In the globalized and technological world in which we now live, school leaders must be prepared to engage in complex and interdependent systems. Hierarchical power and authority will not provide the leader with the capacity to challenge people and systems to adapt and change to the emerging needs of students from differing social, political, and cultural contexts. Principals require a model of leadership that transcends epistemological boundaries to nurture learning organizations that produce students who are equipped to engage in the global knowledge economy and to participate as citizens of the world. This article presents participant perspectives of a model of leadership development that has resulted in over 60% of graduates obtaining school or district leadership positions within two years of program completion and recognition by the Wallace Foundation as a recipient of their 2011 funding program aimed at improving the pipeline to the principalship.