This mixed methods action research study describes the benefits of a Team Leadership Community of Practice group for six early career special education teachers who supervised paraeducators. Problem-posing conversations with peers were a catalyst for professional learning and leadership transformation. The theoretical framework included Experiential Learning Theory, Transformational Leadership, and Communities of Practice—combined as a tri-theory lens. Data collection instruments included individual interviews, a focus group, content logs from audio recordings, a researcher journal, and two researcher-created instruments—the Intentional Leadership Actions and Paraeducator Outcomes Survey and the Teacher Group Reflection Survey. Findings indicated that team leaders favored collaborative partnerships with paraeducators rather than supervisory roles. Given perceived communication barriers as team leaders, participants spent time preparing for conversations with paraeducators. Together, they co-constructed understandings and stretched one another as a learning Community of Practice (CoP), as defined by Wenger (1998). The CoP was a framework for Experiential Learning when team leaders gathered together to share their concrete leadership experiences, reflect, conceptualize abstract meaning, and discuss possible strategies for future experimentation. Additionally, team leaders experienced individual reflection following CoP gatherings as they considered peer suggestions, fine-tuned ideas, and planned leadership actions. As team leaders implemented new leadership ideas and experienced positive outcomes, they reported increased efficacy and desire for additional leadership opportunities in their classrooms and beyond. A trilogy of poems complements the discussion of findings.