How to Become a Better Conversationalist and Connect With Anyone

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9 Strategies to Help You Become a Better Conversationalist

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Growing up as an introvert, I used to dread having conversations with people I didn’t know well.

My face would swell with heat as if I had just swallowed an entire chili pepper. My mind would frantically race in an attempt to find the right words to say—and draw a blank. And I would worry too much about things like my mismatched outfit, the gigantic zit on my face, or whether someone could smell my lunch on my breath to really feel at ease.

Not to mention, I was scared to death of awkward silences. You know, those moments when the air would stiffen and the already dwindling conversation would come to a complete halt. Moments like these almost always made me want to run and go bury my head in the sand.

And awkward silences weren’t the worst. What was even more devastating was when a look of boredom would glaze over people’s eyes. When that happened, I could almost hear my heart shatter into a thousand pieces.

Any of these sound familiar to you?

I’m guessing you’re here reading this post because, like me, you weren’t born with the gift of conversational charm. And you probably have an event coming up—a party, an interview, a meeting, or a date—where you’re going to have to converse with someone you don’t know, and you want to leave a good impression.

The good news is that conversation skills, like many other skills in life, can be improved with practice. Take myself, for example, although I still get butterflies at times, now I’m confident that I can carry out a conversation with someone I’d just met without drowning in cold sweat.

How did I get here? It all started with the realization that I had to become a better conversationalist.


how to become a better conversationalist Pinterest image of a woman with big hair smiling


My Quest to Become a Better Conversationalist

I remember the first time I attended a networking event. It was shortly after I began my first year of business school. A few alumni who had graduated from the school came to give a talk to the freshmen—you know, motivational speech, sharing wisdom, that sort of thing.

Afterward, there was a cocktail reception for everyone to mingle.

Within minutes of the drinks being handed out, a horde of bright-eyed business students formed around the alumni like bees around their queen.

The ones who couldn’t get close enough to the stars of the day quickly engrossed themselves in conversations with professors, Teaching Assistants, or classmates.

I desperately wanted to join in, but I couldn’t. I didn’t know how to strike up a conversation in a place like this or what to say once I exhaust the usual “how did you like the talk?” or “who do you have for Accounting 110?”

So the entire time, I just hung around the sushi station until I found a moment to slip away.

As I rushed down the dark corridors of the school as if I was running away from a crime scene, I realized something important:

Unless I quit business school and became a genius solitary scientist (which was unlikely), and stayed away from all social situations that involved meeting new people (which was unappealing as even the most introverted part of me still craved connection), this would not be the last time I’d have to talk to people who were outside my realm of familiarity.

Instead of running away from conversations with strangers in fear of awkward silences and forced small talks—I would have to learn to be a better conversationalist.

But the question was: how?

To answer that question, first I had to know what made a good conversationalist, well, good.


Qualities of a Good Conversationalist

What qualities do people like Oprah, Barbara Walters, or Katie Couric—women I admire and regard as queens of conversation—have in common?

I boiled them down to these 5 things:


1. They have an amazing ability to build trust

Trust is a fundamental element of a good conversation. If there’s no trust, there’s no real sharing of information and genuine connection. Good conversationalists are able to build trust with people they talk to, often within seconds of meeting them.


woman with a hat smiling


2. They’re clear and concise without seeming aloof

There are people who talk a lot but say very little. Their conversations are filled with jargon, empty flattery, or random jumps from one thought to another without a clear idea of what they’re trying to say. Good conversationalists are the exact opposite. Their words are simple, clear, and to the point without being rude or distant.


3. They understand emotional cues and respond appropriately

Good conversationalists watch for—and respond to—emotional cues from others. They can pick up the slightest change in someone’s expression, tone of voice, or body language. This helps them make the appropriate adjustments in themselves to fit the situation. They know how and when to switch topics, change the pace, or stop the conversation altogether before it derails.


4. They’re funny at the right moments

Humour is like a spice—it can add a punch of flavour to a conversation and even save a tense situation from the brink of disaster. But humour is only effective when it’s used sparingly and at the right moments. Good conversationalists understand this. They know the exact moments to inject humour in their conversations and deliver just the right amount.


5. They’re jack-of-all-trades when it comes to knowledge

Good conversationalists may not be experts in many fields, but they know a bit of everything. From art and science to European history and the emerging science of epigenetics, a good conversationalist can dabble in a wide range of topics with many different kinds of people.


Now think of a good conversationalist you know in your life. Could be a celebrity, a friend, or even someone you’d just met briefly. Do they possess any of the above traits?

I bet you’re nodding your head.

So the next question is, how can we adopt these qualities ourselves?


How to Be a Better Conversationalist: 9 Things You Can Start Doing Today


how to become a better conversationalist Pinterest image of a group of people talking at a park


Here are 9 strategies I learned in my own quest to become a better conversationalist. They’re simple things you can do starting today to make your conversations more engaging and build a real connection with people you meet.

Ready to become a better conversationalist?

Keep reading!


1. Connect Instantly With Anyone By Doing This One Simple Thing

A few years ago, I attended a communication class for work. The purpose was to help me learn how to build rapport with different kinds of people that I work with (I work in human resources).

And I stumbled upon one of the best communication tips EVER. I promise you, this simple tip will help you communicate in a way that establishes trust and connection:

Identify and validate the other person’s values.

There are a number of fundamental values that are important to people. For example: family, love, honesty, integrity, and so on. These fundamental values naturally seep through the way we talk in our everyday lives.

So if the conversation is about the weather, and the other person makes a comment that goes “well I’m going to have to find something else to do with my kids in this weather”, that’s an indication that “family” is likely an important value to them.

Instead of asking what they’re planning to do, which leads to another generic and meaningless topic, simply smile and ask:

“Sounds like family is very important to you?”

99.99% of the time, the person will smile back with their eyes as bright as the stars and start telling you why and how their family is important to them.

And that’s instant connection right there.


2. Get a Library Card

Because in order to be a great conversationalist, you’re going to have to read. A lot. Current events, social trends, economics, science, art, you name it.

Reading not only strengthens your knowledge base, it also expands your world view and changes your perspective. The facts, ideas, insights, and questions you find in various kinds of publications are going to be the source of fuel that keeps your conversations not only alive, but engaging.

Reading is what helps you become more interesting from inside out.

And here’s a free app to help you read more, it’s called “Libby”. It connects to your local libraries and allows you to search their catalogs, download and listen to various audiobooks for free. Libby has helped me “read” dozens more books this past year and revived my love for the written word.


woman reading a book by the side of the road


3. Check-In Often With Yourself

Raise your hand if you’ve ever done any of the following in the middle of a conversation:

  • Jumped in before the other person finished their sentence
  • Hijacked a conversation by doing most of the talking
  • Allowed your mind to wander elsewhere
  • Decided on a response before you’ve had a chance to hear everything the other person had to say

We’ve all been there. Although we like to think of ourselves as good listeners, most of us don’t listen well. Researchers from the University of Minnesota ran tests that showed that the average person—no matter how good of a listener they believe they are—only retains half of what the other person says in a conversation.

That’s why it’s important to check in often with ourselves during a conversation. Are we talking more than listening? Are we giving the other person ample space to finish their thoughts? And are we fully present in the here and now?


4. What Do Walt Disney and Richard Branson Have in Common?

They’re both amazing storytellers.

If there’s a secret to being a good conversationalist, storytelling would be it. As humans, we’re naturally fascinated with stories. No one knows for sure why, but there appears to be an evolutionary advantage to storytelling.

So how can we become better storytellers ourselves? For some inspiration, watch this TED talk by international speaker, author, and presentation skills coach David JP Phillips:



5. Ask This Type of Question

The best kind of question to ask in a conversation is this:

Open-ended follow-up questions.

Not only will they help keep the conversation flowing, they will also send a clear message to the other person that you’re listening and interested in what they’re saying.

Here are some examples of open-ended follow-up questions:

“Tell me more about…”
“What did you mean by…”
“How did you feel when…”

Notice how they differ from close-ended questions such as “do you like apple pie?”

A close-ended question can bring a conversation to a sudden halt because the answer is short and generic. There’s not a lot of material for you to work with in a “yes” or “no” response.

An open-ended question, on the other hand, can bring in a flood of new information for you to explore further.

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6. Strip Naked

Your Language That Is.

Strip down everything that’s not simple or common in your message until you’ve got sentences a sixth-grader could understand.

That means no jargon, legalese, or tech speak—because you might as well be speaking Martian. At best they hinder clarity, at worst they cause costly errors and unnecessary conflict.

And while you’re at it, ditch any vague—but often trendy—terms like “paradigm shift”, “value-add”, or “deep dive”. They can make you seem less trustworthy.

Last but not least, pay attention to filler words we say out of habit.

Here’s one great trick I learned from a presentation class on how to catch them in our vocabulary:

Record yourself giving a presentation, or with the permission of a friend or family member, record a normal day-to-day conversation with them.

You might pick up like useless words that you can like cut out from your speech because they’re like sooooo annoying.


7. Remember You’re Not Seth Rogen

If I’m talking to Seth Rogen, I expect that he’s going to make me laugh at least a few times every minute.

But you’re not a comedian (probably).

No one expects you to make them laugh every other sentence, so relax! You don’t have to try so hard to be funny. In fact, humour—according to researchers at the Wharton School of Business—is risky. If not careful, you could really miss the mark with your humour, sometimes spectacularly.


Here’s my golden rule when it comes to using humour in a conversation:

Never insert jokes and funny stories into a conversation for the sole purpose of “being funny”.  But if the conversation gets to a point where it’s appropriate to tell a funny personal story that’s relevant to the topic, go ahead and share your story. Funny things that happen in our daily lives come off more natural and sincere compared to jokes.

But before you tell any funny stories or jokes, always be mindful of cultural differences. What may be funny in North America may offend somebody from Asia, and vice versa.


8. Practice This Language

Your body language is just as, if not more important than the language that comes out of your mouth.

So much of what we communicate is in the non-verbal cues. We can send a message about whether we like and trust the person in front of us with things like how far or close we stand, where we put our hands, or even something as subtle as whether we squint our eyes when we smile.

When you understand the power of body language in communication, you can adjust your body language to enhance your message. You’ll also become better at reading other people’s emotions too—which—as I mentioned earlier, is a key trait of a good conversationalist.

Now here’s an excellent presentation by interpersonal intelligence expert and public speaker Vanessa Van Edwards on how we can use microexpressions and body language to help us become better conversationalists:




9. Don’t Be a Know-It-All

Have you ever talked to somebody who’s a “know-it-all”?

I knew someone like that. Whenever he spoke—usually to correct someone or to give unsolicited advice—the room would fall silent. One time, he gave me a piece of unsolicited advice about how to run my wedding based on his “years of event planning experience”. After I politely voiced a different opinion he rolled his eyes at me as if I was about to make the gravest mistake of my life and I was too stupid to know it.

Needless to say, we didn’t talk much after that.

The lesson here is don’t be a know-it-all. Don’t go correcting someone’s grammar or shove your nuggets of wisdom down their throat. These are some of the fastest ways to turn a conversation off.

There’s nothing wrong with sharing your knowledge and experience from time to time, but for the most part, stand back, keep your mouth closed, and learn from others. And we can all learn something from another person, even someone much younger or less experienced than us—if we stay curious and humble.


That’s it for my 9 strategies on how to become a better conversationalist. Now it’s my turn to learn from you. When was the last time you had a great conversation with someone you didn’t know well? What made it great? Let me know via the comment section below!

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