Perspectives
Reflections on leadership, place, and the conversations that change how we think.
cohort design
Every design decision in a Waypoint program is deliberate. The cohort size is no exception. Twelve is not a logistical convenience. It is the number at which something specific becomes possible — and above which it reliably stops being possible.
expedition leadership
Boardrooms are designed to make leaders look competent. Wilderness is designed to do nothing of the sort. That difference is precisely why the most revealing leadership development happens far from any conference room.
adventure leadership
Ruth and I just returned from seven days on the coast of Sardinia — hiking the deepest gorge in Europe, kayaking to hidden sea caves, and cycling through pinewood forests to a beach most people never reach. It was not a Waypoint program. But it reminded us, viscerally, why everything we build at Waypoint is designed the way it is.
executive wellbeing
We have built entire careers on the premise that speed is a virtue. But the leaders I have watched navigate complexity with the most grace are not the fastest ones. They are the ones who know when to stop.
decision-making
The higher you climb, the more your decisions affect people who will never know your name. That asymmetry — between the executive who decides and the thousands who live with the outcome — is the defining moral reality of senior leadership.
career transitions
There is a moment in every executive career when the organization you built your identity around stops being the right container for who you are becoming. Recognizing that moment — and acting on it — is one of the hardest things a leader will ever do.
executive leadership
Running technology for a city of 854,000 people is not a technology problem. It is a leadership problem. The lessons from that scale have shaped what I believe about how executives think — and where they get stuck.
global collaboration
The most consequential decisions of your leadership career may depend less on your expertise than on who is sitting across from you — and where.
strategic leadership
The demands on senior leaders have never been more complex. The question is not whether you can handle the pressure — it is whether you are thinking at the right level.
executive development
Conferences transfer information. Retreats change how people think. The distinction matters more than most organizations realize — and the gap is widening.
