This dissertation presents two case studies of educational leadership, followed by an extensive discussion of methodological, historical, and philosophical issues that pertain to education research, policy, and leadership development. The case studies utilize qualitative research methods and the theoretical framework of complex systems to ascertain how and to what extent principals fostered cultural and educational change at their schools, with attention to how principals leveraged distributed leadership, instructional leadership, and the generation of cultural norms. Findings from the study were consistent with literature on systems leadership, and reinforce the significance of history and path dependence in school systems, the need to limit disequilibrium and turbulence within sustainable ranges, the importance of trust within social networks to facilitate productive change processes, and the importance of shared cultural norms to align staff values and behavior. Following the explication of the two cases, a meta- analysis is presented to address the methodological and interpretive limits of the study. The role of human development and the influence of cultural ideology and social infrastructures are highlighted as crucial dimensions of reality that warrant integration in educational research. Integral Theory is utilized as a means to explore the cultural, social, and psychological factors involved in achieving more comprehensive interpretations of social reality. Key topics include: complex systems, Integral Theory, modernity, postmodernity, education reform, neoliberalism, and developmental psychology.