Introduction Leadership curricula in medical student education require assessment - to determine if leadership skills can be taught to medical students and applied during clinical and medical team interactions to aid in medical student leadership development. Objectives To examine whether medical students applied principles of their pre-clerkship leadership curriculum (character, competence, context, and communication elements across four levels: personal, interpersonal, team, and organizational) during an internal medicine clerkship. Methods Using art as a prompt, Uniformed Services University (USU) internal medicine clerkship students completed a structured reflection on a critical incident. Medical student essays written during a 10-week internal medicine clerkship at USU in 2019 were collected. 158 medical student submissions were de-identified and analyzed. Results Sixty-four submissions (40.5%) focused on leadership or leadership and professionalism. Students identified as male (n = 34, 53%), female (21, 33%), or not reported (9, 14%). Most, 48 (75%), did not describe PITO explicitly in their essay. They instead focused on personal and interpersonal aspects (17, 27%) of leadership, the attending physicians they worked with (33, 52%), and effective leadership strategies (46, 72%). The most common themes written about were responsibility (30, 47%), teamwork (18, 28%), competence (17, 27%), and character/integrity (15, 23%). Conclusion Although the students’ explicit use of the PITO model was limited, student essays centered on themes that reflected leadership concepts taught in pre-clerkship years, such as character, competence, and responsibility. This study demonstrates that an internal medicine clerkship rotation can feasibly implement a leadership reflection.