Although work-based assessments (WBA) may come closest to assessing habitual performance, their use for summative purposes is not undisputed. Most criticism of WBA stems from approaches to validity consistent with the quantitative psychometric framework. However, there is increasing research evidence that indicates that the assumptions underlying the predictive, deterministic framework of psychometrics may no longer hold. In this discussion paper we argue that meaningfulness and appropriateness of current validity evidence can be called into question and that we need alternative strategies to assessment and validity inquiry that build on current theories of learning and performance in complex and dynamic workplace settings.