In this chapter, Hannah Arendt’s work on “enlarged thought” is deployed to illuminate the centrality of professional judgement in school leadership. The chapter argues that sound judgement necessitates engagement with a range of relevant perspectives, and that it possesses inherent persuasiveness rather than that being reliant on a leader’s people skills. These insights run counter to much current policy and practice but suggest that plurality, communication and professional judgement need to be promoted both within teacher development and in school leadership practice for good decision-making to flourish and for the risk of error to be minimised.