Homer’s Iliad provides several examples of key leaders disregarding the advice of subordinates. This case study investigates a series of examples assessing what is at stake for the leader/follower relationship. Homer seems especially interested in occasions where subordinates speak up to leadership, providing information that directly challenges the leader to make a tough decision. That is to say, these examples highlight a test of leadership and decision-making skills as seen from the perspective of the follower. We will work through key examples of Kalchas and Thersites on the Hellenic side, and Antenor and Poulydamas on the Trojan side. Each subordinate speaks up to leadership in either presenting accurate information or interpretations, or in being representative of larger concerns. As the consequences of decisions play out, Homer warns leaders what is at stake in refusing to listen. Students will be invited to see things from the follower’s perspective.