According to John Carver (1990), no single relationship in an organization is as important as that between the board and its chief executive officer. That relationship, well-conceived, can set the stage for effective governance and leadership. However, the line between governance and administration in community colleges is not always as clear as the experts define it, and this lack of clarity sometimes leads to significant issues for boards and their CEOs. This chapter relates some cases, based upon observations of the author, on the types of dilemmas that occur in the real world and how trustees and CEOs have dealt with them. The lessons learned from these examples can serve to strengthen the relationship between CEOs and boards and inform the important work they do.