This conceptual article critically examines the view that, in complex adaptive systems (CAS), organizations are moved toward the edge of chaos and will exhibit “order for free” behaviors. Will organizations naturally self-organize to seek greater fitness? We suggest that, as hierarchies, organizations may be collectively led to establish a dynamic system where bottom-up structuration emerges to increase the long-term viability of the organization. Thus, it is our contention that while there is order for free, a desired order is not. To examine if a desired order for free emerges calls for analyses emphasizing the interplay among leadership, organization hierarchy, and CAS perspectives where these are systematically compared and contrasted. Based on such compare and contrast interplay, we argue that leadership researchers can help foster the evolution of a new type of dynamic emergent hierarchy that yields a sustained desired order across time.