This qualitative case-study examined a workshop where academically or socially struggling middle school math intervention students taught university students. The theoretical framework included critical pedagogy and the instructional core to explore how both the adults and the children benefited when children performed the role of instructional leaders. Data collection included focus groups with the middle school students and university students, interviews with middle school administrators, a researcher journal, field notes, and a video recording. A qualitative content analysis was conducted, with the results interpreted in a thematic analysis. The findings of this study indicate that, when middle school students led instruction for university students, both groups received a host of academic and social benefits; however, the children had significant barriers they needed to overcome in order to participate in the workshop. The study concludes with implications for theory, practice, and recommendations for future research.