Teachers at the present time face continuous changes in their work and organizational practices. However, we lack empirical evidence as to what this implies for teachers and their work. This paper describes how two Finnish educational organizations restrict or enable teachers’ professional agency, in terms of how the teachers influence the conditions and contents of their work. The paper further addresses how agency is related to: (i) organizational and educational transformations, (ii) teachers’ professional development and identity negotiations and (iii) teachers’ commitment to the educational organization and well-being at work. This paper provides the comparative research evidence on both the strengths and weaknesses of different management practices of different educational organizations, identified here as a loosely coupled organization and a tightly coupled organization. It seems that strong agency supports teachers’ diverse learning, the practice of their professional orientations and also their well-being and commitment. Conversely, all these are threatened by teachers’ weak agency. However, teachers’ strong agency as individuals also appears to act as a brake on organizational transformation and collective learning. Based on our findings, we suggest novel future directions for the management of educational organizations and for the leadership of teachers’ work in terms of agency-centred coupling practices.