Efforts to improve education occur in complex landscapes, where policy, research, history, experiences, and communities shape practice in ways that have both intended and unintended outcomes. These landscapes change over time; however, there appear to be several core challenges that persist and which likely influence why it is difficult for policy to improve education in intended, effective and sustainable ways. Drawing on New Zealand and international research, this position paper identifies some of these key challenges and explores possible leverage points to navigate these. These include developing adaptive expertise, engaging key stakeholders in decision making, and developing a learning culture.