The over all functions of education is changing the behavior of the leamers sornas to make them playa proactive role in a changing world. The roles will bernplayed if teachers are professionally competent and transmit knowledge, skillsrnand attitudes. To strengthen this competency, the attention given to teachers,rnparticularly to be engaged in men to ring teachers as a mentor and men tee is arnbasis for their professional development, is promising. Thus, the purpose ofrnthis study was to examine systematically the practices and challenges ofrnmentoring in govemment high schools of Addis Ababa. Accordingly, the mojorrnvariables were the Purposes of the mentoring, Practices of mentees andrnmentors, Orientation and Training on Mentoring, Timing and Frequency ofrnmeetings for discu ssions, Judgments of the practices of mentoring, andrnChallenges/ Barriers of men to ring were the fo cus of the study. In order tornachieve the pUlpose of the study, a descriptwe survey method was employed.rnThe study w as conducted in three sub-cities found in Addis Ababa that werernselected based on simple random sampling technique . Among 15 h igh schoolsrnin these three sub-cities, 8 were selected with stratified random samplll1grntechniques. From 8 high schools, all mentees and mentors were selectedrnpurposefully. Moreover, 6 officials of sub-cities educational departments (i.e., 2rnfrom each sub-city) and 2 from AAEB were also selected purposefully too. Datarnwere gathered from sample respondents through a s urvey questionnaire,rninte rview, and data analysis. The data were analyzed using statistical toolsrnsuch as frequency count, percentage, mean, and t-test were used for datarnanalysis. The findings of the study revealed that mentees do not havernawareness that mentoring program comes out with built team spirit andrnshared wisdom that pertain cooperation when compared with mentors. As tornthe practice of relationship, both mentees and mentors have relatively a widerngap to put their expected roles, skills, responsibilities and qualities intornpractice. In addition, orientation and training given was not adequate, longrnlasting and continuous, and; timely. On the other hand, the major challengesrnexperienced were poor clarity ' of roles, lack of well experienced expertisernregarding mentoring and the absence and mal distribution of hand book andrncourse materials for mentees and mentors. In general, the current practices ofrnmentoring was judged as being less effective in achieving the major objectivesrnthat it intended to serve. Therefore, due emphasis should be given onrnimproving the mentoring activities by being proactive toward the success.rnMoreover, timely, adequate and appropriate orientation and/ or training onrnmentoring and its elements should be focused on in order to build commitmentrnand team spirit. All the suggestions should be taken as a package and needsrnjoint planning and monitoring and evaluation.