This chapter identifies common barriers and themes identified by campus diversity leaders in their efforts to facilitate an intentional and coordinated program of diversity organizational learning across a campus ecosystem. It explores the reasons why diversity education programs may or may not be successful and identifies practices that enhance the potential for systematic diversity organizational learning. Transformative learning is a process that examines the assumptions that underpin values and perspectives and through reflection and rational dialogue transform these assumptions to be more inclusive and well justified. The organization development aspect of faculty development addresses strategic institutional initiatives that include diversity and inclusion and intersection with teaching and learning. The chapter focuses on two case studies. The first is the Lehigh University which addresses the prominent role of diversity in academic transformation. The second is the University of Maryland at College Park, which examines the evolutionary movement from compositional diversity to a focus on inclusive diversity learning programs.