This paper reports a Rawlsian thought experiment to propose an approach for developing contextually specific theories of educative leadership. From a position of ignorance, it notes the considerable degree of coherence between a preliminary and practical theory of educative leadership devised in the early 1990s, seven leading twenty first century theories of educative leadership (transformative, distributed, instructional, system, ethical, culturally responsive and adaptive leadership in education) and regarding leadership in education as a moral art. It uses descriptive metaphysics to show that metaphysical and moral philosophies align in cultures to mitigate cognitive dissonance as systems, institutions and individuals find meaning, plan, act, and create theories of practice. It suggests that theories of educative leadership will be more compelling when they use a culturally relevant, pragmatic, holistic, and integrative approach, while acknowledging that potential limitations can include conceptual ambiguities, oversimplification, and challenges in empirical validation and generalizability. A non-foundational theory of knowledge is recommended to create culturally specific theories about educative leadership. It employs pragmatic holism to refine knowledge to solve problems in context, inevitably displacing singular, overarching, and culture-blind models. It proposes the construction of a culturally specific web of belief comprising metaphysical and moral philosophies, exhibiting internal and external coherence and providing a comprehensive and adaptable framework for developing and understanding educative leadership in context.