Researchers have spent years investigating the demands, multiple roles, and critical nature of organizational leaders in postsecondary educational settings. Overall, the research indicates agreement that leadership at all levels in postsecondary education is complex and multidimensional. During the past thirty years, though, much of the research has concentrated specifically on the capacious role of midlevel leadership, with the main focus on academic department chairs within colleges and universities. Research validates that leading from the middle is no easy task. Given these research findings over the past thirty years and the range of issues facing higher education in the first few years of this new century, it appears logical to predict a continuing increase in role demands and complexity. The purpose of this chapter is not to reiterate the roles or to predict specific future roles and responsibilities, but to argue for the integration of what is known and can be predicted about expansive academic leadership duties at the midlevel in postsecondary organizations. This chapter focuses on these issues and describes the six critical components of skills and competencies as they relate specifically to transformational leadership. The authors cite the Academy for Leadership Training and Development (Mesa, Arizona) as an example of professional development that offers leaders the knowledge and skill competencies to meet the challenges of leadership in today's postsecondary settings.