Information technology has transformed the “heartland” of education around the world. Classrooms are global, students international, but traditional methods and their adjacent challenges persist or are exacerbated in online schoolhouses. There is reason to believe that team performance of online students completing team projects can be significantly improved by the active participation of a facilitator. What could explain such improvement? Given the communication barriers that learners can experience using e-learning technologies, the skill of a teacher at facilitating an understanding of e-collaboration and the prescient need to facilitate collaborative skills at all times is essential to a successful educational result. There may also be generational learning style issues to consider. One practical, proven tool is progress reporting. This paper reviews the literature and reflects on author experiences in the online education of Management students at universities in the United States and Australia to draw theoretical connections with communication, leadership, and punctuated equilibrium relevant to contemporary educational practice. The implications of effective facilitation of student teams for Management education and management of student performance are explored.