To be successful in their future careers students need to develop diverse skills and qualifications. Firstly, in addition to learning the course content and the theory, students need to learn how to work effectively in multidisciplinary and multicultural groups. Secondly, they need to familiarise with collaborative technologies (CTs) since these are increasingly used in the workplace to facilitate communication and collaboration between distant co-workers. To address these needs it is essential to incorporate CTs (such as videoconferencing systems) in the curriculum and provide opportunities to students to gain hands-on experience. Nevertheless, what technologies are used does not make the difference between motivated and unmotivated students; it is how these technologies are used that matters. Whilst innovative technologies can be fascinating, they must be properly evaluated and adjusted to specific educational, individual, and group needs in order to be successfully adopted by students. This evaluation entails taking into consideration the context within which technology will be used (appropriateness evaluation) and the social-psychological motives for user acceptance (evaluation of user satisfaction). This paper reports the findings from an interpretive case study in postgraduate business education where students were using a videoconferencing system as part of their workshops and group discussion sessions. This setting provided a suitable social milieu for post-implementation evaluation of this collaborative technology. Qualitative methods were employed including participant observation, focus groups, and analysis of videoconferencing sessions captured on video. The findings indicate that computer-supported collaborative learning (CSCL) helps students become confident with using CTs, learn best practices of how to communicate and collaborate in technology-mediated settings, and appreciate the impact that technology has on everyday social practices. The videoconferencing exercises also engaged students to actively participate in the learning process. Given the duality of technology presence (in educational and business contexts alike) the findings can inform the design of new pedagogical models that maximize the learning potential of CTs.