Where Leadership Really Lives with Deb Cupp
What an incredible 6.8-mile walk with Deb Cupp at Percy Warner Park in Nashville.
Each mile was filled with deep conversation, laughter, and, most importantly, a reminder of why true connections matter. Deb is one of those rare people who brings immense joy into my life, and spending the day with her was nothing short of magical. She has a unique ability to make people feel heard, seen, and challenged in all the right ways.
Throughout the walk, we explored a wide range of topics — leadership, navigating the realities of aging parents, and the importance of staying connected. Whether that connection is with family, friends, or the teams we work alongside every day, the thread of relationship runs through everything we do as leaders.
One of the highlights of the day came when members of Deb’s team joined us briefly on the trail to say hello. It was special to see the curiosity, respect, and rapport that had already formed between us after hearing so much about each other. Meeting the people who help shape Microsoft’s impact on the world felt like stepping into a circle of trust and innovation.
Moments like that reinforce something important about leadership.
When you really boil it all down, great leadership is about the people and relationships that make the work possible.
Dialogue Miles™ walks often create space for the kinds of unfiltered, authentic conversations that rarely happen in a traditional meeting setting. Whether the conversation unfolds across miles of trail or across a conference table, these exchanges are often where the most meaningful insights emerge.
Sometimes the most valuable leadership conversations happen when we simply slow down and give them room to unfold.
Deb, thank you for another unforgettable Dialogue Miles™ walk, and for always bringing joy, wisdom, and positivity to every step we take together.
We also happened to be wearing our Dialogue Miles™ hoodies on the hike, which made the experience feel even more special. I’ve been toying with the idea of creating more of them for others who enjoy these walks. Just something we’re tossing around.
