This article critically1 reviews three key research challenges that emerged as a result of developing gender-sensitive indicators for an NGO in South Africa. The first challenge faced was finding an appropriate balance between an 'expert-led' and an inclusive participatory research process. The second challenge was identifying a set of criteria, based on explicit research values, to guide indicator development. Third, we were confronted with the task of ensuring that the indicators developed could be implemented in the context of a resource-poor, service-driven NGO setting. A discussion of the challenges faced exposes the complex and sometimes murky process of developing indicators that are relevant, appropriate, and usable.