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While prior research exists that high schools need to make changes to meet the needs of the students of the 21st Century, no research exists from the perspective of the teacher who must implement the changes. This qualitative study provides a comparison of two rural model 21st Century high schools in West Virginia, both members of the High Schools That Work network, and factors that impacted their initial benchmarking of 21st Century through a cross case analysis. The purpose of this study was to add to the body of knowledge concerning the factors that affecting the West Virginia framework of 21st Century schools. Through an analysis of the data, factors that had a negative or positive effect on the benchmarking were identified.