This qualitative study sought to understand the views of aspiring principals about teacher supervision and evaluation issues, including their perceived definitions of each, as well as concerns about performing either duty in their first administrative role. Thirty-­two educational administration graduate students enrolled in an instructional leadership class participated in on­-line instruction on teacher supervision and evaluation. Findings indicated participants understood the concept of formative supervision but were less clear when defining teacher evaluation. Specifically, aspiring principals used many terms associated with supervision as a role of principals when evaluating teachers. Participants' primary concerns with completing supervision and evaluation requirements during their first administrative job included having adequate time to be an instructional leader, and being able to deliver constructive feedback to low-­performing teachers to influence and improve instructional practice quickly. Recommendations for university preparation programs that train pre-service principals are included.