How to Get People to Open up and Share their story with you:

A cool technique from Humans of New York

It’s pouring rain and a young man towering at 6’4 gets under the umbrella of a small elderly woman on the sidewalk. Her face is worn with wrinkles and set with bright blue eyes, and she reminds him of the woman from Titanic, the movie.

The odd pair under the umbrella has never met before, and passersby are hurrying on without a thought to their conversation, catching nothing. But in the next few days, they will likely hear of this encounter.

“When my husband was dying” she says, “I asked him ‘Moe, how am I supposed to live without you?’

He told me, ‘Take the love you have for me and spread it around.’”

This woman has shared the deepest recesses of her heart and life’s story with this stranger in a moment. He bids farewell and steps back out into the rain, then turns a corner and begins to cry.

Soon, as he shares this encounter on social media, over one million people around the world will be touched by this woman’s story.

This is not a fluke for the man. His name is Brandon Stanton, and he has earned a strong and loyal international following of over 16 million people on Facebook as he blogs story after story of ordinary strangers he meets on the street.

The Astounding Secret Everyone Asks For

The most astounding part of Brandon Stanton’s work that amazes everyone is … ‘How does he do it?’ How does he get strangers to open up to him like that? People are telling him all about their deepest fears, embarrassments, pains and secrets and letting him share with the world.

Everyone has a story. We know that. But what we don’t expect is that people will just open up to us and share their story with us. And we don’t exactly know how to ask them to tell us, even when we’re interested to know more about them.

Whether you’re trying to get to know someone better in your personal life or researching potential customer needs, you might be afraid of coming across as weird. It is awkward approaching people to get to know them better, when you don’t really know them at all.

For one, you struggle with the questions you should ask. ‘Interviewing.’ It’s hard digging deeper with someone in a way that doesn’t make it all stiff and awkward and a complete one sided barrage of questions that is as uncomfortable to ask as it is to answer.

Yet listening to someone’s story can help you. It can help you figure out stuff, and know which way to go.

I’ve been interested to know more about Brandon’s style, and while doing my research I learned an important technique from his work that I share here that can help in conversations when you want to hear more detail around someone’s experiences.

The Science behind Getting to Know Someone’s Story

Here’s how Brandon describes it:

“It’s the taking an atmosphere of fear and strangeness and uncomfortableness, and turning it into an atmosphere of intimacy, where people feel comfortable to disclose in a very short amount of time.. and the way that I figured this out was by doing this 10,000 times and getting beaten down, beaten down, beaten down, beaten down…”

What he’s saying is that thousands of experiences have shown him it is about flipping things around — from complete strangers to two people connecting with an intimate conversation.

Now, allow me to go all fan girl and say that if you’ve followed his work and interviews, Brandon is just that really cool human who stands above that icky-ness associated with the culture and notion of celebrity. I’ve rarely seen an artist less narcissistic about what they do. Even a fiercely private person like me picked up on his positive, deeply authentic and sincere vibe and thought — ‘I’d probably open up to him right there.’

But other than the fact that Brandon is inimitably Brandon and a decent, trustworthy photojournalist on a world changing mission, there is one technique he shows that can help make it easy and more natural, for those of us who need to learn how to sprinkle a little HONY magic in our own work with learning more about people.

The Way to Make them Open Up to You More

When he’s listening, As Brandon demonstrates in his approach, he makes sure to appear as non threatening and humble as possible, and then when they say yes, will often sit down on the ground near them, position himself comfortably, like a kid about to chat with a friend or grandparent. And then mostly listen.

Brandon will punctuate with just a few questions along the way to dig deeper. And therein lies the secret to his secret:

He is leading them up to telling a story from their life, by making them go from very general statements to specific examples of their experiences.

He doesn’t start by telling them he’s going to ask them deeply personal questions. Remember he’s just stopped them on the street, and asked permission to take their photo. Can’t ask for much more just yet. 
Brandon called this ‘escalating commitment’ as he described taking things further one step at a time gently in an interview with Chase Jarvis:

“The process is I always start with very very broad questions. Like one thing that I’ll ask is ‘If you could give one piece of advice to a large group of people, what would your advice be?’”

Think about this for a second. You’ve been stopped and asked this question by Humans of New York. What advice would YOU give?

Let’s say you say something like

‘Eat more Pasta.’

(I don’t know, this was the first thing that came to my mind as I wrote just now. I’ve never actively thought about it before, really)

Or you go all saint and say,

‘Forgive yourself.’

Alright, cool. 16 million people can hear that from you right? You’re safe with your privacy, and you’ve said something wise to the world when HONY stopped you on the street, you urban sage, you.

Not so fast. He’s not letting you go just yet. (*Swoon*…)

‘Was there a time in your life you couldn’t eat as much pasta as you wanted?’

‘What was the hardest time you ever found it to forgive?’

Stop reading again, and think of an answer to the question. When was a time in your life you found yourself struggling to forgive, and felt like you couldn’t? What happened? Why did you blame and beat yourself up about it?

Did you feel your chest tighten maybe, draw in a sharp breath perhaps? It happens when we think back to those hard times we relived too many times over. And you’ve just thought back to that time now, haven’t you?

You’ve been put on the spot to tell something deeply personal about yourself that reflects huge insight into your experiences, but you’ve been led to it very gently and respectfully. No manipulation, no unwelcome prying.

Simply asking people to get specific with a story to explain themselves.Boom.

Getting people to open up to you with their stories is like striking gold. Stories tap into their emotions. It tells you what they really did, what they do, and what they’re likely to do. How they react. How they feel. What they want. What they love and hate. What they think about, and why they think about it. Oh stories will tell you so many whys about a person! Suddenly it makes sense why one person is afraid of the dark, or another flinches when someone makes a sudden move, or why they appear to be unmoved when hearing of a tragedy or find a certain type of joke offensive. Stories are clues to understanding human behavior, and key to glimpsing the human spirit.

Now I’ll trust you’ll be responsible and want that gold with the best of intentions, so I’m going to help you a little bit more.

How You Can Put this Technique into Practice

How you can do the same? How can you lead an immersion interview or chat at work or personal conversation into clearer territory and get people to start talking more in detail to reveal insightful clues without you having to ask so many damn questions and come off looking weirdly interrogative and feeling bad?

When Brandon asks someone for some advice, they may give a generic response. Infact they often do. But he expects that, as he deliberately asked a broad question like we just discussed.

You’re to do the same:

1.Start off with a broad question relevant to the topic you want to explore.

2. Then ask to get specific. Ask for an example that demonstrates their point X. Questions you ask could include

‘What’s an example of …?’

‘What’s a time when…?’

‘Have you had an experience with that?’

‘Do you remember the last time you felt this way? What happened?’

Let’s say you’re a stylist who is trying to help people dress better at work. You want to interview your target audience to get to know how they really feel, their burning pains and hopes and dreams. Yet, you can’t get them to really open up in the level of detail that you want, even as they’re willing to give you time answering your questions. You can ask them, ‘How do you really want to feel when you come dressed in for work?’

They might say ‘Confident and feeling great about myself’.

Now, that’s good but let’s see if we can get it specific, so you can derive a story to work with and maybe even write about.

You could ask them the ‘most’ they’ve ever felt.
‘What is your most memorable experience coming in to work and feeling really great about yourself?’

Or the last time something like that happened.

‘When is the last time you felt really confident coming into work?’’ 
‘Last Monday.’
‘That was five days ago. What was different on Monday from all the rest of the week?’
And they could say.. ‘Well, I’d finally got time to do my laundry on the weekend, and actually put together an outfit the night before instead of being too exhausted and leaving it to chance the next morning. I went to bed early and woke up feeling rested, and in a good mood especially after relaxing with my favorite people over the weekend. I even picked out matching accessories and blow dried my hair which I usually don’t have time for and just felt really good. I even got a few great compliments on how fresh I looked..’

(Don’t forget to ask about the compliments! ‘Oh that’s nice.. what did they say?’)

Or you can ask about a time when they felt the opposite of how they needed to. And then go into that story.

Brandon often asks people who have just given a general response if they can cite an example of a time they experienced something around that, and that is when they will get specific with a story that is unique to them.

The Gold you’re digging for lies beneath the surface

Dig deeper. Go one level deeper if you can, two, three or more. If you want your subject to keep talking once you’re on track and give you even more detail, just feel free to ask for details. ‘Why?’ 
‘Who said that?’
‘Why were you afraid?’
‘How old were you?’

‘Did you consider Option A?’

‘What did they say?’

‘Did they ever reach out again?’

‘What was a moment you’ll always remember?’

Repeat the process, for as many levels deep as you can go. Often the answer that lies two levels deeper tells you more about the person and story than the surface level answer. It’s not that the person was being dishonest with you, but often stories reveal what people concealed, whether they meant to be concealing something or not.

‘I’m looking for a story.’ Says Brandon.

And so are you.

Call it a Two Step Formula if you will. — One, Two. There, it can be that simple. Don’t worry about blowing it. The beauty of it is that you get to explore any way you want with this technique. 
You’re open to discovering new things about someone, and see if you find your answers. If not, you just ask a different question, and lead again with that.

Now think of one way you’re going to use this, and plan it out in the comment section. Or if you use it, do tell me how it went for you.

Gonna devour every comment and give you excessive attention. Because I want to hear your story… ;)

And if you liked what you read, please hit recommend so others can benefit and I’ll know I did the right thing with my first post on Medium.