It is indispensable for the Japan Self-Defense Forces (JSDF) to secure and nurture high-quality human resources in order to effectively accomplish various missions. It is very important to promote further recruitment of women and assign more active roles to female personnel with motivation and abilities. It is also urgent to maintain a working environment in which those female personnel can fully continue to work even in any challenging circumstances and to demonstrate their abilities. The purpose of this chapter is to examine the necessary leadership as a leader to female personnel with work–family conflict in the JSDF in order to promote their success. What kind of work–family conflict do female personnel have? How should a leader respond to work–family conflict for female personnel? What are the characteristic leadership requirements for work–family facilitation? This chapter will consider and answer these three questions.