Leadership at the level of a school site matters with the school principal serving as a central source of influence (Dodson, 2015; Wallace Foundation, 2013). Leithwood et al. (2004) found principal leadership just behind teaching in terms of the impact on student learning among school-related factors. School principals are tasked with being or becoming leaders of learning who can develop a team who delivers the multifaceted aspects of effective instruction with transformational effects (Kim, 2020). Transformative Leadership Conversation (TLC) was constructed for the purpose of leading transformation in schools yet is atypical of most discourse leveraged by school leaders (Adams et al., 2023a). This study defines TLC and describes its elements. The case for principals’ use of TLC is made by describing the relational and contextual nature of principal leadership and the power of conversation to influence the minds and actions of people. This study describes the extent to which teachers report principals using the structural elements of TLC including reflective questions, deep listening, and affirming language. Teachers did not report routine use of TLC. The study also demonstrates school leaders need training to use elements of TLC, missing elements of TLC are vital to sensemaking and learning dialogue, and context of school leadership conversations matter, particularly in regards to the types of schools and the school accountability grade where principals and teachers perform their work.