This study was conducted to allow us to understand the subjective experiences of medical students participating in rowing exercise classes at a medical school in South Korea and to derive implications for medical education. Accordingly, we analyzed their reflective journals, focusing on leadership and teamwork development. The study involved 40 second-year premedical students, and Colaizzi’s analysis was employed to understand and structure their experiences. The comprehensive analysis revealed 149 meaningful statements expressing students’ thoughts and experiences regarding the rowing exercise. From these statements, 13 meanings were synthesized, resulting in nine themes and four overarching categories, which provided a multilayered understanding of students’ experiences. The factors that enhanced teamwork included communication, trust, respect among team members, and a sense of responsibility. By contrast, the hindering factors were competitiveness, impatience, and avoidance of responsibility. Before the class, a mix of anticipation, excitement, and dissatisfaction regarding the rowing exercise course was observed. However, after the class, students realized that the role of the entire team, rather than individual ability, is crucial, and collaboration with peers is key—the concept of shared leadership. This study is significant in that it demonstrates rowing’s potential as a team sport to serve as an effective program for fostering collaboration and leadership within the medical school curriculum.