This case study illustrates the importance of goodwill, if coordinated with an informed view, opinion, or judgment (doxa) and opportune moment (kairos). It examines Isocrates’ concept and use of goodwill (eunoia) in his speeches Nicocles, On the Peace and Antidosis. Students will start by reflecting on the modern concept of emotional intelligence (EI) and the definition of goodwill by Aristotle, then analyze how Isocrates (436–338 BCE) uses goodwill as a precursor of emotional intelligence. They will examine the role of the teacher as an advisor to leaders such as Nicocles, the king of Cyprus, and Timotheus, the Athenian general. Then, they will be asked to discuss the role of Isocrates in advising leaders on the use of goodwill and the configuration of goodwill–judgment–opportune moment. Students will also examine the relation between a teacher, a counselor, a mentor, and a leader, the qualities of a leader, and the challenges posed by winning over the goodwill of a community.