Participatory-democratic organizations seek to redistribute decision-making authority, but doing so raises a practical question: how do participants learn to exercise that authority in nonhierarchical, collective ways? This paper theorizes how participatory-democratic organizations address what I term the collective-practice gap: the gap between the individualistic capacities shaped in hierarchical institutions and the relational, participatory capacities required for nonhierarchical, collective participation. Drawing on ethnographic research in two participatory-democratic organizations—a democratic school and a community-governed philanthropic project—I examine how democratic capacity is cultivated through everyday organizational practice. I identify two dilemmatic pedagogical strategies used by experienced participants: the non-exercise of influence and taking the long view. Through these relational and temporal practices, experienced members strategically withhold outcome-directing intervention and tolerate slow, inefficient, or uncertain processes, creating conditions for others to develop the skills, values, and behaviors needed to function in a democratic, collective setting. These strategies, however, carry organizational risks—including delay, conflict, and uneven participation—because the practices that support democratic learning can also strain organizational functioning. Therefore, these strategies are best understood not as fixed solutions but as partial, situational responses to the tension between cultivating egalitarian participation and preserving organizational viability.