Group decision-making can result in important benefits for organizational effectiveness. However, collaborative environments do not emerge organically. Effective leadership is critical for group success. Educational leaders must understand group processes and the importance of creating a culture that supports collaboration. Student discipline for off-campus behavior is an example of a complex situation that offers opportunity for group decision-making. Legal questions have yielded new twists in recent years with districts taking a more aggressive stance toward off-campus behavior that has a spillover effect at school. In this case study, team leadership and legal aspects of discipline are examined in the context of Superintendent Carter's attempt to lead a group through a complex, ambiguous, emotionally charged situation that has potential consequences for a wide variety of stakeholders.