This article describes a project in which first-year administrators in Pinellas County, Fla., were members of a professional development cadre. The major purpose of the study was to determine the problems encountered by first-year assistant principals. During cadre meetings, participants were encouraged to record in journals and discuss with their peers their experiences as new administrators. Journal entries and highlights of small group discussions were analyzed using a general analytical strategy as outlined by Miles and Hubennan (1994) in their text "Qualitative Data Analysis". Through this process, the researchers discovered that the participating first-year assistant principals were most challenged by heavy job responsibilities, negative impact on their personal lives, difficulty in managing staff and working with large numbers of parents (many of whom were difficult or demanding), relationship problems with principals, and troubles in student management (specifically discipline issues and their unpredictable nature). The findings from this study support previous research on problems faced by first-year administrators and support the need for professional development in these areas of challenge. (Contains 1 figure.)