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Higher education leaders need to identify differences among generations of employees and students and develop a strategic plan for managing and motivating across the generations. This case study addresses the following question: “How do higher education leaders lead and motivate multigenerational employees and online students?” An understanding of the common characteristics of each generational group is the first step for developing a strategy for motivating all employees and students in higher education. Communication, mentoring programs, training, respect, and opportunities for career advancement are components valued by all. It is important for higher education leaders to understand the values, work ethic, and communication style of the different generations. The implications for higher education leaders lie in establishing an organizational culture that promotes satisfaction for all individuals in the higher education setting.