Most education systems struggle to recruit qualified headteachers for their schools with a worrying shortage of candidates. Strikingly, Italy confronts an increasing mass of applicants, whose selection risks turning into a lottery; Italian headship, like the French, is obtainable through recurrent national competitions open to all qualified teachers, constituting their main career improvement. Assuming that headteacher recruitment is part of a broader process of “designer-leadership” (Gronn, 2002) which has a strong impact on professional and personal identity, the paper unravels the underpinnings, mechanisms and implications of such competition. It aims to provide a critical analysis of the strategies, forms of organisation and procedures deployed by the ministry and the candidates, in preparation of the selection. It shows how the competition policy framework “articulate[s] particular leadership roles and responsibilities and excludes others” (Ball, 1994, p.85). Data include official policy documents and statistics, however the focus is on experiences of existing and “hoping-to-become” headteachers, collected through in depth interviews within a broader study on leadership. The analysis shows a dramatic gap between the candidate’s culturally and historically shaped aspirations and their translation into everyday experiences, providing evidence of the ways in which policy enactment occurs and its distance from written policy texts.