This chapter captures reflections and sheds light on the problematic aspects of evaluating youth music programmes. We start with the critical context of evaluation in England today with Trekkah’s experience as a practitioner vis-a-vis Frances’ academic expertise. We identify five key tensions through our joint evaluation experiences, which are illustrated by three evaluations of NottinghamCAN’s projects: The Phlexx Incubator, Reviving the Chapel and Under the Bridge. Through these examples, we experiment with a range of evaluation methods, building on the premise that as Artists we can respond to the evaluation through creating pieces of art.