This research combines recent discussions in the cross-disciplinary areas of e-learning, social software, and training motivation. On the one hand, e-learning with its role in a fast paced knowledge society, its potential to revolutionize education and the gap between research and practitioners is already in discussion for years. Discussions are becoming more intense with the rise of social software. On the other hand, human resources, life-long learning, and motivating employees to participate in trainings appear critical to organizations. This research focuses on e-learning in the corporate context and examines the impact of social software features on user motivation based on a review of training motivation literature and on 39 interviews conducted in an international IT services company. Findings suggest that the impact of social software features is still unknown, and that differentiating them by the learner’s needs leads to further insights.