This chapter explores contemporary research into leadership development, noting the emergence of a new leadership paradigm strongly influenced by women's global contribution to the workplace. Leadership is a process that involves influence and goal attainment and occurs within a group context. The concept of "distributed leadership" suggests that leadership "practice" comprises a series of interactions between educational leaders, followers and their situation, rather than being the culmination of one leader's competence and knowledge. The chapter focuses on feminization of leadership to refer to the spread of traits and qualities generally associated with women in the process of leading organizations and women's entry into a customarily male occupation. The glass ceiling has historically represented the promotion of men over women into senior leadership positions. For women who aspire to senior leadership positions, we need to understand the various obstacles that make up this labyrinth and discover how some women have found their way around them.