The integration of technology into classrooms, the education of gifted learners, and the challenge this presents to classroom relationships as a result of engaging with computer technology are significant issues for teachers in this decade. The evolving paradigm of technology use, the deep learning of computer skills that students will require for future employment and how this can be incorporated into appropriate pedagogies for gifted learners also poses challenges for teachers. This thesis reports on a unique mentoring program that was developed to utilise desktop videoconferencing (DVC) technology and designed to specifically address these challenges. The study was undertaken in a large independent school (K-12) in New South Wales, Australia and involved six students and six teachers, none of whom had any previous experience of DVC or mentoring. The aim of the study was to investigate learning outcomes for teachers and gifted students. This study employed DVC as a didactic strategy over a 10-week period. The mentoring sessions of the cohorts and their post-mentoring interviews were evaluated using grounded theory methods of data gathering and analysis over a 2-year period. The findings demonstrated that the nature of learning during DVC could be constructed as an emergent theory, based on the teaching philosophies of the teachers and their goals for their students. Technical support, relational mentors and motivational tasks created supportive environments for DVC. Perseverance, enthusiasm and resilience enhanced the uniqueness of mentoring program. Several recommendations are also posited for further research.