Re-working the Gramscian idea of the ‘organic’ intellectual from the cultural-political sphere to Higher Education (HE), suggests the need to develop critical and questioning ‘counter hegemonic’ ideas and behaviour in community education students. Connecting this reworking to the Habermasian theory of communicative action, suggests that these students also need to learn how to be constructive in developing such knowledge. Working towards critical and constructive capacities is particularly relevant for students who learn through acting in practice settings where general principles and purposes acquired in the academy need to be interpreted in response to the unique demands of specific situations. From a Gramscian perspective, enabling students to develop the qualities of organic intellectuals means that lecturers have a duty to teach critical knowledges which the student will be unfamiliar with and unlikely to possess. If teaching is not to become simply didactic, however, there is also a need to acknowledge Habermas’s contention that all knowledge is contingent. This does not mean that knowledge is merely relative, subjective, or essentially interest serving, as some postmodernists would have it. In Habermasian terms, knowledge is developed through a rigorous process of contesting validity claims according to procedures appropriate to discipline areas. In these procedures, contestation occurs to the point where there is general agreement about the best current understanding, until such time as this is overtaken by ideas with a better claim. The danger is that over commitment to contestation in the classroom undermines subject knowledge and ultimately the authority of the educator. Speaking Habermas to Gramsci, and vice versa, helps socially and politically committed educators to construct a space in which didactic and discursive moments purposefully alternate.