This paper examines an account of a practitioner-initiated transformation of workplace-based social relationship within a grassroots adult education institution. This tripartite relationship among adult students, staff and teachers, abbreviated as AST, is a major driving force for activities and missionary functioning of the XinZhuang Community University (XZ-CU) and thus constitutes an indication of conjoint collaboration. Grafted from historical context and the development stage of AST, the initiative and the intervention focused on redefining AST relationship from a distributed leadership perspective and represents a democratic core and alternative to school leadership that would render new opportunity to create "democratic structures and processes" that a Democratic School advocated. This work has led to the conception and practice of joint educational experiment with elementary schools. The objectives of this research (as a professional engagement) are two-fold: first, to outline the major observables of this engagement, including reviews of facilitating the evolution of AST relationship in past three years. Second, with the Cultural Historical Activity Theory (CHAT) and its variant as the theoretical lens for framing and understanding the phenomena, we then identify the critical contradictions and concerted efforts of transformation, along with outcomes that emerged and artefacts employed, as well as further impacts of school reform on structures and processes.