Paradox mindsets have been proposed as a way of increasing capacity to deal with the competing tensions that present themselves in organizational life. It has been argued that having a paradox mindset can help individuals to work creatively and productively with tensions to produce solutions. Increasingly paradox scholars have also began to highlight the relational element of paradox mindsets, how we work through paradoxes with others. Less explored, however, is how individuals explore paradoxes through collective processes that help them to understand the tensions that they are experiencing. This paper offers a deliberative approach to paradox mindsets that integrates individual development with the novel forms of collective deliberation that are a feature of democratic organizations (those that use collective and deliberative decision-making procedures). Based on the learning processes involved in our own experiences, in setting up a democratic organization, we consider how paradoxes became more salient through collective collaboration with experienced practitioners within the field. We offer suggestions to how management education can be developed to help practitioners begin the process of learning to live with and indeed thrive, collectively, in paradoxical situations.