The prefaces of Cicero’s late dialogues indicate that they share a pedagogic function with the philosophical practices of the Hellenistic Academy. In the first part of this chapter, we give a few examples showing how the late dialogues serve this end, and use them to argue that Cicero’s texts systematically enact, as well as represent, an Academic pedagogical methodology. In the second part of the chapter, we use these results to propose that Cicero’s earlier, “Platonic,” dialogues are equally sophisticated in the modes through which they effect Academic aims concerning philosophical education. As starting points for further inquiry, we indicate a few of the devices the early dialogues employ to prompt the reader to reflect on her job as a philosophical critic.