Abstract This study explored the heuristic value of Janis' (1982) groupthink and vigilant decision making models as explanations of failure and success in top management team decision making using the Organizational Group Dynamics Q-sort (GDQ). Top management teams of seven Fortune 500companies were examined at two historical junctures—one when the team was successful (defined as satisfying strategic constituencies) and one when the team was unsuccessful. Results strongly supported the notion that a group' decision making process is systematically related to the outcomes experienced by the team. Ideal-type Q-sorts organized around Janis' analysis of groupthink and vigilance were substantially correlated with Q-sorts of failing and successful groups, respectively. The fit was, however, far from perfect. Ideal-type Q-sorts derived from other frameworks correlated better with the failure-success classification than did the Janis-derived ideal types. Successful groups showed some indicators of groupthink (e.g., risk-taking, cohesion, and strong, opinionated leaders), whereas unsuccessful groups showed signs of vigilance (e.g., internal debate to the point of factionalism). The results illustrate the usefulness of the GDQ for developing and empirically testing theory in organizational behavior from historical cases.