The article presents analysis of the epistemological, pedagogical and methodological processes and dilemmas that unfolded during our efforts to transform the conceptions and understandings of our participants' thinking about ways of managing land-related conflicts. The paper reports our evaluation of the thinking and perspectives that guided our interventions and how we dealt with the situational challenges we encountered. It reports what we did to emerge out of the dilemmas we encountered in our efforts to help others think over and learn from their situations. The educative value of our efforts and encounters for other similarly situated practitioners and change agents will be stated at the end. We emphasise the educative potential of establishing links between contexts and thinking processes toward transformative and critical learning.