This teaching case study is meant to help current and future school leaders become change agents who lead effectively and improve their schools. I discuss one case in a fictitious city and school that is representative of many other American schools. In particular, I examine adaptive challenges that educational leaders commonly face. This case encourages administrators to participate in meaningful conversations with stakeholders to solve complex issues around leading change. The hope is to better understand how school leaders can transform schools, embrace adaptive challenges, and use change as opportunities for growth. I also pose questions designed to make future and current educational leaders think how they would resolve similar issues.