Stop Feeling Awkward

Today’s Sponsor

When I asked you, "What's your biggest networking challenge?" you clearly said it was feeling awkward starting conversations with people you don't know.

Which reminded me of a not-so-fun fact about why starting conversations with others can sometimes feel weird:

You're not feeling awkward because you don't know what to say.

You're awkward because you're trying too hard not to be awkward.

I’ve been there, and just thinking about it takes me back to a conference a few years ago.

I'd just delivered a presentation to a room full of people.

Felt great.
Confident.
In my element.

Then I spotted someone in the hallway who could potentially collaborate on my next project.

Suddenly, I wasn't the confident presenter anymore. I was someone who needed something.

I spent about 20 minutes standing near the coffee station, rehearsing opening lines in my head.

• "Hi, how's the event?" Too boring.

• "Great presentation, right?" What if they missed it? 

• "I'm Girvin, nice to meet you." Too formal.

While I was perfecting my approach, others were just walking up and saying, "Hey, how's it going?"

There are a number of reasons you may feel anxious socializing, and a number of ways to calm your anxiety.

But here’s a hot take on conversation anxiety: 

The people who seem naturally good at conversations aren't doing anything special.

They're just not overthinking it.

Why Experts Struggle More Than You'd Expect

Here's what makes conversations especially awkward for subject matter experts and leaders:

You're comfortable when you're "on":

• Presenting your expertise to audiences

• Leading meetings where you're the authority

• Delivering results in your domain

But informal relationship-building conversations are different:

• You're not presenting; you're connecting

• You might need their support for your initiative

• You're building rapport, not demonstrating expertise

• The dynamic is peer-to-peer, not expert-to-audience

The shift from "I have expertise to share" to "I want to build a relationship" creates vulnerability.

And vulnerability feels awkward when you're used to being the authority in the room.

The Truth About Confident Conversationalists

Here's what I discovered watching people who seem naturally social:

They feel awkward too. They just don't let it stop them.

• They expect conversations to feel slightly uncomfortable at first

• They focus on the other person instead of their own performance

• They use simple, genuine openers instead of clever lines

• They're okay with conversations that don't go anywhere

• They start more conversations, so they get more practice

The secret isn't confidence. It's acceptance.

When you stop trying to eliminate awkwardness and start accepting it as normal, conversations become much easier.

I know, I know. Easier said than done, right?

Well, you know I’ve got a framework for you.

Conversations Without the Awkwardness

After studying my own awkward moments and watching smooth conversationalists, here’s my take on how to make starting conversations feel natural:

E - Expect Initial Discomfort
A - Anchor in Simple Curiosity
S - Start with Situational Comments
E - Embrace the Other Person's Perspective

Let’s get it…

E - Expect Initial Discomfort

Know that the first 30 seconds of any conversation will feel slightly uncomfortable, and that's completely normal.

• Tell yourself, "This might feel awkward for a moment, and that's okay"

• Remember that they probably feel the same initial uncertainty

• Focus on getting through the first exchange, not the entire conversation

• Recognize that discomfort fades once you start talking

When you expect awkwardness, you don't panic when you feel it.

A - Anchor in Simple Curiosity

Approach conversations with real curiosity about the other person rather than trying to impress them.

• Think "I wonder what their experience is like" instead of "I hope I sound interesting"

• Ask questions you actually want to know the answers to

• Focus on learning something rather than saying something smart

• Remember that people enjoy talking about themselves

Curiosity shifts attention away from your performance anxiety.

S - Start with Situational Comments

Open with observations about your shared environment or experience.

• "How are you finding the conference so far?"

• "That last speaker had some interesting points"

• "Have you been to one of these events before?"

• "This coffee line seems to be the place to meet people"

Situational comments are natural, relevant, and give you something obvious to talk about.

E - Embrace the Other Person's Perspective

Focus entirely on their experience and responses rather than monitoring your own performance.

• Listen to understand, not to prepare your next comment

• Ask follow-up questions about what they share

• Show genuine interest in their perspective

• Let the conversation flow based on what they find interesting

When you focus on them, you forget to be self-conscious.

POLL

In Case You Missed It!

• Someone at work is playing games with you

• Grab your Pocket Guide to Impromptu Conversations
  (Essential questions and cues to connect quickly—without sounding rehearsed)

• Train Your Attention, Improve Your Memory

• Transform small talk into deeper connections with proven conversation strategies

• Grab your Heads-Up Framework Checklist for initiating difficult conversations early with clarity, control, and mutual respect.

The Bottom Line

The most socially confident people aren't the ones who never feel awkward.

They're the ones who feel awkward and start conversations anyway.

They understand that slight discomfort is the price of meeting new people, and they're willing to pay it.

So…accept awkwardness as the normal first step and connect with someone new.

Thanks for reading. Be easy!
Girvin

P.S. What's the most awkward conversation you've ever started that turned out great? Hit reply and tell me.