5 Tips for Introverts That Can Make You a Great Conversationalist
By: Anthony J. Yeung
Tags: Communication, Life Lessons, Personal Development, Self Improvement, Self

Back in high school, I was extremely shy and deathly afraid of talking to people I didn’t know. In college, I hit a breaking point and gave myself a challenge: For 90 days, I forced myself to talk to at least one stranger every day and even took notes to analyze how it went.

It was painful. It was embarrassing. It was uncomfortable. To make matters worse, I had body image issues because I was short, skinny, and covered with acne.

90 days later, however, I became a new person.

Since then, I spent years refining what works and what doesn’t and learned how to start conversations, build connections, and make new friends, no matter the language, country, or situation.

Without a doubt, few life skills can make a bigger impact on your life than learning how to have great conversations and create strong connections. And if I could do it, trust me: So can you. Here are my five best tips that work whether you’re shy or introverted—that I had to learn the hard way:

1. Stop Asking So Many Questions.

Almost every article online about conversations tells you to ask a lot of “open-ended” questions, which are questions that don’t have a yes-or-no answer. (Closed-ended: “Are you from here?” vs. Open-ended: “Where are you from?”) The reason behind that is to get people talking and push the conversation forward.

And when I started talking to strangers, I definitely relied on this tactic too. Sometimes it would go okay, but other times I felt like it was only going because I kept asking questions. Worse, if I couldn’t get them to ask me questions in return, the conversations would eventually die.

But while it’s okay to ask a few questions, here’s why relying on them is actually a bad tactic:

It creates “question trains,” which are situations where you ask question after question until it sounds like an interview. “What do you do? How long have you done it? What do you like about it?” (Often, people do this when they don’t know what to say and just use questions as a crutch.)

which are situations where you ask question after question until it sounds like an interview. “What do you do? How long have you done it? What do you like about it?” (Often, people do this when they don’t know what to say and just use questions as a crutch.) It forces conversations. Sometimes, people ask a lot of questions to try to keep someone talking with them; the other person is losing interest so you just keep asking them things so they don’t leave.

Sometimes, people ask a lot of questions to try to keep someone talking with them; the other person is losing interest so you just keep asking them things so they don’t leave. Questions take value. Rather than sharing anything unique about yourself, you just ask questions to get information and push the conversation (and make them do all the work).

Instead, make more statements. Statements are opportunities for you to share something about yourself, your personality, and your perspective.

Even better, when you make a statement and they respond, they won’t feel like they’re being “forced” to interact with you. Instead, they’ll voluntarily talk with you because they feel comfortable opening up.

Bad Example:

You: “Where are you from?”

Them: “New York.”

You: “Where in New York?”

Them: “Queens.”

You: “What’s your favorite thing about living in New York?”

Them: “Uh, I don’t know.”

Here, you’re making them do all the work without sharing anything about yourself or even hinting at why you’re asking. (You also asked three straight questions; the last one a really big one that takes a lot of work to answer.)

Good Example:

You: “Where are you from?”

Them: “New York.”

You: “I’m jealous: I love New York. I’m always amazed at how much there is to do there.”

Them: “Yeah, it’s a really great city. I love it too.”

You: “I never got cussed at though; so I never had the real New York experience.”

Them: “Haha, I yelled at someone last week.”

You: “That’s hilarious! I gotta hear about it!”

Them: [tells a story]

Here, you shared about yourself, your experiences, and your perspective. You only asked one question and built off it. You never forced them to talk to you; instead, your statements invited them to respond.

That, ultimately, is the goal: Getting people to feel comfortable opening up about themselves. And the only way to do that is for you to open up first.

I’m not saying you should never ask a question, but try to limit how many questions you ask. And if you do ask a question, make sure it’s an interesting one: “What’s the easiest way to tell someone isn’t a native New Yorker” is much more interesting than “What’s your favorite thing about living in New York?”

2. Start Your Conversations Strong.

I used to think that I needed to have a great “opener” to start a conversation—something brilliant to say that would start an awesome conversation 100% of the time. A witty observation. A funny comment. (After all, you’ll find countless articles with tons of conversation openers.)

But the hard truth is no opener works 100% of the time. In fact, if you learn only one thing from an article, let it be this:

What you say is the least important thing when starting conversations. The most important thing is your vibe, energy, and tone.

You see, people often initiate conversations weakly — talking with their bodies facing away or while looking at their phones. But when you’re timid and hesitant, no one leads the conversation and odds are it won’t last. (Being tentative usually means you’re afraid to put yourself out there and protect yourself from rejection.)

Instead, start a conversation strong. It should be like trying to break a wooden board in karate—if you commit, you’ll succeed, but if you’re hesitant, you’ll fail. Go all-in and put your full attention and energy behind your words. Make it crystal clear you are initiating conversation. Commit to talking to them. It shows a lot of confidence and lets the other person know your intention.

At a certain point, I stopped trying to think of a clever opening “line” or “question;” I often just walked up to a person and said, “Excuse me… hi, how’s it going?” And it worked! More importantly, whenever I committed fully to talking to someone, I never got brushed off. Here are some tips to do so:

Point your body directly towards the person

Maintain solid eye contact

Speak at a good, audible volume

Add more tonality to your voice (so you don’t sound monotone)

Don’t pull out your phone or try to distract yourself

3. Increase Your Vibe And “Overact.”

When you first talk to a stranger, they’re not really listening to what you say; they’re assessing your vibe and energy. Are you friendly? Dangerous? Creepy? (That’s how our brains are wired.)

So, when you begin a conversation, don’t just start with the energy level you’re currently at; always have a little more energy than the other person.

That way, you have enough enthusiasm, energy, and passion to elevate them and draw them in without going overboard and having way too much energy compared to the other person. (In my experience, I always start better conversations when I’m in a light, fun, and bouncing mood.)

Also, try to “overact” so your emotions are clear. Add more tonality to your voice, add more enthusiasm, feeling, and energy behind what you say, and be more animated. (ex. saying “I love this place…” vs “I love this place!”) This is even more critical when having conversations over a video or phone call.

Here’s why: When you’re with your friends, you could slightly lift one eyebrow and everyone would know how you’re feeling. But when you’re talking with someone who’s never met you before, that context doesn’t exist—by overacting, you can be understood. (It might seem weird to you, but to the other person, it seems fine.)

If you struggle to have the right vibe, one trick I used when I was doing my 90-day challenge in university was to listen to music before I started my day. Something with a good beat and with good energy was enough to give my spirit (and conversations) a boost.

4. Don’t Being Interesting; Be Interested.

Two years ago while I was staying in Budapest for a few weeks, I met this girl who was traveling through as well. We ended up talking, hitting it off, and going on an impromptu date that lasted the rest of the night.

“You know,” she said and we were sitting hand-in-hand, overlooking the river, “I actually don’t much about you. You didn’t really say much about yourself.”

I laughed inside.

Some people converse by boasting about all the things they’ve done to make themselves look cool so others will be impressed and want to talk to them. Talking to them eventually turns into a competition and an exercise of one-upmanship. (“Oh, you when to Budapest?! I went there 15 times!”)

But from what I’ve seen, the key to great conversations is to make other people feel cool and interesting. Take an interest in them. Be fascinated with what they do. Make them the star of the show.

Don’t be interesting — be interested.

When you take a genuine interest in others, great things can happen. Most surprising of all, if you do this right, others will find you interesting. After all, it’s rare to encounter a person like this. (In fact, only people who are actually interesting people don’t need to take center stage.)

5. Appreciate What They Say.

While everyone teaches you to “listen,” I’ll go one step further. During a conversation, when someone shares something unique or interesting, don’t just nod—genuinely appreciate what they did and explain why.

Years ago, I was at a Starbucks, taking a break from a cross-country drive, when I saw three guys hitting on the female baristas. During their “chat,” a barista said she lived in Okinawa for three years teaching English.

A good-looking guy said (I swear), “Nice. So what time did you open today?”

My jaw dropped. Can you imagine how much courage it took to make that life decision? Or the learning, culture shock, and challenges she endured? You have to appreciate that.

Needless to say, they left empty-handed. (Funny thing was, I ended up talking to the baristas, had a great conversation, and got a free drink.)

When someone tells you something awesome, unique, deep, or detailed, you must appreciate what they said. For example, if they tell you that they’re backpacking through South East Asia by themselves, tell them that you admire the courage. If they tell you that they moved to a new country to chase a dream, tell them that you're impressed by their story.

It shows that you value their input. It helps them feel comfortable and safe to open up about themselves and share experiences, feelings, and emotions with you — while you do the exact same thing. (But if you skip this step, you’ll show that you don’t really care.)

Use these tips and watch what happens—it might just change your life.