While some of Paulo Freire's readers understand his pedagogy as a rejection of any and all directive teaching methods, there are many scholars who do recognise Freire's emphasis on teacher directiveness in its appropriate form. In light of this tension between directiveness and dialogue, it seems that students of Freire must inevitably come to a crossroads: is Freire's pedagogy directive or is it not? However, even this question does not get at the more critical dilemma: if Freire's pedagogy is directive, is such directiveness incompatible with Freire's overwhelming emphasis on egalitarian dialogue? This paper establishes three readings of the issue of directiveness in Freire and ultimately provides an exegetical defence of what is termed the compatibilist reading--that directive teaching, properly construed, is compatible with dialogic teaching in Freirean pedagogy. The question this paper seeks to answer is how Freire can have it both ways. In sum, Freire undeniably supports teacher directiveness and philosophically justifies directiveness as compatible with problem-posing education through his concepts of virtue education, utopia and criticality.