Purpose. Health-system pharmacy directors, managers, practitioners, students, and employers were surveyed to assess the situation of current and future leaders in pharmacy and generate recommendations for preventing shortages. Methods. Online surveys were sent to pharmacy directors, pharmacy middle managers, current pharmacy practitioners, pharmacy students, and employers recruiting for management positions using ASHP's membership and CareerPharm databases. Directors, managers, and practitioners were asked about their job satisfaction and future plans. The trends in demographics and attitudes toward the balance between family and work were assessed among directors, managers, practitioners, and students. Employers were asked about their perceived ease of filling managerial positions. Results. While most pharmacy directors and middle managers were satisfied with their current positions, 80% of directors and 77% of middle managers anticipated leaving their jobs in the next decade. Men comprised 72% of directors, 50% of middle managers, 62% of practitioners, and 21% of pharmacy students. The majority of pharmacy students and practitioners reported being married to a working spouse and having children and expressed a desire to balance their personal life with their career. The top reasons cited by students and practitioners for not seeking leadership positions were having to give up clinical practice and competing responsibilities. More than half of employers felt it was more difficult to recruit managers now than it was three years ago. Conclusion. A significant gap in pharmacy leadership in the next 5-10 years is expected, as well as a shift in work force composition and attitude. Mentoring and residencies are important methods of fostering new leaders in the profession.