The research began with a personal question about how one learnt educational management. The research participants consisted of 19 principals who were selected on the basis of distribution between primary, secondary, male and female. Two questions guided the research. How did these principals perceive that they learnt to be principals? How did they perceive that their learning impacted on their practice? A self-study paralleled the study of the principals, as a study of an educational manager who was not a principal. The qualitative methodology applied in the study was grounded theory. The methodology and the retrospective, biographical nature of the study through interview, meant that the research was phenomenological and interpretative. The main source of raw data was the transcripts of interviews, documents and literature. These principals perceived that their critical learning related to educational management was learning of attitudes and values as well as knowledge and skills. This learning could be traced in the first instance to family and upbringing, to their own education and their careers in teaching and middle management. Because this learning was the foundation on which their learning as principals, was based, I called this foundational learning. The research indicated that foundational learning influenced the nature of the principalship. The learning of principals after appointment was conceptualised as experiential and intentional. Experiential learning occurred in the contexts of initiation, dealing with crises and problems, routine management, managing change, taking part in specific events, and through the process of being a principal for an extended period. Experiential learning appeared to consist of two main types, situational and emergent. The latter comprised new learning created by learning over time from a variety of experiences. Intentional learning aimed to meet learning needs and included all the deliberate formal and informal learning activities such as gaining qualifications, attending courses and conferences, visiting other institutions and reading professional literature. Barriers and limitations to learning constituted another relevant aspect of principals’ learning. The principals perceived that their foundational learning had a major impact on practice as the source of values, attitudes, systemic knowledge of educational management and management skills. They perceived that their experiential learning had the most direct and significant impact on their practice because it was most likely to produce practical and relevant learning. Intentional learning had a subsidiary function, supporting and growing experiential learning. In this way, intentional learning impacted on practice. Personal, systemic and external learning barriers and limitations appeared to impact on practice in idiosyncratic ways. Foundational, experiential and intentional learning was cumulative, contextualised within particular schools and situations and inter-related through impact on practice. Consequently each principal’s story was different and unique. I concluded that each principal was a unique product of learning, accumulated over a life time and developed within schools, each of which represented a unique environment. As a result, each particular combination of principal and school represented a unique configuration in terms of learning to be and being a principal. The self-study supported these conclusions. On the basis of the findings of the research, I drew out a number of professional development implications. If heeded, the professional development implications could reorient educational management education by focusing on the unique configuration of principal as sum of foundational, experiential and intentional learning, and his or her particular school or organisation as a particularised environment of educational problems. These problems may need to be defined uniquely to be resolved.