As school leaders, novice principals faced some challenges within the first years of their leadership journey. This mixed-methods study explores the initial challenges faced by novice principals while leading their schools. At the same time, their countering strategies in handling the initial challenges are also being explored. A total of 168 novice principals responded to all items within a questionnaire on their initial challenges and their useful strategies to overcome the challenges. In addition, 11 novice principals were interviewed for in-depth information on their challenges and possible strategies in overcoming them. Findings revealed that dealing with a previous principal’s legacy and heavy workloads were major challenges faced by novice principals. In terms of their countering strategies, novice principals employed various approaches such as organizing an initial meeting with teachers, getting parents involved in school activities, and sharing leadership practice.