How to Keep a Conversation Going

How to Keep a Conversation Going: Tomasz and Jon at Angloville

If you’ve ever found yourself at a loss for words during the middle of a conversation, don’t feel bad. You’re not alone.

We’ve all had experiences where we’re not sure what to say next. We’ve all had moments when a conversation stalls. It happens to everyone, including the people who seem to have it together the most.

Conversation is a double-edged sword. It’s both thrilling and nerve-wracking at the same time. It can add novelty to the listless routines of our daily lives. But conversation can feel like navigating a minefield, too. One wrong step, and you’re toast.

Whether you’re dating or making friends in a new city, conversation doesn’t have to feel like life or death. Instead, it can be rewarding when you see it as a skill you can improve.

Before Getting Started

When learning how to keep a conversation going, it’s important to acknowledge one thing.

Nerves are normal.

Talk to hundreds or even thousands of people. The way you feel before you begin a conversation is always the same. You’ll start off with a little bit of anxious energy.

But, those initial nerves serve a purpose. They’re a biological response to remind you that you’re human and not some emotionless robot. Our brains don’t like uncertainty, and every new conversation enters us into the unknown.

For most of my twenties, I resisted this fact. It took me a while to accept that nerves would always accompany a conversation with someone new.

Working in the NBA, I spoke with some of the most intimidating figures in professional sports. You’d think that interviewing the likes of Kobe Bryant or Kevin Garnett immuned me from anxiety. But even after close to a decade working in the League, that wasn’t the case.

To this day, I still get nervous whenever I talk to somebody new. But most of the time, I don’t let that anxiety scare me away. The difference is that I’ve had enough practice thanks to my career and experiences with travel. I’ve learned to see that nervous energy as a good thing.

Working on your conversation skills won’t be easy. In fact, you won’t be very good when you start. But with practice, you’ll learn how to manage your anxiety and make progress.

In time, that anxious response will also overwhelm you less. Learning how to keep a conversation going is a lot like working out. You can’t expect to lose 10 pounds in a week. You need to play the long game instead.

How to Keep a Conversation Going: 4 Reliable Tips

Conversation isn’t rocket science. In fact, the last thing you want to do is overthink.

Keep it simple. When you do, the thought of conversation feels much less daunting, instead. You’re more likely to stick with the task at hand when it isn’t complex.

“The good program you practice is better than the perfect program you quit,” author Tim Ferriss said in a podcast with former Navy SEAL Jocko Willink.

In my experience, there are only four tips you need to follow to become better at conversation.

Tip #1: Live an Interesting Life

Above all else, your life is what you have to work on first. In fact, if all you do is work on this, everything else will take care of itself.

You need to live a life that you take pride in talking about. When you do, learning how to keep a conversation going becomes an easier equation. You’ll never run out of things to say when you live a life that’s worthwhile.

If your life consists of a job you hate and hanging out with people you merely tolerate, you’re in trouble. Along with sleep, these are things that take up a significant amount of time. Spending more than half your day doing things you don’t appreciate gives you very little to talk about.

How, Then, Do You Live an Interesting Life?

Find out what you enjoy. The only way to do this is through the process of trial and error.

For me, travel has brought plenty of value to my life. It’s afforded me memorable experiences and given me plenty of material to discuss. I have a wider perspective on life that I enjoy discussing with those who care to know.

Follow what sparks your curiosity. This will sometimes terrify you because things won’t always work out. But, don’t let the specter of failure stop you from at least trying.

If you change your perspective, failure can work in your favor. Rather than repressing an experience that didn’t work out, turn it into a talking point instead. This can actually make you more likable.

There is no universal definition for an interesting life. There are plenty of people who travel and work prestigious jobs, yet still feel unfulfilled. It’s your responsibility to figure out what an interesting life looks like for you.

Tip #2: Let the Silence Do the Work

For many of us, silence is the death knell of a conversation. We can’t stand moments of brief pause, because they always feel like an eternity. Many of us learned at a young age that situations like this should always be avoided.

But, try the opposite some time. You might find that it can work to your advantage. There’s power in being able to embrace those subtle moments of silence.

This is a concept supported by storyteller extraordinaire Cal Fussman. He’s used this tactic speaking to some of the most influential people of the past century. If it’s worked for Cal, it can work for you.

The Benefits of Quiet

Learning how to embrace these breaks seems contrary to the point of this article. We have an idea in our heads of what good conversation looks like, and moments of silence don’t fit the bill. But, there are a handful of reasons why they should.

First, silence gives you and your conversation partner time to process. When conversations go deep, they can often get heavy. Those brief moments of pause are like short water breaks in the middle of an intense workout.

Second, it relieves you of unnecessary pressure to drive the conversation. A good talk between people requires engagement from everyone involved. By letting the silence do the work, you give your partner some ownership of the conversation.

Finally, learning how to embrace silence also improves your non-verbal skills. When you become comfortable with quiet, it shows in your body language. You communicate beyond words that silence is OK. That, in turn, can make your conversation partner more relaxed, too.

Tip #3: Abandon Your Filter

No one enjoys being disliked. It’s not a pleasant feeling. To protect ourselves from this outcome, it’s normal for most of us to say things that others want to hear.

In other words, we try to appease in the conversation.

But many times, this ends up backfiring. More often than not, pandering makes conversation much harder than it needs to be. Most people can read right through it.

To learn how to keep a conversation going, you need to abandon your filter. Whenever you can, practice the chance to say whatever’s on your mind. The results won’t always be pretty, but it’s a valuable skill to have.

Knowing and Handling the Consequences

Speaking without a filter, though, doesn’t allow you to be rude. With practice, you’ll learn how to talk from a thoughtful, well-intentioned place. Understand and accept that there will be many mistakes made as you develop your sense of tact.

Here’s a general rule of thumb. Abandon your filter in any circumstance meant to protect your ego. If you’re afraid of saying something that might make you look dumb or weak, say it. Vulnerability can make you more relatable.

Being candid in conversation does carry some risks. The biggest one of all is that not everyone will like what you have to say. You might even discover a few people dislike you as a result.

To deal with this, embrace this resistance as a blessing instead. You face nothing but an uphill battle trying to win the hearts and minds of those who don’t like you. You’ve saved yourself from wasting time trying to convince people that don’t want convincing.

Be grateful for the flip side as well: Those who appreciate your unfiltered approach won’t only like you; they’ll love you. By being open and candid, you’ll enjoy much stronger connections with the people who matter most.

And one last thing – know that most people are forgiving. Saying something dumb doesn’t always kill a conversation in an instant. There are plenty of kind people out there who are willing to give you a second chance.

Tip #4: Ask and Listen

Don’t be afraid to ask questions. Being curious takes care of most of the work in learning how to keep a conversation going.

When you’re curious, you shift your focus from yourself to the other person. Most people want to talk about what’s going on in their lives. Asking good questions gives them a pathway to share.

Likewise, it’s important to remember that conversation isn’t all about talking. It involves listening, too. Pay attention to what someone has to say rather than ruminating on a response.

Aim for the Heart, Not the Head

This is the first lesson that Cal Fussman teaches people who want to ask better questions. It’s a lesson that can help you in your quest to learn the art of conversation.

“Once you get the heart, you can go to the head,” Cal said in Tim Ferriss’s book Tools of Titans. “Once you get the heart and the head, then you’ll have a pathway to the soul.”

Explore topics of conversation that resonate on a deep level. Ask others questions that have substance. Talk about things that get to the root of what makes others who they are.

Need some examples? Ask about people who’ve made a mark on someone’s thinking. Ask how someone’s past has influenced his or her present. And as a follow-up, you can always rely on a simple and reliable one-word question: Why?

After you’ve followed your curiosity, listen. Seek first to understand rather than be understood. This is a concept supported by my friend Rob Lawless, a man with a mission to meet 10,000 people, one-on-one, for an hour each.

“Be a consumer of opinions rather than a provider,” he said.

Most people just want to be heard. Through conversation, this is a gift you can give.

Making the Most of This Article

Read and refer to it, but don’t use this article as a crutch. Sometimes, people get so carried away with studying that they never execute. Don’t be one of those people.

It’s easy to fall into the trap of analysis paralysis. The internet is a bottomless hole of information. It makes it simple to overthink rather than act. You can wind up in a research loop that feels productive, but isn’t actually moving the needle.

Knowledge derives itself from action. That’s how this article came about. You do something, and then you reflect on how you did it. Only through experimentation can you come up with tips and repeatable tactics.

So go out and test the following concepts in the real world. That means talking to real people! Find out for yourself if these recommendations hold up for you.

Put yourself in situations where you have to talk to others. Strike up a conversation with someone at work whom you don’t usually talk to. Go to a cafe, and chat with the person standing in front of you in line.

Initiating these conversations will feel awkward, but that awkwardness will fade away. These conversations might even stall, but when they do, learn to laugh at yourself for trying.

Experience is the best teacher.


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Jon is a freelance writer who authors this site. Learn more about him here. You can also follow Jon on Twitter or Instagram.

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