To boost the existence of career-learning environments in Dutch vocational education, the innovation project 'Career Orientation and Guidance (COG) in Secondary Vocational Education' started in 2012. In this article, we describe the effects of this project on the level of policy formulation and implementation by means of three case studies. Data were collected at three schools through interviews, observations of meetings and teacher training, and analysis of policy documents. We conclude that a dialogue between managers and teachers, as well as among teachers is essential for changes in the learning environment of the students, since formulating a school-wide strategic policy requires communication between the different levels of the organisation, and clear tactical policy or operational plans require teacher teams and their team leaders to engage in substantive dialogues about the Career Orientation and Guidance innovation process. Instructional as well as transformational leadership stimulates a dialogical work environment for teachers and their managers, which is necessary for a dialogical career-learning environment for students.