When history education researchers discuss historical inquiry they describe a process of asking questions about and investigating human experience using skills and concepts from history and the social sciences. Classroom teachers often see inquiry quite differently. As noted in Teaching History for the Common Good, purpose has a great deal to do with how (or whether) teachers implement practices as challenging as historical inquiry. Purpose alone, however, cannot prepare a teacher to conduct instructional practices for which their own experience as learners has ill-prepared them. Questioning, for instance, is an often over-looked feature of historical inquiry. Too often teachers do not see questions as opportunities to engage students in reflective, disciplined inquiry—using historical skills and concepts to build a deeper understanding of the world or encourage civic engagement. Rather, their purposes focus more on motivating students to learn content covered on a test. As a result, teachers tend to be less interested in students building evidence-based interpretations than in whether students got the “right” answer for a test. Drawing on a number of studies that examine this and other challenges involved in formulating questions that motivate and sustain historical inquiry, this paper argues that teachers must themselves learn skills, concepts and content so deeply that inquiry initiated by historically compelling questions becomes normal practice.