Transitions from one school level to another or from school onwards to working life are crucial phases for students’ individual lifelong learning pathways and, in this way, for their academic success. The paper presents, in the light of distributed pedagogical leadership (DPL), some key factors in incorporating transition-supportive pedagogical practices to the organizational structures in a Finnish upper secondary vocational education organization. The results provide evidence both of threatening and advancing issues in order to adapt successfully proven practices onto the whole organization through distributed ways of action. The results come from a larger study called ENTREE (Collaborative Enhancement of Transitions in Lifelong Learning Pathways by means of Distributed Pedagogical Leadership). The target of the study introduced in this paper is the personnel of the vocational school in question as 500 persons representing all organizational levels, sectors and duties. The data was collected by means of interviews and observations of the members of the leadership teams and as a survey of all staff. The multi method analyses were done through an instrumental model called TenKeys®. It consists of ten critical points or keys which render to examine DPL from different and overlapping viewpoints.