Leadership studies have been conducted for decades; however one of the leading studies about principals’ career path belongs to Peter Ribbins who carried it out in the United Kingdom in 1997. After this research a collective research project involving Singapore, Hong Kong, Cyprus and Malta was carried out under the leadership of Peter Gronn and Peter Ribbins. The purpose of this study is exploring principals’ career path as well as updating the previous research in Cyprus (Pashiardis & Ribbins, 2003) and Malta (Bezzina & Cassar, 2003) in the same field. The study has been carried out in Ireland, Cyprus and Malta with fifteen primary school principals, five principals from each country. In order to have an in depth idea about their career development, one of the qualitative methods, the interview method, was used for gathering the data. The analysis showed that the reasons for becoming a teacher are various; on the other hand the reasons for becoming a principal are similar. The majority of them wanted to become a principal to have power and because they believed they could manage the school better than the previous principals as they had the managerial skills to do the job. However there is no initial training to prepare the principals for the role. In terms of management they all stated that they are supportive, respectful, democratic, a role model, honest, collaborate and approachable and that they delegate, give responsibility and pay attention to good communication. Irish principals stated that they use these features in enabling more effecting teaching and learning. However both Cypriot and Maltese principals said bureaucracy and administrational work does not allow them to be involved in the teaching and learning process, and this is the reason that they cannot play an effective role in enabling better teaching and learning in the school. Their educational and managerial values include being democratic, collegial, a team worker, fair, transparent and respectful. However sometimes they experience difficulties in putting these values into practice. All of the principals stated that they dislike managerial tasks and bureaucracy as well as dealing with difficult people. On the other hand in spite of these difficulties, the majority of the principals stated they still enjoy principalship. In conclusion the results show that the findings of this study correspond to previous research in Cyprus and Malta. However some differences were spotted. Results also show that principals experience similar challenges to those they stated in earlier studies. These results can hopefully be used by policy makers to design new policies and improve the education of principals for the future.