In this paper, descriptive assessment method for middle school mathematics was evaluated by developing a framework for designing and grading problems for descriptive assessment and analyzing the effectiveness of the problems. The new descriptive assessment problems were developed by reviewing the current 7th National Mathematics Curriculum of Korea and aligned mathematics textbooks to define a set of problem design principles and evaluation framework for the assessment strategy. The developed problems were first pilot tested and then revised based on the feedback from the test. The final version was field tested by 100 students in 7th grade middle school. After the field test, the problems were graded by two middle school math teachers and one math education researcher to determine the overall correlation between graders and also to analyze effectiveness of the evaluation framework of the test. This result of this study is expected to assist in the further development of descriptive problems and grading framework by providing a reference work for teachers to better understand the process and the limitations of executing the new assessment strategy.