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The purpose of this quantitative study was to identify and compare differences in leadership behaviors of senior student affairs officers (SSAOs) based on their generational cohort (Baby Boomer, Generation X, Millennial). The Multifactor Leadership Questionnaire (MLQ) was used to measure nine leadership behaviors and three leadership outcomes. Surveys were administered electronically to 3,361 individuals identified as a chief student affairs officer or director of student affairs in the Higher Education Online Directory (2014). The 449 respondents included 246 Baby Boomers, 192 Generation Xers, and 11 Millennials. Due to an uneven sample size, the Millennial group was removed from the data analysis. The total respondents consisted of 215 male and 219 female SSAOs with 260 employed at four-year private institutions and 170 employed at four-year public institutions. A MANOVA was utilized to determine whether or not statistical differences existed between the nine dependent variables (leadership behaviors) and independent group variables (generational group). The findings showed that whereas Generation X SSAOs exhibited more transactional leadership behaviors, Baby Boomer SSAOs were more transformational. The results of this study have implications for the field of student affairs in that research and practice support the need for more transformational leaders in senior administrative positions in higher education. If Generation X SSAOs who represent the next generation of administrators are more transactional in their leadership, college presidents and professional associations may need to develop a new, more transformational generation of SSAOs to replace Baby Boomers as they retire.