How to Keep a Conversation Going

Darkness inked the nightclub as he walked in.

I was alone until now, setting up a DJ system worth well over $1,000 for my gig later in the night. I could feel my heart pound in the back of my hands.

Thief? Murderer? No, worse…

Janitor… I’d actually have to talk to this guy.

We were alone in a small club and the fact that we should talk felt like one of those 20,000 lb weights from Looney Tunes hanging in the air.

But what to say? And after that, what next? How would I keep the conversation going? Years ago, that huge cartoon weight would’ve floated in the air uncomfortably. And while I still get those “shy-guy jitters,” at least now I know what to do.

I did start the conversation and kept it going great. That’s what I’ll show you in this post; how to keep a conversation going.

Use What They Give You

Here’s a golden nugget: In most cases, you can use what the other person says to keep the conversation going. So instead of constantly thinking up new things to talk about, you simply use what they give you.

It seems obvious, but how many of us actually do it on a normal basis? And do it right?

In communication lingo, “what they give you” is called free-information. I’ve also heard it called offers or hooks or threads. The idea is that while talking, people give extra information about their lives.

When I say extra, I mean in addition to what you were initially talking about. You can then ask a question or make a statement about this new information to keep the conversation hoppin’.

Let’s take my janitor experience as an example.

Examples of How to Keep a Conversation Going with Free-Information

When the janitor walked in, I knew nothing about him. Or did I?

I knew he worked for the club I was playing. I knew he was at work. I knew it was late. So I could’ve started the conversation about any of those things:

“Working late, huh”


“Must be interesting to work here…bet you see a lot of crazy stuff.”

I actually chose something much less inspired. I talked about the weather. BUT it worked which is why I chose to tell this story. Simple remember?

Me: “Hey, how’s it going?”

Him: “Oh, pretty good, pretty good.”

“Good. Man, it’s been raining like crazy lately, huh? Bet that makes for a lot more clean-up?”

“Yeah, you right. It’s ok though, I’ve been praying for rain. My plum trees need it.”

So can you spot the free information? That’s right, it’s the part about his plum trees. I didn’t ask about that or expect it. That’s now a possible topic ripe for the picking…(sorry).

He also said he was “praying for rain.” This implies he’s religious or spiritual. That could be another direction to take the conversation.

Here’s another example. You might ask someone at the gym:

You: “Is it just me or are there a lot of new workout machines in here?”

Other Person: “Yeah, they expanded the aerobic section. I’m SO glad; it really helps my training.”

The bit about training is the extra information. So guess what? Yup.

You: “Oh really? That’s good. What are you training for?”

Here’s another example:

You: “I’m jealous; you have a really nice tan.”

Other Person: “Thanks! I went tubing this weekend and got a lot of sun.”

You: “Oh really? I’ve never been tubing before and it sounds fun. What’s it like?”

You see? People leak free-information all the time. You just need to be more open to hearing it. When you notice something of interest in the conversation, comment on it or ask a question to open up a new path in the interaction.

Improv Comedy can teach tons about thinking on your feet and using what's given to move forward

Simply wash, rinse and repeat to keep a conversation going.

Grandparents and Desserts

Back at the club, I talked to the janitor about his plum trees. His grandfather had planted them and now they were his to care for. I shared that my grandparents also have a plum tree and how we look forward to the plum desserts they make.

We started talking about tasty home-made treats.

That’s how to keep a conversation going. ACME’s heavy weights department would be proud.

Take Action

Actively try to recognize free-information when it seeps into your conversations. When you notice an offer, go ahead and make a statement or ask for more information about that topic.

You’ll be amazed how liberating it is to enter a conversation knowing they will give you what you need to continue!

But here’s a secret:

Keeping conversations going is even easier once you get to a state of flow.

It’s that space where you naturally think up more fun things to talk about than you have time for.

This is where you really want to be socially, as much as possible.

For more about how to create this state of flow, Click Here for my social success video e-course & newsletter.

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