Supervisory practice has evolved since its origins in colonial times, and its effectiveness as a means of improving instruction depends on the ability of educational leaders to remain responsive to the needs of teachers and students. An educational leader’s resolve to remain adaptable also depends on an appreciation of the changing and evolving nature of supervision, especially in the new millennium. An educational leader who understands the history of supervision and how current demands are influenced by that history will be better able to confront the technological, social, political, and moral issues of the day. Educational leaders also will have to develop the requisite knowledge, skills, and dispositions that are the foundation for effective supervisory practice. This chapter explicates how supervision has evolved to its current state, how you might respond to ever-increasing supervisory needs and demands, and how your beliefs and attitudes affect how you react to daily challenges.