How to Have a Curiosity Conversation

We’ve talked throughout A Curious Mind about how to use questions, how to use curiosity, to make your daily life better. But maybe you want to try what I did: Maybe you want to have some curiosity conversations, to sit down with a few really interesting people and try to understand how they see the world differently than you do.

Curiosity conversations can help give you a bigger life. They can do for you what they have done for me—they can help you step out of your own world, they can widen your perspective, they can give you a taste of experiences you won’t have on your own.

 

Starter Conversations

Everyone has their own style, but I’d recommend starting close to home. That’s what I did, in fact. Think about your immediate circle of relatives, friends, acquaintances, work-related colleagues.

Maybe there are a few people with intriguing jobs or very different experiences—of education, upbringing, culture, or people who work in your business but in a different arena.

That’s a great place to start, a good place to get a feel for how a curiosity conversation works. Pick someone, and ask if they’ll make a date to talk to you for twenty minutes or so— and specify what you want to talk about.

“I’ve always been curious about your work, I’m trying to broaden my sense of that world, and I was wondering if you’d be willing to spend twenty minutes talking to me about what you do, what the challenges and the satisfactions are.”

Or . . .

“I’ve always been curious about how you ended up as [whatever their profession is], and I was wondering if you’d be willing to spend twenty minutes talking to me about what it took to get where you are—what the key turning points in your career have been.”

Here are a few tips for when someone agrees to talk to you—whether they are a family member, an acquaintance, or a friend of a friend:

• Be clear that you want to hear their story. You’re not looking for a job, you’re not looking for advice about your own situation or any challenges you’re facing. You’re curious about them.

• Even if the person you’re talking to is someone you know well, be respectful—treat the occasion with just a tinge of formality, because you want to talk about things you don’t normally; dress well; be on time; be appreciative of their time even as you sit down to begin.

• Think in advance about what you’d most hope to get out of the conversation, and think of a handful of open ended questions that will get the person talking about what you’re most interested in: “What was your first professional success?” “Why did you decide to do [whatever their job is]?” “Tell me about a couple of big challenges you had to overcome. “What has been your biggest surprise?” “How did you end up living in [their city]?” “What’s the part of what you do that outsiders don’t appreciate?”

• Don’t be a slave to your prepared questions. Be just the opposite: Listen closely, and be a good conversationalist. Pick up on what the person you’re talking to is saying, and ask questions that expand on the stories they tell or the points they make.

• Don’t share your own story or your own observations. Listen. Ask questions. The goal is for you to learn as much about the person you’re talking to as you can in the time you have. If you’re talking, you’re not learning about the other person.

• Be respectful of the person’s time, without unnecessarily cutting off a great conversation. If they agree to give you twenty minutes, keep track of the time. Even if things are going well, when the allotted time has passed, it’s okay to say something like, “I don’t want to take too much of your time and it’s been twenty minutes” or “It’s been twenty minutes, perhaps I should let you go.” People will often say, “I’m enjoying this, I can give you a few more minutes.”

• Be grateful. Don’t just say thank you, give the best compliment for a conversation like this: “That was so interesting.” And send a very brief follow-up email thank you, perhaps highlighting one story or point they made that you particularly enjoyed, or that was particularly eye-opening for you. That thank-you email shouldn’t ask for anything more—it should be written so the person who gave you his or her time doesn’t even need to reply.

 

Curiosity Conversations Farther Afield

Conversations with people outside your own circle or with strangers are harder to arrange, but they can be fascinating, even thrilling.

Who should you approach? Think about your own interests—whether it’s college football or astrophysics or cooking, your community almost surely has local experts. When you read the paper or watch the local news, pay attention to people who make an impression on you. Search out experts at your local university.

Setting up curiosity conversations with people outside your own circle requires a little more planning and discretion:

• First, once you’ve identified someone you’d like to sit and talk to for twenty minutes, consider whether you might know someone who knows that person. Get in touch with the person you know, explain who you want to talk to, and ask if you can use your acquaintance’s name. An email that begins, “I’m writing at the suggestion of [name of mutual acquaintance],” establishes immediate credibility.

• If you are trying to meet someone who is totally outside of your circle, use your own credentials and strong interest up front. “I’m a vice president at the local hospital, and I have a lifelong interest in astronomy. I was wondering if you’d be willing to spend twenty minutes talking to me about your own work and the current state of the field. I appreciate that you don’t know me, but I’m writing out of genuine curiosity—I don’t want anything more than a twenty-minute conversation, at your convenience.”

• You may hear back from an assistant asking for a little more information—and some people may find the request a little unusual. Explain what you’re hoping for. Be clear that you’re not seeking a job, or advice, or a career change—you are simply trying to understand a little about someone with real achievements in a field you care about.

• If you get an appointment, make sure to do as much reading as possible about the person you’re going to see, as well as their field. That can help you ask good questions about their career track or their avocations. But it’s a fine line: be respectful of people’s privacy.

• Pay attention not just to what the person you’re talking to says, but how they say it. Often there is as much information in people’s tone, in the way they tell a story or respond to a question, as in the answer itself.

• The tips about starter conversations apply—along with your own experience of having those starter conversations. Have questions in advance, but let the conversation flow based on what you learn; make your side of the conversation questions—not your own thoughts; be respectful of the clock; be grateful in person and in a very brief follow-up email. If an assistant helps set up a curiosity conversation, be sure to include that person in your thank-you note.

 

Curiosity Takeaways

What you’ll discover is that people love talking about themselves—about their work, about their challenges, about the story of how they arrived where they are.

The hardest part is the very beginning.

In a formal curiosity conversation, I would recommend not taking notes—the goal is a good conversation. Taking notes might just make someone uncomfortable.

But when you’ve left a person’s office, it’s valuable to spend just a few minutes thinking about what the most surprising thing you learned was; what the person’s tone and personality was like, compared to what you might have imagined; what choices they’ve made that were different than you might have made in the same circumstances.

And you don’t need to have curiosity conversations in formal settings that you set up. You meet people all the time. The person next to you on the airplane or at the wedding quite likely has a fascinating story and comes from a world different from yours—and all you have to do in that setting is turn, smile, and introduce yourself to start a conversation. “Hi, I’m Brian, I work in the movie business—what do you do?”

Remember that if you’re trying to learn something, you should be asking questions and listening to the answers rather than talking about yourself.

 

Curiosity Conversation 2.0: The Curiosity Dinner Party

You can take the principles above and extend them into a group atmosphere by hosting a gathering. Think of two or three interesting friends or acquaintances—they can be people who know one another or do not—preferably from different lines of work and different backgrounds.

Invite those people, and ask each of them to invite two or three of their most interesting friends or acquaintances. The result will be a group of selected people who are interconnected but (hopefully) very different from one another.

The dinner party can be as formal or informal as you like, but it should be in a place that is conducive to mingling. Use the suggestions above to kick off the dinner conversation and encourage each person to follow their own curiosity, ask questions, listen, and learn about one another.