Contemporary strategic planning tasks require new, more research-oriented design education methods. Architectural projects are here essentially interventions aimed at unfolding site-specific development potential. Site analysis and design thus become an integrated, creative process. Based on a teaching experiment in landscape architecture education, this paper proposes teaching creative site analysis as a translation process of observed site conditions into desirable future site conditions. Guided by actor-network theory, the paper outlines, first, a conceptual framework for creative site analysis. Second, it presents the applied educational procedure, with a focus on the decisive step from inventory to intervention which is the formulation of a design problem. The teaching experiment shows that onsite studies of spatial controversies in the form of recent physical changes, emerging new activities and uses, and people’s ideas and desires for future development can be a pertinent starting point. Furthermore, a clearly defined programming phase where design problems are formulated by different representational media and collectively assessed by students and teachers proved helpful for the students. Overall, the produced design work and the student evaluations show that translation offers an operational framework for teaching a creative approach to site analysis.