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A methodology, for assessing a user's skill grade is a key technology for developing adaptive user interfaces. The methodology presented assesses a user's skill grade by analyzing the tendencies of the user's operations. In order to analyze these tendencies, we categorized user's operations into three categories and extracted data from the logs on which the user's operation behavior was recorded. We discuss the methodology for assessing a user's skill grade and the system architecture, and then we describe the results of a preliminary experiment and a new experiment with the prototype based on the new architecture.