It is often a struggle for classical schools to articulate how their math classrooms are different from a typical school. This presentation will begin with a look at how mathematics fits in a Socratic, liberal arts school. When teachers regularly ask meaningful questions, they open up a year-long discussion with their students about the order, beauty, and wonder in mathematics. All students, from math whizzes to the greatest strugglers, benefit from this humane approach. After discussing these philosophical issues, we will cover practical issues like when discussion is and is not appropriate, how to build questions into your daily routine, and how to construct good questions for longer classroom discussions.