This chapter presents a series of supervision-related case studies of situations that midlevel managers might face. Individuals enrolled in a midlevel management professional development course recommended the topics selected for this chapter. Drawing upon her experience teaching the course, the author selected four case studies that individuals in the class found most helpful to their work and/or evoked some of the most lively discussions. The case studies outlined in this chapter are designed to stimulate discussions about the cases themselves and to offer the author's professional perspective on how she might respond to the cases, if presented with similar scenarios. Embedded throughout each of the cases, and in the discussion section that follows each case study, is a series of questions for the reader to ponder. The perspectives offered that relate to each of the case studies presented are through the lens of someone who identifies herself as a "Baby Boomer," African American, female, Vice President of Student Affairs. In her 30-plus years of working in higher education, this author has worked at both public and private universities, supervising many of the traditional student affairs areas such as residence life, new-student programs, student health and counseling, the career development center, recreational sports, multicultural student affairs, and student activities. Other senior-level managers in student affairs with different backgrounds and experiences might approach the case studies differently. Thus, the case studies are offered as a means of encouraging discussion about the various ways one might respond when presented with one or more of the case study scenarios.