This paper outlines some challenges involved in developing creativity support tools (CST) aimed at serious creativity. Such domains include: academic research, patent creation, literature-based discovery, creative ideation, etc. By referencing a common workflow model, we focus on the role of evaluation within the development cycle and finessing of a CST. Our focus lies in gathering expert evaluations by recognised leaders and critics whose opinions hold respect within that community. Such evaluations are typically; difficult to acquire, involves experts with very narrow field of expertise and necessitate detailed and complex evaluations. We outline an approach to evaluation that is based on pre-selected evaluators for whom personalised artefacts are created for evaluation.