The history of assessment and evaluation in education has been characterized by a continual search for objective indicators, absent the critical role played by subjective factors that affect the education process. This chapter presents three separate Q studies to increase understanding of subjective issues. Study 1 examines perspectives of faculty and staff on the purpose of a college education and reveals how divergent views on the purpose of education problematizes the development of a meaningful assessment program. Study 2 examines the culture of assessment of faculty and administrators from different institutions with suggestions offered regarding strategies for reconciling dueling narratives on outcomes assessment. Study 3 involves students in a research methods class given the task of assisting two community organizations in doing a survey to provide data on the need for affordable housing in the local community. This study examines how student essays provided the basis for the Q study revealing how the students experienced the class differently.