In this chapter, this complex nexus involving politics and education leadership operations in the ASEAN region is discussed and transformation form of leadership mediates between the two. Findings indicate that educational leaders operating under positive political environments are much better leaders in terms of transformational form of leadership behaviors which further influence education practices positively. The study will fill the gaps within the existing literature by throwing light on the key nexus between the political environment and the leadership processes within the educational sector that would bring insights into the issues to the policymakers and educational leaders in a bid to facilitate effective leadership practices within the political environment. The chapter concludes the future research and practical implications on how educational form of leadership is practically implemented in the ASEAN region and the fact is that adaptive strategies should be implemented in the consideration of political peculiarities, which influence educational form of leadership.