How To Hold a Conversation and Build Deeper Connections

Think back to the last conversation you had that lasted for a few minutes. How did it make you feel?

Was it dull or inconsequential? 

Was it awkward or uncomfortable? 

Or was it compelling and memorable? 

One of the wonderful things about conversations is that they’re all unique—but they’re not always pleasant. And if you’re someone who hasn’t practiced how to hold a conversation, you may find yourself anxious when it comes time to strike up a chat. 

Surely you’ve heard the phrase “the art of conversation”—and in a way, a good conversation really is artful and nuanced. All parties involved must have the skills and drive necessary to make the conversation productive, whatever that means to the people involved. 

If you’re someone who finds more of your conversations falling into the uncomfortable camp, this article is for you. Below, I’ll run through some of the common reasons why people struggle to carry on a conversation. Then, I’ll give you tips on how to hold a conversation that will keep people engaged and build deeper, more meaningful relationships.

  

What makes it hard to hold a conversation?

Even the most skilled conversationalists will still have a lousy conversation every once in a while. Sometimes, the chemistry just isn’t there, or the situation is inherently awkward. 

But if you’re someone who dreads conversation and frequently finds yourself walking away from a chat feeling deflated, then there are a few common issues that may be at play.

 

Anxiety about how others will perceive you 

Conversations can often be places of vulnerability—we have to share things about ourselves, think on our feet, and run the risk of doing or saying something embarrassing. 

This kind of vulnerability can lead to intense feelings of social anxiety. You may play up embarrassing scenarios before the conversation starts or replay what you consider to be your worst moments during the conversation well after. This can happen even if the other person enjoyed the conversation and did nothing to make you feel this way. 

If you’re someone who struggles with this kind of anxiety, there’s a lot you can do to alleviate the problem. I’ve written about overcoming anxiety extensively in these articles if you want to go deeper: 

 

Dreading awkward silences and moments

Sometimes, it can feel like avoiding a conversation altogether is easier than having to deal with any long, uncomfortable pauses or awkward moments. Some people will really go out of their way to avoid this—they may even be unwilling to call a restaurant to book a table or skip social engagements altogether. 

No one enjoys long silences in conversation, and they’re often unavoidable. If you follow the tips later in this article, you’ll learn how to keep awkward silence to a minimum—and even use them to deepen and improve a conversation.

 

You devalue what you have to say before you even say it 

Does this sound familiar? 

You’re in the middle of a conversation, and suddenly you have the desire to contribute something or ask a question. 

But before you do, a voice inside your mind says something like, 

Nobody cares about that. 

They probably already know that. 

Bring that up, and you’ll kill the conversation. 

While it’s a good idea to think through what you plan to add to a conversation, it’s very easy to shoot down what would have been excellent talking points. 

That little voice has been responsible for ending some of the best conversations before they’ve started. The next time you hear it, try ignoring it and saying what you want to say anyway. You may be surprised by the results.

 

Someone isn’t carrying their weight 

Conversations require active participation from all parties involved—otherwise, it’s just one person delivering a monologue. The most common reason conversations fall short is because one person isn’t pulling their weight. 

They may not be asking questions or only giving one-word responses. Perhaps they seem disinterested, hostile, or uncomfortable. There may be any number of reasons why someone isn’t pulling their weight, and not all of them mean that person is a bad conversationalist. 

The best way to diagnose this problem is to look for patterns. Is there one person with whom your conversations always feel stilted and awkward? If so, they might be the one who needs to work on their conversation skills. 

If you find that all of your conversations feel off, then the common denominator may be you. But don’t worry if that’s the case—virtually anyone can learn how to hold a conversation well with a bit of practice, and the tips below. 

 

Cultural, social, or power dynamics get in the way

Sometimes, conversations are difficult because of the differing dynamics between the various people involved. 

Conversations with your work bestie are likely easy and fun.

Conversations with your boss, on the other hand, are likely more stilted and stress-inducing. Even if you like your boss, the fact that they hold power over you adds an additional barrier to every conversation. 

Similarly, speaking to people from different cultures or backgrounds than you can be hard. It’s natural to feel intimidated by these differences. You may be worried about saying the wrong thing, or misunderstanding something because of your differences. 

Paradoxically, the only way to overcome these kinds of barriers is through open and honest communication. Conversations—even the awkward ones—help us understand one another on a deeper level.

 

How to hold a conversation: 10 tips to keep in mind

If possible, prep, plan, and practice

Some conversations happen unexpectedly and off the cuff, but sometimes you might know an important conversation is coming on the horizon. You could spend hours leading up to the conversation feeling anxious, or you could make the most of that time to lay the groundwork for a really excellent convo. 

Here are a few questions you can reflect on before the conversation—try writing down your answers, or mulling them over on a long walk or during a hot shower. 

By answering these questions ahead of time, you can enter the conversation feeling prepared and confident.

Think of it like studying for a test—the more you “study” what would make for a good conversation, the better the conversation will be when it happens.

 

Consider any “digital dynamics” at play 

Most of the tips I’ve put in this article are applicable to both IRL and digital communications. But when you’re having a conversation with someone through digital means, there are a few additional considerations to take. 

Written communication can be powerful, but it also can be easily misinterpreted. We rely so much on facial expressions and tone of voice when it comes to understanding others—and with written communication, these things are taken away. 

As a result, humans have come up with ways to inject more clarity into our digital comms. Punctuation is one very old method, and more recently, the advent of emojis and other text-speak (like /s to signify sarcasm) have helped overcome some of these online barriers. 

But whenever you’re communicating through a device, try not to jump to any conclusions about others’ tone. Someone who sounds angry or short online may simply be pressed for time, or not terribly thoughtful about how they are coming off. 

On that note, when you’re carrying conversations online, re-read what you’ve written before you send it. Try reading it out loud, and see if your words match the tone you want to communicate. 

A few extra seconds before sending a message can make online conversations a lot easier.

 

Think of silences as natural inhalations 

Pauses in conversation feel awkward—there’s no way around that. But they really shouldn’t, because those silences are totally normal and could even be good for the conversation at large. 

When you experience a lag in the convo, your brain may start to panic.

You start desperately trying to think of what to say next, or wondering if the person you’re talking to thinks you’re socially awkward or bored.

Next thing you know, you make things worse by trying to force conversation just to fill the gap. 

This will take some practice, but try reframing how you see silence in conversation. Rather than thinking of it as something horrible that must be avoided at all costs, consider it like the conversation itself is taking a deep, inhaling breath. 

A pause will allow the convo to reset briefly and take a new direction. It can also give your conversation partner a chance to bring up something they’ve been wanting to address. 

Try counting slowly to 5 or 10 the next time you find yourself in a long pause. In that time, your partner may fill the silence on their own, or your brain may pull up a new question or topic you’d like to discuss.

Giving your convo partner and your mind the time to breathe is what the silence is for.

 

How to open a conversation

Beginning a conversation can be really tough, especially if it’s with someone you don’t know very well (or at all). But the opening of a discussion is so important because it will set the tone for at least the first few minutes of the exchange. 

It’s perfectly fine to start a conversation with simple, reliable open-ended questions: How are you? What’s new? And the old Zoom standard—How’s the weather where you are? 

These kinds of niceties are sort of like dipping your toes into a pool before diving in. They allow both you and your conversation partner to settle into the conversation easily. 

But after you get the preamble out of the way, then what? 

It’s useful to have a number of conversation openers to keep the conversation moving beyond small talk. When coming up with your own conversation starters, keep these tips in mind:

 

Practice active listening 

Have you ever been talking passionately to someone, only to realize that they’re more focused on their phone or just staring off into the distance? 

That kind of listening is known as passive listening—when you listen to someone but don’t really engage with them beyond a nod and the occasional “mmmhmm.” 

Active listening, on the other hand, makes conversations much richer and easier. This is when you give someone your full attention as you listen. Instead of focusing on what you want to say next, you ask questions to take the conversation deeper. 

The more active listening you can do, the better—it is truly the key to good conversations. In fact, I’m so passionate about active listening that I’ve written an entire guide on how to add this skill to your conversational arsenal. Check it out here: 

 

Pay attention to body language

When you think about conversation, you may only think about the words you’re exchanging. But conversations take place in other parts of our body beyond the vocal cords. 

The body language you use, and your ability to read your partner’s body language, will have an enormous impact on how you carry a conversation. 

It’s a lot easier to convey the right body language and read the signals of others if you know some common signs to look for. 

 

Draw upon shared memories or interests

Once you’ve used a good opener to kickstart the conversation, one of the best ways to keep it going is to steer the conversation toward common ground. 

This is a lot simpler if this is someone you already know. It’s easy to ask a close friend about their new colleague or their upcoming vacation because you probably talked to them about it recently. 

Even if you have only met this person in passing, you can still use what shared history you have together to deepen the convo. For example, you might say something like, “Last time I saw you was at Sandra’s birthday party. Remember that amazing DJ she hired?”

Finding common ground can be trickier when you are meeting someone for literally the first time ever, like at a party or networking event. In these cases, you can still try to find some common ground by using the situation or an observation to spark conversation. 

For example, at a party, you might say something like, “I like your Maine sweatshirt. I’ve visited that state a lot—are you from there?” 

At a networking event, you may ask, “Who’s been your favorite speaker so far?” 

 

Use humor naturally, and laugh at others’ jokes

Humor is one of the best ways to deepen a conversation. When people laugh at something together, it forms a bond—and it may even establish an inside joke you can use later (see my tip below on going for a throwback). 

A word of warning: Don’t force humor. You don’t want to be that person who tries to make everything into a joke or lets one funny joke go on way too long. Instead, crack jokes if and when you can, keeping them light and appropriate. 

If your conversation partner makes a joke, react! It takes courage to say something funny in a conversation, and if you don’t at least crack a smile, they’ll begin to feel self-conscious. Even if the joke wasn’t terribly funny, use the moment to add some levity to the conversation with a smile.

 

Deal with difficult conversations

In this article, I’ve mostly given tips about how to hold conversations that are enjoyable for all involved. 

But not all conversations are pleasant. In fact, we often have to have very hard conversations with colleagues, friends, partners, or family members. 

Many of the tips we’ve covered so far, like being an active listener and reading body language, can certainly help with difficult conversations. But there are other tips you may find useful for those challenging but but necessary talks. 

For help with those kinds of conversations, check out these resources:

 

Be inclusive of everyone involved

This tip is for conversations with more than one other person. 

Most people know what it feels like to be left out of a group conversation. Maybe at a party, you had to listen from the sidelines while a group of friends chatted as if you weren’t there. Or perhaps you’ve been stuck in the backseat of a car while your parents discussed something up front, without your input. 

No one likes being left out, and doing so will make the conversation a total failure for at least one other person. Part of the art of conversation is making sure everyone feels included—and as a skilled conversationalist, you can be the one to fix the problem.

(Trust me, this is going to make you a very likeable person.)

If you notice someone in the group hasn’t contributed in a while, ask them a direct question the next time there’s a break in the conversation. 

If you’re in a group you’re close with, that also contains a few newcomers, try not to fall back into talking exclusively about past experiences or inside jokes. Use your conversation openers to expand the conversation, so everyone is included.

 

Go for a throwback 

Conversations can be unpredictable, and it’s best to let them move in different directions naturally. But sometimes, the conversation may move on from a point that you wanted more information on, and bringing up that point later in the conversation does two wonderful things: 

1. It lets your conversation partner(s) know you are actively listening 
2. It builds a deeper bond and keeps the conversation moving 

This is also a great way to fill in one of the silences. If there’s a pause in the convo, simply say something like, “Hey, can we go back to that project you’re working on? I want to know…” 

These throwbacks also work when you have multiple conversations with someone over a long period of time. In later convos, mention something you picked up on or remember from the most recent conversation. Bonus points: Bond over an inside joke from the last chat.

 

Reflect on the conversation

This is the most important tip if you really want to focus on learning how to hold a conversation.

When you’re done chatting with someone, try meditating on a few of these questions: 

As you reflect on questions like these, you’ll begin to see patterns of things you’re doing well (or conversation tactics you need to improve). Over time, you’ll get better and better at this until you really have mastered the art of conversation. 

Conversations can certainly be intimidating if you let them. But they are the best way to deepen relationships with the people you love and care about, and they’re key to making new friends and acquaintances.

The tips in this article will help, but only if you put them into practice! So get out there and start talking—the more you work at it, the sooner you’ll be a supreme conversationalist.