Creating settings that support diversity has been a long-standing concern of community psychology. In this paper, I propose two qualities as important aspects of organizational contexts that support the meaningful participation of diverse groups:(a) a culture of connection and (b) recognition of multiple “realities.” For each theme, I first examine countervailing values that can undermine meaningful participation of nondominant groups. I suggest that organizational values for independence and a press for sameness can contribute to settings where members of traditionally oppressed groups will be prevented from meaningful participation. I also suggest that fostering a culture of connectedness that actively legitimizes multiple realities is a constructive alternative. To illustrate these points, I share observations based on experiences in manufacturing, educational, and community-based settings. Then, I explore two dynamics that are important when confronting the countervailing values and building more inclusive contexts: (a) accountability for impact and (b) privilege dynamics. Last, I turn to some possibilities for change through a stance of connected disruption.