Portfolios are emerging as a tool for documenting learning progression and assessing competency. ePortfolios are appealing as a portable and fluid means of documenting both learning and relevant experiences in a large number of students. Competence and learning can be especially difficult to document in important aspects of education and training, such as patient-centeredness, the cultural context of disease, and social determinants of health that do not lend themselves to fact-based assessment methods. Successful implementation of a method such as an ePortfolio requires explicit faculty development, as many faculty members have limited expertise with modern educational assessment technology. As part of the authors’ introduction of a Sociocultural ePortfolio Assessment Tool in the undergraduate medical curriculum, three faculty development workshops were held to expand faculty skills in using this technology. In addition to gaining comfort using a new Web-based technology, faculty members also needed to develop skills with providing mentored feedback and stimulating student reflection. Workshops were modeled after other successful programs reported in the literature and allowed faculty to develop a structured format for evaluating student content. Faculty members were given multiple opportunities to practice their newly developed skills providing mentored reflections using an ePortfolio. The workshop evaluations were positive, suggesting that faculty participation in the workshops were a necessary component for them to develop sufficient assessment skills for providing mentored reflection. Faculty members who participated in this program—whether or not they had content expertise in sociocultural medicine—valued the hands-on faculty development program.