The middle school years are among the most formidable, as students transition from youth to adulthood. Self-esteem, consequently, is a significant attribute in developing the strong character necessary to successfully navigate middle school. Because a student's grades can influence how the student feels about his or her ability to learn, teachers and administrators have an imperative to strive to report grades that are an accurate measure of the student's achievement in a subject. A mistake some middle school teachers make is to use grades as a behavioral motivator. Many teachers view grading and behavioral management together as one and the same. Whenever these teachers need to motivate their students, they attach some effect to the student's grade. The authors argue that grades should not be based on a student's behavior, but should remain exclusively a reflection of the student's command of the subject. With initiative and forethought, teachers can devise a system that motivates students to complete and turn in the assigned work. The key is for teachers and administrators to recognize the limits of various grading practices and to embrace the idea that student assessment need not be constructed with inflexible rules. The authors stress that the right grading policies can promote both self-esteem and academic success among middle schoolers. (Contains 2 figures.)