This study adopted design and development research methodology (Richey & Klein, "Design and development research: Methods, strategies, and issues," 2007) to systematically investigate the process of applying instructional design principles, human-computer interaction, and software engineering to a performance support system (PSS) for behavior management in a classroom. The purpose was to examine how a proposed instructional design framework based on Ausubel's ("The psychology of meaningful verbal learning," 1963) advance organizer theoretical approach could be used to address inherent problems of technically driven PSSs. Development data were collected from a six-phase participatory rapid prototyping process using both qualitative and quantitative methods. Findings indicated that (a) the advance organizer concept combined with a matrix design metaphor provided an effective way to illustrate conceptual connections and relations among PSS modules and their elaborated information, (b) the system served as a reference to support participants for exchanging ideas with other teachers as well as with parents of students, and (c) the rapid prototyping process established parameters that helped the project team maintain a focus on users and collect data useful for advancing to a higher phase of system development. Potential drawbacks pertaining to the proposed design strategies and their possible corrective actions are also reported and discussed.