The contemporary school leadership is not just a gear of technical and professional skills. It has literally evolved into a complex combination of social, moral and educational values and their translation through the art of leadership practices. The school leadership and administration has turned into a value-laden rather a value-saturated arena of interactions. Within the broader and complex framework of values, the personal values of the school leadership play a critical role in the everyday life of a school. Therefore, this study is intended to explore the types of personal values, the motivational bases for acquiring them and the influence of such personal values on the leadership practices of the school principals. Consequently, this study entered the field of exploration with a set of three questions. First, what are the main types of personal values endorsed by school principals?; secondly, what are the motivational bases for acquiring those personal values? And finally, the main question of how do these personal values influence the leadership practices of the school principals? To address the above stated queries, a comparative case study method followed within the qualitative research paradigm. Two community based school principals were purposefully selected as study participants from the private secondary school context of Karachi, Pakistan. Semi-structured interviews, observations, reflective journal and document analysis were used as the main data collection tools for the study. The data gathered is qualitatively analyzed through thematic interpretation and of the participants' perspectives. The study found that the types of personal values and the motivational bases for the acquisition of such values are very much contextualized. A deep-rooted connection exists between the value types and the motivational bases. There are various regulating factors that steer the acquisition of such personal values by the principals. This research further explored that the leadership practices of the principals are considerably influenced by their personal values in terms of cultivating a school culture, establishing structures and marinating relationships with the external community. Based on the study findings an effort has been made to put forward a contextualized model. The findings of this study can be significant to the educational leaders in exploring new dimensions in their leadership practices. It may help the educational leaders in the developing context to understand their own personal values in order to see how they are getting translated through their practices. The findings may provide practical and contextual information to the teacher educators and professional development organizations in designing leadership training programmes for the educational leaders of the developing societies. This study may provide useful insights in recruiting better fit principals by the management authorities of schools.