A discussion of the importance of skeptical probing in educational administration considers fundmental philosophical concerns, issues in inquiry, several theoretical frameworks, sociology of knowledge perspectives, and implications for educational administration programs. Philosophy suggests the best source of knowledge in a field as diverse as educational administration is not "facts" but the interplay of ideas and observations--or inquiry--which encourages multiple perspectives and methods. Phenomenology, for example, with its focus on essences, provides a valuable perspective. Moreover, no attempt to affect ethical outcomes can ignore people's social circumstances. Despite limitations, positivism, emphasizing meaning and exposition, and ethnography, emphasizing observation, are valuable in educational administration. Similarly, a theoretical framework such as public choice theory, which identifies self-interest as the primary motivation of teachers and administrators, is useful but easily criticized when focused too narrowly on schools or confronted with contradictions such as effective educational programs. The sociology of knowledge perspective emphasizes historical, social, and psychological contexts in shaping ideas. This perspective also furnishes such assessment norms as universalism, disinterestedness, and organized skepticism. Practitioners and students of educational administration would be well served by greater awareness of philosophical issues. (PB)