Implementation of a Multi-tiered System of Support (MTSS) has proven to be a ‘big hairy audacious goal’ within the literature and applied settings. Positive Behavior Intervention and Support (PBIS) has utilized a similar framework and was represented under the MTSS umbrella. If implemented with fidelity, both MTSS and PBIS have been shown to have positive outcomes for learners, staff members, and school systems. To implement one component of PBIS, a coaching procedure which consisted of instruction, modeling, rehearsal, and feedback was provided for three middle school teachers. Two Tier 1 PBIS classroom management practices were the focus of the coaching intervention—opportunities to respond and encouragement of appropriate behavior through positive points of contact. This study utilized a mixed methods approach which incorporated a single-subject design, specifically a nonconcurrent multiple baseline design across participants, to assess the effects of the coaching intervention on the implementation of the two classroom management practices, student on-task behavior, and the social validity of the intervention. Findings indicated an increase in both practices as well as an increase in student on-task behavior, from baseline to intervention phases of the study. Additionally, all participants reported high levels of social validity of the coaching intervention. The discussion was focused on triangulation of the quantitative and qualitative data, which indicated these findings were complementary. Connections of the findings to the research literature, implications for future practice and research, limitations, and conclusions have been provided.