Ask better interview questions: 3 lessons from Humans of New York

When Brandon Stanton was laid off from his job as a bond trader in 2010, he took a risk that many aspiring artists take: He moved to New York to pursue photography.

Several years later, his blog Humans of New York has developed a following of millions on social media and spawned a New York Times-bestselling book.

His success has brought him to unexpected places, like the Oval Office, where he interviewed President Obama, and Europe, where he shared stories of refugees as part of a project with the UN.

Stanton’s work features street portraits and short-form interviews, often reduced to a few lines, of people in New York and around the world. His subjects, who are almost always strangers he approaches on the street, share personal details. The result is a series of portraits that is humane, insightful, and kind of magnetic.

“I’m rebooting my life entirely, again. It’s time for Andrew 5.0.”

A post shared by Humans of New York (@humansofny) on

How does he do it? To get good answers, you have to ask good questions. Here are three interview lessons from Humans of New York:

#1: Get to the heart of it

Human moments are captivating. Vulnerability and honesty stand out. Stanton could ask people, “What do you do for a living?” or “How’s your day going?” Instead, he asks things like:

  • What are you most afraid of right now?
  • What’s the happiest moment of your life?
  • What’s the saddest moment of your life?
  • Who is the most influential person in your life?

Ask for the facts when you need to, but also ask the questions that elicit emotion. The answers will be illuminating.

#2: Ask one question at a time

Stanton’s questions are simple and direct, and he asks them without much explanation or context.

This is harder than it sounds. As interviewers, we often think we need to provide a lot of lead-in to a question to help the interviewee open up. We think that if we talk more, our interviewee will share more.

In fact, you make your interviewees feel comfortable by giving them your full attention.

“It’s not about what I say, it’s about the energy I’m giving off,” Stanton said when asked how he gets people to open up to him. “I’m genuinely interested in what the person has to say.”

Remember, the best interview questions are simple. Avoid double-barrelled or back-to-back questions, and learn to be OK with the silence as your subject thinks of his or her answer.

#3: Seek out the unexpected

You may spend an hour with your subject and walk away with a small nugget of gold. That’s OK. That’s good. I’m willing to bet that 93 percent of Stanton’s material is just not that noteworthy. He’s intentional about what he publishes, acting more like a curator than a reporter.

Your job, similarly, is to identify the most captivating interview answers. So what do you look for? One clue is a narrative that violates your expectations.

Your questions can help you get to this place (“What would people be surprised to know about x?”) but it may come up organically during the interview. When it does, take the time to dig deeper.

Content creates relationships

Stanton has over 6 million followers on Instagram, but his growing community isn’t just about popularity or book sales.

He partnered with Tumblr to raise more than $300K for Hurricane Sandy victims. He helped raised more than $1 million for a Brooklyn school after one of the students appeared on his blog. He reportedly raised more than $5 million for philanthropic projects in 2015.

He uses these portraits to connect with his community, but it didn’t happen overnight. It came from consistently sharing these stories over time — and in the process, sharing himself. In turn, these relationships help benefit the people whose lives he shares. That’s much more powerful than any interview tactic.

Open Eye Creative is a small video production company with a huge vision: to use the power of story to strengthen and propel organizations that are changing the world. Read more.