Case studies continue to be a signature teaching tool for developing leadership educators in a classroom setting. However, many of these cases tend to be generic and may limit student learning. In order to maximize the learning potential of case studies, we advocate for the use of peer-authored, real-to-life case studies written from a first-hand experience as a training tool for graduate and doctoral-level leadership students. Students author a case based on a real-to-life issue, share with a classmate, and analyze collaboratively. This form of training allows leadership students to examine a case through multiple lenses while processing with a peer who may still be dealing with the leadership issue in real time. The culminating process allows students to examine the issue with direct feedback from another who lived the experience, completing a true 360-degree examination of a real-to-life controversy. This process supports deep reflection, leadership competencies, and metacognition of a dilemma. The assignment outlined in this application manuscript can be completed face-to-face or online and can be modified to work with any leadership learner group or program.