This chapter focuses on the changing process of the relationship between a corporation and its stakeholders in response to the CSR movement. Not all companies have responded positively to the CSR trend and embedded CSR in their stakeholder relations. This chapter clarifies how companies tackle the practical challenges in reconsidering and restructuring the relationship with stakeholders at the new stage of CSR, in which it is developed and implemented. This chapter holds up Japanese companies (JCs) as a case and, by interviewing managers in 20 major companies, explores how CSR management and stakeholder relations in JCs have been changing through the implementation of stakeholder engagement efforts. Until recently, JCs had never engaged with stakeholders with regard to social and environmental issues and have hesitated to meet with consumer groups and NGOs outright. After the CSR boom in the mid-2000s, they began to conduct to engage with stakeholder, albeit perfunctorily, as part of the scope of activities covered in CSR reports. However, going through the experimental leaning in dialogue with stakeholders and receiving critical responses from external parties, some companies have gradually begun to understand the significance of stakeholder engagement and change the nature of their relationship with their stakeholders. Almost all major JCs have introduced CSR systems since the CSR boom, and the institutionalization of CSR management has rapidly developed. Every newly-established management systems do not automatically work, as CSR in particular has been formally introduced in the initial stage. However, many JCs have learned since then how they should go about implementing CSR management and formulating constructive relationships with stakeholders. This paper sheds light on their experimental learning process.