Twelve Miles with Jeff Buckeye at COS25

Last week, I had the privilege of walking 12 miles with Jeff Buckeye while in Redmond for the COS25 event at Microsoft, co-sponsored by Jeff and The Chief of Staff Association.

We walked along the Sammamish River and ended up at Willows Lodge from the Redmond Town Center, without a car involved, just following the path and letting the conversation flow.


A Few Things That Stayed with Me

  • Networking
    Common connections often lead to meaningful new relationships. The starting point is rarely random.

  • Clarity
    Simplicity brings the strongest insight. The more complex things become, the more important it is to strip them back.

  • Reflection
    The plan behind the plan often reveals what actually matters. That is where the real thinking happens.

  • The Rhino Lesson
    Big. Powerful. And vulnerable. Strength and openness are not mutually exclusive.

  • Direction
    Sometimes the right turn on a path leads to opportunities you did not expect.


Walking alongside Jeff was a powerful reminder of what Dialogue Miles™ is all about: connection, reflection, and the power of shared experiences. The walk gave us time to pause, reflect, and build on our ideas—and those lessons carried over into the amazing conversations at the event.

Grateful for the walk and the opportunity to share the stage with incredible leaders at the event. It’s all about connecting, learning, and moving forward.

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Six Miles at Percy Warner Park with Robin Satyshur

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Three Miles in Dayton with Chris Eifert