Turns Out Being Awkward is Actually Good - Here's How to Use It As Your Superpower

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THIS ISSUE

1. Feature: Best-selling and award winning author and workplace performance coach Henna Pryor shares how awkwardness is the secret to confidence and charisma.

2. Key Lesson: Awkwardness isn’t something to avoid; it’s a tool to deepen connection.

   • ❤️ Heartset: Awkwardness Is How You Connect

   • 🧠 Mindset: Confidence Comes From Showing Up, Not Being Perfect

   • 🧰 Skillset: How to Use Awkwardness to Build Relationships

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FEATURE

Listen on Apple, Spotify or on the web.

The Truth No One Tells You About Coaching

When I started my journey as a solopreneur, I had the opportunity to work 1-on-1 with people. Something I’ve never done. Sure, I’ve managed people, but doing a 60 minute coaching session for $?

I was worried. And I was right.

The truth is you will fumble. You will mispronounce someone’s name, pause awkwardly mid-thought, or ask a question that lands like a lead balloon. And you know what? It happened to me when I tried coaching, but that’s exactly how you’ll win.

Let me explain.

Think about the coaches, mentors, or leaders you admire. Is it their polished perfection you love—or the way they made you feel understood, seen, human?

Here’s the twist: perfection doesn’t build trust; awkwardness does.

How? 👇🏽

Main Lesson: Awkward Moments Build Bridges

Henna Pryor, author of Good Awkward, teaches that awkwardness is your secret weapon for connection. She learned this the hard way during her first professional job when her boss called her “Helen” for months. Too afraid to correct him, Henna created a bigger, messier situation when she finally had to admit her name was actually “Henna.” But when she embraced the awkwardness, her relationship with that boss improved—it even became a running joke.

If you’re stepping into 1-on-1 coaching, this lesson could be the difference between hesitating and thriving. Those first few calls? You’ll feel vulnerable. You might stumble over your words or lose track of what you wanted to say. But here’s the opportunity: your “human moments” make you relatable.

❤️ Heartset: Awkwardness Is How You Connect

Your fear of fumbling on a call stems from a lie we’ve all been fed: that confidence equals flawlessness. Spoiler alert: it doesn’t. People don’t want polished robots—they want real, imperfect humans who listen, care, and get them.

Henna reminds us:

Awkwardness is your opportunity to connect on a deeper level. That pause, that flubbed question, that nervous laugh? Those are the cracks in the armor that let people see the real you.

🧠 Mindset: Confidence Comes From Showing Up, Not Being Perfect

Here’s the shift you need: Confidence isn’t about avoiding awkwardness—it’s about getting comfortable with it. Think of it like a muscle. Every time you stumble through a question or laugh off a blunder, you’re strengthening your ability to recover.

🧰 Skillset: How to Use Awkwardness to Build Relationships

Let’s make this practical. Here are 4 ways to transform your fear of awkwardness into your secret weapon for connection:

1. Name It to Tame It
   If you fumble or lose your train of thought, call it out with humor or honesty.

   “Wow, I just blanked on what I was about to say—give me a second!”

   “Oops, I totally butchered that. Let me try again.”

   Acknowledging awkwardness releases the tension and makes both you and your client feel more at ease.

   (Catch an awkward moment during our recording! Watch it HERE.)

2. Lean Into Silence
   Ask a powerful, open-ended question (think: “What’s holding you back right now?”) and then stop talking. If they say, “I don’t know,” resist the urge to fill the silence. Sit with it. Let them process. Awkward? Sure. But that silence often leads to breakthrough moments.

3. Be Curious, Not Perfect
   Shift your focus from “How do I sound?” to “What can I learn about this person?” People sense when you’re genuinely curious—it makes them feel valued. And when you’re focused on them, you’re less likely to get caught up in your own mistakes.

4. Celebrate the Awkward Wins
   After every call, reflect on what went well. Did you misstep but recover? Did an awkward laugh lead to a meaningful connection? Highlight those moments. They’re proof that you can fumble and still win.

   Revel in the complexity of non-verbal communications

Your Awkward Superpower

Your fear of awkwardness isn’t a sign you’re not ready—it’s a sign you’re growing. It’s the proof that you care about the impact you’re making.

When you embrace those moments of discomfort, you’ll find they’re your greatest opportunity to build trust, authenticity, and even charisma.

So take the call. Fumble through your first few sessions. Laugh at yourself. Because the more you lean into awkwardness, the more magnetic—and successful—you’ll become.

Your superpower isn’t perfection—it’s your humanity.

Go be awkward—and go be legendary 🤘🏽,

Howie Chan

Creator of Legend Letters

​Read my story​

​Follow me on LinkedIn

SOURCES

1. Chan, Howie, Charismatic Influence: The Surprising POWER of Awkwardness & How You Can Harness It with Legend Henna Pryor, The Legend Effect Podcast, January 21, 2025 - LINK

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