This study is a hermeneutic investigation into the phenomenon of organizational role conflict as experienced by five long-term department chairpersons, four long-term department heads, and two former long-term department chairpersons working at universities and colleges located in Indiana, Illinois, and Massachusetts. Organizational role conflict for department chairpersons and department heads is a byproduct of their frontline manager position. By occupying a position between the collegiate and administrative branches of their institution, these managers serve as an important link in the chain of command, but suffer from ambiguous, contradictory, and competing expectations placed on them because of their hybrid status as faculty members and administrators. While over six decades of research has established organizational role conflict as elemental to the department chairperson position, people who occupy this frontline manager position on a long-term basis are neglected in these investigations. This study addresses this deficiency in the research canon, as it provides an examination of the academic long-term frontline manager's experience of organizational role conflict. In-depth interviews and field notes were used to collect data, which were analyzed through the lenses of organizational role theory and organizational and management theory. Study findings indicate that the participants, guided by a strong sense of purpose and duty, mitigate their organizational role conflict while enacting their frontline manager role by employing strategies and embracing perspectives that reinforce their hybrid roles as scholar/educators and frontline 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.]