Singapore has attempted to prepare her students for the knowledge economy by implementing a series of Information Technology master plans. The need to train teachers on how to use the master plan provision of video production tools prompted the author to develop a course for pre-service teachers that focused on collaborative critiquing using computer-supported collaborative learning, an area of scant literature. This study focused on the online discussion part of the course and examined how online scaffolding can be used to support pre-service teachers in acquiring video production knowledge, in developing critiquing technique and Socratic Thinking through critiquing video design examples. Findings has shown that scaffolding strategies can be successfully employed to encourage learners to improve their knowledge, generate active debate on many contentious issues, keep discussion organised and make in-depth contributions from multiple perspectives. Implications to five areas of practice were drawn: online discussion, learner development, the teaching of design studies, staff development and design of learning environments.