In this case study, I describe my experiences as a novice researcher in conducting focus groups with high school students to learn about their participation in a high school dropout prevention program. The dropout prevention program was a partnership among the high school, the local state university, and the Phoenix Suns of the National Basketball Association. The program consisted of academic mentoring and tutoring from local university student-teachers, as well as financial and logistical support from the Phoenix Suns. While prior analyses of the dropout prevention program indicated it was effective in increasing students’ academic achievement and decreasing students’ dropout rates (Dialynas, 2015), the Suns, along with the high school administration, wanted to ensure the program was not just effective but was also meeting the perceived needs of the students, student-teachers, and high school teachers involved. Thus, this research involved surveying the student-teachers and high school teachers and conducting focus groups with the actual dropout prevention program student participants. This account discusses my experiences regarding various aspects of the focus groups, including participant sampling, question generation, and discussion facilitation, as well as challenges encountered and practical lessons learned.