Effective teaching practice focused on encouraging deep engagement helps all students learn and succeed. Considerable work by researchers and change agents, encouraged by national organizations such as the National Science Foundation (NSF) and the National Research Council, has promoted greater use of evidence-based educational practices, such as peer learning, the use of authentic assignments, and problem-based learning known to improve learning and reduce disparities in outcomes across learners. However, although much is known about what effective teaching looks like and the power of its impact, universities and colleges have found that changing teaching practice is challenging. One way to change faculty teaching behaviors is through explicit recognition and reward of those who use effective practices. However, doing so requires evaluation processes that better align to those practices. The interest in discussing teaching evaluation and creating more effective approaches is evident across the country, as well as internationally. At the national level, the NSF is funding a project, on Transforming the Evaluation of Teaching (TEval), involving multiple universities engaged in institutional change to advance science, technology, engineering, and math (STEM) undergraduate education through efforts to create more effective approaches to teaching evaluation. The cross-case analysis examines the ways that institutional context affects the cultural change process of adoption of this new approach, one of numerous efforts across the country to determine best practices around teaching evaluation.