This is an adapted transcript from the Love To Lead Podcast. Listen to the full episode The Leadership Moment That Taught Me What Not to Become as a Woman Business Owner

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There’s a specific kind of leadership moment that makes your stomach drop.

It’s when you hear yourself say something sharp.
Or dismissive.
Or overly simplified.

“This shouldn’t be that hard.”
“I don’t want to have to explain this again.”
“Everyone just needs to step up.”

And later — when the house is quiet and you’re replaying the day in your head — you realize:

That didn’t feel like me.

Today we’re talking about tone-deaf CEOs.

The ones who oversimplify everything.
Who operate disconnected from their people.
Who communicate in ways that make everyone around them feel small or confused.

And before you click away thinking, “Jillian, I’m not a tone-deaf CEO” — stay with me.

Because even the most caring, values-driven women slip into tone-deaf leadership patterns when they’re overwhelmed, disconnected from their work, or trying to squeeze themselves into systems that were never designed for women.

This isn’t about shame. It’s about awareness. And awareness is where powerful leadership begins.

The Corporate Moment That Changed Everything

When I was 22, I worked as a graphic designer for a major retail brand.

At the time, it felt magical. Seeing a display I created inside a store? Chef’s kiss. It felt creative. It felt purposeful. It felt like I had made it.

But corporate also showed me exactly who I didn’t want to become.

One afternoon, the VP of Sales walked into our design office holding a roll of new print material. He was hyped. Like he had personally invented the iPhone.

“This material is revolutionary,” he said. “You can stick it to windows, drywall, brick — ANY surface — and it’ll peel right off and reapply somewhere else.”

And to demonstrate this incredible innovation?

He chose my face.

Before I even processed what was happening, he pressed the adhesive material onto my cheek and into my hair. Then he ripped it off. In front of my entire team.

It pulled my hair.
My makeup.
My dignity.

And I stood there frozen.

Because I was young.
Because he was powerful.
Because no one knew what to do.

That was the moment my disdain for tone-deaf leadership was born.

Not just because it was inappropriate — which it absolutely was.

But because it showed me what happens when leaders:

• Don’t understand the impact of their actions
• Don’t see the humans in front of them
• Don’t read the room
• Don’t take responsibility for the energy they bring

Tone-deaf leadership isn’t just about big dramatic failures. It’s about disconnection.

Tone-Deaf CEOs Exist in Small Business Too

Here’s the uncomfortable truth:

Tone-deaf CEOs aren’t just in corporate.

They show up in small businesses — especially when women are overwhelmed, overworked, and disconnected from their purpose.

You don’t become tone-deaf because you don’t care.

You become tone-deaf because you’re drowning.

Let’s talk about the patterns.

The 3 Traits Tone-Deaf CEOs Have in Common

1. They Oversimplify What They Don’t Understand

My VP treated that “revolutionary” material like a toy. And he treated me like a surface.

Tone-deaf leaders reduce complexity to:

• “Just do it like this.”
• “It shouldn’t be that hard.”
• “Why didn’t they just figure it out?”

Women entrepreneurs slip into this when they’re overwhelmed and functioning without clarity.

It sounds like:

• “I handed it off. Why didn’t they just get it?”
• “Why can’t she just read my mind?”

Oversimplification is a symptom of disconnection.

When you’re unclear, exhausted, or carrying too much, you shortcut communication. And those shortcuts cost you trust.

2. They Aren’t Connected to Their People (or Their Work)

Tone-deaf CEOs lead from a pedestal — not from partnership.

In corporate, that VP didn’t see a human. He saw a prop.

In small business, disconnection looks like:

• Hiring without clarity
• Delegating without context
• Expecting initiative without instruction
• Being unavailable but still expecting excellence

Women don’t disconnect because they’re careless.

They disconnect because they’re carrying everything — business, family, mental load, emotional labor — and they’re doing it silently.

But disconnection always creates dysfunction.

When you aren’t connected to the work long enough to understand it, you can’t delegate it clearly.

When you aren’t connected to your people, you can’t lead them well.

3. They Communicate in Blanket Statements

Tone-deaf leaders speak in sweeping language:

• “Everyone needs to step up.”
• “This should be done by now.”
• “I don’t want to explain this again.”

These statements don’t create clarity.

They create fear.
Confusion.
Resentment.

Blanket statements are usually signs of:

• Exhaustion
• Lack of structure
• Internal overwhelm

And women battle this constantly inside systems that weren’t built with their mental load in mind.

When you’re tired, you default to emotion.

But leadership becomes light when communication becomes precise.

The Bonus Pattern: Emotionally Expensive Decisions

When you’re disconnected, you make expensive decisions.

You:

• Hire without a strategy
• Overpay for help you don’t know how to use
• Invest in tools hoping they’ll magically create clarity

Not because you’re irresponsible. But because you’re tired.

Overwhelm breeds impulsive decisions. And then you resent the very help you hired.

So How Do You NOT Become a Tone-Deaf CEO?

This is where we shift. Because the goal isn’t perfection. It’s self-awareness.

1. Stay Connected to the Work Long Enough to Understand It — Then Let It Go

Women feel guilty both for holding on and for releasing. But true leadership is knowing when and how to release responsibility. You cannot delegate what you don’t understand. And you cannot hold everything forever. Connected first. Then released with clarity.

2. Stay Connected to Your People

Honor the human in front of you. Clarity and compassion can coexist.

Say things like:

• “Here’s what success looks like.”
• “Here’s what I need from you.”
• “Here’s what support looks like in this role.”

Specifics create safety. And safety creates ownership.

3. Communicate in Precision, Not Emotion

No more blanket statements.
No more assumptions.
No more “shoulds.”

When you’re triggered, pause. When you’re overwhelmed, slow down. Precision builds trust.

4. Lead Yourself First

Self-awareness is the antidote to tone-deaf leadership. Your energy is your most valuable business asset. When you are aligned, grounded, and clear — your business reflects that. When you’re scattered and resentful — your team feels it. Leadership isn’t about control. It’s about responsibility for your presence.

The Hard Truth (And the Relief)

You are not a bad leader. You are likely a tired one. You are likely a woman trying to lead inside systems that never accounted for your invisible responsibilities.

But that doesn’t mean you get to stay disconnected.

It means you get to redesign how you lead.

Ownership isn’t carrying it all. It’s knowing what’s yours to hold — and what isn’t. And the moment you choose awareness over autopilot?

That’s when your leadership changes.

If this hit a little too close to home, I encourage you to sit with it.

Notice where you’ve oversimplified.
Notice where you’ve disconnected.
Notice where emotion replaced precision.

Not with shame. With grace.

Because tone-deaf leadership isn’t a personality trait.

It’s a pattern. And patterns can be changed.

This is an adapted transcript from the Love To Lead Podcast. Listen to the full episode The Leadership Moment That Taught Me What Not to Become as a Woman Business Owner