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Want to enrich your life? Surrender to conversations with strangers.

On my computer screen is a drawing of a lobster on crumpled paper. Thick black outlines define its crude shape and uneven red crayon fill the body. Next to the creature is a question written in large blue child-like handwriting. “Is this the lobster that killed your mother?” An answer in the corner, black and neatly written, reads, “Yes, yes it is.”

A woman named Amarisse found the lobster drawing. It was stuck to a city information sign outside of the Malt Shop in downtown Bellingham, Washington. I don’t know Amarisse and I’ve never been to Bellingham. The only reason I’m looking at it, from my work desk in San Francisco, is because of Davy Rothbart.

Davy gathers conversations, stories, and bits of life. He turns them into explorations on humanity—as radio interviews on This American Life, as essays in his book My Heart is an Idiot, or as collages in FOUND Magazine. It’s on FOUND’s website that I see Amarisse’s lobster. Surrounded by love notes, old photographs, and to-do lists, it’s one of many pieces that have been sent in by strangers like Amarisse and at the behest of Davy.

These scraps of life could easily be disregarded as garbage. But on FOUND they’re given the space to be seen as parts of a larger conversation on humanity and relationships. And that’s Davy’s driving philosophy—we can learn so much from each other’s shared experiences and stories, we just need to take the time to listen. Or as Davy puts it, “surrender to the conversation”.

An interview with Davy

Davy spoke with me about the power of listening, how to talk to strangers, and why being a better conversationalist can help you in business and in life.

How did you get into collecting stories?

My curiosity of other people and their stories came from the way both of my parents interact with the world. My dad is one of those guys who’s never met a stranger. When we go to a diner, the waiter or waitress will end up sitting in the booth with us because my dad is asking so many questions.

As a kid, I sometimes felt embarrassed by the way he talked to everyone. But then again, often an interesting encounter would take place that wouldn't otherwise. I developed fondness for that style of interacting with the world around me and the people around me.

Listening is a superpower

On a deeper level, my mom is a meditation teacher and counsels people over the phone. She’s also deaf. Now she has an operator-assisted phone that does voice-to-text translation. But, when I was younger, I was her translator—listening to the person on the phone and signing to my mom.

I was eight years old and people would call in and share really intense stories. My heart went out to people who were struggling and at the same time, it was spellbinding to get a sense for the triumphs and incredible heartbreak that people go through in their lives. I was exposed to all the ways people manage hurt and what directions they go during a crisis.

It sharpened my antenna. After that, I was always aware that people constantly carrying a whole slate of complex emotions and situations in their hearts.

It sounds like your mom and dad gave people who needed to share their story the opportunity to do so.

Absolutely. What was incredible is that yes, my mom is a wise a woman and she would give some meaningful and often profound advice. A lot of times though, she didn't actually say that much. Just the act of sharing these painful experiences with somebody seemed to unburden people in a noticeable way. I learned that there's power to just listening.

What is the true power of being a good listener?

To be a good listener, you need to be genuinely curious about the person. Otherwise, you will come off as fake. Real listening shows that you care about the person. This is the real power because it makes people feel excited to share with you and comfortable being around you.

To be a good listener, you need to be genuinely curious about the person. Otherwise, you will come off as fake.

Also, it's not an entirely selfless act to be an engaged listener—you discover yourself in other people. When somebody else is sharing themselves on a deep level with me, I feel a strange high that comes from recognizing myself in other people. If somebody sends in a pitiful love note to FOUND, I might be laughing and I'm not laughing at the person, I'm laughing at myself because I realize I've written the same pitiful love note like a hundred times myself. Listening is a way for you to know you aren’t alone in your life experiences.

How can people practice being better listeners and conversationalists?

Just be interested, ask questions, and listen. Don’t turn the conversation into something about you. Keep exploring their experience. Most people are afraid to ask questions. Afraid it will appear like they’re prying or getting nosy. When you converse with sensitivity and genuine curiosity, They're happy that somebody cares, wants to know who they really are, and what's really on their mind.

Plus, you have to be willing to talk to strangers.

How to talk to strangers

When and why should we talk to strangers?

As for when? You can do it anytime. I recommend those times though when you are stuck somewhere—a grocery store line or the security line at an airport.

And why talk to strangers? Your experience of the world is richer with the more people that you get to know.

I remember one trip where I was feeling a little tired while in the security line at SFO. This guy behind me started talking to me. At first, I was trying to deflect him because I was tired, but then I surrendered to the conversation. We had this awesome 15 or 20 minute chat. Had I deflected him, I would have been standing in that line impatiently checking my phone or something. Instead, I got to know another person. He shared stories with me, I shared stories with him. That day I talked to a couple of other people on my flight and on the shuttle bus from LAX back to my house. Later that night, it hit me that what would have been really boring or tedious hours, instead felt like memorable and interesting times. Everyday there are incredible opportunities to connect with people.

Can you imagine striking up a conversation with a new stranger every single day? On the Relate podcast, hear from one man who did… and about the life-changing relationships he developed along the way.

What is your advice for starting a conversation?

Remember that it's just a few words. You share a look with somebody or you both observe the same funny thing at the same time. Say a couple of lines to them and see how it goes. You don't have to corner anybody or rant and rave to them. Just engage with people.

Say you really want to talk to someone but you're so nervous about being rejected, maybe you're at a conference or it's someone you want to ask to be your mentor. What is your advice there?

Rejection doesn't have to be painful if you just attach less of yourself to the rejection. Trust me, it's not like I'm immune to rejection or fear of rejection, I'm not.

But, the most successful people I know are the ones who are the least ruled by a fear of rejection. They're just fearless. They just will share their story or pitch their ideas to anybody. In a kind of relentless way. It's not always the person with the most talents or the most natural ability who wins in life. Sometimes it's the person who's the most willing to run forward with their ideas until they find the people who don't reject them. Keep going until you find the person who will give you a chance.

How conversations make you more successful in life

You've talked a lot about the value of having these conversations. Where do you see the good listening and the interviewing skills helping someone out in their professional relationships?

People make professional decisions based on personal relationships. There's no faster or more effective way to build a personal relationship then by having an actual conversation of substance with somebody. I don't think that I necessarily engage with people as a business strategy but I think I do it because I like to do it. It's the way I live my life. You can't help but notice the advantages and the benefits and the good things that come out of having these genuine conversations with somebody.

How is this different from networking?

It’s a cynical approach to connect with people just to get help from them. Plus, people are really good bullshit detectors. People have eerily sensitive to your intentions, so I think if the strategy is to get in good with somebody so you can, with ideas in mind, yeah, it's a fine distinction but I think it makes a difference.

If your goal is to connect with as many people as deeply as possible because it's interesting to you and it's a meaningful way of engaging with the world, the benefits happen in so many ways. New friendships, new romantic relationships, just a deeper enjoyment of everyday life. The same happens in your professional life too. Such as improved new business relationships and connections that you wouldn't have found otherwise. I think your motivation has to come from a good place though or people see through you.

Say you don’t get along with someone at work, how can these skills help smooth out those relationships?

I would challenge people to say, "I'm here with this other person. Maybe they're annoying me for some reason. Maybe there's something we're failing to connect. What can I discover about their life and their story that will resonate with me, that will be interesting to me?" The truth is it's really on you. If you're asking that question and come with the right approach, even the person you feel like you have the least in common with or the least interesting conversations, it can turn into something meaningful and revealing. It can change your relationship.

The customer service connection

We look at a lot of customer and business relationships at Relate. How can those be improved with better conversation and listening skills?

Well, let’s look at a call center from the customer’s perspective. It’s sort of roll the dice when you call a call center. You need help with something and you have no idea how interested the person on the other line is going to be with really helping you. One thing I like to do, when they answer, is to ask them how are they doing and not just, "How are you?" But, "How are you really?" It just stops them and takes them out of their day.

They're talking to a hundred people, think about how draining that must be. Just acknowledging their humanity, it might take me an extra minute, it might seem like it's going to add a minute to your call, but what you get out of it is a completely engaged person who actually really wants to help you with whatever issue you're calling about. It's really dramatic the difference it makes.

That’s good advice for customers. What can the business do?

By the same token, customer service agents can spend that extra minute getting to know their customers. For example, instead of just being like, "What are you calling about? What can I help you with?" try "How are you doing? How's everything going with you?"

When you drop the business speak, the customer will feel more like they are talking with another person, not a robot. The customer and the agent can converse freely and actually creatively problem solve. This can also help mitigate frustrations. Some people are calling because they're mad at the business. When an agent is personable, it can diffuse the situation before it escalates. Customers just want to feel listened to from the get-go.

When you drop the business speak, the customer will feel more like they are talking with another person, not a robot.

So focusing on customer service?

Customer service is the most interactive face of your company. By investing more in your customer service team’s conversation skills, Customers aren’t interacting with your engineers that design your product or the CEOs; they're interacting with the customer service people. Your customer service agents are the people making customers want to keep coming back and buying your product or your service. Give them the skills and freedom to engage with customers as fellow humans. It will pay off.

Davy’s advice can be boiled down to this: take the time to have a real conversation with people because it will enrich your life. Whether you want to improve your conversation skills at professional events or just make the security line at the airport seem shorter—surrendering to conversations, listening better, and being genuinely curious can make your life richer. Even if it’s just an interesting drawing of a lobster.

Chelsea Larsson is a content marketer for Zendesk and a frequent contributor to Relate. She believes any problem can be solved with a pen, paper, and Pimm's cup. Find her on Twitter: @ChelseaLarsson.

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