This article looks at the practice of educational questioning using the philosophical hermeneutics of Hans-Georg Gadamer. It first looks at questions and statements from a hermeneutic perspective, demonstrating some of the differences and similarities between the two. It then details Gadamer's notion of the "true question", asking whether it is possible for teachers to ask "true questions". Then, it turns to some concrete ways to rethink educational questioning. Three themes are proposed, themes to keep in mind when educational questions are used: non-superficiality, humility, and circuitry.