The purpose of this paper is to describe a self-assessment assignment which details how an industry analysis and manager interview can be used to provide a realistic perspective of a student's desired future management position. In this assignment students conduct a comprehensive analysis of the industry and position which they desire to hold in the future. One of the central themes and part of the assignment is conducting a qualitative interview with a sitting manager in the job they wish to pursue in the future. Students are encouraged to conduct interviews with more than one manager and if possible, to engage in a day (or longer) of shadowing the manager. The assignment highlights the importance of understanding the work environment and position sought for graduating students and how a classroom exercise can be used post-graduation. In addition, suggestions on adding interview questions and post-assignment assessment are given. While this assignment has been used in the author's MBA Leadership class, it can easily be adapted and modified for use in other graduate or undergraduate curricula within, or outside, of business disciplines.