Despite persistent calls for institutions to offer internal leadership development programs for administrators, colleges and universities struggle to prepare mid-level administrators for professional advancement. Colleges and universities also face problems with employee retention. The experiences of those who occupy the organizational middle are lesser known than well-documented experiences of executive-level administrators and faculty. The purpose of this study was to explore the experiences of mid-level administrators who currently hold Director or similar positions in academic or career advising at small, residential, private liberal arts institutions of higher education. This collective case study involved interviews with mid-level administrators to explore their leadership development experiences from within their institutions. Qualitative coding was deployed in data analysis to generate categories and themes that helped gain an understanding of the experiences that shaped the leadership development of these professionals. Fourteen participants were interviewed from twelve small, residential, private liberal arts institutions of higher education. Five themes emerged from the data analysis: Challenges, Experiences, Initiative, Leadership, and Relationships. This study revealed the significant impact supervisors have on leadership development along with an underdeveloped state of resources to promote and facilitate internal leadership development. Institutional and industry-wide challenges also surfaced as key influences in the leadership development experiences of mid-level 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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]