As educators, we seek engaging ways to demonstrate how crucial leadership is to advancing organizational success. This exercise uniquely emphasizes how much leaders can learn from their predecessors in the same role. Participants explore leadership by researching two former Bishops of Rome—John Paul II and Benedict XVI—and the incumbent pontiff, Francis. They investigate personal traits, biographies, and accomplishments of each pope in order to understand each leader’s style and effectiveness. The exercise can be adapted to other contexts where executive leadership is essential. The aim of this exercise is for participants to make recommendations to Pope Francis—using situational data of his predecessors. In doing so, the exercise creates perspective for how participants might enhance their own leadership skills within their own professional organizations.