How to Be a Better Conversationalist and Build Stronger Connections, According to Experts

Holding your own in a conversation is a powerful life skill. Honing this skill, though, can be tricky if making small talk and asking follow-up questions isn’t your strong suit. Isolation practices during the COVID-19 pandemic have “significantly worsened our ability to converse,” adds Racheal Turner, LPC, an Arizona-based therapist. “As a therapist, I see firsthand how many people are still struggling to find their voice, with long-lasting effects continuing into 2024,” she says. “This issue is particularly pronounced among the children I work with.” Even if you’re not a naturally chatty person, it’s possible to be a good conversationalist.

Once you learn how to be a good conversationalist, the positive ripple effect is noticeable. In practice, knowing how to be a good conversationalist might help you land a job interview, connect with a stranger, or score a repeat invite to a dinner party. A 2022 study² published in the Proceedings of the National Academy of Sciences reported that people tend to underestimate how much they can learn from and enjoy conversations with strangers. So, putting yourself out there by striking up a conversation with a friend of a friend at their birthday party might feel awkward at first, but it could also lay the groundwork for a useful connection or a meaningful friendship.

Because we can all benefit from working on our interpersonal skills, we tapped a few experts to learn more about how to be a better conversationalist, what healthy conversations look like, and how to start a conversation without being awkward.

How can I be a good conversationalist?

With the right approach, you can learn how to keep a conversation going and reap the benefits of connecting with others. Below are six expert-backed tips for how to be a better conversationalist.

1. Listen closely

Giving someone your undivided attention and listening closely to what they say goes a long way. By paying attention, you’re communicating that you care about their thoughts and opinions, says Dave Smallen, PhD, a research psychologist who studies relationships and human connection. “For example, if we are speaking with someone who we are just getting to know, we might find ourselves thinking about what to say next, focusing on the impression we are going to make with our next comment, rather than what the other person is saying,” he explains. “Yet it is the spaces between what we say that often make the biggest impression on others, where we are communicating to them that we are warmly open to what they are sharing, and so we are going to cultivate a more meaningful conversation if we are present in that way.”

To practice active listening during a conversation, make eye contact with the other person and avoid looking at distractions like your phone, adds Turner. “One helpful technique is to rephrase what the other person said, ensuring they know you were paying attention,” she says.

2. Be curious and open to other perspectives

It helps to approach a conversation from a place of curiosity and interest in what the other person has to say, according to Dr. Smallen. “This allows us to hold back from imposing our perspective on others, which can feel intrusive and shut down the flow of a conversation,” he says. Of course, this is easier said than done as being open to other people’s perspectives also means hearing them out when they express opinions that differ from your own. “If there is nothing at stake and you hope to connect with this person, simply hearing their perspective and story will be meaningful to them, rather than expressing that you believe they are wrong,” Dr. Smallen says. “We are not likely to change anyone’s mind, and so, if we want to connect, we benefit from openness and curiosity.”

3. Allow for awkwardness

Your conversations won’t always flow perfectly, and that’s okay. “We can’t expect to just be immediately on the same wavelength as everyone else; we have to find that shared wavelength together, in collaboration,” says Dr. Smallen. “For example, if we are talking to someone we just met, there might be some false starts, some talking over one another, some nervous laughter.” All of this is completely normal, and the conversation can carry on smoothly even if you hit a few bumps along the way.

4. Allow each other to speak without interruption

While it may be tempting to immediately jump in when a thought strikes, ideally you’ll give the other person the floor to speak without interrupting them. “Let the other person finish what they are saying, as interrupting it can come off as rude and disrupt the flow of conversation,” advises Debra Roberts, LCSW, conversation expert and creator of My Communication Tools. “And while waiting to chime in, don’t start thinking about what you are going to say next as you’ll miss out on the active listening part of being a good conversationalist.”

5. Ask open-ended questions

If the other person’s comments bring a question to mind, ask away. “A good conversationalist contributes to the conversation but also engages with the other person by asking questions on a wide range of topics, such as how they like to spend their free time, if they’ve taken any interesting vacations, their favorite music, or their work,” says Roberts. Ideally, you’ll ask open-ended questions—which often begin with “why,” “how,” “what,” “tell me about,” or “describe”—rather than closed questions—which usually start with “an,” “did,” “will,” “was,” or “have,” and elicit a yes or no answer—says Turner. “This approach encourages more detailed responses and fosters a deeper connection,” she says.

6. Use self-disclosure

Even if you’re hesitant to open up with other people, doing so can make a big difference in determining whether you connect with someone on a deeper level. For example, if someone asks how you’re doing, your first instinct may be to say “I’m fine,” or “I’m good, how are you,” says Turner. “Instead, share more about yourself during conversations,” Turner advises. “This not only invites the other person to open up but also helps build stronger relationships.” While this situation is relatively simple, taking the time to really consider how you’re doing and express that to the other person may lead to a meaningful conversation.

Why are some people better at communicating than others?

Some people are better at communicating than others, and sometimes even excellent communicators find themselves struggling to converse with people. According to Turner, the rise of social media—specifically modern reliance on virtual communication over face-to-face conversation—may be exacerbating some people’s subpar communication skills. “When conversing on social media, people often overlook nonverbal cues and emotional expressions, which are crucial for meaningful interactions,” she says. “As a result, this lack of genuine engagement can increase disconnection and strain relationships.” Not great, since the presence of close relationships benefits your overall well-being. According to a 2017 article¹ published in American Psychologist, close relationships can help you cope with stress and maximize positive emotions around achieving goals and personal growth.

It’s also important to remember, though, that the specific situation you’re in and the people you’re interacting with also impact how your communication skills may come across. Like pulling a handful of random cards from a deck, you never know what mix of interactions you’re going to draw on a given day. That is to say, it’s completely normal if you’re having an “off” day when it comes to conversation or if you have a few unpleasant conversations mixed with a few more satisfying ones. This doesn’t make you a bad conversationalist and you can turn things around. “There are many ways to have a meaningful conversation, and there are no wrong ways to connect with others,” says Dr. Smallen. “We are all going to feel more competent conversing in certain environments or with certain people rather than others.”

What are the characteristics of a good conversationalist?

“A healthy conversation happens when two people are engaged in an interaction where they each feel heard and respected, even if they disagree.” —Debra Roberts, LCSW

Good listening skills, confidence, eye contact, and the ability to ask thoughtful questions all contribute to making someone a better conversationalist. That said, anyone can be a good conversationalist as long as they learn how to adapt according to the scenario. “Because there are so many different types of people, with different personal and cultural backgrounds, different languages, different interests and expertise, different comfort expressing personal information, and so forth, it is beneficial to approach conversations with a curiosity as to what will best allow a conversation to thrive here in this unique moment and place,” Dr. Smallen says. “A person who is going to feel more competent conversing with people across situations, and across cultures, will likely have some flexibility to adapt to variations in what is appropriate conversationally, but this kind of flexibility is enhanced by simply having more experiences connecting with various kinds of people.”

What makes you a bad conversationalist?

When you interrupt people during a conversation and steer the conversation to your own experiences, you can come across as a “bad” conversationalist, says Shannon Garcia, LCSW, a psychotherapist in private practice at States of Wellness Counseling. Instead, you can practice sharing your experience briefly and then steering the conversation back to the person you’re talking to, suggests Garcia. “For example, you might say, ‘Something similar happened to me the last time I traveled! What happened next for you?’” she says. “This way you give them a chance to share more if they want and it keeps the conversation balanced.”

What do healthy conversations look like?

As stated above, a healthy conversation is balanced—all parties involved are giving and receiving information equally. This requires active listening skills that allow you to navigate the conversation more smoothly by asking questions or making relevant comments that encourage your partner to continue talking. “When individuals are present and open to listening, you have more productive conversations, healthier interactions, and better outcomes even if they were addressing a challenging topic because both parties are willing to listen,” says Roberts. A healthy conversation is also characterized by mutual respect. “A healthy conversation happens when two people are engaged in an interaction where they each feel heard and respected, even if they disagree,” Roberts adds. “They make eye contact, nod, smile, and their body language shows interest rather than being closed off.”

How to start a conversation without being awkward

Striking up a conversation can feel intimidating, especially if you don’t know the person. First, try to cut yourself some slack. “We tend to hold a much more negative view of ourselves as conversationalists than others do,” notes Dr. Smallen. “Research also shows that if we already feel lonely, we are more likely to interpret others as rejecting us. When we are putting ourselves out there and starting a conversation, we need to be our own advocate and remind ourselves that however it goes, there is absolutely nothing wrong with us.” If you want to start chatting with someone, look for common ground, as people tend to feel more comfortable in conversations where they’re fluent in the topic being discussed, suggests Dr. Smallen. “This is why small talk is actually beneficial,” he adds. “As banal as it can be to talk about the weather, the weather is something we are all experiencing at any given moment. We can move on to discussing something deeper from there if we feel like we might connect with this person.” That said, awkward moments in conversation will arise, and it’s okay to acknowledge that they happened and change the subject.

What to say to keep a conversation going

Starting a conversation is half that battle; from there, it’s a matter of listening to your partner and contributing to the conversation to keep it balanced. You can keep a few phrases in your conversational toolbox to use whenever you want to keep a discussion going. “Using, ‘Then what happened?’ helps the other person know you are interested in what they are saying and encourages them to elaborate,” says Garcia. Or, “the phrase, ‘Earlier you mentioned…’ is great to use when the conversation feels like it’s slowing down or maybe has stalled out,” Garcia says.

Depending on the circumstance, you may be interested in evolving from small talk to a deeper conversation. This involves experiencing what psychologists refer to as “emotional intimacy,” or exposing your innermost thoughts, feelings, beliefs, etc. during a conversation. According to Dr. Smallen, there are two ways to move toward deeper discussions during the conversation: listening with sincere presence and openness so that the other person feels comfortable sharing about themselves, or using self-disclosure, aka being vulnerable. This process can be a gradual build-up. “When I study people’s experiences of meaningful connection, they often move from small, only slightly vulnerable disclosures of personal information to more vulnerable and meaningful sharing over the course of a conversation,” says Dr. Smallen. As long as you’re willing to share your thoughts and hear the other person out, the conversation can keep going on indefinitely.

How do you recover from a boring conversation?

Boring conversations are salvageable, and it’s possible to move the conversation into a more interesting direction. That said, abruptly changing the subject as soon as you lose interest isn’t typically the best approach. “But it’s important to do this tactfully and with kindness because most often, you are taking an active step to change the direction of the interaction, so you want to be sensitive that you might be quasi-interrupting the other person,” says Roberts. It can be helpful to steer the conversation in the direction of a topic that’s related to something that they said but leaves room to dive into other subjects. For example, if you’re talking to a friend about their recent trip to Italy with their family and they can’t stop venting about their sister’s poor planning skills, maybe ask about a different trip they’ve taken with friends in the past or express your own interest in traveling to a specific location. “Now you’ve redirected the interaction to something potentially more interesting,” says Roberts. “You can also ask if they mind that you change the subject because you want to ask them a question or tell them about something else.”

Talking to people can bring value to your life, whether you’re deepening your social connections or taking the time to acknowledge a stranger’s perspective. Making an effort to stay present, avoid interruptions, and ask open-ended questions can improve your ability to interact with people in any scenario and ultimately lead to richer, more solid interpersonal connections.