The vices rampant now among students in Nigeria secondary schools, such as acts of indiscipline, stealing, cheating, truancy, rioting, cultism, and raping, together with population explosion, call for special skills on the part of the school administrators to be able to cope with these challenges. Consequently, this paper examines the uniqueness of the principals' position to make or mar the image of the educational system and the need for these principals to be well equipped to meet these challenges in the educational system of the third world, with particular reference to Nigeria. This is so because it is now clear that the pre-service skills acquired by present school administrators, through formal education, may not be adequate to meet with these sustainable challenges. Recommendations on probable improvement of these staff development programmes for effective and efficient performance of these principals on their jobs concluded this paper.