Complex organizations are characterized by distributed decision making, and require a sharing of perspectives among distributed decision makers if they are to coordinate activity and adapt to changing circumstances. This paper explains the process of perspective taking and its roles in human communication, mutual trust, and organizational learning. SPIDER is a software environment for enriching communication among managers by improving their ability to represent and exchange understandings of the situations they face. Cognitive maps linked to underlying assumptions are used as a basis for sharing their perspectives and enabling coordination of distributed decision making.