This study examined the perceptions of a cross section of new and experienced assistant principals regarding the realities of their jobs. Findings indicated that their challenges pertain to workload and task management, conflicts with adults and students, and curriculum and instruction issues. Novice and experienced assistant principals' responses were similar, suggesting that their duties did not change substantially the longer they were on the job. Implications are raised for how leadership preparation and professional development programs can prepare aspiring and practicing assistant principals to become more competent in dealing with these persistent job realities. (Contains 5 tables.)