This article discusses the decision of the Art Institute of Pittsburgh (AiP) in Pittsburgh, Pennsylvania to implement a rigorous writing program assessment in order to obtain the Middle States accreditation, and it describes the process of determining which assessment model would be the most appropriate for AiP's needs. The use of a quantitative model recommended by experts hired as consultants for the improvement of AiP's assessment practices was seen by the faculty as decontextualized and impersonal. Eventually, AiP's writing professionals won approval for conducting a qualitative assessment, which the author used previously at LaRoche College. A qualitative assessment provided an opportunity for, and record of, faculty development through transcripts and later analysis of instructor discussions about the writing courses, their portfolios, and the grading procedures.