Traditional, standardized instruction and assessment practices are insufficient to promote the development of skills such as critical thinking, creativity, collaboration, and communication, which have been deemed necessary for post-secondary success (Darling-Hammond & Adamson, 2013; Milner, 2018; Rickles et al., 2019). They also serve to magnify inequitable conditions in education (Kearns, 2016). The disconnect between traditional educational practices and the needs of contemporary students led to this action research study exploring the ways in which performance assessment shifts the nature of teaching and learning. Performance assessment is defined as complex activities that require students to apply or transfer understanding of meaningful content to create an original product or solve a problem (Darling-Hammond & Adamson, 2013). Engaging in multiple cycles of qualitative data analysis of semi-structured interviews, observations, artifacts, surveys, and focus group conversations led to findings suggesting that performance assessment is associated with benefits to student learning and educators engaging in student-centered pedagogies. Additionally, the data suggest that achieving those benefits requires certain conditions to exist that provide the time and embedded support necessary for educators to develop deep levels of assessment literacy. Results from the study provide insight into organizational actions that can be taken to promote instruction and assessment practices that will enable all students to achieve post-secondary success. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]