Teaching is one of many professions for which personalized feedback and reflection can help improve dialogue and discussion between the professional and those they serve. However, professional development (PD) is often impersonal as human observation is labor-intensive. Data-driven PD tools in teaching are of growing interest, but open questions about how professionals engage with their data in practice remain. In this paper, we present ClassInSight, a tool that visualizes three levels of teachers’ discussion data and structures reflection. Through 22 reflection sessions and interviews with 5 high school science teachers, we found themes related to dissonance, contextualization, and sustainability in how teachers engaged with their data in the tool and in how their professional vision, the use of professional expertise to interpret events, shifted over time. We discuss guidelines for these conversational support tools to support personalized PD in professions beyond teaching where conversation and interaction are important.