This paper demonstrates the challenges that those working to strengthen democracy confront in putting their strategies into practice, using the Westminster Foundation for Democracy’s (WFD) work with civil society as an example. While formulating effective interventions is a significant challenge, how to go about implementing them is often just as problematic. This probelm is particularly acute when it comes to supporting key democratic institutions through programmes that seek to harness civil society. The paper begins by situating WFD’s support to civil society within its broader strategy, considering why WFD supports civil society and where it fits in its theory of change. It then explores how WFD implements that strategy on the ground using a current programme in Macedonia as an example. The paper analyses strategy and implementation in light of existing research on the role of civil society in democratization and the way in which the international community supports it. This allows us identify the strengths and weaknesses of the current approach, as well as options for mitigating risks and windows of opportunity for increasing impact. These have implications beyond WFD; the Department for International Development’s recent Civil Society Partnership Review demonstrates that other organisations face similar issues.