Inter-school networks have been promoted in many school systems globally to facilitate: knowledge generation and dissemination; responsiveness to increasingly diverse student and societal needs; and emotional and practical peer support for educational professionals. In understanding contemporary education as a ‘wicked’ problem, this paper explores case studies of inter-school networks in Aotearoa New Zealand (New Zealand) and England through the lens of complexity theory. We focus on how the conditions necessary for complex emergence identified by Davis and Sumara operate and how these conditions, along with their ‘enabling constraints’, facilitate the emergence of new perspectives and practices that enable the achievement of network objectives. This analysis indicates that where particular forms of leadership are in place, challenges – such as fragmentation, competition and the absence of social capital – can be overcome. We argue that network leaders need to balance and bridge three overlapping leadership approaches: operational leadership, entrepreneurial leadership and enabling leadership. We conclude by exploring the implications and insights for school, network and system leaders.