The focus on grades and what they represent happens in every middle grades classroom--some students completely understand the concepts when reviewed, but perform poorly on the quiz; some gifted students score high on tests but appear bored in class. With the current emphasis on school accountability by standardized test scores, middle level teachers find they must consistently adjust their instruction in ways that highlight the relationship between learning and assessment (Anfara, 2009; Faulkner & Cook, 2006). All middle grades teachers consistently face the challenge of assessing student work and equitably translating student thinking into a grade (Tovani, 2011), yet effective assessment is not limited to a single quiz or a test at the end of a unit. Teachers and researchers have shared evidence that there is a direct, positive effect on student learning by assessing students throughout the learning process, rather than merely at its conclusion (Larsen, Butler, & Roediger, 2009; Roediger & Karpicke, 2006). Formative, ongoing assessment helps identify how student knowledge and understanding is developing, while traditional, summative assessment yields information about what learners may know at a particular point in time. Since both measures provide useful data that can guide instruction, what systematic assessment strategies can middle grades teachers use that allow learners to show what they know and understand throughout instruction? This article presents PILOT, a classroom assessment strategy that highlights five essential elements of instruction that can support student achievement.