Challenges for novice school leaders evolve as information is managed differently and as societal and regulatory expectations change. This study addresses unique challenges faced by practicing principals (n=159) during their first three years of the principalship. It focuses on their perceptions, how perceptions of present novices compare to those of experienced school leaders, and how pre-service programs can better prepare them for these challenges. Findings revealed that two themes shared relatively the same prominence among experienced leaders as they did with novices: navigating politics and gaining a sense of credibility. Experienced leaders expounded more on specific political hurdles with school boards, other teachers, and parents, and—regarding these same populations—experienced leaders voiced that they wished they had been more successful in their earlier years in developing credibility more quickly with stakeholders. A theme not occurring at all among present novices but noted by five experienced leaders was that of adjusting to the culture of a new school as its leader. This phenomenon may be explained by the value more seasoned leaders have developed for factors inherent in a campus culture. As they look back on their novice years, seasoned leaders may realize how more effective they could have been and how much credibility they could have earned had they become more proficient in understanding the culture of the school environment they were charged to lead. Further comparison of novices to experienced leaders demonstrates the following differences. When approaching the open-ended questions, present novices and experienced leaders alike identified time management and balance as the most challenging.