This paper serves as an exploration and thick description of job performance outcomes based upon the manner in which self-directed learning activities of employees are conducted, mediated by the use of Web 2.0 technologies in organizational settings. It provides a collective view of the role that Web 2.0 technology plays in self-directed workplace learning and job performance outcomes to benefit employees, organizations, and human resource development professionals. To expand further the knowledge base of adult learning and self-directed learning activities, this paper places its focus on the role of Web 2.0 technology in adult learners’ engagement in self-directed learning. Part of the discussion focuses on learners’ preferences in relation to the emergence of Web 2.0 technology. This discussion of learner preferences explores learning environments that participants engaged in and the motivation behind their engagement. This paper contributes to the field of human resource development by providing a new lens that views the role of Web 2.0 technology in self-directed learning and job performance within an organizational setting, thereby enabling its integration into a blended-learning site. A practical application resulting from this paper is to provide insight to human resource development professionals into best practices and recommendations for the adoption and application of Web 2.0 technology.