Dialogue is essential for transforming institutions into learning organizations, yet many well-known characteristics of academic health centers (AHCs) interfere with open discussion. Rigid hierarchies, intense competition for resources, and the power of peer review in advancement processes all hamper difficult conversations, thereby contributing to organizational silence, and at great cost to the institution. Information necessary for critical decisions is not shared, individuals and the organization do not learn from mistakes, and diverse perspectives from those with less power are not entertained, or worse, are suppressed. When leaders become more skilled at inviting multiple perspectives and faculty more adept at broaching difficult conversations with those in power, differences are more effectively addressed and conflicts resolved. In this article, the authors frame why this skill is an essential competency for faculty and leaders alike and provide the following recommendations to institutions for increasing capacity in this area: (1) develop leaders to counteract organizational silence, (2) develop faculty members' skills in raising difficult issues with those in positions of power, and (3) train mentors to coach others in raising difficult conversations. The vitality of AHCs requires that faculty and institutional leaders develop relational communication skills and partner in learning through challenging conversations.