This phenomenological qualitative pilot study explores the barriers and facilitators that affect the implementation of social participation interventions through occupational therapists’ perceptions in a school-based setting. Study participants were recruited using purposeful, convenient, and snowball sampling within the researcher’s work environment. A total of eleven participants volunteered for the study. Each participant engaged in a 1:1 semi-structured interview that was recorded for analysis. A total of six themes emerged: three barriers and three facilitators. The barriers included a lack of role clarity, resource shortages, and a skill gap, and the facilitators included core occupational therapy skills, people connections, and learn/reflect/evolve. Core occupational therapy skills yielded three additional subthemes: therapeutic use of self/rapport, purposeful activity/occupational profile, and contextual factors. The qualitative study results concluded that the participants acknowledged the value and importance of involving social participation interventions in practice. However, it is often an area not formally recognized as a focus of occupational therapy intervention. Implementing social participation interventions was observed to become more integrated into practice as therapists sought more learning ventures, reflected, and developed more confidence, experience, and awareness, often leading to a more holistic approach to services. Considering the positive effects on well-being, academics, and mental health, as shown in the literature and the voices of the participants, more awareness, support, and instruction are needed to help occupational therapists implement more social participation interventions in the school environment to promote positive development in the students’ lives.