This paper aims to explore ways to enable designers, researchers and practitioners to share, discover and critique alternative and creative evaluation techniques. It draws on case examples of piloted enlightened evaluation approaches derived from a partnership between the Glasgow School of Art and Highlands and Islands Enterprise, a regional development agency with a remit of the Highlands and Islands of Scotland. Due to the complex initiatives, collaborations and partnerships involved in such a process, measurement frameworks that more appropriately support understanding and learning than traditional approaches have been being piloted. Despite a demand for more flexible techniques, there is a significant gap in understanding and knowledge regarding the most effective approaches, techniques and tools for enlightened evaluation.