The political work of school leaders is initially mapped from the findings of a 2019 mixed-method study involving principal participants in primary and secondary schools. A range of tensions derived from the research are described, with emphasis on those originating in the dissonance between the authoritative requirements of centralised policy and the profusion of local practices that mark the implementation work of school leaders. Using these tensions as a backdrop, the case is made for coalitions of school leaders – here illustrated in the work of formally constituted principal associations – directing their advocacy to a critique of calls for consensus voiced by powerful, centralized agents of education policy. This critique is founded on understanding how unequal power relations invite principals to perform certain preferred subjectivities aligned to current policy, while discouraging (and being disparaging of) versions of the principal that criticise, challenge or resist the status quo. Working from the claim that more productive possibilities are found in the dissensus of diverse opinions, and in alliances that rouse the curiosity and mitigate the risks for individuals, new theoretical and practical possibilities for the political participation of school leaders are explored. Relevant theory is drawn from the concept of agonism, with the ideas of Chantelle Mouffe, William Connolly and others used to propose and explicate an ‘ethos of democratic participation’ in the political arrangements between systems and schools. These empirical observations and theoretical arguments are then illuminated in the practical work of principals associations. A local example is initially drawn in the form of a pilot program, called The Thriving Principal, which was developed as a direct response to the various ambiguities, paradoxes and tensions revealed in the 2019 study. Using a professional learning communities (PLCs) methodology the program aims to help participating principals to become better equipped to navigate the terrain between system compliance, on one hand, and principal agency and autonomy on the other. A final move in the paper is to connect the advocacy function of principal associations (which was heavily favoured by participating principals in the 2019 study) with the political participation of principals and, relatedly, to test the theoretical possibilities of agonistic democracy against the complexities of practice. This move is the stepping off point for an interactive discussion, with the audience invited to share their own thoughts and experiences.