In this chapter, we further explore and contextualize school development amidst the tensions between contemporary policies and the educational needs of students. We conceptualize school development as a process that mediates among tensions that result in a Zone of Uncertainty. We then describe our application of school development in the Arizona Initiative for Leadership Development and Research (AZiLDR). Content was initially drawn from findings from the International Successful School Principalship Project (ISSPP) exploring leadership in high-needs, culturally diverse schools and related leadership studies. Our approach differs from other school development models in at least four ways. First, the approach is grounded in education theory as explicated by John Dewey and others. Closely related, our approach attempts to balance evidence-based values with humanistic values. Third, our approach is grounded in our empirical research and related studies of leadership in culturally diverse schools and communities. Fourth, our approach is process oriented and contextually sensitive for schools as they are situated in the larger community and serving culturally diverse populations. Finally, we develop leadership through a collaborative approach in that we work with school teams as a unit.