10 Keys to Having a Good Conversation

Our mission is to make people better overall communicators. Whether that means in a public speaking setting, in a small office meeting or at the dinner table.

As a writer, professional interviewer, and radio show host, Headlee has learned a thing or two about having engaging conversations. She dismisses the traditional “techniques” often used to show that you’re listening (i.e., head bobbing and parroting back what you heard). Those techniques aren’t wrong but could be perceived as inauthentic at times.

“There is no reason to learn how to show that you are paying attention if you are in fact, paying attention,” Headlee said. “We’ve all had really great conversations. We’ve had them before. We know what it’s like. The kind of conversation where you walk away feeling engaged and inspired, or where you feel like you’ve made a real connection or you’ve been perfectly understood. There is no reason why most of your interactions can’t be like that.”

Headlee’s 10 Keys to Having a Good Conversation

1. Don’t multitask.
“I don’t mean just set down your cell phone or your tablet or your car keys or whatever is in your hand. I mean, be present. Be in that moment.”

2. Don’t pontificate.
“You need to enter every conversation assuming that you have something to learn.”

3. Use open-ended questions.
“Take a cue from journalists. Start your questions with who, what, when, where, why or how…Try asking them things like, “What was that like?” “How did that feel?”

4. Go with the flow.
“That means thoughts will come into your mind and you need to let them go out of your mind. Stories and ideas are going to come to you. You need to let them come and let them go.”

5. If you don’t know, say that you don’t know.
“Err on the side of caution. Talk should not be cheap.”

6. Don’t equate your experience with theirs.
“If they’re talking about having lost a family member, don’t start talking about the time you lost a family member. If they’re talking about the trouble they’re having at work, don’t tell them about how much you hate your job. It’s not the same. It is never the same. All experiences are individual. And, more importantly, it is not about you. Conversations are not promotional opportunities. Stephen Hawking was once what his IQ was, and he said, “I have no idea. People who brag about their IQs are losers.”

7. Number seven: Try not to repeat yourself.
“It’s condescending, and it’s really boring, and we tend to do it a lot. Especially in work conversations or in conversations with our kids, we have a point to make, so we just keep rephrasing it over and over. Don’t do that.”

8. Stay out of the weeds.
“Frankly, people don’t care about the years, the names, the dates, all those details that you’re struggling to come up with in your mind. They don’t care. What they care about is you. They care about what you’re like, what you have in common. Forget the details. Leave them out.”

9. Listen.
“I cannot tell you how many really important people have said that listening is perhaps the number one most important skill that you could develop… When I’m talking, I’m in control. I don’t have to hear anything I’m not interested in. I’m the center of attention. I can bolster my own identity. But there’s another reason: We get distracted. The average person talks at about 225 words per minute, but we can listen up to 500 words per minute. So our minds are filling in those other 275 words. And look, I know, it takes effort and energy to actually pay attention to someone, but if you can’t do that, you’re not in a conversation. You’re just two people shouting out barely related sentences in the same place.

We have to listen to one another. Stephen Covey said it very beautifully. He said, “Most of us don’t listen with the intent to understand. We listen with the intent to reply.”

10. Be brief.
Be interested in other people.

Watch Headlee’s TedTalk here: