Art classrooms and museums are places where teachers and students talk about artworks. However, there is a lack of empirical research into dialogue—the most basic component of classroom teaching and the most used education strategy in museums. I investigated the development and experimentation of a dialogue-and-questioning framework for art classrooms and museums. I conducted a design-based research study with seven primary schoolteachers and 187 6th-grade students in Hong Kong. I found that the total number of questions asked by the teacher participants increased significantly. Teachers’ performance, when asking personal connection, observation, interpretation, and evaluation questions, also improved significantly. They became more conscious of relating artworks to the students in a personal way and developed a practice that fostered a more comprehensive understanding of artworks. Student participants began to approach artworks from different perspectives and engaged in more in-depth examinations. Copyright © 2022 National Art Education Association.