Through a guided discussion, this article explores a five-year cross-cultural evaluation relationship comprising multiple projects involving an evaluator from Canada and a group of Indian colleagues working on educational reform in India. The initiative was funded through a multilateral consortium of donors and involved Western evaluation specialists working in collaboration with Indian colleagues to (a) develop evaluation capacity within the country and (b) produce evaluative knowledge about education quality initiatives associated with large-scale educational reform. This article is based on a conversation between the principal investigator from Canada and three Indian colleagues who had been involved in all phases of the work. It focuses on their respective perspectives and experiences, including the benefits obtained and the challenges encountered in the process of bridging Western and Indian knowledge systems. The article begins with background about the initiative and continues with a conversation among the participants about their cross-cultural evaluation experience. It concludes with an analysis of the issues that emerged and generation of lessons learned for evaluators interested in cross-cultural evaluation.