Healthcare organizations offer numerous clinical and academic leadership pathways for physicians, among which the position of program director (PD) is considered to be a prominent educational leadership role. As PDs are instrumental in the recruitment and training of the next generations of physicians, PD gender distribution can affect the present and future of a medical specialty. This study offers a dialectical perspective in understanding how international PDs negotiate gendered understanding of their work/role by using the framework of Relational Dialectics Theory 2.0. Thirty-three interviews of PDs from Qatar, Singapore, and the United Arab Emirates were conducted and, using contrapuntal analysis, the competing discourses of meanings of gender in the PD work/role were examined. Competing discourses where structural, cultural, and professional meanings of gender were interrogated revealed inherent multiple meanings of how gender is understood in PD work/roles. In making sense of these meanings of gender, PDs express dilemmas of traditional gender binaries of masculine/feminine work/role meanings to explain the term in different ways in their everyday organizational and cultural struggles. The findings have implications for PD recruitment and retention in teaching hospitals.