Over the past 15 years, the adult model of transformative learning has gained attention among language educators for its ability to explain moments of perspective-shifting, a process that involves deep, conscious decentering of the self from existing beliefs and values. Given that transformative learning represents a highly individual experience requiring effort on the part of the individual to engage critically with one's own assumptions as they pertain to particular experiences, such learning cannot be guaranteed, but can be fostered in instructional contexts. Indeed, scholars have noted the inherent challenge in evaluating transformative learning, suggesting that process rather than product should be the focus of assessment. This chapter explores how the transformative pedagogical tool of written structured reflection can be used by language instructors to identify moments of perspective-shifting among their learners and understand the crucial skills that underlie the ability to transform one's meaning perspective. Examples from beginning L2 learner reflections illustrate what success can look like in a transformative learning assessment framework.