The Pathways for Transversal Skills and Orientation (PCTOs) are the result of a specific training program introduced by the Ministry of Education, University and Research (MIUR), aimed at enriching the educational process of secondary school students. Joining PCTOs can help to develop awareness of one’s own skills, including design competences, especially in view of future training and/or professional processes and scenarios. In this context, tutors and headmasters play a particularly important role as they are actively involved in the design and implementation of projects. In fact, in principle, each project is defined and structured by all the stakeholders involved, according to a logic of co-design. On the other hand, each school has the opportunity to configure PCTOs ad hoc, both according to its own resources (human, technological, skills, etc.) and the specific territorial/sociocultural fabric. Based on these premises, a complex dataset was designed and constructed, corresponding to an integrated multistakeholder matrix, which collects and intersects data from three surveys – respectively addressed to: students (No. 4,045), tutors (No. 264) and headmasters (No. 73) (a.y. 2021/2022) – and from content analysis as a survey applied to projects uploaded by a sample of Italian schools (No. 251 projects from 78 institutions). The goal of this paper is to trace, taking a micro-macro analysis perspective, the most prevalent governance styles and the main trajectories undertaken by Italian schools in implementing policy. First, studying the different configurations that PCTOs have taken in the selected schools and tracing common traits and/or specificity-gaps with respect to the territorial context and the school chain (territorial-curricular framing) constitute the main intents. Furthermore, focusing on students and the degree of consistency between school design and policy directions, other objectives are: 1. to study the mechanisms of adherence to and evaluation of the PCTOs experience by girls and boys (induced participation vs. open and autonomous participation; design more or less centered on student needs); 2. to estimate the effect of participation on variables related to individual self-perceptions, expectations and aspirations. The multilevel and multistakeholder model of analysis offers both the opportunity to reconstruct dense relationships among variables and to identify forms of vulnerability and inequality in the school context, for an explanatory reading of them, combining different levels of analysis. This articulated research instrumentation is also fruitfully usable in other complex fields of study within which it is crucial to recognize forms of inequality and social exclusion, as well as to counter them.