The purpose of the study was to assess the practices of school leadership and the challenges that school leaders face in performing their duties in Secondary Schools of Bole sub city. The study employed a descriptive survey design. Principals, vice principals and supervisors were selected using purposive sampling. Semi structured interview was also utilized to substantiate the data gained through the questionnaires. Both primary and secondary sources were used. The primary sources of this study were principals, vice principals, supervisors and teachers of the selected schools. On the other hand secondary sources were relevant documents of the schools in the study area. To gather the necessary data three types of data collection instruments namely questionnaire consisting of closed ended item, structured interview and document analysis were used descriptive approach such as percentage, frequency, mean, standard deviation and grand mean were utilized to analyze the data .The qualitative data obtained through interview was analyzed using themes. The results of the study revealed that all school principals have qualification in school leadership but some of school vice principals involved in leading the school without having prior qualification in school leadership and trainings. The study concluded that principals are less effective in their leadership due to problem of working with parents and community, work overload and lack of sharing the problems of school leadership by higher officials. Finally, the point of the recommended that qualified secondary school principals and vice principals be assigned it is on the basis of their experience and academic merits, providing in-service and pre-service training and build productive relationships with parents and the wider community.