In this chapter we analyse the link between multidisciplinary design and team learning, which, we argue, need to be supported in equal measure during Web design projects. We introduce a new approach to collaborative Web design, called the “Design and Learning Methodology,” as a way to support these two processes. The approach involves many stakeholders, including future website users, in design decision-making. It structures stakeholder participation through multidisciplinary design teams (MDTs). It uses professional facilitators to guide design and learning processes. Facilitation tools are drawn from a combination of action learning methods, which help MDTs reflect and act on new knowledge gained from design experiences, and human-centred design, which is an international protocol for achieving quality in interactive systems design (ISO 9000 series). Based on our research, we describe how facilitation of the process of learning from design contributes to continuous improvement in collaborative competencies needed for Web design.