This paper explores how designers’ core competencies relate to the emerging paradigmatic shift in design practice, and provides suggestions for design education. The shift is due to the increased interest from design in engaging with social and political contexts and issues the last fifteen years. Designers have several core competencies and in this paper prototyping and thereby the capacity to work with wicked problems are explored. More explicitly, we suggest that designers can design relevant propositions with the help of successive prototyping. Tightly integrating designing propositions with problem setting is necessary when dealing with wicked problems. This works well when designers deal with signs and things. However, in order to deal with increasingly complex contexts, we suggest that design students should get more relevant experience of prototyping in complex contexts and improved reflection by making use of theories from STS in order to deal with these complex contexts.