After a decade of calls for healthcare transformation, there is a convergence of themes in our general orienting models. The core metaphor of health system as machine (with closed boundaries, linear functions, and controlled predictable outputs) has given way to health as ecosystem (with open boundaries, non-linear functions, multiple interdependencies, and no single locus of control over outcomes). Current developmental psychology theory suggests that people construct their reality, and interact with their world, based on the epistemology (or "action-logic" or "mindset") of their stage of development. Through this lens, the skills for leading large-scale change in our increasingly complex world require significant cognitive and interpersonal development. The concept of vertical development may be an underemphasized aspect of system change. This article will discuss a new set of leadership skills and frameworks that emerge in the nexus of complex adaptive systems and adult development theory.