The problem with most strategies is that they're built for a world that doesn't exist. When Strategy Meets Reality is for leaders who have followed the established playbook - off-sites, frameworks, cascades - and discovered that the more they plan, the less the organization seems to adapt. Strategy produces documents, not direction. The truth is that organizations are complex adaptive systems, not machines, which means strategy cannot be designed and then implemented in a linear sequence; it must be oriented, adapted and sustained through structures that enable intelligent action at every level. Drawing on complexity, systems thinking and decentralization, When Strategy Meets Reality reframes strategy as orientation: the ongoing work of making sense, acting and adapting when the map no longer matches the territory. Rather than control and prediction, it focuses on coherence, adaptation and viable decision-making in uncertainty, supported by information that flows freely and authority that moves to where knowledge lives. This is a book for CEOs, COOs and strategy leaders who want strategy to produce decisions and direction that survive contact with the world.