This basic qualitative study, using interviews and document analysis, examined reflections from a Work Based Learning (WBL) program to understand how utilizing digital collaborative communication tools influence the educational experience. The Community of Inquiry (CoI) framework was used as a theoretical frame promoting the examination of the three elements including: social reflection (communication), cognitive exploration of work-related curriculum in a real-world environment (work based learning), and teaching presence within technological structure and process (facilitating collaborative technologies). The central research question guiding this study was: What are the perceptions of high school work based learning coordinators about digital collaborative communication tools in enhancing students' educational experience? Findings of this study demonstrate that digital communication skills: Promote ongoing student portfolio creation that aligns with work force skills; Amplify student sharing and discussion capabilities; Require patience to provided beneficial results; Increase efficiency and convenience; Improve the ability to regularly update learning material and provide continuous access; and Increase the availability of a student safety net for those struggling or adapting to the new digital skills. Implications for practice and future research are discussed. [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.]