Ongoing learning may be one of the few sustainable competitive advantages for organizations. Historically, research efforts and organizational resources have been primarily directed toward understanding and enhancing learning in formal settings, as in classroom training. Yet most learning at work occurs through more informal means. This research sought to enhance our understanding of informal learning by studying effective and ineffective developmental interactions between two individuals. Capturing stories and using a participant-guided qualitative coding process, the research explored factors that had an impact on the effectiveness of developmental interactions and whether those factors worked differently depending on the topic of the interaction (career advice, work-life support, or job or task guidance). Results suggest that several personal and relationship factors influenced developmental interaction effectiveness, but communication factors had no impact. Furthermore, with just a few exceptions, these same factors were important across all three topics explored in this research.