Institutions of higher education are required by U.S. accrediting bodies to articulate their conceptual framework and develop a viable program improvement plan through a continuous reflective process of progressive problem solving that enables data-driven decision-making practices. To meet or exceed national accreditation standards for leadership, institutions of higher education develop viable improvement plans based upon analytical processes that include data-driven decision making. To meet or exceed accreditation standards, the program improvement plan at the action research site where this study took place was based on the collection and analysis of data retrieved from their program annual review assessment process. However, at this action research site, program evaluators responsible for the analysis and evaluation of program annual review data worked in a limited silo-like isolated manner to complete the program improvement process. The purpose of this action research study was to identify the benefits and challenges of implementing a critical friend approach in collaboration with program evaluators during the program annual review assessment process. Qualitative and quantitative data were collected from multiple sources and yielded patterns and themes to address and find solutions for the problem. Three questions guided this action research: (a) how and to what extent did the critical friend analyze data in collaboration with the program evaluators to improve the program annual review assessment process? (b) what safeguards, if any, did the critical friend implement to help ensure systematic analysis and accountability of assessment? and (c) what are the benefits and challenges of collaboration between a critical friend and program evaluators? Twelve voluntary study participants provided data collected from interviews, observations, a survey questionnaire, and confidential notes documented in the researcher's journal. A thematic analysis of the collected data identified three themes: (a) program evaluators collaborate with a critical friend to evaluate program annual review practices, (b) program evaluators and a critical friend identify leadership practices that influence program annual review practices, and (c) program evaluators and a critical friend identify decision-making practices that impact program annual review assessment processes. Each of these themes supported the importance of working with a critical friend during the assessment process in higher education. The results of this study support the importance of collaboration with a critical friend during the process of assessment in higher education. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]