The future of evaluation is at a pivotal point, driven by the powerful interplay of demographic shifts (including a youth bulge and an aging global population) and the rapid evolution of digital technologies, particularly AI. This session explores this dynamic convergence, revealing how these megatrends are revolutionizing and shaping the evaluation landscape. It will examine practical applications of AI in evaluation, address crucial ethical and responsible innovation considerations, and discuss how AI can empower the next generation of evaluators and strengthen intergenerational partnerships in evaluation.