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Q methodology provides a unique mixed-methods means of examining subjectivity through the use of an activity called a Q sort in which participants must sort a list of given items within a predetermined sorting form. Although Q methodology has a long history as a research tool, its use as an instructional tool has not been extensively explored. This is unfortunate because the Q sort activity—an element of Q methodology—offers instructors with an evidence-based approach to helping individual students understand their own subjective points of view while also helping to reveal distinctive subjective profiles or perspectives held by all students in the class. One reason why Q sorts may not have been embraced by instructors is perhaps the fact that it is difficult to prepare a Q sort in its traditional, paper-based form. A prototype of a Q sort software tool was built to meet this challenge. The purpose of this paper is to present the story of the current design of this tool. Four categories of design iterations developed over a four-year period are presented and discussed.