The Leadership Moment That Taught Me What Not to Become as a Woman Business Owner
Wed Feb 04 2026
In this episode, we unpack what tone-deaf CEOs actually have in common—and why even the most caring women can slip into these patterns when they're carrying too much inside systems that were never built for them.
Through a powerful (and painful) corporate story, I share the moment I learned firsthand how disconnected leadership impacts real humans—and why awareness, not intention, is what actually matters.
You'll learn:
The three core traits tone-deaf leaders share (and how they show up in small businesses) Why oversimplification, blanket statements, and emotional decisions are symptoms of disconnection—not failure How overwhelm quietly erodes leadership clarity What human-centered, grounded leadership actually looks like How to lead with honor, precision, and self-awareness—without becoming hardened or cold This episode is a reminder that you're not a bad leader. You're just tired. And leadership becomes lighter when awareness comes first.
Connect with Jillian:
Instagram.com/jilliandolberry
Reach out to Jillian: www.jilliandolberry.com/contact
Resources:
Check out The Peaceful Business Ebook by Jillian Dolberry
Here is my free resource that gives you real insight into how your team is actually experiencing their role.
If this episode resonated with you, subscribe for new episodes and share it with a woman in your life who carries more than she ever admits out loud. She needs it.
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In this episode, we unpack what tone-deaf CEOs actually have in common—and why even the most caring women can slip into these patterns when they're carrying too much inside systems that were never built for them. Through a powerful (and painful) corporate story, I share the moment I learned firsthand how disconnected leadership impacts real humans—and why awareness, not intention, is what actually matters. You'll learn: The three core traits tone-deaf leaders share (and how they show up in small businesses) Why oversimplification, blanket statements, and emotional decisions are symptoms of disconnection—not failure How overwhelm quietly erodes leadership clarity What human-centered, grounded leadership actually looks like How to lead with honor, precision, and self-awareness—without becoming hardened or cold This episode is a reminder that you're not a bad leader. You're just tired. And leadership becomes lighter when awareness comes first. Connect with Jillian: Instagram.com/jilliandolberry Reach out to Jillian: www.jilliandolberry.com/contact Resources: Check out The Peaceful Business Ebook by Jillian Dolberry Here is my free resource that gives you real insight into how your team is actually experiencing their role. If this episode resonated with you, subscribe for new episodes and share it with a woman in your life who carries more than she ever admits out loud. She needs it.