Organization studies has a substantial literature on why employees stay silent when confronted by dysfunctional or unethical behaviour. Within this literature, organizational silence is typically depicted as having negative effects. This chapter builds on a smaller literature that sees silence more positively and productively. Intellectually, it draws on Hannah Arendt’s ideas on thinking as an internal aporetic dialogue that finds expression in dialogue with others. Thinking, for Arendt, is not about producing knowledge or practical wisdom but about discovering the meaning of things through connecting the private (silent) space of thinking with the public space of the political world of common action. Her ideas are well-illustrated in the meeting practices of the Quakers, a non-conformist Christian denomination that originated in the mid-17th century. Quaker meetings for business enact a political space where participants share their thoughts as equals, bound together in a unity of difference, where one’s silent thoughts and the contributions of others become entangled in a manner that allows for some collective sense to emerge (or not). This chapter proceeds to consider how formal rationality can threaten to obliterate the possibility of thinking and, conversely, how thinking without reasoning is equally dysfunctional. Finally, the chapter points to how our inquiry into Arendt, silence, and Quaker meetings can help us reflect on the concrete practices that exist in other contexts that might enable the enlargement of mind and collective sense-making.