9 Tips for Becoming a Good Conversationalist

Some people have the gift of gab and can talk to anyone about anything. And some people struggle to make small talk. What separates the two isn’t knowing what to talk about; it’s polishing up your communication skills so you can keep a good conversation going.

“Good conversations require a give and take, just like keeping a ball in the air during a game of catch,” says Anne Green, president and CEO of CooperKatz & Company, a communications and media-training firm with clients that include Richard Branson. Thinking of a conversation as a game of verbal tennis will keep things flowing, but becoming a good conversationalist requires having more skills in your communication toolbox. Here are 9 habits that the best conversationalists have mastered to practice the next time you need them.

Why is being a good conversationalist important?

Being a good conversationalist can help you make a lasting impression. Whether you’re engaging in small talk at a networking event, or engaged in an intense negotiation, how you communicate with others will determine the outcome. Even in our digital world, knowing the art of the conversation is key to building strong relationships.

Good relationships require trust. When you trust the people you work with, for example, you are more likely to let them know when you’re struggling with a task or just feeling burned out. You let them know about your half-baked ideas, which might become the germ of something significant. Part of that trust comes from knowing the people around you, and how do you find out about the people around you? Through communication and conversation. 

As a good conversationalist, you are also better able to learn from the people you speak with, which can lead to career growth and opportunities and stronger connections.

Tips for becoming a better conversationalist

Here are 9 methods for improving your conversation skills.

1. Listen.

It may seem counterintuitive, but the best conversationalists aren’t those who always have witty things to say, but are those who are genuine listeners. Communications specialist Sasha Quintana, cofounder of Chatter Republic, says good listeners don’t just listen with their ears, but with their whole body. They lean into the conversation, establish eye contact, and provide their undivided attention to the person they’re speaking with.

Being a good listener also means that you’re not crafting your response as the person is speaking. “Too often we find ourselves thinking ahead to what we want to say next, not what the person we’re speaking with is saying,” says Quintana. Having a good conversation requires understanding the other participants. Shared understanding starts with really listening to what other people have to say.

2. Don’t try to dominate the conversation.

Good conversations aren’t a competition. They’re fundamentally cooperative. One person speaks. The other builds on that initial statement. The cooperation that builds trust can fall apart if the conversation becomes competitive. When you try to “win” a conversation, you may feel energized by the encounter, but it doesn’t deepen your relationship with your opponent.  

Sometimes, people spend conversations trying to impress each other, which means that each story becomes an attempt to one-up the one just told. Other times, the topic of the conversation focuses on a point of disagreement and the discussion becomes a debate in which each side tries to convince the other that their point of view is correct without truly engaging in discussion. 

But the most common type of conversational competition is when one speaker dominates the airspace, making it difficult for the other person to get their point of view in or even speak at all.  A good conversation should be a give-and-take of information, like a ping-pong game. If the ball stays on one side of the court for too long, both parties will soon lose interest in the game and move on.

3. Pay attention to body language.

Riaz Meghji, a human connection expert and author of Every Conversation Counts, says that if you want to build a human connection with the person you’re talking to, you need to focus completely on the other person. “Listen to what isn’t being said. Listen for tone and watch their body language for clues about how they’re feeling,” Meghji says.

Good conversationalists listen with their eyes, looking for body language or changes in mood that provide information about the other person’s interest level in the conversation. This can help you redirect or improve the conversation in the moment, says Parker Ellen, professor of management and organizational development at Northeastern University

4. Be informed and come with interesting topics.

Be a person of interest by reading and informing yourself on a variety of topics from world affairs to business and culture, says Suzanne Bates, author of All the Leader You Can Be, the Science of Achieving Extraordinary Executive Presence. “Be bold in getting beyond pleasantries to introduce high-interest topics likely to enliven a conversation,” she says. “Be attuned to each person to meet them where they are and be curious about their views.”

Being well read allows you to introduce ideas and stories from other domains, adds Mark Levy, president of the branding firm Levy Innovation and author of Accidental Genius: Using Writing to Generate Your Best Ideas, Insight and Content. “When a businessperson wants to make a point in conversation, they’ll often rely on an idea, opinion, or story from the world of business,” he says. “After a while that gets old. We’ve all heard the same business stories, and we start to mentally check out.”

Good conversationalists “seed a conversation with jolts,” says Levy. “If you’re talking about, say, workplace productivity, it’s fine to talk about [the Civil War battle] Pickett’s Charge or black holes or an idea from an Elizabeth Gilbert book that, in some way, relates to workplace productivity. Bringing in ideas from other domains keeps people awake and interested, and it’s actually how paradigm shifts are born.“

Be careful, though. Don’t listen just to bring up something you’re interested in discussing. And of course, stay aware of your conversation partners: if they’re not interested in the latest article you read, don’t drone on and turn the conversation into a lecture.

5. Be empathetic.

Another way to build rapport is to show empathy. “Don’t just put yourself in the shoes of a friend or a close colleague,” Meghji says, but “challenge yourself to realize the perspective of someone who’s really different from you.”

You can also practice being empathetic even when you don’t agree with the other person. How? “Be less quick to take issue with that person,” says Meghji. Instead probe. Ask someone whose idea seems far-fetched: “What would it take to make that work?’”

Meghji explains, “It’s so easy to jump to judgment, so suspending that judgment is an act of empathy.” The conversation becomes “us together, rather than me versus you.”

6. Ask strong questions.

“As someone who had little to no experience in business–outside of running my own one-man freelancing operation–all that’s really saved me (so far) from madness are the skills I used as a journalist,” says Evan Ratliff, who wrote for magazines like The New Yorker before founding his startup, The Atavist. One of those skills, he says, is “being able to formulate questions that deliver useful answers, whether from advisors or clients or whomever.” Good questions can move your business, organization, or career forward—as well as any conversation. 

“Great conversationalists know that communication is a dance,” says Quintana. Look for commonalities between you and the person you’re speaking with. Open-ended questions, those that require more than a “yes” or “no” answer, are the best type of questions to ask if you’re looking to establish common ground. Asking, “Where are you from?” “How long have you been in the industry?” and “What did you think of that speaker?” are great starting points, but after the ice is broken, you need to keep going.

Here are some tips on asking strong questions:

  • Don’t ramble on–terminate the sentence at the question mark. When people are nervous, they tend to ramble, and their questions tend to trail off into a series of possible answers. (“What’s the most effective way to find a good programmer? Is it to search on Monster or to go on LinkedIn or to talk to people you know or … uh… uh… yeah, is it to, um…is there another job site that’s good …?”) You’re the one with the question; why are you doing all the talking? 
  • Get comfortable with silence. Allow your respondent to think; don’t jump in after a few seconds pass. You won’t get answers if you keep talking, and you’ll rarely learn anything if you offer all the answers.
  • Start with “who, what, when, where, how, or why” for more meaningful answers. These have a high probability of thoughtful responses, whereas those that begin with “would,” “should,” “is,” “are,” and “do you think” can limit your answers.
  • Don’t fish for the answer you want. “The really ‘bad’ questions are leading ones–the questions where you’re fishing for a particular answer,” says veteran journalist Clive Thompson, who writes for Wired and The New York Times. If you know the answer, why are you asking? If you’re seeking confirmation on something you already suspect, ask objectively, and ask directly. You’ll come off as confident, and you’ll get more honest answers.

7. Give strong answers.

“When someone directs a question your way–when the ball is thrown to you–you should always respond with an answer that will continue the flow of dialogue, passing the ball back and never letting it drop,” says Green.

If a musician is asked, “What kind of music do you play?” for example, Green says the response “many different kinds” will shut down the conversation. “The key is to answer and elaborate,” she says. “A more effective response to that same question would be, ‘I play many different kinds of music, but I spent my early twenties in the South playing a lot of country music, which I’ve since brought to my music career in New York City.’ That gives the other person something to work with, creating a more stimulating conversation.”

8. Dig deeper.

 Meghji recommends going “big” with your small talk. We often engage in chitchat that doesn’t build a connection. So abandon tired old questions like “Hey, how are you doing?” and “What’s up?” Such conversational chatter is, according to Meghji, “a defense mechanism to keep us from getting emotional in front of another person.” 

Instead, he advises that you should show genuine curiosity by replacing stock phrases with more pointed expressions of interest. Instead of generic questions like “How are you?” be more specific. 

“When you say to someone “how’s work” they’re going to say ‘pretty good’ or ‘good’ or ‘great’ or whatever,” says Debra Fine, author of the bestseller The Fine Art of Small Talk. Instead, “dig in deeper, let them know you’re sincere with one more question. Say something like, ‘So, what’s been going on with work, Bud, since the last time we talked?’ Or if you say to somebody ‘How were your holidays,’ and they say ‘great,’ you can follow up by saying, ‘What did you do over the holidays that you enjoyed the most?’” Let them know you are sincere. 

9. Don’t try to be perfect. 

A good conversationalist isn’t afraid to show they don’t understand, Levy says. “So many people shoot themselves in the foot, because they’re trying to come across as all-knowing or perfect, but letting the other person in on your lack of understanding can actually be flattering to them,” he says. If you’re confused, Levy suggests asking, “I want to make sure I really understand what you mean. Can you say what you just said in a slightly different way?”

Additionally, don’t be afraid to look vulnerable, says Meghji. Social media encourages us to look “camera ready,” visually perfect, engaged in enviable activities, wearing the best outfits, showing perfect bodies. This pressure means “it’s tough to open up and show vulnerability, especially for millennials,” he says. “They worry that ‘if I share my truth I might say the wrong thing, and alienate myself from my community.”

Conversations provide a perfect context for breaking from the “perfection” trap. Suppose a new group of recruits joins a company, and on their first day they are nervous and scared. The leader has a great opportunity to show that they don’t have to feel perfect. He might say, ‘Welcome, I know first days can be scary; I remember I felt that way when I joined. But we’re here for you, and glad to have you aboard.’” By being honest ourselves, we encourage that in others, Meghji says.

LISA EVANS, BUD BILANICH, SHANE SNOW, ART MARKMAN, and JUDITH HUMPHREY also contributed writing, reporting, and/or advice to this article and a previous version. 

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