Illustrating Leadership Lesson: Connection Over Loneliness

In this episode of Illustrating Leadership, I had the joy of talking with Vicki Bradley, founder and CEO of Women in Leadership Empowered and Chief Executive Coach at Vicki Bradley and Company.

Vicki’s work is rooted in service, advocacy, and helping women bring their authentic voices not just to the table, but to the world. After years in corporate environments, she realized that the work she cared most about was helping women navigate complexity, trust themselves, and lead with greater confidence.

When I asked Vicki about a leader who shaped her, she shared about Dave, a former boss who had a profound impact on how she understood leadership.

One of the lessons he gave her was simple, but it took years for her to fully understand:

It’s lonely at the top.

At first, Vicki did not understand what he meant. She was in his office often. They talked, strategized, and worked closely together. How could he feel lonely?

But later, when she became president of a company, she understood.

Leadership can be lonely because leaders often carry information they cannot share. They have responsibilities that require discretion. They want to connect deeply with their teams, but they also have to protect what is not theirs to reveal.

That is why connection outside of the immediate team matters so much.

Mentors.
Advisors.
Past bosses.
Industry peers.
People who can challenge, support, and help you see differently.

Dave also taught Vicki the importance of slowing down enough to understand the people and places around her. On one business trip to Newfoundland, he did not simply take her to the location and move on. He encouraged her to experience the culture, the history, the people, and yes — even the tradition of Screech and kissing the cod.

That lesson stayed with her.

Leadership is not just about showing up in the room.

It is about seeking to understand.

It is about being present.

It is about seeing the human being, the culture, and the context in front of you.

Today, Vicki brings those lessons into her coaching, courses, leadership development work, and her podcast, Women in Leadership Talk. Her work reminds us that good leadership requires courage, curiosity, trust, and connection.

And perhaps most importantly, it reminds us that even when leadership feels lonely, we do not have to lead alone.

Connect with Vicki

Please make sure you check out Women In Leadership Empowered's website and go say hi to Vicki on LinkedIn, Instagram, and Facebook!

Connect with Jessica

Learn more about how your host supports leaders by visiting her website...and definitely send a connection request on LinkedIn and let her know you listened to this podcast!