The contemporary operational environment (COE) is rapidly evolving - what worked recently may not work now and probably will not work next week. As the Army operates increasingly as an expeditionary force, it will become even more important to share lessons learned quickly and to promulgate best practices widely. Training requirements are therefore also becoming increasingly dynamic and complex. Instructors must develop timely teaching points that rest on solid doctrinal foundations while addressing current issues. Accordingly, through the sponsorship of the Army Research Institute and the Office of the Secretary of Defense, we are exploring educational strategies and technologies that can close the gap between the classroom and the operational environment. The goal is to provide capabilities that support interactions between students and outside experts in the Contemporary Operational Environment under the control of a Small Group Instructor. The central idea is to enable students to relate classroom concepts to current issues through the guidance of outside experts. In this manuscript we describe the problem, the theoretical background for our approach, and results from our efforts to identify requirements.