This chapter introduces the evaluative perspective of a funder – the National Endowment for Democracy (NED) – that advances a portfolio of highly diverse and multifaceted democracy, human rights, and governance (DRG) projects. The chapter explores the underlying political character of democracy assistance work – which is therefore viewed by some as partisan – and second, the variable dynamic forces intrinsic to complex operating contexts, both of which affect how the NED is able to both standardize and provide flexibility in grantee evaluation. This analysis draws attention to the challenges and opportunities inherent to grantmakers operating on a global scale as well as structuring adaptable evaluation methodologies commensurate with that scale of work yet relevant to grantees.