This research was conducted mainly to assess the existing leadership training practices and its challenges in the government high Schools in Addis Ababa City Administration. A descriptive survey design was used in this study. The researcher used simple random sampling method. The Primary data were gathered from Principals through interview and vice principals, department heads, unit leaders and supervisors through questionnaires. Nine high schools were selected and the total distributed 109 questionnaires, 83 questionnaires were properly filled and returned, with a very high response rate of 97.1% although some respondents missed questions from the questionnaire. Then, the data that was found out of the questioner, the descriptive analysis, part was done using SPSS version 21 to find the frequency, and percentage of the data. According to analyzed data the findings of the research indicate three gaps. The participants of the study were valid to the population they represented. The findings also show the existence of Leadership training practices in the schoolsâ€™ plan, before the plan they do proper identification of needs in all areas. In-consistency is seen in the practices, according to the leaders, because of routine administrative work of leaders, lack of enough support from the woreda or kifleketema education office, and shortage of finance were seen as major. The researcher recommends that the schools need to find a way of putting consistency in to the human resource development program especially to the leaders. It is recommended that responsible parties including Addis Ababa City Administration Education Bureau (AAEB), kifleketema Education office, woreda Education office and higher educational institutions are advised to fill the knowledge and skill gaps of the principals and other school leaders by designing and providing long and short term professional training and development programs on: how to evaluate and plan a strategy to hold trainings and developments by their own for their leaders and to have self-sufficiency programs in the schools for the problem of finance.