You Can Learn To Be A Better Conversationalist. Here's How.

You have to admit that many of us have lost the art of conversation. It’s easy to point to our phones and social media as the main culprits. The effects of COVID didn’t help either. Even the growing acceptance of introversion plays a role.

But becoming a better conversationalist is a skill that could benefit many of us. It requires curiosity, genuine interest and a willingness to connect — qualities that not only strengthen your social skills but also lead to more meaningful interactions.

Recently, I attended a cooking class, and my station was next to a woman who was far more adept at cutting and slicing and dicing than I was. I wanted to engage with her — for a moment I thought about asking how she became so good at her knife skills, and then thought better of it. Ultimately, I didn’t end up talking to her. I told myself all sorts of excuses — she was busy, she didn’t want to be interrupted — but really, it was because I got in my head about how to start small talk. Basically, I didn’t want to sound like an idiot.

According to psychologist Dr. Ashley Smith, my reaction is completely normal. “It’s that sense of awkwardness that is the biggest barrier for a lot of people when it comes to small talk, starting conversations, or just connecting and networking,” she said. “For a lot of people, awkwardness triggers anxiety, so we need to break that connection. Doing so allows people to feel awkward without fear or nervousness.”

The real goal, said Smith, is to learn to tolerate awkwardness — and that takes intentional practice: “The best way to overcome any fear is to face it. In this case, that boils down to taking small steps by doing things that feel a little awkward to you. That could be saying hello to strangers as you pass them, asking questions of sales clerks at stores, or asking servers, baristas or Uber drivers questions,” she said. “The goal is just to get used to putting yourself out there. The more you do it, the easier it gets. Anxiety will go down, and your threshold for awkwardness will increase, meaning that it will take more of it to make you uncomfortable.”

One of the biggest misconceptions about conversation, said Kati Morton, a licensed marriage and family therapist, is that it’s a talent some people have and others don’t.

“In reality, conversation is a skill, and like any skill, it gets easier with practice and a little structure,” she said. “Most people struggle not because they’re bad at talking, but because they feel pressure to be interesting or say the ‘right’ thing. That pressure can make us overthink and actually shut down our natural curiosity.”

A helpful shift, Morton said, is to focus less on performing in a conversation and more on being curious about the other person. “People tend to feel most comfortable with those who ask thoughtful follow-up questions and show genuine interest. Good conversation often follows a simple rhythm: share a little, ask a little and build on what the other person says.”

So how do you actually get better at making conversation, especially when it feels awkward? Experts say it starts with a few small, practical shifts.

Conversation takes practice, not confidence.

One of the biggest mindset shifts, Smith said, is understanding that confidence doesn’t come first — action does.

“People tell me that they want to feel confident. If they felt confident, then they would go do XYZ. It’s a backwards process, though. Confidence doesn’t come first. Action does. You have to go do things, over and over and over. Then, you’ll feel confident,” she explains.

If you’re shy or socially anxious, she recommends starting small and thinking of it like building a muscle. “It takes a ton of repetition to build comfort,” she said. Simple ways to get those reps in include saying hello to strangers, giving someone a compliment or asking an employee a question at a store. “Your mind will tell you it’s awkward, but your mind is lying. It’s not awkward, even if it feels that way. Feelings aren’t facts.”

When it comes to the conversations themselves, small tweaks can make a big difference. One of the easiest ways to move beyond surface-level small talk is to ask more engaging questions. Instead of the usual, “What do you do?,” Smith suggests trying, “How do you like to spend your time?” or “What do you do for fun?” — questions that naturally open the door to more interesting and meaningful exchanges.

Another strategy is to share something a little personal. “When you open up and are a little vulnerable, the other person will return in kind,” she said. “This starts a deepening loop of trust.”

Don’t sleep on these conversation starters.

Of course, putting yourself out there is only part of it. The next question is: What do you actually say once you do? In my cooking class example, what could I have said to get the conversation going — something that didn’t necessarily start with talking about knives?

Morton said building better conversation skills often comes down to a few simple, repeatable habits:

Being present counts for a lot. 

Being a good conversationalist isn’t just about what you say — it’s also about being present with the person you’re talking to.

“To stay present when you feel nervous or distracted, first, put your phone away. It’s tempting to have it out or in your hand, but a phone disrupts connection, even if you don’t look at it,” Smith said. “Then work to maintain eye contact — or focus on their forehead or nose if direct eye contact feels too uncomfortable. Practicing mindfulness regularly strengthens your ability to control your attention, so you can focus on the parts of the present moment that matter, rather than being hijacked by anxiety or distractions.”

Another tip? Listen to understand, not to respond. “If you tend to jump ahead in your mind, planning what you’re going to say next, you’re not really being present,” according to Smith. “Instead, try silently repeating the other person’s words along with them in your head. This helps train your focus, allowing you to pick up more of what they’re actually saying and respond more thoughtfully.”

Morton adds: “Stop planning your response while they’re talking. Instead, pay attention to what they’re saying and how they’re feeling. Then reflect it back: ‘That sounds really frustrating’ or ‘So you felt caught off guard?’ Feeling understood matters more than saying the ‘right’ thing.”

Silences don’t need to be awkward.

For many people, avoiding conversations means avoiding the awkward silence that might come after putting yourself out there. No one likes the sound of crickets, but Morton points out that most people are “relieved when someone else starts the conversation. If there’s a pause or moment of awkwardness, that’s not a failure, it’s just part of normal human interaction. Silence isn’t failure, it’s processing time. Most people don’t notice it as much as you think.”

If the silence stretches, Morton suggests gently re-engaging with something simple: “Wait, I’m curious, how did that go?” “You don’t need perfect flow,” she said. “Just presence.”

Yes, you can start a conversation with anyone.

You don’t need to only talk to people from your generation or in the same industry or even the same barista at your favorite coffee shop. It might feel more comfortable to do so, but Smith said you can talk to just about anyone, anywhere.

“I’m a bigger believer that you can find common ground with anyone if you’re willing to set aside judgments and preconceived notions and make the effort to find it,” she said. “Ask questions: What do they like to do? What was the last thing that made them smile? What kind of music, movies or books do they enjoy? Where was their last vacation? Treat it like a fact-finding mission — you’re trying to find one thing you have in common. Side note: Research shows that we have more in common than not. Everyone wants security, safety and for their kids to be happy.”

Smith suggested breaking the ice with a compliment or a story. When someone shares something about themselves, ask a follow-up question before relating it back to you. If they share good news, amplify it by asking more about it rather than just saying “That’s great!” or “Congrats!”