This chapter describes the assumptions underpinning the International Study of Principal Preparation. It outlines how cultural reference points for leadership have changed. It explores the changing conceptualization of contemporary leadership, highlights the new economic dimensions of leading, and discusses the changing face of educational personnel. It notes that educational leaders must utilize knowledge of how technology has altered how we perceive the world, live our lives, relate to others, and practice our profession. It highlights the complexities for leaders who must thrive in a milieu characterized by a desire to preserve a civil society, balance student–professional–union–community needs, develop cultural literacies for learners, and respond to accountability demands. Other complexities include the multiple allegiances of leaders, conflicting loyalties of community members, varying levels of digital awareness, and the need for interpersonal and intrapersonal intelligences. The chapter closes with a set of principles and considerations for leadership development.

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