In this reflective article, we offer innovative approaches to creating opportunities for leadership learning through questioning the intentions versus impacts of leading short-term study abroad courses. We consider the critical relevance of approaching a course like this from a learning disposition--recognizing our roles as learners, as well as facilitators of learning. We note the impacts of hegemony and identity, the effort and skills of dialoguing across difference, the complexities of constructive ambiguity, and the necessity to be adaptable as we navigate liminal spaces, concepts, and efforts for peace leadership. In the end, although this was a brief, 10-day experience, we came to realize our entire outlook on facilitating leadership learning shifted to recognize and grapple with these complexities.