The major objective of this study is to assess the most common school leadership practices in the Dire Dawa Administrative region and their relationship with student achievement. To this end, it used a cross-sectional and correlational study design. Sample schools were selected using purposive sampling techniques and principals and vice-principals were selected using the availability sampling method. Accordingly, 16 schools and 48 principals participated in the study. Data was collected using a self-developed questionnaire, interview and document analysis. The reliability of the self-developed questionnaire was .77. Student achievement data for the three years the principal/vice principal was assigned were collected from the regional education bureau data set. The collected data was analyzed using narrative analysis, descriptive and inferential statistics. The relationship between leadership preparation and student achievement was analyzed using correlation and simple regression. The findings indicated strong relationship between leadership development and student achievement with r=0.18 at a p<0.05 level of significance. The relationship is moderate but significant at a p<0.05 level of significance and with rho=0.426. Whereas the most common leadership preparation strategy employed is experience sharing, with other strategies such as short-term training and job assignments being less common.