This dissertation considers in turn the role education plays in civil, democratic society; the role assessment plays in education; and the role theoretical constructs and cultural contexts play in assessment. Then, through literature review, document analysis, and interviews, the analysis investigates, identifies, and recommends grounded-theory-derived practices for improving qualitative assessment in higher education settings. The process of qualitative assessment is understood as being heuristic and continual, requiring re-examination and revision to maintain both its validity and reliability. To this end, rubrics are essential to efficiently and reliably assessing everything qualitative, whereas the realities of institutional culture and politics require adroit leadership from educators and administrators, drawing from manifest praxes in organizational theory, management theory, and political theory, to affect progressive change. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]