Undergraduate students, particularly those with limited experience in business, struggle to appreciate the complexity of organizational communication dynamics. Communication complexities such as role conflict, position power, and individual perception—and their influence on effective communication—are particularly challenging for this population. This article describes a classroom exercise based on the children’s game “Telephone” that connects organizational communication with considerations of role conflict, power and influence tactics, and individual perceptions as they influence engagement with communication involving a new initiative. During the full class reflection and debrief, students identify the connections between their role in the activity and how individual organizational elements and experiences may inform effective communication. Designed for an undergraduate organizational behavior course, the exercise is adaptable to other management topics or levels where communication is a consideration.