For students to develop the capacity to produce complex works of consistently high quality, they need to be able to monitor the quality of their work during its production. This requires that they know what constitutes high quality; how to compare the quality of their emerging work with their model of high quality; and how to modify their work accordingly. A common approach to assessing complex works is to apply a set of fixed criteria. This practice gives rise to various anomalies, two of which are analysed in this chapter. This phenomenon calls into question the fundamental validity of using preset criteria as the preferred approach for judging quality. Instead, holistic judgments are required. A teaching approach that deliberately blurs the boundary between pedagogy and assessment so students can develop the ability to make holistic appraisals is outlined in the second part of this chapter.