To what extent and in what ways do issues about content and the teaching and learning of content figure in the conversations between novices and their mentors? This paper explores that question by means of four cases drawn from a large data set about two different first-year teacher programs, an induction program sponsored by a university and a local school district, and an alternate certification program for secondary teachers sponsored by a school district and employing mentor teachers. Conversations between experienced and beginning teachers are discussed in relation to four aspects of learning to teach academic content: (1) deepening one's own understanding of subject matter; (2) learning to think about academic content from the students' perspective; (3) learning to represent subject matter in appropriate and engaging ways; and (4) learning to organize students for the purposes of teaching and learning academic content. (JD)