This study aims to explore the reasons and challenges of junior high school principals participating in reappointment and transfer principal election. It also explores the various strategies and effects on school management. The study adapted qualitative method and typical case sampling to select eight principals from junior high schools in Taipei city, and used semi-constructed interviews to collect data. The findings of this research were: 1. Principals used a conservative method and hoped to gain support from teachers and parents in their first election. 2. The strategies used during reappointment were dependent on their willingness of staying. 3. Transfer election could be divided into two types, an offensive strategy used by those who had fulfilled their term and were waiting for a brand new start; a conservative strategy used when one intended to have reappointment and transfer, but were mostly invited to participate in the election. 4. The influence on school management of different strategies included: (1) The operation of school staff affects the principal election and school management; (2) School satisfaction as the foundation of reappointment affects principal leadership; (3) The election system is stressful to principals as they had to meet the needs of students’ parents and the school staff. They also had to show their persistence and outstanding achievements; (4) Their fair attitudes to inappropriate behaviors of teachers would bring uncertainty to their election; (5) The election system hinders the innovativeness of principals; (6) Principals should lead by personal example and fully focus on winning trust and identification from school management.