This paper summarises a research-intervention in a setting of vocational education and training (VET), where mentoring schemes for faculty managers are changed by participants themselves. Participants comprise mentees, who are faculty managers in VET, and their mentors, who are more experienced colleagues in the same institution. Informed by Marx’s conception of dialectical contradictions, with a theoretical framework of Cultural and Historical Activity Theory (CHAT), and using a Change Laboratory methodology, participants envision, negotiate, and enact change to mentoring activity. In this study, technology enhanced learning (TEL) is of interest to participants in two interrelated domains of work and learning: TEL describes their own development, including the mentoring schemes examined in this paper; and TEL describes the pedagogical development of faculty and students in VET, the development of which is their managerial responsibility. By collaboratively exposing and aggravating contradictions in their past, present and future activity, participants recognise local dilemmas as manifestations of contradictions in mentoring. The paper examines how they trace primary contradictions of use versus exchange value: a tension in capitalist economies, between inherent worth and exchange as a commodity. Double stimulation tasks enable these participants to collaboratively expose, model and call upon contradictions to enact change. The changes to mentoring activity are modest yet expansive for mentors and mentees, indicating the developmental potential of primary contradictions: countering the pretence of managerial consensus in mentoring relationships; challenging business-focused outcomes of mentoring schemes; and confronting top-down coercion during mentor-mentee interactions.