Purpose: The purpose of this qualitative case study was to explore how using technology tools during mentoring impacts the desired outcomes, as defined by the mentor-mentee contract, of the mentoring relationships of technology workers at a private graduate university with the main campus in Southern California. Methodology: This was a single qualitative case study designed to investigate skill transfer in mentoring relationships using technology. The sample was selected from information technology workers who participated in a pilot mentoring program at the identified university. Open-ended and semistructured questions were asked in face-to-face individual interviews with the mentors and mentees. Subsequently, the supervisors of the mentees were also individually interviewed using semistructured face-to-face interviews for an independent assessment. Findings: Participants reported that technology enabled them to transfer both technical and soft skills during mentoring. The data also showed that technology enabled learning and promoted the development of technical skills, such as 3D programming skills, web application development, and project management skills, and the development of soft skills: communication skills, interpersonal skills, and time management. Mentors and mentees were comfortable with technology and therefore used technology during mentoring. The perceived quality of the mentoring relationship was enhanced through the use of technology. Conclusions: Mentors and mentees who have an acceptance of the usage of technology can help improve the quality of their relationship by using technology to expedite communication and enhance the transfer of skills. For information technology workers, the type of technology used should be relevant to the technical skills the mentee seeks to develop. Soft skill development regarding communication skills can be successfully developed during mentoring when technology designed for communication is utilized. Recommendations: The researcher recommends three categories of future studies: (a) exploring user acceptance of technology and its impact on mentoring success (including populations of technology workers and others in fields outside of technology in hybrid and e-mentoring relationships); (b) exploring gender influence on mentoring needs for technology workers (with specific focus on women, keeping their technical skills current, and advancing in male-dominated profession); and (c) quantifying newly explored themes and patterns in user acceptance of technology, and gender influences, as related to mentoring success. [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.]