As educators, we seek engaging ways to demonstrate how crucial leadership is to advancing organizational success. This exercise uniquely emphasizes how much leaders may 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. Participants investigate the personal traits, biographies, and accomplishments of each pope to understand each leader’s style and effectiveness and make recommendations to Pope Francis using this situational data of his predecessors. In doing so, the exercise creates a perspective for how participants might enhance their own leadership skills within their own professional organizations. Variations for other organizational contexts where leadership is essential are included as well as variations for online delivery modes.