The purpose of this qualitative, multiple-case study was two-fold: 1) to describe, analyze, and interpret the experiences of school principals and superintendents who use multiple social media tools such as blogs, microblogs, social networking sites, podcasts, and online videos with stakeholders as part of their comprehensive communications practices, and 2) to examine why the principals and superintendents have chosen to communicate with their stakeholders through social media. Qualitative, semi-structured interviews with 12 principals and 12 superintendents purposefully selected from four regions of the United States and Canada were conducted. Social CRM served as the framework for the study. Findings revealed four themes that applied to both groups: 1) Social media tools allow for greater interactions between school administrators and their stakeholders; 2) Social media tools provide stronger connections to local stakeholders, to fellow educators, and to the world; 3) Social media use can have a significant impact on a school administrator's personal and professional growth; and 4) Social media use is an expectation; it's no longer optional. Implications for practice, for boards of education, for educational leadership programs, and for expanding the definition of Social CRM are included. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]