Assessment of transformative learning is challenging because key aspects of the transformative experience are often difficult for faculty to recognize and for students to communicate. Also, there is an affective component involved in the struggles students face when encountering disorienting dilemmas and the subsequent perspective shifts that must occur to accommodate new ways of making sense of self, others, and the world. There are ways to track and measure student progress across an arc of development in those important beyond-disciplinary and life skills and mindsets that are the hallmarks of good employees, entrepreneurs, artists, citizens, and family members – humans that are, in short, creators, not just consumers. Faculty generally must be trained in this process because creating good reflective prompts and spotting individual students’ idiosyncratic expressions as they attempt to put into words felt shifts of worldview are not typically part of PhD curricula. One Midwestern, regional state university in the US has met the challenge of eliciting and assessing transformative learning. Lessons learned and specific, replicable processes and tools are shared in this chapter.