<p>This paper offers a transdisciplinary and socio-cultural exploration into the way cities are planned and governed. It focuses on the concept of “constructive discussion” and uses the housing system of Sydney, Australia as a case study. Mobilising qualitative analysis of interviews with people that influence, or represent, key sectors of the public in relation to housing, the paper has two aims. First, it presents an analysis of how constructive discussion appears to relate to housing issues in Sydney. Doing so shows how constructive discussion can provide a new vantage point to consider and conceptualise complex social issues influencing governance and planning in cities. In our case, a focus on constructive discussion enabled ideation of social interventions and democratic innovations that complement technical and policy responses and understand Sydney’s ‘housing system’. We document both the diagnosis, and potential responses, in the paper. Most broadly, the paper shows that a focus on constructive discussion can offer new insights for researchers and practitioners seeking to achieve transformative system change in urban and democratic contexts. Our research emerged from a transdisciplinary collaboration between university academics and civil society actors in Sydney, Australia and we propose the ongoing integration of systems science, socio-cultural perspectives and transformative agendas can benefit from such endeavours.</p>