Participatory arrangements have become a popular way of addressing modern challenges of urban governance but in practice face several constraints and can trigger deep tensions. Facilitative leadership can play a crucial role in enabling collaboration among local stakeholders despite plural and often conflictual interests. Surprisingly, this style of leadership has received limited attention within debates linking urban governance and participatory democracy. We summarize the main insights of the literature on facilitative leadership and empirically develop them in the context of participatory urban governance by comparing recent participatory processes in two Italian cities. Whereas in one city facilitative leadership gradually emerged and successfully transformed a deep conflict into consensual proposals, in the other city, participatory planning further exacerbated pre-existing antagonism, and local democratic culture was only later slowly reinvigorated through bottom-up initiative. These diverging pathways explain how facilitative leadership is: (1) important for making things happen; (2) best understood as situated practices; (3) an emergent property of the practices and interactions of a number of local actors and (4) a democratic capacity for dealing with continuous challenges. Key to this style of leadership is understanding participatory urban governance as an ongoing democratic process.