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This chapter describes the potential role that deliberate attention to developing resilience can play in novice female school administrators’ efforts to overcome challenges associated with leadership transition from the role of classroom teacher to the position of vice-principal or principal. It examines the changing nature and roles of principalship, the role of women as school administrators, the key barriers and challenges for women in the role of school administrator, and the experiences of newly inducted female school administrators. The chapter concludes with the discussion of how novice female school administrators can develop their resilience to successfully transition to their new roles during the period of induction and socialization into leadership positions.

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