This paper presents the outcomes of a training and collaborative research program carried out in the academic year 2025/26 with approximately one hundred teachers from early childhood, primary, and lower secondary schools in Central Italy. The program emerged from the need to rethink teaching practices in a context characterized by an increasing distance between students and school meanings, as well as by the growing complexity of the teaching profession. Adopting a decolonial and intersectional perspective, the study interprets educational practices as situated configurations of knowledge and relationships, shaped by power dynamics and multiple forms of meaning-making. Particular attention is devoted to the distribution of knowledge and to students’ forms of agency across different educational contexts. The training program was structured into a phase of “distant yet participatory” observation and a phase of experimentation. The findings highlight the decisive role of context and organizational arrangements in making visible competencies that often remain invisible in everyday practices. The analysis identifies four main themes: the centrality of the teacher’s observational stance, the emergence of situated competencies, the role of devolution and redistribution of decision-making power, and the structuring function of spatial and temporal contexts. The experience shows how it is possible to engage with uncertainty while ensuring a more liveable school environment and fostering more democratic forms of educational coexistence.