This chapter is based on an interview between one of the Handbook’s editors and an expert on humanitarian monitoring and evaluation. It explores a variety of historical and contemporary issues around the inequalities of monitoring and evaluating humanitarian action with a focus on organisational learning, capacity building, and accountability. From the Rwanda crisis of the humanitarian sector in the 1990s to real-time evaluations in Ukraine today, the power of Terms of References to shape evaluation outcomes and the importance of listening to local partners the chapter covers a range of issues. Based on Sokpoh’s long-standing expertise as local and global manager of evaluations for a range of international organisations this practice-informed chapter concludes with reflections on the use of technology, gendered dimensions of evaluation teams, and decolonising yet another important area of the humanitarian sector that tends to replicate existing inequalities.