South African Universities are tasked with increasing student throughput by offering additional academic support. A second task is to teach students to challenge and question. One way of attempting to achieve these tasks is by using Information and Communication Technology (ICT). The focus of this paper is to examine the effect of using an ICT tool to both increase academic support to students, and to teach critical thinking skills. A field study comparing a Project Management course at the University of Cape Town over two successive years was conducted. In the second year an ICT mediated constructivist approach (DFAQ web site) in which students acquired project management skills was used to increase support and teach critical thinking skills. Structuration theory, in particular the notion of practical and discursive consciousness, was used to inform our understanding of the role of questioning on teaching project management. The conclusion is that a constructive approach, mediated by an anonymous web-based consultative environment, the Dynamic Frequently Asked Questions (DFAQ) improved support to students and had an effect on student learning of project management and students acquired some questioning skills as evidenced in the examination performance. The efficacy of the approach was evaluated both through an interpretive study of DFAQ artefacts and the performance in the examination. The paper examines relevant literature, details the research objectives, describes a field survey, and the results. (Contains 1 table and 2 figures.)