How to Keep a Conversation Going

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Book Excerpt

Conversation Mastery

This post is an excerpt from Conversation Mastery: Conversation Topics, Techniques, Tips & Tricks to Make Conversation Easy.

Pick up Conversation Mastery today to learn more about how to be more confident, charismatic and commanding when making conversation.

Man thinks about how to keep a conversation going
Don’t worry – keeping the conversation going is easier than you think

True conversational masters don’t just know how to start a dialogue with someone new, but how to put other people at ease and make them want to keep the conversation going and continue engaging with you. 

Fortunately, just as the “Ask about them” framework covered earlier in the book provides an easy-to-remember tactic for starting conversations, there’s an equally effective (though slightly less alliterative) strategy you can use to take your conversational skills from adequate to awesome (OK maybe I was wrong – this one’s a little alliterative, too).

It piggybacks on the body language technique you learned in Chapter 5, and ensures you don’t just use the right words, you use the right tone, body language, inflection and cadence.

In short, you use the right mood.

How to Keep the Conversation Going

Breaking Down the Best Strategies for Continuing a Conversation

Match Their Mood

Two people talking excitedly
Match your conversation partner’s mood to make continuing the convo seem natural and easy

So, what’s the “right” mood for conversation?

The answer is simple: whatever mood your conversation partner is already in.

This tip leapt off the page at me when I read it in the Leil Lowndes book How to Talk to Anyone.

As Lowndes explains, “Small talk is not about facts or words. It’s about music, about melody. Small talk is about putting people at ease.”

Therefore, she concludes,“The first step in starting a conversation without strangling it is to match your listener’s mood, if only for a sentence or two.”

When you think about it, this makes perfect sense. You’ve probably had experiences where you were tired, nervous, or otherwise quiet and low-energy.

If, in those moments, a super-friendly, loud, bubbly or energetic person starts chatting or interacting with you, it can often be off-putting or downright annoying, no matter how nice the person seems or how kind-hearted their intention.

But if someone whose tone of voice, body language and overall energy seems similar to yours starts asking a few innocuous questions – “How are you doing today? What did you get up to last night?” – you’ll feel much more inclined to answer them and engage in conversation.

Create a Kinship That Keeps ‘Em Talking

Two people having a warm conversation

In fact, you’d probably even feel a certain kinship with the person who’s asking, because you’d get the sense that they’re a lot like you.

By taking a few seconds to determine whether or not your conversation partner is high or low energy, then adjusting your own speech to match their mood, you can instantly form a strong connection that will make continuing the conversation seem natural and easy.

Pairing the “Match their mood” technique with the first few opening queries you make using the “Ask about them” framework provides a one-two punch that will immediately endear you to even the most intimidating conversational partner, helping you rev up their conversational engine.

The Best Questions to Keep a Conversation Going

A man and woman laugh as they chat amicably

Once you’ve got the conversation started by matching their mood and asking them a few questions about themselves, you’re going to need a way to continue it without getting to that dreaded awkward silence.

That’s where this next trick, also from Lowndes’ book, comes in.

Let’s say you start with one of the common small talk questions I mentioned above: “What did you get up to last night?”

If the person you’re talking to is a good conversationalist, this might be enough for them to take the ball and run with it.

But there’s also a chance that the response will be short-lived.

They might just say something like, “I watched a movie” or “I went out to a restaurant” and leave it at that.

Being a Word Detective

A woman listens intently as another woman and a man converse
Listen closely for key words that can lead to natural follow-up questions

This is where this next trick becomes tremendously valuable. In her typically insightful (if admittedly schmultzy) way, Lowndes calls it “being a word detective.”

The idea is simple: no matter what they say in response to your initial question, you listen for the main phrase they mention, and then ask them a follow-up question specific to that topic.

For instance, imagine they say “I stayed in and watched a movie last night.”

You can then ask them what movie they watched, what else they’ve seen lately, what their favorite movie of all time is, what Oscar contenders or big summer blockbusters are coming out soon, or literally any other question related to movies.

If they say “I went out for dinner” you can ask them about the restaurant they went to, other restaurants in town, how often they go out versus staying in to cook, and so on.

This move remains within the “Ask about them” framework because it focuses on something you already know they’re interested in.

And like that move, this one doesn’t actually require you to know anything about the topic in question – all you have to do is ask them questions about it.

Avoid The Dreaded Conversation Killer 

A young man talks to a young woman

Using open-ended and fairly broad questions to find out something about your conversational partner, then asking a series of follow-up questions related to their answer, will help you to avoid that dreaded conversation killer:

Awkward silence.

After all, even if the first topic of conversation runs its course and naturally tapers off, you can easily start a new one by asking them a fresh question about themselves, which will elicit a whole new set of responses, providing you with more conversational gold to mine.

The Foundation for Conversational Confidence

A man and woman smile while walking down the street together

It’s hard to overstate just how much these two techniques have bolstered my conversational confidence.

I went from feeling nervous, afraid and insecure about small talk to actually enjoying it—and even looking forward to opportunities to talk to other people.

I now feel like parties, networking events and other social settings are a great way to flex a little social muscle.

And as a result, I get to meet and forge connections with all sorts of interesting people.

Of course, not all people are interesting.

While it’s great to know that you can make conversation with anyone, it’s hard to call yourself a conversational master if you frequently find yourself getting trapped in discussions with boring, dull, rude or otherwise uninteresting people.

That’s why, in the next chapter, you’ll learn how to implement the third and final stage of conversational mastery: smoothly and effectively ending a conversation by… 

Strengthen Your Social Skills & Bolster Your Conversational Confidence ↓

Pick Up Conversation Mastery Today

Are you sick of feeling scared, timid or insecure when talking to other people?

Do you find yourself wondering how to be more confident, charismatic and commanding when making conversation?

Do you ever wish that you could be less awkward at parties, bars, job interviews or professional settings?

Conversation Mastery is a master class for overcoming those obstacles and unlocking all the opportunities that come from confidently interacting with other people. 

Learn More ➤

More Advice on How to Improve Your People Skills from Irreverent Gent
More Advice on How to Continue a Conversation from Around Ye Olde Interwebs: 

Banner image via William Fortunato on Pexels (Thanks William!)

About Dave Bowden

Dave Bowden

Irreverent Gent founder Dave Bowden is a style blogger whose advice on how to look good and live well has been featured in some of the world’s most trusted publications, including New York Magazine, The Wall Street Journal, Business Insider and more.

When not obsessing over style and self-improvement, he can usually be found spending time with his wonderful wife and son, indulging in a hoppy craft beer, or sobbing over the woeful state of Toronto's sports teams.

Check out Dave's Style Story to find out how a chance encounter with his friend's step-dad taught him the value of looking good and living well. (Don't worry—it's less creepy than it sounds!)

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