In this article, the author describes how high-inquiry questions, wait-time, assessment, and reflection can yield deep learning connections for elementary and middle school students in the world of theater-making. He explains that building understanding of theater-making processes for students is supported when they: (1) Use theater vocabulary; (2) Express understanding through language that describes relationship similarity; (3) Ask penetrating questions prior to and during an art making experience as a framework for performance assessment; (4) Ask reflective questions during and after an arts experience to encourage critical thinking; (5) Ask questions whenever they want about issues they care about to make connections and generate ideas; and (6) Wait in the sacred sometimes awkward space of silence to think after a question has been posited. Stages of Learning was an arts-in-education organization that focused on learning through theater making in the New York City metropolitan area from 1994 through 2010. Throughout its lifecycle, the organization reached approximately 40,000 third- through eighth-grade public school students and their classroom teachers. The aim of this article is to share the most promising of the reflection and inquiry practices of the organization and to demonstrate their credibility based on research conducted by thought leaders in non-arts disciplines (such as the sciences) because the resources are robust and provide a compelling case for inquiry-based learning in the arts. The theater-based reflection and inquiry processes at Stages of Learning might otherwise be forgotten or lost.