Curiosity and Connection: A Dialogue Miles Walk Before COS25

Managing time is a constant challenge for CEOs and their Chiefs of Staff. Maximizing opportunities for meaningful, impactful connections becomes a high priority, no matter the size of the company. So when the opportunity arose for Keziah Wonstolen and me to meet ahead of the COS25: Chief of Staff Dialogue in Redmond, it was an easy decision.

Keziah is the Founder and CEO of Vannin Chief of Staff, and someone I had been hoping to connect with in person since our first email introduction from Jeff Buckeye back in February of 2023.

Two years later, we finally made it happen. We walked six miles and the conversation never slowed down.

Dialogue Miles™ often works that way. Movement changes the pace of the conversation, and ideas flow differently when you’re not sitting across a table.

Here are a few reflections that stayed with me from our walk:

Ask Questions

Curiosity opens the door to deeper connection. When leaders approach conversations with genuine curiosity, it creates space for perspectives that might otherwise stay hidden.

Be Patient

Meaningful relationships rarely develop overnight. They take time, repeated conversations, and shared experiences that build trust over time.

Leverage Common Bonds

Shared experiences often become the foundation for stronger professional relationships. When leaders discover common ground, whether through business challenges, personal stories, or entrepreneurial journeys, conversations move quickly from surface to substance.

Safety in Action

During the walk, a local resident went out of his way to share a few important safety tips about the area. It was a small moment, but one that reinforced how simple gestures can make a difference during shared experiences.

After the walk, we continued the conversation over dinner, discussing ways we might collaborate and support each other as entrepreneurs.

The small business community has a unique way of creating these moments of connection. I’m grateful for the walk, the conversation, and the opportunity to finally meet in person.

Sometimes the most meaningful professional conversations happen when we simply decide to go for a walk.