A study abroad program can be a transformative experience for students, but these programs rely on the support of program leaders who play a crucial mentoring role. Program leaders can also learn from their experiences abroad, but their experiences are less studied than those of students. To better prepare future program leaders, this paper describes the experiences of program leaders during a two-week study abroad program. We introduce a novel data collection approach, autonomous focus groups, to capture real-time perspectives. Through the lens of Kolb's Experiential Learning Theory, we characterize the process of leading a study abroad program and the conceptualizations that program leaders form about students during their time abroad. Our findings provide a more nuanced view of the day-to-day experience of leading a study abroad program than previous studies, which can inform the preparation and training provided to program leaders.