The article examines organisational challenges in the Finnish vocational education and training (VET) to support students' lifelong learning pathways. Investigation of organizational challenges is done through the students' transitions either within one school level or from one school level to another or to working life. For supporting the students' learning pathways, it is argued here that specific attention has to be paid to collaborative practices of the personnel in order to guarantee the transitional fluency. This kind of collaboration is here called distributed pedagogical leadership. For examining the shared practices in the frame of distributed pedagogical leadership, the article introduces both quantitative results from a national survey and a Finnish VET case school and qualitative results from this particular school as several interviews of the leadership team and the teachers. (Contains 3 tables and 1 figure.)