There is something incalculable about teacher expertise and whether it can be observed, detected, quantified, and as per current educational policies, used as an accountability tool to hold America's public school teachers accountable for that which they do (or do not do well). In this commentary, authors (all of whom are former public school teachers) argue that rubric-based teacher observational systems, developed to assess the extent to which teachers adapt and follow sets of rubric-based rules, might actually constrain teacher expertise. Moreover, authors frame their comments using the Dreyfus Model (1980, 1986) to illustrate how observational systems and the rational conceptions on which they are based might be stifling educational progress and reform.