The purpose of this study was to identify the leadership competencies and characteristics that are "preferred" by student affairs administrators, and to compare these preferences across generations to determine if there were any differences. The term "preferred" was used to indicate that the study asked respondents to assign a value or a level of importance to each competency, thus indicating preference. This study built on the work of McDaniel (2002) and Smith (2007). By utilizing the previously developed Higher Education Leadership Competencies (HELC) survey as the instrument, the data collected from this study has the potential to add new and valuable knowledge and insight into our current understandings of perceived leadership in the workplace, specifically the working environment of student affairs at institutions of higher education (Smith 2007). This cognitive approach to leadership perceptions highlights differences in preferences of leadership in terms of specific leadership competencies. The data reduction technique of factor analysis resulted in 10 components with correlation coefficients above 0.50: Organizational Behavior, Communication, External Relations, Diversity, Professionalism, Institutional Culture, Inclusiveness, Humor, Partnerships, and Technology. The top 5 ranked competency items from the HELC included: Communicates effectively, Acts consistent with core values and integrity, Learns from experience, Supports leadership of others, and Encourages professional development. The 4 most common "greatest challenges facing higher education leaders in the next 5 years" cited by respondents related to the budget, mental health issues, technology and diversity. The ANOVA results indicated that 7 of the 10 components were found to have significant differences in means between groups: Communication, External Relations, Diversity, Professionalism, Institutional Culture, Humor and Partnerships. An ANCOVA analysis confirmed this finding while testing the variable "years of experience" as a covariate. The research question and main hypothesis were confirmed and supported--there are significant differences in preferred leadership competencies between different generations of student affairs administrators. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]