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Promotion to the principalship is a great privilege but with it comes great responsibilities. Research suggests that novice principals around the world face challenges which are similar. This chapter highlights some of the issues that new leaders are likely to encounter in their journey as educational leaders. It seeks to assist new principals or novice educational leaders to navigate the challenges they may face by guiding readers, first, to reflect on their definition of leadership and then to identify and craft their leadership philosophy. This journey of self-discovery is done through a conversation which includes anecdotes (both positive and negative), emotions, beliefs and reflections of the author; all the while intertwining research findings and pertinent questions. The author emphasizes that a leadership philosophy is personal because it is based on one’s beliefs, attitudes, experiences, and personality.

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