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Educational leaders find themselves in multiple contexts when they need to lead difficult conversations, for which they are often not prepared through their leadership preparation programs. Researchers have long called upon educational preparation programs to explicitly prepare educational leaders to become skillful communicators, often with the focus on being prepared to lead difficult conversations (Kowalski et al., 2007; Lasater, 2016; Tyler, 2016). However, little is reported on how programs are leading this explicit preparation, if at all. The purpose of this study is to examine how one educational leadership program prepares its graduates to navigate difficult conversations.