One of the top domestic issues of concern to Americans is access to high-quality and affordable health-care, and there is a growing concern about how institutions struggling to survive within this trillion-dollar industry will increase their effectiveness in the future. This chapter outlines a process of leadership development using an action learning approach in one Midwestern health-care system over a period of three years. The process addresses both the development of the individual leader as well as the collective leadership capacity in an effort to sustain organizational learning and effectiveness over time. A model is presented that covers four phases or Four C's of development, which includes movement from individual Competency development, to the development of social capital through the enhancement of Connections and Creation of shared understanding, ultimately expanding Capacity for change within the organization. We also address other factors that must be taken into consideration that will either enhance or impede the concentric movement such as culture, sponsor support, and alignment of systems and structures.