The authors of this article each bring a different theoretical background to their evaluation practice. The first author has a background of attention to culturally responsive evaluation (CRE), while the second author has a background of attention to systems theories and their application to evaluation. Both have had their own evolution of thinking and application of their respective conceptual traditions over the last 20+ years, influenced considerably by their involvement in the American Evaluation Association. They recently worked together to build evaluation capacity among evaluators of science, technology, engineering, and mathematics (STEM) education programs, in which they explored how these two conceptual and theoretical paths connect. In this article, the authors present their current thinking about the relationship between CRE and systems-oriented evaluation. In a case example, they illustrate the value of integrating the two perspectives to determine the guiding questions for an evaluation of a STEM education project.