All Hail Conan

For a role model on how to draw information out of people, look no further than late-night talk-show hosts. Their sole job is to make a celebrity, often no funnier than you or I, appear immensely charming and intelligent. That’s a tough task sometimes. Think about the energy, focus, attention, and listening they employ to make this happen. That’s what is possible.

All Hail Conan

I’ve found that the absolute best mindset to emulate for deep listening is that of a talk-show host—Jimmy Fallon, Jimmy Kimmel, Conan O’Brien, whoever your favorite is, they all do the same thing. Just ask yourself what they would do if you’re struggling for what curiosity looks like and how you can wield it. Conan O’Brien happens to be my favorite, so let’s think about the traits he embodies in a conversation with a guest on his show.

Visualize his studio. He’s got a big open space, and he is seated at a desk. His guest is seated at a chair adjacent to the desk, and it’s literally like they exist in a world of their own. When Conan has a guest on his show, that guest is the center of his world for the next ten minutes. They are the most interesting person he has ever come across, everything they say is spellbinding, he is insatiably curious about their stories, and he reacts to anything they say with an uproarious laugh and an otherwise exaggerated reaction that they were seeking. He is charmingly positive and can always find a humorous spin on a negative aspect of a story.

His sole purpose is to make his guest comfortable on the show, encourage them to talk about themselves, and ultimately make them feel good and look good. In turn, this makes them share things they might not otherwise reveal and creates a connection and chemistry that is so important for a talk show. The viewers at home are desperate to learn about this celebrity guest, so Conan acts as a proxy for their curiosity. Also, the viewers can tell in an instant if either party is mailing it in or faking it, so Conan’s job literally depends on his ability to use his curiosity to connect on a deeper level.

Even with grumpy or more quiet guests, he is able to elevate their energy levels and attitudes simply by being intensely interested in them (at an energy level slightly above theirs) and encouraging them by giving the great reactions they seek. It’s almost as if he plays the game “How little can I say to get the most out of people?”

Of course, in your life, this applies to those people you come across that are like pulling teeth to talk to. A little bit of friendly encouragement and affirmation can make even the meekest clam open up. Numerous questions, directing the conversation toward them, and the feeling that you actually care are also integral. Imagine the relief you can create at dreaded networking events. People like those who like them, so when you react the way they want, it encourages them to be more outgoing and open with you.

Another talk-show host would later go on the record lamenting how often he disliked his guests and how boring he found the actors and actresses that he would be forced to speak to. But that’s a testament to how highly trained his habit of curiosity was. He started by making a conscious decision to be curious, built the habit, and engaged his guests easily; do you think his guests could tell if he was truly interested or not? Never.

Curiosity allows people to feel comfortable enough to speak freely beyond a superficial level—because you are demonstrating that you care and that you will listen when they open up. People won’t be inclined to reveal their secret thoughts if they think they’ll be met with apathy, after all. So even if you have to fake it till you make it, Conan O’Brien is who your mindset and attitude should feel like.

In case Conan O’Brien’s curiosity still isn’t coming naturally to you, here are some more specific patterns of thought you can use to improve your people skills.

I wonder what they are like? When you start to wonder about the other person, it changes your perspective on them completely. This is an inkling of curiosity. You start to care about them—not only about their shallow traits, such as their occupation or how their day is going, but what motivates them and makes them act in the way they do.

Having a sense of wonder about someone is one of the most powerful mindsets you can possess because it makes you want to scratch your itch. Scratching the itch of curiosity will become secondary to everything else because you simply want to know about the other person.

Suppose you had a sense of wonder about computers as a child. You probably irritated others with how many questions you asked anyone that seemed to have knowledge about computers. Now as an adult, what kind of attention span are you going to devote to computers, and what kind of questions are you going to ask? You are going to skip the small-talk interview questions and get right down to the details because it’s what you care and are curious about.

Keeping the mindset of wonderment will completely change the way you interact with people because you will suddenly care, and much of the time, we don’t notice that we don’t care about the person we are talking to. You’ll dig deeper and deeper until you can put together a picture of what you are wondering about.

What can they teach me? Don’t read this from the perspective of attempting to gain what you can from someone. Instead see others as being people worthy of your attention. Everyone has valuable knowledge, whether it applies to your life or not. Everyone is great at something, and everyone is a domain expert in something that you are not, no matter how small or obscure the subject.

The main point is to ignite an interest in the other person as opposed to an apathetic approach. Imagine if you were a huge skiing junkie and you met someone who used to be a professional skier. They may have even reached the Olympics in their prime.

What will follow? You’ll be thrilled by what you can potentially learn and gain from the other person, and that will guide the entire interaction. Again, there will be a level of interest and engagement if you view others as worthy of talking to. But you’ll never know unless you dig below the surface.

Whether we like to admit it or not, sometimes we feel some people are not worth our time. It’s a bad habit, and this line of thinking is one of the first steps toward breaking it. Everyone is worth our time, but we won’t be able to discover it if we don’t put in the work.

What do we have in common? This is an investigation into the life experiences you share with someone. It instantly makes them more engaging and interesting—because we feel that they are more similar to us! It may sound a bit egotistical, but we are undoubtedly more captivated by people who share our same views and interests.

Finding commonalities may even elevate people, especially if we are surrounded by people different from us. For instance, if you discovered that a new stranger was born in the same hospital as you were, despite being in a different country, you would instantly feel more open to them. This person must share similar worldviews, values, and humor. But you wouldn’t have discovered that if you didn’t make an attempt at excavating beneath the surface.

You will need to go on a hunt, and you will ask the important questions that get you where you want to be. You might jump from topic to topic, or you might dive in and ask directly.

Perhaps it’s just because you will have something to fixate on besides talking for talking’s sake, but these attitudes will drastically change how you approach people. Curiosity can still be tough to maintain, which is why my final suggestion for creating curiosity is to make a game of it. Your goal is to learn as much about the other person as possible. Alternatively, assume there is something extremely thrilling and exciting about the other person and make it your quest to uncover it. Eventually, you’ll find what you’re looking for.

The next time you go out to a café or store, put these attitudes to the test with the captive audience of the baristas or cashiers you come across—the lucky few who are paid to be nice to you. Do you perceive these workers to be below you, or do you treat them differently than you would a good friend? Do you have a sense of wonderment and curiosity about them? What do you think they can teach you, and what do you have in common with them?

Do you tend to ask the baristas or cashiers about their day and actually care about their answer? If not, do you think you’ll be able to simply “turn it on” when you’re around people you care about? Practice changing your mindsets concerning the people around you. It’s the easiest practice you’ll have because you don’t have to lift a finger, but it drastically transforms the quality of relationships you’ll create.