Purpose: The purpose of this study is to advance the preparation of prospective school administrator students by extending the Web 2.0 application of blogging to discover students' strengths and successful leadership experiences. During the blogging process, students reflected on and responded to appreciative inquiry (AI) blog posts that encouraged reflective responses highlighting and identifying their inherent leadership strengths and successful leadership experiences. Design/methodology/approach: A qualitative case study model was used to explore the reflective blog contributions of prospective school administrators to discover patterns in the blogging data by grounding the study in an AI theoretical research perspective. A bounded case study delimited the scope of the study to participants who were: masters or doctoral students in a school administration preparation program at a large Midwestern United States research extensive university; and enrolled in four graduate administrative preparation classes taught using reflective blogging over three instructional quarters. Findings: The Web 2.0 application of appreciative inquiry blogging: confirmed personal strengths and successful leadership experiences; bolstered a supportive learning environment; confirmed the students' history of successful leadership experiences; and increased social capital among students. Social implications: Future research using AI in Web 2.0 applications can influence the positive preparation of school administrators by preparing them to lead schools in an evolving digital world. Researchers may examine how an AI blogging Web 2.0 application contributes to changing personal perceptions of contemporary deficit views of schooling to what is possible in light of stakeholders' strengths. Originality/value: The importance of integrating Web 2.0 applications into educational administrator preparation programs is critical in an age where elementary and secondary school students live in a Web 2.0 world and build social networks with peers throughout the globe. Moreover, the evolving global workplace demands fluency in Web 2.0 applications.