The experience of undergraduate students in American higher education is curated by student affairs and student services professionals. However, there is not a great deal of scholarship focusing on how these practitioners' leadership style impacts this experience. This study seeks to analyze how student affairs and student services directors' leadership style impacts the undergraduate student experience at a small, private liberal arts college. Participants and data collected in Cycle 1 used individual interviews, focus groups, and surveys. Action steps, including a "Personalized Leadership and Career Coaching for Student Affairs and Student Services Professionals" tool, were designed, implemented, and evaluated in Cycle 2 to provide a developmental experience that blended discipline-specific job functions, personal leadership style, and organizational culture. Findings included an acknowledgement of the butterfly effect analogy, the concern on a leader's future and burnout, and the causal relationship between leadership and self-efficacy in the organization. Implications for the organization include continued communities of practice and evaluating the relationship between continuing education and leadership identity. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]