How to Join a Conversation (Without Being Awkward!)

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How to Join a Conversation Without Being AwkwardCRASH!

Glass shards fly in all directions. The crowd cheers. They want more.

People are throwing (and missing) bottles into a trash can 25 feet away from them. It’s some kind of contest. Apparently they do this every Thursday.

My wife signed up for a kickball team, and they were having a meet-and-greet at a local dive bar.

All these people seemed to know each other, they were laughing and joking around.

I was sitting there, my shoes felt uncomfortable. Why did I wear this shirt? I wanted to leave.

“What the hell is wrong with me?” I thought.

At one point or another, we’ve all felt like this.

We want to connect with groups of people, make new friends, or meet new people, but sometimes we get in our own way.

Group conversations can be unpredictable, and a little wild.

How can we reliably feel confident in group conversations?

How can we smoothly contribute without having much time to think of what to say?

And how can we do all this while feeling authentic?

In short, how do you join a group conversation without feeling awkward and out of place?

You’re about to learn the mindsets, skill sets, and routines that will help you effortlessly join and enjoy group conversations.

Let’s dive right in.

How to Join a Conversation Without Being Awkward

How to Join a Conversation
Without Being Awkward

Here’s How to Effortlessly Enter Group Convos

How to Join a Conversation Without Being Awkward

Mindset #1:

Everyone in the group has a shared goal: have a good time.

How to Join a Conversation Without Being AwkwardSomething never said by a group of people: “We’re having too much fun.”

Typically, groups want to have a good time. Keeping this shared goal in mind is great, because it takes away any thoughts of “winning and losing.”

When you’re thinking about winning and losing, you’ll be subtly comparing yourself to others. Not good.

With the mindset of “everyone wants to have a good time,” you’re in a much better position to perform because your social compass will be pointing in the right direction.

This mindset is also effective because it places you in an external mindset (e.g. What can I GIVE socially) instead of an internal mindset (e.g. What can I HAVE socially).

Mindset #2:

No one is judging you. They’re too busy wondering if you’re judging them.

How to Join a Conversation Without Being AwkwardAlmost without fail, I see concerns from clients and readers that other people are thinking the worst about them.

Why do we do this?

Because of a wonderful concept Dave’s written about before called the negativity bias.

The negativity bias was a great thing for our ancestors. It was effective for avoiding sabretooth tigers. It’s not great for reading people’s minds at a dinner party.

When we are in an uncertain environment, our brains constantly try to fill in the gaps. And our default mode as humans skews negative because staying alive is good.

Helpful reframe:

We’re all hardwired to fear social judgment, so ask yourself: How can I help other people feel more accepted?

The benefit here is twofold:

  1. Awareness of the negativity bias will help you process those feelings of perceived judgment. You can even say to yourself: “That’s just the negativity bias thinking.” This will help you move on from that unproductive emotion.
  2. It levels the playing field. If everyone struggles with perceived social judgment, you can be the guy who helps buck the trend by helping people feel accepted.

Mindset #3:

Being bold will have a much higher payoff than hesitating.
How to Join a Conversation Without Being Awkward
“OK, I’m going in.”

Ever notice how some people are bold?

They’ll walk up to a new group without hesitation.

They’ll ask for a woman’s phone number smoothly.

They’ll speak up in a meeting.

Ever wonder how they do that?

There’s a quote that I like: feel the fear – and do it anyway.

They still feel fear. They take action anyway.

In a group setting, being bold doesn’t mean you have to dominate the conversation.

But it does mean:

  • When you speak up, you do so in a louder voice.
  • When a new person joins the group, you take the lead by introducing yourself, or catching them up on the topic at hand.
  • When the group doesn’t know where to grab a bite to eat, you step up and propose a solution.
How to Join a Conversation Without Being Awkward
Think of yourself as a host to help put you in a bold state of mind

A good role to assign yourself is that of the host. A good host is bold.

When you hesitate, you’re stuck in an uncomfortable “in-between” state that leaves you unsure about what actions to take.

Fortune favors the bold.

Mindsets are a great place to start because they lay the groundwork for skill sets.

The interesting thing is. The more you take action with skill sets, the greater shift you’ll notice in your mindset. It’s a virtuous cycle, a fly wheel that spins faster and faster as you practice.

When we’re bold, we’re rewriting our story of “I’m not the kind of person who could own a room, connect with anyone, or be charismatic.”

It’s time to be bold.

Here are crucial skill sets that will help you succeed in a group.

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Skill Set #1:

The +10% Rule

How to Join a Conversation Without Being AwkwardGroups want to have fun. So why do people join a group and immediately talk about how they had to put their dog to sleep last week? Not good.

Why we do this: It may feel cheesy or unnatural to pump up our energy, so we default to the safety of lower energy.

When you’re joining a group conversation, you’ll want to enter with as much energy as the group – or even better, 10% more.

Having slightly higher energy is effective because the group senses that there’s a low chance that you’ll drag down the group’s energy.

How to practice this:

When joining a group, be more enthusiastic about topics, smile more, and speak a little louder.

When you join a group with 10% higher energy, you’ll never run the risk of awkwardly hovering on the outside of a group and nodding along. (We’ve all done it.)

It’s okay to make a little splash when you join a group. Remember, fortune favors the bold.

Here are a couple of helpful scripts to get you started joining group conversations:

Script #1:

“Hey guys, do you mind if I hang out for a couple of minutes?”

Why this works: You’re asking for permission to join their group, coupled with a time constraint.

Asking for permission is a very subtle form of persuasion. It takes the other person’s feelings into consideration.

A time constraint is crucial because it answers a main objection in people’s minds: “Will this person overstay their welcome?”

Script #2:
How to Join a Conversation Without Being Awkward
“Hey, were you guys just talking about Game of Thrones? Because my theory is…”

“Excuse me, I couldn’t help but overhear, are you guys talking about XYZ? Because [reason].”

If what you overhear seems super serious, maybe don’t use this one. But if someone’s talking about travel plans for a summer vacation, rock on.

Why this works: A dash of permission, and a good segue into the current topic.

Create your own (mix and match):

Here are the effective building blocks of a good script:

  • Permission
    • Take the group’s feelings into consideration. Get verbal or nonverbal permission to continue. Key phrase: “Would you mind…”
  • Time Constraint
    • Answers the main objection in people’s minds: “Will this new person hang around too long?!” (If you’re cool, no one cares how long you stick around.) Key phrase: “I can only hang out for a couple of minutes…”
  • Environment
    • What kind of environment are you in? Is there something interesting you can comment on?

Skill Set #2:

How to Join a Conversation Without Being AwkwardSpokes

Does your mind ever go blank right when you had the perfect opportunity to say something?

Doesn’t that suck?

What if I told you there’s a way you can always have something to talk about and never run out things to say?

There is. It’s called the Spokes Method.

Imagine a bicycle wheel.

In the center of the wheel is the hub.

The hub is the current conversational topic. As an example, let’s use superhero movies.

Radiating out from that hub are spokes. Think of the spokes as topics that loosely relate to the topic at hand.

For superhero movies we have quite a few to play with:

  • Favorite superhero movies coming out soon
  • Favorite superheros
  • Favorite movies
  • Comic books
  • Special effects
  • TV shows that you love to binge watch

So we don’t just have that one topic to play with. We have six. Plenty of options.

Let’s kick it up a notch with a harder topic.

How to Join a Conversation Without Being AwkwardLet’s say you’re at a dinner party and someone mentions that they’re a mechanical engineer.

And let’s say you’re like me and you don’t know much about mechanical engineering.

What are your spokes?

Play along while reading this: come up with three possible spokes.

I’ll wait.

So, what did you come up with?

Here are mine:

  • What got you into engineering?
  • What kind of things do you engineer?
  • Working on anything exciting right now?
  • Have you ever seen an object that made you stop because it was engineered so well?
  • As a kid, did you like taking things apart?

Notice how our focus shifts from the topic to focus on the person.

Even if you’re not interested in mechanical engineering, you can still have a great conversation.

As you practice spokes, you might run into what I call the “perfection paradox.”

This is when you try to find the perfect thing to say, then self-edit because you feel like what you were going to say isn’t good enough.

Perfection is the enemy of action.

Don’t edit yourself into silence. It’s okay to open your mouth. Everything you say won’t be perfect…and that’s not only okay, it’s expected.

This next skill set will help you rebound.

Skill Set #3:

Flush, Fix and Forget: How to rebound from any awkward moment

How to Join a Conversation Without Being AwkwardA while back, my wife and I went to our city’s huge public library downtown. It has columns, stone lions, and I assume ghosts.

1:02 PM

We take the elevator up to the 5th floor, where they have study rooms, periodicals, and the quiet room. The quiet room exists so that people can work and study in peace.

1:03 PM

We settle into the quiet room; we’re the only two people there.

1:03:30 PM

Thinking that the room was soundproof, and also wanting to make my wife laugh, I devise a hilarious (to me) plan to play five seconds of gangster rap.

1:04 PM

I press play. My wife quotes me as whispering “This is what I think of your quiet room.” (I do not remember this.)

1:04:10 PM

A library employee opens the door and politely tells me that the quiet room is (shocker) meant for being quiet. She asks if we might rather use one of the nearby meeting rooms. My wife thinks this is a fantastic idea.

1:05 PM

I sheepishly grab my messenger bag and we walk to the meeting room.

Quiet Room: 1 Jeff: 0

What can we learn from this?
How to Join a Conversation Without Being Awkward
There’s no sex in the champagne room – and, apparently, no rap in the quiet room
  • A. I clearly did not respect the nature of the quiet room.
  • B. I have a strong aversion to being a obedient rule follower.
  • C. I love gangster rap.

Looking back, I realized something interesting…

If something awkward happened to me years ago, I would have gone through a familiar cycle:

  1. Obsess over the event: “What the hell was I thinking?!”
  2. Second guess myself: “What I should have said was THIS!”
  3. Internalize my actions to my identity: “I am so stupid.”

The most important takeaway is: Separate your actions from your identity.

How many times have you talked with a group and:

  • A joke didn’t land.
  • There was an awkward pause.
  • You ran out of things to say.
How to Join a Conversation Without Being Awkward
How many times have you convinced yourself that your awkward moment looked like this?

And later you replayed the conversation in your head over and over.

Even worse…you started to meld that interaction into who you are, and associate it with your identity.

Not ideal.

So what’s the fix?

I use the three Fs: Flush, Fix, and Forget.

Flush it

Destroy the link between your actions and who you are. Delete all thoughts of “What do these actions say about who I am as a person?” When you flush that raw emotional connection, you have enough space to fix it.

Fix it

Is there anything about the situation that is within your control? Mentally adjust your approach for next time. (For me, that means not playing gangster rap in the quiet room.)

Forget it

Move on. Close the book. Replaying an event will almost certainly lead to “because that’s who I am” thinking. Often the biggest key here is simply giving yourself the permission to move on.

As you use the three Fs, you’ll find that you can move from flush to forget almost instantly.

This could be the difference between:

A fantastic night out.


A night spent beating yourself up over that awkward thing you did.


Tiny, Life Changing Moments
How to Join a Conversation Without Being Awkward
Routines can help you make being bold as habitual as brushing your teeth

We’ve covered mindsets.

We’ve covered skill sets.

Now, we’re going to cover something that I rarely share publicly.

This is the single most important step to learning any new skill.

This is how you take the theory that you’ve learned, and start applying it.


What you think of as your life is a collection of routines:

After you brush your teeth, you put your toothbrush away.

When you sit down in the driver’s seat of your car, you buckle your seatbelt.

When you realize your scrambled eggs are cooked, you turn off the stovetop burner.

We can use routines to our advantage.

My favorite type of routine to use is the If-When-Then routine.

If-When-Then routines give you an in-the-moment blueprint for new behaviors.

(I learned If-When-Then from Robert Cialdini’s book Pre-Suasion.)


How to Join a Conversation Without Being AwkwardWhen I’m in a group conversation at happy hour, if a new person joins, then I’ll be bold and introduce myself first.

When I walk into work, if there’s a group of people at the water cooler, then I’ll join their conversation.

Using the If-When-Then routines will help you turn something intimidating, like joining a conversation, into something you do automatically.

It’s your turn.

Take five minutes and brainstorm two typical scenarios where you could use If-When-Then.

When I _______, if there’s someone _______, then I’ll _______.

Next step:

We’ve covered some powerful mindsets, skill sets, and routines for group conversations. If you want to take a deeper dive into group conversations, download my free audio training on group conversations.

In the audio training, you’ll learn how to systematically destroy the fear of approaching people using Conversational Muscle Memory, the best body language to use while joining a group and how to jump into a conversation that has no opening. And you’ll also get a word-for-word script builder worksheet. Get it here.

Want to Make
Great Small Talk?

Discover exactly  what to say.

Enter your email address below to learn how to start – and sustain! – great conversations.

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