Technical grading is a complex task, the mastery of which requires considerable time and repetition to develop the necessary levels of expertise. Mastery of technical grading is not expected in an educational setting; however, competence should be. Through a review of Cognitive Load Theory literature and an analysis of instructor responses to student educational needs when learning technical grading, novel technical grading instructional methodologies were theorized. These methodologies are supported primarily by two-dimensional visualization tools to diagnose levels of student expertise and enhance the development of independent skill and efficiency, which will lead to higher degrees of technical grading competence in landscape architecture students.