It is believed that the effectiveness and efficiency of school administration can be enhanced in a privatized system of education. However, such belief is narrowly based on studies on school choice and such impact on the quality of teaching and learning. The issue of staff management in understanding school administration is essentially overlooked. Using Macao as a case study for illustration and drawing on data from a qualitative study, this paper seeks to argue that school administration against a specific context of privatization can actually contribute to the unprofessionalism of teachers. The study illustrates that staff management should not be merely taken at an individual level as an interpersonal issue about trust or a matter of conflict management, but should be understood against a wider context, and also shows that schools in a privatized system of education are not necessarily effective or efficient in managing their staff.