The purpose of this study is to explore the perceptions of academic student support program leadership regarding best practices, experiences, and behaviors that influence their work toward retention and graduation efforts. Three research questions resulted from the study's purpose: (a) What are program directors' perceptions regarding their leadership practices and behaviors in student success units? (b) What leadership pressures, obstacles, and challenges do program directors face as they seek to achieve institutional student success goals? (c) How do program directors' current leadership perceptions inform/impact potential challenges and initiatives for the future? The current research incorporates ideas from the literature related to leadership in higher education, their perceptions of the role as middle leaders, understanding of and current trends in student support services, and an overview of student success. Furthermore, a conceptual framework was applied based on the leadership challenge model's five principles (Kouzes & Posner, 2012). The principles include "modeling the way, inspiring a shared vision, challenging the process, encouraging the heart, and enabling others to act." The exploration of the program director leadership is necessary because there is limited research devoted to the work of this type of middle manager in higher education. For this qualitative study, a phenomenological design was used to understand the shared, lived experience of the participants (Creswell, 2013; Eddles-Hirsch, 2015; Moustakas, 1994). The researcher used semi-structured interviews with an open-ended question format to understand each participant's experience and the connection to student retention and graduation challenges and successes. Analysis of interviews for common themes was done using Nvivo software. Interviews were transcribed, and member checking was utilized after each transcription. Coding and emerging theme analysis were completed through Nvivo. Emerging themes included (a) mentoring relationships, (b) student success with variations, (c) understanding of collaborative challenges, and (d) perceptions of middle leadership. Future implications for this research include more directed mentoring for leadership in managing the duality of their roles and their potential for advancement into senior administration roles. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]