This paper reports on research that was undertaken to determine the problems experienced by deputy principals in secondary schools, and the extent to which these problems were experienced. Although some research was conducted on the deputy principalship, no research treats the problems that deputy principals experience upon appointment comprehensively. An understanding of the problems experienced by secondary school deputy principals is a necessary precursor of an induction program to address the problems. A quantitative approach which was underpinned by the post-positivist paradigm was adopted. In order to determine the extent to which the problems were experienced, a survey was conducted among one hundred and fifty seven secondary school deputy principals in the North West Province. The participants came from a diverse context of rural, township and urban schools. The deputy principals who participated in the study included those who were newly appointed (one to three years of service) and those who were experienced (more than three years of service). Data were analyzed by means of descriptive statistics such as frequencies, means and percentages. There were no significant differences in the responses of both newly-appointed and experienced deputy principals. The results revealed that deputy principals experienced administrative, financial management, work pressure, personal and physical resources problems. In an attempt to address the problems identified, a context-specific induction program is recommended. The induction program should be an on-going program of professional development and should preferably include specific aims, action steps to be taken to achieve the aims that are set and measures to evaluate progress.