There remains much to be learned from searching exploration of the great authors who have meditated on education. Montaigne is one such thinker and this essay endeavors to draw together the strands of his pedagogy and to demonstrate how they gain purchase in the business of teaching and learning. The article also proposes to supplement his vision with practical examples from fiction and autobiography. Perhaps the most striking theme is the need to be able to decentre from the comfort zone of acquired beliefs and convictions and the crucial role played by conversation in cultivating the intellectual and moral openness in order to do so. At the heart of Montaigne's writing on education is what can be called a pedagogy of conversation.