Stewarding Complexity: Why the Old Maps No Longer Work
Stewarding Complexity: Session One — Why the Old Maps No Longer Work
The central challenge facing boards, executive teams, and senior leaders today is easy to name—and notoriously hard to navigate:
How do you steward institutions in environments that refuse to hold still?
How do you lead strategically when political, technological, social, and organizational conditions are constantly shifting beneath your feet?
Most governance and strategy practices still assume a world that no longer exists. They’re built for stability: linear plans, if–then logic, fixed goals, long planning cycles, and tidy impact metrics designed to lock outcomes in place. But leaders today aren’t operating in stable systems. They’re operating in complex, adaptive environments—where cause and effect are unclear, change is ongoing, and surprises are the norm.
The result? A growing gap between the reality leaders face and the tools they’ve been given to lead.
The first gathering of Stewarding Complexity is a reset.
In this opening session, we’ll surface why so many familiar approaches to strategy and governance keep failing—and what it actually means to lead when prediction and control are no longer reliable. Charley and Aarn will open the conversation by naming a core tension at the heart of modern leadership: our systems are complex, but our inherited tools are not.
From there, we’ll turn outward. Participants will be invited to bring real, lived challenges—moments where plans keep breaking down, decisions feel stuck, or governance structures lag behind reality. Together, we’ll begin practicing a different way of thinking and working: one that emphasizes sense-making, adaptation, and stewardship over control.
This session isn’t about offering quick fixes or new buzzwords. It’s about building the shared language, mental models, and practical muscles leaders need to operate responsibly and strategically inside complexity.
If you’re feeling the vertigo of constant change—and suspect the problem isn’t your leadership, but the tools you’ve been handed—this first session is where the work begins.