Through a series of conversations, Fintan McCutcheon and Joanna Haynes explore McCutcheon's reflections on school leadership in the contexts of the Educate Together movement (in the Republic of Ireland) and, specifically, in his aspiration to build an optimally democratic school in Balbriggan. Much of the academic and professional literature on school leadership depicts the role of school leaders as expressing a strong vision for the school, with charismatic communication and strategic skills, and putting explicit emphasis on high educational standards. On the ground, the school leader is required to maintain executive governance standards, is accountable to a range of hierarchies and audiences and is in a custodian role to traditions of school culture and human resource relationships. Taken together, these academic, professional and contractual obligations can corral the school leader into practice of limited scope, obstructed by protocol, risk-averse and curtailed in creativity and, in relation to developing a democratic school, lacking in the necessary room for innovation. The conversation focuses on the rough ground of incident and messiness, identified through critical moments of school life when the aspirations to be democratic, to lead democratically, to teach democracy and to create a sustaining democratic school culture are lived-out. Through this dialogue, the conversants observe a practice of school leadership grounded in practical reason. The dialogue touches on and threads congruence between the on-the-ground risk-taking, rule-breaking, action orientation, nuanced dialogue, passionate engagement and deep reflection that characterise day-to-day school leadership practice. It concludes with ideas concerning the dynamics of forms of democracy that can prevail.