This paper draws on recent research which was grounded in theory-building with civil society practitioners in two Aotearoa NZ leadership learning contexts (Malcolm, 2014) to draw out their tacit wisdom about leading amidst complexity. The research challenges dominant, implicit assumptions about leadership, for example as strong, heroic, decisive, visionary heroes and heroines. An alternative understanding of leadership is explored, drawing on complexity thinking constructs, to see leadership as a whole, multi-layered, dynamic learning system. What may look to the outsider as messy, disorganised or contradictory leadership responses, are instead understood as polarities within a complex adaptive system that is always in movement.