Youth Futures is a complex program supported by a local partnership aimed at increasing access to post-secondary education among youth from lower-income family backgrounds. Although program stakeholders have recognized the importance of evaluation since the program's inception, embedding an evaluative culture and building capacity for evaluation practice in the context of this partnership-led program has been challenging. We describe our experiences and the lessons that have been learned about generating and sustaining interest in evaluation among a diverse group of stakeholders. The article proposes some recommendations for others who endeavour to conduct evaluation work in community contexts.