Even though student-led small-group book discussions about fiction have been a curricular staple, teachers still contend with surface-level discussions and students who have difficulty with creating meaning together. Based on their previous findings, the authors explore building a foundation for discussions (for teachers new to literature study) and scaffolding deeper discussions (for teachers working on deeper, dialogic discussions). Suggestions emphasize scaffolding students to expand their perspectives, become more metacognitive, and use transmediation to communicate the abstract. The activities/strategies taken together demonstrate that teachers have a dual responsibility in their classrooms: teaching students how to engage in deeper conversations and helping students value what can be accomplished through them. When teachers commit to this dual responsibility, students are more able to learn deeply.