them feel safe, and quickly conveying the idea that you don’t have an agenda, that you’re just being friendly or curious. She found that older people are much more likely to initiate a conversation, for instance, whereas younger people require a little more assurance. But she also found that in all her own attempts to speak to strangers, the vast majority of those interactions were substantial, and many went great.

She came to believe, too — and this is important — that making a practice of talking to strangers could offer more than a jolt of good feeling for an individual. There was joy in it, profundity, real communion. If practiced widely enough, she believed it could help repair a fracturing society. “We’re not just talking about a few individualized things,” she says. “We’re talking about a different way to live.”

Nightingall stands before our class, bright, engaging, and articulate, and walks us through what to expect over the coming days. She wants to take us “from unconscious incompetence to conscious incompetence, and from conscious competence to unconscious competence,” she says. In other words, we are currently bad at this and we’re unaware of why or how. We will learn what we are lacking. We will improve on it. And we will, hopefully, become so proficient that it will become second nature to us.

Our first lesson is small talk. A lot of people hate small talk, which is understandable, because a lot of small talk is deadly boring. Nightingall concedes the point. Yes, she says, small talk can be dull. But that’s because most people don’t understand what it’s for. It’s not the conversation. It’s the opener for a better conversation. It’s a way to get comfortable with one another and cast around for something you want to talk about. That, she says, is why it’s important to be aware of your response when someone asks something like “What do you do?” You are failing to understand what that question is really asking, which is this: “What should you and I talk about?”

Nightingall came to this insight via a couple of sources. She had done improv comedy in the past, and in improv, you start a sketch with something familiar to everyone in the audience — something relevant, timely, or present in the room — to bind the room together. Only then can you really take the audience on a ride. That’s small talk. But Nightingall has also followed the work of social anthropologist Kate Fox, who has studied, for instance, the seemingly inexhaustible English desire to discuss weather. While some critics have pointed to this affinity as evidence of a listless and unimaginative people, Fox argued that weather wasn’t the point. Instead, it is a means of social bonding, a greeting ritual. “English weather-speak is a form of code, evolved to help us overcome our natural reserve and actually talk to each other,” Fox writes. The content is not the point — familiarity, connection, and reassurance are. Once those are in place, a real conversation can happen.

When you recognize that small talk is just a door to a better conversation, Nightingall says, then it can be useful, because it’s structured in a way that naturally leads you toward common ground. We have all experienced how these conversations, if given the time, can move in ever-tightening circles until you both zero in on something you have in common and want to talk about. With that in place, you can wander, get a little personal, go deeper. But it’s probably on you to take it there, Nightingall says. “Everyone is interesting, but it’s not up to them to show you — it’s up to you to discover it.”

The best way to discover that interesting stuff, Nightingall says, is by “breaking the script.” That means using the techniques of small talk, but resisting the temptation to go on autopilot. For example, you go into a store and say, “How are you doing?” and the clerk says, “Fine; how are you?” and the conversation contains no information and goes nowhere. That’s a script. We use scripts to make interactions more efficient, particularly in busy, dense, fast-moving places like big cities. But in doing so, we deny ourselves the chance at a better experience and maybe a new contact, and we wall ourselves off from all the benefits that can come from talking to strangers.

So how do you break those scripts? With specificity and surprise, Nightingall says. For example, when someone says, “How are you?” she doesn’t say, “Fine.” Instead, she says, “I’d say I’m a 7.5 out of 10.” She briefly explains why she’s a 7.5, asks them how they’re doing, and then just waits. This is when mirroring kicks in; it’s a phenomenon where people naturally follow the lead of their conversational partners. If you say something generic, they will say something generic. If you say something specific, they are likely to as well. Thus, because Nightingall gave a number, her partner is likely to give a number themselves. If they say they’re a 6, Nightingall will ask, “What’ll it take to get you to an 8?” This specificity creates a light atmosphere and makes it harder for the other person to maintain the belief that you’re of a lesser mind, because it instantly demonstrates complexity, feeling, and humor: humanity, in other words. “Straightaway, they’re like, ‘Oh, you’re a human,’ ” Nightingall says. “You have that bond, and then, naturally, things open up.”

Here are other ways Nightingall suggests breaking a script. When a shop clerk asks, “Can I help you?” you can reply, “Can I help you?” Or instead of asking people at a party what they do, ask them what they’d like to do more of, or what they don’t do. Or instead of asking someone how their day went, ask, “Has your day lived up to your expectations?” All these things require a certain measure of confidence to pull off, Nightingall says. But they work. And when they do, they will reveal a little nugget of what it’s like to be that person. That is meaningful, because that nugget is indicative of what is beneath the surface. “How you do anything is how you do everything,” Nightingall says. That nugget tells you where to go next in the conversation.

Image Credit: Nicolás Ortega

Once you’ve established a little connection, what do you do? I normally start asking questions. Which makes sense: I’m showing an interest in the other person, and I demonstrate my interest by indulging my curiosity. But one paradox about talking to a stranger, Nightingall explains, is that while curiosity is indispensable, a barrage of questions out of the gate can feel like prying, or an interview. They don’t quite know where you’re coming from yet, and they don’t know if you have some kind of agenda. Even one personal question asked too early can create an uncomfortable dynamic because you’re asking something of someone. You’re making a demand.

Nightingall suggests that statements, not questions, can be a better way to open a conversation. A question compels an answer, whereas a statement leaves it up to the other person to decide whether they want to talk. It’s not a demand; it’s an offer. You notice something about your shared surroundings, offer an observation, and leave it to the other party to respond. If they do, you respond with another statement that builds on what they said.

These observations should ideally not be moronic — “I noticed that the sun came up today!” — but they can be simple. Like weather talk in England, the point is to indicate a shared experience. Nightingall has found that proximity helps, too. If you are at a museum, walking right up to someone looking at a painting and blurting out “What do you think?” is very different from making an observation about a painting after standing next to them for 30 seconds looking at it. That’s because you have been in their proximity. They have adjusted to your being there, and you have demonstrated a measure of self-control. Then you can speak. It feels less like an invasion.

One day in class, my fellow students and I pair off to practice our technique. I’m partnered with “Paula,” who tells me that one of her favorite things is making a cup of good coffee for herself on the weekends and just sitting alone. I try to remember Nightingall’s advice about opening with statements, not questions, but now we’re in a groove — so I dig in. After four questions, Paula is talking about how resentful she is at having to work for other people. I’m obviously quite pleased with myself as I trot back to Nightingall with this pheasant in my mouth. But she is less impressed. She delicately explains that while “it’s clear you’re a person who asks questions for a living,” everything about my body language suggested I was looking for something to pounce on. I asked questions too quickly, she said. I was leaning forward. This wasn’t a conversation; it was an interview. Possibly an interrogation.

Nightingall suggested asking simpler and more open-ended questions. Instead of saying, “Do you think this was because you were a control freak?” just echo, or say, “Why do you think that is?” That is the opposite of what I usually do, but it’s what I must learn to do. In a good conversation, you must relinquish control. Your job is to help your partner arrive at their own conclusion and surprise you, not to ferret out whatever it is, slap a bow on it, and go, Next! There’s a powerful lesson there: If you’re interested only in things you know you’re interested in, you will never be surprised. You’ll never learn anything new, or gain a fresh perspective, or make a new friend or contact. The key to talking to strangers, it turns out, is letting go, letting them lead. Then the world opens itself to you.

Why don’t we talk to strangers? The answer I heard, over and over again from experts, is simply that we don’t talk to strangers. In many places, for many reasons, it has become a social norm, and social norms are really powerful. That is why Nightingall uses what she calls a foolproof method to not just violate the norm — but to openly acknowledge that you are violating the norm.

She asks us to imagine riding mass transit — which, as we know, is the last place anyone ever talks to a stranger. There is someone who strikes us as interesting. We can’t turn to that person and say, “Why do I find you so interesting?” because if you said something like that to a stranger on the subway, they’re going to assume this is the initiation of a chain of events that will ultimately conclude with their becoming crude homemade taxidermy. So Nightingall suggests something called a pre-frame. It’s an idea based in the field of neurolinguistic programming, which coaches people to “reframe” the possible negative thoughts of others — in essence redefining their expectations for the interaction to come. Ordinarily, we might be wary if a stranger just starts talking to us. We don’t know who they are, or what they want, or whether they’re right in the head. What a pre-frame does is reassure them that you know all this.

To do it, you acknowledge out of the gate that this is a violation of a social norm. You say something like “Look, I know we’re not supposed to talk to people on the subway, but…” This demonstrates that you’re in full possession of your faculties. You’re not erratic, disturbed, or otherwise off in some way. It helps alleviate wariness and opens the possibility of a connection. Once that is established, Nightingall says, you follow the pre-frame with your statement — “I really like your sunglasses,” for instance. Then you follow that with a justification: “I just lost mine and I’ve been looking for a new pair.” The justification eases the person’s suspicion that you have some kind of agenda and allows you to talk a little more openly.

That’s when questions become more important, Nightingall says. Questions serve a multitude of functions, which is why, as I learned in my exercise with Paula, they can be so complicated. Yes, questions help you obtain information. And yes, on a deeper level, they help your conversational partner clarify the point they are trying to make. But they also help us emotionally bond with other people. In a series of studies in 2017, psychologist Karen Huang and her colleagues discovered that “people who ask more questions, particularly follow-up questions, are better liked by their conversation partners.” Those who ask more questions, the authors found, are perceived as higher in responsiveness — which is defined as “listening, understanding, validation, and care.” In other words, people like us because we are interested in them.

And yet, the researchers noted, people tend not to ask a lot of questions. Why? Several reasons. “First,” Huang writes, “people may not think to ask questions at all…because people are egocentric — focused on expressing their own thoughts, feelings, and beliefs with little or no interest in hearing what another person has to say. Or they may be so distracted by other aspects of the conversation that they do not realize that asking a question is an option.” Even if a question does pop into someone’s head, they may not ask it, because they worry it’ll land badly and be “perceived as rude, inappropriate, intrusive, or incompetent.” In these cases, people will probably just talk about themselves, which studies show they do twice as often as they talk about other matters — which, ironically, makes people like them less. (Good work, everybody.)

But what’s a good question to ask? Nightingall has us complete an exercise in which we are given banal statements — the sort commonly offered in small talk—and tasked with coming up with good questions. For instance, one student says she ran along the Thames yesterday. There is almost nothing in the world less interesting to me than running, and usually I’d take this as my cue to begin plotting my escape. But, working from the idea that small talk is the means, not the end, the class brainstorms good questions to ask that might lead to something more personal or interesting: “Do you run every day?” “Is that a passion for you?” “What would you do if you couldn’t run every day?” I suggest, “What are you running from?” which is meant as a joke, but the class seems to go for it.

Then we move on to the flip side of question-asking: It is listening. When people do start talking, you must listen, make eye contact, and generally show you’re engaged. We know this, of course. But we are not always good at showing it. Two effective techniques to signal engagement are paraphrasing what people have just said — “It seems like you’re saying…” — and echoing — which is simply occasionally repeating things your partner just said—both of which are commonly used by therapists and hostage negotiators to foster connection and build trust. For instance, if they say, “I guess at that point I was frustrated,” you say, “You were frustrated.” This seems deeply weird and unnatural, and feels awkward to do, and if you overdo it, your partner is going to think something’s wrong with you. But I am here to attest that, done well, it is extremely effective. It’s like a magic trick. Researchers have concluded as much. According to the French psychologists Nicolas Guéguen and Angélique Martin, “Research has shown that mimicry…leads to greater liking of the mimicker” and helps create rapport during a social interaction.

Nightingall breaks down listening into three levels. There is listening for things you know about. That’s the most superficial level. That’s when someone says something about baseball and you jump on it and start talking about baseball. Then there is listening for information — you show curiosity about someone but your questions are about collecting factual data. That’s also more about you and your interests. And then there’s the deepest level of listening: listening for experiences, feelings, motivations, and values. That kind of listening is more than simply hearing, or self-affirmation. It’s paying attention and endeavoring to understand. It is demonstrated with eye contact, echoing, and paraphrasing, and it can be deepened by asking clarifying questions — Why? How? Who? — that help the person get to the heart of the matter.

In other words, at this level of listening, you are not simply listening for something you want to talk about, or offering advice, or trying to think of something smart to say in response. It’s not about your agenda. It is a level of engagement that is about helping your partner get to what they really want to talk about, and you going along for the ride. You still want to talk about yourself a bit, Nightingall says — to give a little, and not leave the person feeling like you’ve just rummaged around in the bureau of their personal life and made off with a watch. But you want most of the focus to be on them. It is, again, a form of hospitality. You are hosting someone. You are surrendering a measure of control. You are giving them space. You are taking a risk. That risk opens you to the potential rewards of talking to a stranger.

During lunch and after class, I try out some of these techniques around London. I ask a 20-something bartender at a pub if the day has met her expectations, and she confesses with very little prompting that yes, it has. She’s about to quit her day job. She feels she’s been sold a bill of goods about the merits of a straight corporate career, and she’s going to empty her savings and travel the world. She hasn’t told anyone this yet, she says. But she will soon.

At lunch at a Lebanese takeout restaurant, I ask the owner what menu items he’s most proud of — because that’s what I want. He starts taking bits of this and that and dropping them into my bag. I tell him I grew up in a white neighborhood, and when I was a kid, a Lebanese family moved in behind us and used to hand us plates over the fence of what was at that time very exotic food. Since then, Lebanese food has always been among my favorites. Curiously, when I eat it, I think about home. This, as Nightingall instructed, was me opening up the conversation with a statement, not a question. The owner tells me that in Lebanon, that kind of hospitality is a big deal; people always make a lot of food for visitors. While he talks, he keeps dropping more food into my bag. When he’s done, the bag weighs about five pounds and he charges me for maybe a third of it.

At the end of the final day of class, Nightingall tells us that practice will be everything. Some encounters will go poorly, she says, and some will be great, but in time, we will get more comfortable with doing this as we internalize the techniques we have learned. We will be able to get a little bolder or more playful. Our confidence, tone, and body language will alleviate people’s wariness at the flagrant violation of a social norm of long standing.

Indeed, Nightingall is something of a wizard at this. She once started a conversation with a man on the tube just by pointing at his hat, smiling, and saying, simply, “Hat.” She will randomly high-five people in the street, she says. She smiles at people going the opposite direction down an escalator just to see if they’ll smile back. She doesn’t order an Americano; she orders “the best Americano in the world.” And people respond. During a break one day, I walked into the campus Starbucks to get more coffee. Nightingall was already in there, talking animatedly with a barista she’d never met before. When she and I walked out, she told me he gave her the coffee on the house.

Nightingall’s free coffee, my Lebanese meal — these were not coincidences. As I learned repeatedly while testing techniques of talking to strangers, I’d often be rewarded with free food. There are, of course, far more fruitful, meaningful, and valuable reasons to talk to strangers. But the food stuck with me. Then I realized why: When you start a good conversation with a stranger, it’s like you’re giving them an uncommon gift. And more often than not, they want to give you something in return.