Courageous Authenticity in Leadership: Why Speaking Up Isn’t Always the Boldest Move

Courageous Authenticity: What It Is—And What It Isn’t

There’s a moment in every leader’s journey when speaking up feels more terrifying than staying silent.

You’re in the room. You feel the tension. You know you see something others don’t. But the voice inside says, “What if this backfires? What if I’m wrong? What if I say too much?”

That’s the crossroads between comfort and courageous authenticity. And for many women leaders especially, it’s familiar terrain.

In a recent episode of The Enlightened Executive, I sat down with Cindy Adams—executive coach, speaker, and co-founder of The Enneagram in Business Network—to explore what true courageous authenticity looks like in leadership today.

And here’s what we uncovered: It’s not just about being bold. It’s about being wise.

Why This Matters for Leaders

Leadership today demands transparency, but not at the expense of impact.

We’ve been told authenticity means speaking your truth. But unfiltered expression isn’t always useful, especially in high-stakes environments. When you blurt, broadcast, or bare all without context, you risk undermining the very influence you’re trying to build.

That’s why courageous authenticity is a practice, not a personality trait.

It means knowing:

• When to speak and when to pause
• How to frame truth so it can be received
• Why your authenticity serves the mission, not just your ego

And most importantly, it means aligning what you say with how you want to lead.

The Science Behind the Shift

Neuroscience shows us that the brain perceives social rejection as physical pain. That’s why speaking up, especially when your view diverges, can feel like a risk to survival.

For women leaders and underrepresented voices, that risk often feels even more real.

But here’s the paradox: leaders who withhold too much create disconnection. And those who overshare without intention dilute their influence.

Courageous authenticity lives in the balance.
It’s where vulnerability meets discernment.

This is where tools like the Enneagram offer such valuable insight. Because how we perceive authenticity, and how we express it, varies dramatically based on our type.

Your Enneagram Type Shapes How You Show Up

In our conversation, Cindy shared her personal evolution: how she once believed courage meant saying everything. But as her leadership matured, she discovered that wisdom often lies in the how and when, not just the what.

This insight plays out across all Enneagram types:

• A Type 2 (The Supporter) may hesitate to speak up for fear of seeming selfish.
• A Type 3 (The Performer) might share what’s strategic but withhold what’s vulnerable.
• A Type 6 (The Troubleshooter) may rehearse authenticity so much it loses its spontaneity.

Each type has its own reflexes—some help, some hinder.

The goal isn’t to suppress your natural instincts.
It’s to elevate them. To bring self-awareness to the front of the room.

Action Steps You Can Take This Week

If you want to build more courageous authenticity into your leadership, here’s where to begin:

1. Map Your Reflexes
   Notice what you do when things feel tense or uncertain.
   Do you power through, over-explain, withdraw?
   That’s a pattern, and it’s trying to keep you safe. Recognizing it is your first step to choice.
2. Use the Pause + Purpose Formula
   Before you speak up, pause.
   Ask: What’s the outcome I want? Who is this serving?
   Courage without clarity can cause confusion. Clarity without courage can become avoidance. You need both.
3. Tailor Your Expression Through Your Enneagram Type
   Your Enneagram type shapes your blind spots.
   Use courses like our Enneagram Applied course to explore how your instincts influence communication, conflict, and collaboration.
4. Reframe What Courage Means
   Courage isn’t always loud.
   Sometimes, it’s the decision to wait until your message has the best chance to land.
   Sometimes, it’s asking a question instead of making a point.
   Sometimes, it’s being silent when your old pattern would speak to seek validation.
5. Reflect on a Time You Missed the Moment
   We all have those moments.
   What held you back? What would you try now with the awareness you have today?

That’s how you build wisdom. Not through perfection—but through reflection.

Final Thought: Authenticity Is Not a One-Time Act

It’s easy to think authenticity is a checkbox.
“I spoke my truth.” Done.

But courageous authenticity is a continual calibration between honesty, timing, and intention.
It’s the ability to show up fully, but also skillfully.

Because the most influential leaders don’t just share what’s real.
They do it in a way that moves things forward.

And that’s what we’re all after, isn’t it?

Want to understand how your Enneagram subtype shapes your courage, communication, and leadership presence?
👉 Take the Enneagram Applied Assessment