Teachers develop when they critically examine the questions they ask about their work because questions make pedagogical beliefs visible and available for critical reflection and revision. In a standards-based educational climate—a time when writing becomes a set of measurable skills rather than a complex social practice—teachers may feel that a critical examination of their questions is (at best) a luxury or (at worst) a distraction to work they need to accomplish. Therefore, writing teacher educators may find it increasingly challenging to help teachers engage in reflexive inquiry. This essay describes a Deweyian-informed framework that shows how addressing inquiries and critically examining inquiries are processes that complement one another. Using examples from two contexts commonly implemented to promote teacher development, this essay argues the asking/understanding framework provides useful language for helping WTEs and teachers negotiate varying expectations for pedagogical inquiry and teacher development