Traditional instructional methodology in the Information System Design (ISD) environment lacks explicit strategies for promoting the cognitive skills of prospective system designers. This contributes to the fragmented knowledge and low motivational and creative involvement of learners in system design tasks. In addition, present ISD methodologies, including web design methodologies, do not focus sufficiently on technological problem solving and design. Engagement in system design tasks demands critical thinking [Shelly, Cashman & Rosenblatt, 2001, Systems Analysis and Design, 4th edn. Course Technology, Boston] and abstraction skills [Harris, 1999, Systems Analysis and Design for the Small Enterprise, The Dryden Press, Harcourt Brace College Publishers, Fort Worth]. The aim of this paper is to explain a synergy between the technological process and web design methodology and its influence on the development of the cognitive skills of learners in the ISD context. In this research, the Team Structure Software Process (TSSP) methodology was integrated with the stages of the technological process. An interface approach between Information Systems and Technology Education was adopted during the implementation of an Instructional Web Design Program (IWDP), which served as a framework for building a software product. This research was based on a qualitative, action-research approach where individual interviews, focus group interviews, observation and document sources were used to gather data. Seventeen students at an institution of higher education were observed and their experiences were investigated through a focus group interview, journals and an essay. In addition, an interview with the teacher was conducted to investigate her thoughts and feelings during the implementation of the IWDP. During the implementation of the IWDP, multi-method learning was promoted, enlarging learners' insight into the design process and a climate for enhancing intellectual processes and skills created [Jakovljevic, 2002, An Instructional Model for Teaching Complex Thinking through Web Page Design, DEd thesis, Rand Afrikaan University, Johannesburg]