The aim of this research was to investigate how young students can be supported to use Socratic Seminar as a tool for critical thinking skills and deep, dialogic discussion of complex texts through use of picturebooks. In this teacher action research study, a first-time kindergarten classroom teacher supported by a university professor, enhanced the literacy instruction of their 19 students through the use of Socratic Seminar. Data were systematically collected through weekly Harkness models and a speaking and listening rubric. Results from the Harkness models indicate a meaningful change in the dynamics of the student conversation from teacher-led to interactive student engagement. Across the 5-week intervention, participation increased from approximately one-half of the students to full participation. The speaking and listening rubrics demonstrate a positive increase in (a) tracking the speaker, (b) repeating back what is heard, (c) contributing to conversation with multiple exchanges, and (d) following agreed-upon rules for conversation. Students also became better at listening to others' responses, and responding on topic. Through iterative design and intentional reflection, the teacher and university researcher found that while the Socratic Seminar was effective in improving students' participation, multiple scaffolds were necessary to support young participants such as visual supports (e.g., interactive word walls and printed pages from the texts), physical supports (e.g., question cubes and talking chips), and written supports (e.g., student writing samples).