Middle school students experience biological, cognitive, and social changes as they struggle with identity formation, self-concept, self-esteem, and academic success. Psycho-educational groups are an effective and efficient method for confronting social/emotional or academic problems that prohibit middle school students from performing well in schools. An essential component in the successful counseling of middle school groups is the skill and experience of the group leader. Research on school-based groups has focused on all areas with the exception of group leadership. Therefore, the purpose of this study is to explore how experienced middle school group leaders approach and conduct psycho-educational groups. This qualitative study uses a grounded theory methodology to investigate the practices, experiences, and perceptions of fourteen middle school counselors. The theory that emerged is grounded in the data from the participants and represents how they were able to conduct small groups in schools despite barriers many other school counselors experienced. Through educational leadership, relationship building, and an understanding of the systems at work in schools, these participants were able to establish a group program in their schools. The participants in this study also reveal the experiences they used to develop their skills as group leaders. The results of this study may have important implications to middle school counselors, researchers, and counselor educators in understanding the group and educational leadership skills needed to conduct effective groups in a middle school setting.