In this essay, I explore the question of how best to leverage the benefits of dialogue for leadership education. The essay makes the case for studying the work of the ancient Greek historian Plutarch, who provides us with a unique kind of dialogue about leaders and leadership in his "Lives." This text features biographical sketches of important leaders from the ancient Greek and Roman traditions that are intended by the author to be in conversation with one another. In this essay, I present a brief content analysis of two lives, Lycurgus of Sparta and Numa Pompilius of Rome, with the aim of clarifying the leadership themes contained therein and showing how students of leadership can benefit from the conversation between these two biographies facilitated by Plutarch. In general, "Lives" is a resource though which students can enter into a profitable dialogue about important historical examples, revealing truths about leadership that help students to grapple with vital questions.