Purpose: The purpose of this research project is to explore the use of technology in enhancing and creating opportunities for collaborative learning by connecting prospective school leaders and practicing principals from multiple settings. Design/methodology/approach: This was a research project in which an internet-based network system was created in "LiveText" (software) for cross-collaborative learning among intern prospective school leaders, practicing school administrators from different school settings and university faculty. Data were gathered through focus group discussions, surveys, reflections and the interns' portfolios. Findings: Responses from participants indicated that the technology used in this project: created a forum for prospective school leaders to network and be involved in experiences spanning multiple settings and multiple mentors; enabled the participants to better understand issues of urban/inner-city, suburban, rural, elementary, middle, and high schools; created opportunities for interns to assess their own knowledge, skills, and dispositions based on Interstate School Leaders Licensure Consortium (ISLLC) standards; and enabled the development of web-based electronic portfolios through "LiveText." Originality/value: The project demonstrated how technology can be used as a programmatic tool to enhance collaborative learning by: first, countering logistical and structural challenges of organizing multiple setting leadership experiences for aspiring school leaders; and second, dismantling barriers that separate prospective school leaders from diverse practicing school leaders and schools and, thereby, building both strong and weak ties.