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The Art Of Approaching Strangers: Lessons From Humans Of New York

Business and entrepreneurship depend on people. People you work with, people you sell to, people you pitch. This article unpacks what one guy learned forming connections with others by cold-approaching strangers in a famously cold city. As a bonus, I’ve found that talking to strangers is a beautiful counter-response to the arms race for attention that is the ad-driven internet. So let’s learn from a master at the practice.

Imagine walking down a bustling New York City street, camera in hand, with the goal of not just photographing strangers, but getting them to open up about their deepest fears, greatest joys, and most profound life experiences.

This is exactly what Brandon Stanton, the creator of Humans of New York, has done over 10,000 times. His approach is a masterclass in forming human connection on the fly.

This piece is a walkthrough of how he approaches a stranger on the street.

Humans of New York creator Brandon Stanton drops biggest book yet
Brandon Stanton. Looks like a regular guy tbh.

The Dance of Non-Verbal Communication

Brandon’s process begins before he even says a word. “Rule number one,” he says, “never approach from behind.” Instead, he makes a wide, visible approach from the front or side. This simple act immediately sets the tone: I see you, I respect your space, I’m not a threat.

As he nears his subject, Brandon’s body language transforms. He crouches down or sits, bringing himself to eye level (Brandon is 6’4″ so this is crucial). “The goal,” he explains, “is to be as non-threatening as possible.” This subtle adjustment can make all the difference in putting a stranger at ease.

Keep the Opening Line Simple

With his body language setting the stage, Brandon opens with a simple request: “Excuse me, is there any way I can take your photograph?” Notice the phrasing—it’s gentle, it gives the person an easy out, and it doesn’t overwhelm them with information.

If he senses hesitation, Brandon has a backup. He’ll briefly mention his project, sometimes showing that he has a bit of a following and has written a book on his phone. But he’s not attached to the outcome. If someone’s not interested, he takes heed and moves on.

A Humans of NY post

Escalate Gradually

Once he gets a yes, Brandon starts with a full-body shot (i.e., the camera is far away from the subject). “It’s the least intimate,” he explains. This gives the subject time to get comfortable with the camera and with Brandon’s presence. As the interaction progresses, he’ll move in closer for more intimate shots.

After the initial photos, Brandon smoothly transitions to the interview. He explains a bit more about his project, mentioning that he finds out a little about everyone he photographs. This sets the expectation for conversation without putting too much pressure on the subject.

The Art of the Question: From Broad to Specific

Brandon’s questioning technique is where the magic really happens. He starts broad: “What’s your greatest struggle right now?” or “Give one piece of advice.” These questions are easy to answer but open the door to deeper conversation.

From there, Brandon listens carefully, looking for threads to pull on. If someone doesn’t give him much to work with, e.g. “Be optimistic,” he might ask about a time they struggled to be optimistic. The story behind one piece of advice is usually more interesting than the advice itself.

“I’m always looking for something that person has told me that nobody else has told me,” Brandon explains. “It’s almost always a story because we all share similar philosophies, we all share similar opinions on a lot of different issues, but all of our stories are our own.”


Creating Intimacy in a Public Space

One of the most remarkable aspects of Brandon’s approach is his ability to create a sense of intimacy on a busy street corner. He achieves this through his focused attention, his willingness to sit and talk for 15-20 minutes, and his genuine interest in the person’s story.

He also pays close attention to the subject’s energy. Are they giving short, clipped answers, or really thinking about their responses? This helps him gauge how to proceed with the conversation.

Energy Over Words

Throughout the entire interaction, Brandon maintains a calm, friendly demeanor. “It’s all about the energy that you’re giving off,” he insists. “It’s just 100 percent energy.”

This focus on energy over specific words is perhaps the most crucial lesson from Brandon’s approach. A mistake he made was spending years thinking about word choice—should I ask them if I can take a “portrait or a “photo”?. Turns out that did not actually matter that much. Creating an atmosphere where people feel safe, respected, and heard did.

Practice Makes Perfect

Brandon’s skill in approaching strangers didn’t come overnight. It was honed through thousands of interactions, each one an opportunity to learn and improve.

For those of us looking to improve our own skills in connecting with strangers, whether for sales, finding collaborators, or simply to enrich our daily lives, Brandon’s approach is compelling.

Start with respect, move slowly, ask genuine questions, and above all, project an energy of openness and interest. With practice, anyone can learn how to form connections with people they don’t know.

This writing is based on footage from Brandon’s acceptance speech of the James Joyce award given to him by University College Dublin.

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