People who become educational leadership professors usually come to their new occupation with a range of skills and experiences. Most doctoral preparation programs in educational leadership however do not always prepare future faculty members to address conflicts that arise when the actual roles and responsibilities of the new faculty member conflict with either their own norms and values or the institutions' norms, values, or mission. This case is an opportunity to consider how new faculty prepare for entrance into the professoriate. This case guides the reader through an exploration of faculty expectations of their students and themselves and how to plan student evaluations given students' characteristics in the context and the culture of the institution. Future faculty members can benefit from a thoughtful consideration of themselves and how their expectations for themselves and their students affect the teaching and learning process.