The importance of high-quality evaluation is underscored in Learning Forward's Standards for Professional Learning: Evaluation provides information that supports advocates, professional learning planners, and anyone who wants to know "about the contribution of professional learning to student achievement" (Learning Forward, 2011). Most importantly, high-quality evaluation provides the context around which educators make decisions about what professional learning is valuable for them. For most educators, the critical question is not whether professional learning works in general, but whether it works in their situation and context (Hirsh, 2013; Wiliam, 2019). The COVID-19 pandemic and its resulting impacts on student engagement with learning, state budgets, and many other aspects of educational systems underscore why the particular contexts of districts, schools, and students matters. Educators cannot afford to waste limited time and resources on programming that isn't driving improvements in the knowledge and skills of their educators and the outcomes of their students. This article describes the authors approach for balancing rigor with relevance in developing an evaluation plan for professional learning focused on student assessment. Working from a systematic framework for understanding the impact of professional learning (Guskey, 2000), they developed an evaluation plan that seeks to understand the mechanisms through which the professional learning of our organization improves outcomes for students and supports continuous improvement of practice through evidence gathered from multiple stakeholders.