Headteachers in the Czech Republic are a group of employed adults enjoying a relatively wide range of powers within the autonomous school system. This fact is manifested in a specific way in the opportunities available to them regarding planning their own career development and obtaining support for it outside and inside the school. Our objective is to present the history of support to school career development of headteachers and show its dynamics in connection with the dynamics of school and educational system development. We will focus on the situation from the beginning of 1990s till the present, i.e. the period when the Czech system of education as well as careers of headteachers and the corresponding counselling support were developing in a new social context.