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4 tips to have better conversations

For former police chief John Weiss, learning to be a better conversationalist ultimately came down to this one simple thing.
Image: A couple talks in a cafe
Don't fall into the trap of “conversational one-upmanship,” where one talker will consciously or unconsciously put down the person they are talking to. Lumina Images / Getty Images/Blend Images

Arguers, interrupters, long-winded story tellers. Everyone has their own conversation style. For better or worse, how we communicate shapes our relationships and how we’re seen by others. For retired police chief John Weiss, learning to be a better conversationalist ultimately came down to one thing: listening.

Weiss, 55, now a writer and artist who lives in Las Vegas, spent 26 years on the Scotts Valley police force in California, and served the last 10 of those years as a busy police chief.

“When you become a police chief, it’s a very stressful job,” says Weiss. “You have limited time, so you find yourself — and it’s not a good quality — you find yourself interrupting or finishing people’s sentences for them because you are in a hurry.”

Weiss spent 26 years on the Scotts Valley police force in California.
John Weiss says his relationships with his wife, friends, and officers deepened after he became a better listener.Courtesy of John Weiss / Courtesy of John Weiss

Weiss says his wife began to point out his tendency to interrupt. But it wasn’t until a visit with a physical therapist for a shoulder injury that he started to realize what a difference a good listener can make.

“He made me feel so comfortable, so quickly, because he was such a great listener and he asked great questions,” says Weiss.

The physical therapist was the opposite of what Weiss calls an “oppressive talker” — the kind of person who he says “will steer the conversation about themselves.”

Most of us aren’t oppressive talkers or great listeners, observes Weiss.

“I think most people tend to fall more in the middle,” he says, adding that the “trick is trying to calibrate that balance.”

Here’s how Weiss, who originally wrote about his experience in a popular article titled “Do You Make This Mistake In Conversations?,” learned to become a better conversationalist.

He stopped interrupting and started listening

Weiss began to listen. He showed up to the police station earlier and interacted more with his officers, taking the time to talk to them about their home life and learning about what they were going through on the job. His relationship with his officers started to improve, he says.

“People love good listeners, they just do,” says Weiss. “We all have things we want to share that [are] important in our lives, and when you meet someone who is really interested and listens, and you know that they are listening because they ask you questions about what you’re talking about, that’s a wonderful thing.”

He stopped trying to win

Weiss began to avoid what he calls “conversational one-upmanship,” where one talker will consciously or unconsciously put down the person they are talking to. Conversations that devolve into political arguments are a good example, he says, but conversational one-upmanship doesn’t have to be political.

For instance, you tell a friend that you got a raise at work. Instead of congratulating you, your friend starts talking about his own recent promotion. Another example: You tell someone that your son recently got accepted into an Ivy League college — she interjects that her daughter was promoted at work. Both are examples of conversational one-upmanship.

“You would think friends would want to celebrate successes of their friends, rather than feel insecure about something positive that happened in their life, then have to counter with something even better that happened in your life,” says Weiss. “That’s what I mean by conversations turning into competitions.”

He learned to ask good questions

A great conversationalist knows how to ask meaningful questions, observes Weiss. Simple questions like “What’s new with you?” are generic and open-ended, and invite people to respond however they like. Instead, Weiss focuses on asking deeper questions around big issues.

“Trying to focus on ideas more than gossip or about small talk is, I think, a better way to have a conversation,” he says.

But he’s careful about bringing up issues that might be polarizing, noting “we have a divisive society right now with politics.”

If political discussions turn you off, he says, you can bring up books, movies, sports, art, or whatever interests you.

He keeps his phone in his back pocket

Rudely checking your phone during conversations, a habit known as “thubbing,” can be a major conversation killer, says Weiss. That’s why he leaves his phone in his back pocket during conversations.

Another conversation killer, he says, is pulling out your phone to show someone endless photos.

“We all enjoy a picture here and there — ‘Oh, that’s a beautiful picture you took of that sunset in Maui, or oh, yeah, your kid’s getting big, he looks great,’” says Weiss. “ But when it’s 20 pictures it’s like now you’re holding me hostage with all these photos.”

His relationships improved

Weiss says his relationships with his wife, friends and officers deepened after he became a better listener.

“I found that it just made for closer relationships,” says Weiss. “Slowing down to pay attention to what my wife was telling me after work was very much appreciated. It helped me remember things when it came time for an anniversary, a birthday, I knew what was going on with her, I had been paying closer attention.”

Weiss' tips for better conversations

  1. Stop trying to win. Constant interrupting and one-upmanship will be perceived as self-centered.

  2. Reciprocate. Don’t talk only about yourself. Ask questions of the other person.

  3. Focus on brevity. Ask yourself, “How long have I been talking?” 

  4. Don’t hold your listener hostage with small talk or mundane stories. Focus on issues they may find interesting, and show an eagerness to learn about what they think.


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