The rapid growth of cities can compromise their heritage by: diluting the distinctive character of diverse urban areas, destroying historic sites and buildings, and interrupting evolutionary continuity. This paper presents an innovative approach to addressing these problems. Using collaborative experimentation, a School of Urban Interventions was established to test the impact of different development scenarios on a diversity of urban areas in Krasnoyarsk (Siberia, Russia). The School created affordable tools to enable a more gentle, iterative and gradual way of developing often fragile historic areas, allowing hypotheses and design solutions to be examined before permanent changes were made. This collaborative experimentation approach helps participants to find shared collective values in the course of working with territory through negotiation, through participatory methods and grounded initiatives, helping to inform urban and architectural practices and therefore shape the cities’ heritage futures. The approach can also restore broken ties between the city and its inhabitants, empowering young professionals and creating active citizens while revealing hidden cultural potential. Being co-organized by the local university, this project also helped educate students to become activists and involved the university in urban life.