Governing boards have a history of underperformance. Yet, most attempted strategies address the recognized problems of inexperienced trustees, infrequent meetings, and trustees’ lack of understanding of higher education. They include steps such as clarifying board roles and responsibilities, better orientations, more information, and restructuring the board. Yet, these commonly advocated strategies yield few consistent results. This paper looks beyond the typical problems and solutions for underlying causes that might make governance difficult. It synthesizes literature from psychology, business, behavioral economics, group behavior, and related areas to develop propositions that help explain board behavior (or misbehavior) to suggest deeper causes of board misbehavior via a set of propositions. These propositions focus on the nature of high-powered groups, overconfidence, group information bias and group processes, all of which constrain board effectiveness. The paper concludes with a series of recommendations for practitioners and for researchers to further address what look like perennial governance problems.