This paper explores the cultural and organisational conditions required to drive evaluation capacity building (ECB). It shares the principles used to measure current organisational readiness for evaluation, in order to inform the ongoing development of realistic ECB initiatives. The project is driven by the need to improve evaluation literacy and awareness across New Zealand Defence Force (NZDF) Learning Providers and the New Zealand Defence College (the College). Current evaluation ‘readiness’ will be assessed through a diagnostic instrument which focuses on six domains. The results of the organisational readiness assessment will feed into an organisational maturity matrix to provide a benchmark from which to measure future progress, and prescribe a systematic range of ECB initiatives which align with organisational readiness and understanding. The NZDF is a unique organisation, combining three distinct individual service cultures—Army, Navy and Air—together with a growing contingent of civilian staff. It is against this landscape that the NZDF College Performance and Evaluation Team works to embed its core learning evaluation framework. This paper shares a starting point, discusses some challenges encountered along the way and offers potential to provide a foundation for other organisations starting on their own unique ECB journey.