As Montessori schools expand their offerings to become institutions of learning for children ages three to fifteen and even beyond, school administration as a career becomes more specialized and complex. Generally speaking, many administrators today come up through the teacher ranks and are classified as "Montessori-trained administrators." At present, however, there is a shortage of experienced Montessori-trained school principals and administrators.

When a school cannot find a Montessori-trained administrator, it often advertises within the much larger pool of experienced heads of school through the independent schools network. In other instances, an administrator may emerge from within the business office of a school or may be a parent appointed by a parent board of trustees. Frequently, however, schools with parent boards find it important to maintain a separation of power between school management and the board.

Montessori school administration requires a sensitivity to the needs of children from birth through adolescence as well as an awareness of the needs of teachers who work at different age levels. The administrator must address the stages of development in Montessori teachers individually while understanding the evolution of the school community and school culture as a whole. Through conscious planning of faculty development, the administrator builds a common understanding of the whole child and a vision of purpose for the school. At the same time, business and entrepreneurial realities are linked to educational decisions and the school's mission. The administrator must therefore consider financial and community-relations variables as they relate to the various functions of running the school: admissions, hiring, fundraising, legal issues, building and grounds, parent education, budget, and board relations.