Given the dynamic nature of culture as both a social and individual phenomenon, an investigation of assessment culture in student affairs necessitates a look at the reciprocal relationship between individual practitioners and their surrounding environment. The purpose of this study was to explore the range of perceptions of student affairs practitioners regarding assessment of student learning by integrating various individual and environmental variables into a comprehensive framework that encompasses the multiple levels of the social ecological model (McLeroy, Steckler, Bibeau, & Glanz, 1988). The researchers employed Q methodology to illustrate the range of viewpoints of 44 student affairs practitioners regarding assessment in student affairs. Participants representing various functional areas, position levels, and institution types completed a Q sort of 51 assessment-related statements. Participants’ sorting data were subjected to by-person factor analysis, resulting in groupings of respondents who share similar perspectives. Additional qualitative data were collected via post-sort questions and follow-up interviews to assist with interpretation of three participant viewpoints: Assessment-as-Significant, Assessment-as-Irrelevant, and Assessment-in-Isolation. These distinct viewpoints clearly illustrated that the various beliefs individuals hold about themselves and their institution’s culture of assessment interact dynamically to impact participants’ assessment perceptions and practice. Study findings provide further insight into reasons for the gap between the espoused value and actual practice of assessment and reinforce the notion that addressing this gap requires attention to the dynamic interactions of both individual and environmental factors. Implications for the scholarship of assessment and assessment practice are discussed.