The theory of formative assessment highlights the importance of ipsative assessment, which uses internally generated criteria and goals to compare students' performance with their past performance. This study designed a formative ipsative assessment practice as part of inquiry learning in high school and clarified its significance and challenges. The results of three rounds of academic writing for high school freshmen showed that the practice gradually improved students' overall writing skills; thus, qualitative improvement and transformation in performance-centered learning were expected. In high schools, where a single teacher is responsible for many students and is constrained by external standards such as university entrance exams, one strategy is to align learning and assessment by developing abstract higher-order criteria and then developing them into concrete lower-order criteria appropriate for each student. This paper presents five challenges and these solutions.