Currently, the low number of candidates and the complex formation of the teams are great problems in the occupation of the school leadership position. This qualitative study aims to identify the main difficulties experienced from the perspective of the candidates. Based on the data obtained in various interviews, it should be noted how the headteacher selection process is influenced by different variables, both contextual and personal. The variables that condition this process include complexity of the decision to be a candidate or accept the appointment and the difficulty of forming and a team, among others.