In this paper, we compare and contrast our experiences in using standards-based grading in different courses and across two separate institutions to explore the related tradeoffs and subtleties in designing and implementing such grading systems, guided by innovation diffusion theory. We summarize our individual courses, use Linda Nilson's criteria for evaluating grading systems as a framework for our shared reflections, and present questions for instructors to consider when designing a standards-based grading course. Despite the differences in courses, students, and institutions we had considerable overlap in the challenges we faced and the benefits we experienced.