This qualitative study examines the experiences of faculty members who are required to document their teaching practice in a portfolio, first as a tool for professional development, and two years later as a tool for performance evaluation for the emergence of evidence of transformative learning, which is demonstrated in evidence of teaching practice and documented through the portfolio process. The data collection for the research was completed in various stages. The first stage involved the document review of teaching portfolios prepared for the first time in 2013. Next, the researcher reviewed the portfolios of the same faculty members who were required to submit an updated portfolio in 2015 to be used for performance evaluation. After the two-stage document analysis, 10 faculty members were interviewed to further explore the learning that occurred from the start of the process over the two-year period to confirm and expand on the data from the document reviews, in addition to examining the impact of the interview and feedback stages of the process. The findings reveal that many of the faculty found this process of documenting and reflecting on their teaching a disorienting dilemma. For some this triggered the opportunity for transformative learning as evidenced in the differences between the two portfolios over two years, and as discussed in the interviews. This work aligns with the conference theme in the area of intersections between development and evaluation in an institution that does not have the traditional tenure system in place for faculty.