The investigation presented in this paper focuses on the following questions: How can engineering and architectural expertise guide a process of digital optimisation and add structural “awareness” in real time to aesthetic considerations (or vice versa)? How can building geometry be set up computationally in order to render it “sensitive” to structural input? Which tools are required to foster this interaction? The authors of this paper form a team of researchers and practitioners from architectural and engineering background who combine their efforts to address the issue of interconnecting design intelligence across disciplines and advancing work methodologies in practice assisted by academic research. A live case study project is presented as a test scenario in order to find answers the above questions.