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The Only Skill You Need To Be More Interesting

May 18, 2023

"I feel like I could talk to you all night." The woman I'd been enjoying the evening with leaned in and said with a devilish smile. That's when I knew that I was onto something big.

The next day thoughts danced inside my head like ancestral cavemen who had just discovered fire. Over the next month, the same scenario played out again and again and again. It seemed like I'd slipped into a modern version of Groundhog Day.

Would you believe I hadn't really said anything? In fact, I had barely told this person anything about myself. And it wasn't because I was trying to be evasive. I was simply practicing a newfound skill that made talking about myself almost irrelevant.

I used to waste time and energy trying to impress people with knowledge. 

Rather than impress, this tactic often ended with the opposite effect. We don’t know what’s going through other people’s minds unless we ask them. Rather than listening and asking questions, we typically pay attention just long enough so that we can steer conversations in areas that interest us. Then we begin rambling about concepts the listener may or may not be interested in or familiar with.

This potentially creates two undesirable scenarios. 

Scenario 1: The listener gets confused. They have insufficient context unless we pause to allow them to ask questions. This lack of understanding leaves the listener feeling insecure if we don’t give them space to get comfortable with asking “dumb” questions. 

Scenario 2: The listener knows more about the topic than we do. If our logic is flawed, they assume we may become defensive if corrected. This creates tension, as the listener becomes impatient that we are spewing verbal garbage into the streets of their mind. 

In either scenario, the conversation shuts down. The listener withdraws. We learn nothing and are perceived as conversation hogs fattening ourselves on their mental energy. 

“Our modern selves talk more and listen less despite the fact that understanding and responsiveness to one another's stories, ideas, and concerns have defined all our achievements, from hunting woolly mammoths to putting a man on the moon. Not listening to one another diminishes what we can achieve, and in that way, too, can be seen as a moral failing. We not only fail one another as individuals, but we also fail to thrive as a society.” -  Kate Murphy1

So what was this newfound superpower? 

It is simply being interested in the person speaking. This sounds obvious, but it runs counter to how we usually engage in conversations. It took me a long time to understand that people are primarily interested in one thing. Themselves. Most people only care about what you can do for them. Learn to make that work in your favor.

Rather than trying to impress people others with our backgrounds, credentials, and possessions, we should instead focus our attention on answering how we can help them. If we listen carefully, we learn what makes them tick. We begin to understand their worldview. When we understand their perspective, we can demonstrate this back. In doing so, we instantly become more interesting to them. 

''If you want to be interesting, be interested.'' - David Ogilvy

Jay Abraham is an internationally recognized guru of gurus known for his “out-of-the-box” way of thinking about growing businesses. People pay a lot of money to listen to him speak. After pouring himself a drink in a hotel lounge one evening, he sat down next to a man drinking alone. 

Jay told the man only two things about himself. He was from the United States and in town on business. Jay sat back, asked probing questions, and listened to the man speak for the next 90 minutes. Jay then stood up wobbly after his drinks and walked over to the elevator.

The man ran over and said, "Wait, I have to tell you something. You are one of the most interesting people I have ever met." At that moment, Jay learned a valuable lesson. If you want to be interesting, be interested. It's a powerful yet counterintuitive concept. But why does it work? And what can it teach us about how we usually engage in conversation?"

Tactical empathy may be one of the most important skills I've ever learned.

I’ve never been described as someone high on the empathy spectrum. This makes it hard to relate to other people’s perspectives. People sense that we’re ignoring their wants and needs when we don't consider their perspective. We’re not listening. 

Tactical empathy enables you, “the listener,” to recognize the perspective of the person you’re speaking with and articulate that recognition back to them. This demonstrates we are listening well enough to understand their worldview. A person’s worldview can include how they feel, what motivates them, who is influencing their decisions, and what might motivate them to take action in the direction we want them to go. 

The specific exercise I'd been practicing in the introduction to this article is called the "Quick 2 Plus 1". This exercise involves applying two labels, a mirror, and then silence.

You can think of a label as a verbal observation. A verbal observation is a way of describing what we sense the speaker is communicating both verbally and non-verbally. A good label reinforces positive aspects, such as common goals and dynamics, and diffuses negative sentiments the person might have toward you or your goals. Labels often start with "It seems/looks/sounds, like..."

For example, in the scenario above, the woman might mention something that’s troubling her at work. 

A few negative labels might include:

  • It sounds like you’re not feeling well this evening.
  • You look upset when discussing work. 

She might then begin explaining that her boss doesn’t appreciate her ideas. That’s when a mirror comes into play. Applying a mirror involves simply repeating the last 3-5ish words the other person says back to them.

Doesn’t appreciate your ideas?”

I've found this encourages people to expand on what they were saying and allows them to give better descriptions without asking a direct question. 

''The fool tells me his reasons; the wise man persuades me with my own." - Aristotle (maybe)

Once the mirror has been applied, simply remain silent and let the person expand on their points. People hate silence, and when there's silence, they often rush to fill in the gaps. And this is one of the most challenging parts of listening. 

She might say, “Yeah, whenever I speak up in meetings and give an idea, he just shuts them down.” 

Then the process starts again. 

  • “You seem to enjoy generating new ideas for making your job easier.”
  • “You sound like you're excited about the possibility of making improvements.”

People often assume tactical empathy is a manipulation strategy. 

While any effective strategy can be used to manipulate, that’s not the point here. Because if we take advantage of people, they eventually pick up on that and refuse to cooperate.

The point of deploying tactical is to get the other person to recognize that we fundamentally understand what they’re going through. Only then can we create the right environment for reciprocity and collaboration toward a mutually beneficial future state.

Using tactical empathy has transformed my conversations.

As Chris Voss always says, "Everything is a negotiation." People's time, energy, and interest are no exception. In using this new skill, I’ve found that I’m better able to express my understanding of what the person I'm listening to is communicating. As a result, I have better, more meaningful conversations. And that leaves other people interested in learning more about who I am. 

If you're interested in learning more about how to use tactical empathy, I encourage you to pick up Chris's book, Never Split the Difference: Negotiating As If Your Life Depended On It ." 

You won't regret it!


1. Murphy, K. (2020). 16. The Morality of Listening: Why Gossip is Good for You. In You’re not listening. essay, Harvill Secker.

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