Capacity development (CD) is a popular strategy in international development, but studies show that many CD programs fail to develop the expected results. There is no agreed-upon body of theories to guide CD practice either. To address this issue, this research drew upon the workplace learning literature to explore the dynamics of capacity development in the context of Afghan Ministry of Education (MoE), Department of Planning (DoP). The purpose was to understand the perceptions of the MoE-DoP staff on how different factors influenced their workplace learning and how the CD project led by the UNESCO International Institute of Educational Planning (IIEP) utilized those factors for developing their capacities. The conceptual framework— developed using major theories of learning, especially Lave and Wegner (1991) and Billet’s (1990, 2004)—was used to frame the research and analyze the participants’ experiences. The main data collection method was in-depth interviewing. The sample included eight employees with diverse backgrounds, each of whom were interviewed at least three times. The findings include a list of learning incidents reported by the participants and a list of influencing factors classified into three categories: personal (gender, education, language skills, personal vision, and confidence in learning), task-related (cognitive demand, access to information, professional interactions, and combination of theory and practice), and contextual (guidance, a culture of openness and information sharing, incentive structure, organizational structure, and internal politics). The IIEP project was found to have utilized many of the factors to facilitate the participants’ workplace learning such as engaging them in technical tasks like strategic planning and developing projection models, mentoring through technical assistants, creating incentives, and offering opportunities for formal training and education. The project, however, has not conducted a systematic assessment of the influence of personal, task-related, and contextual factors on each individual participant and has not developed individualized learning plans to guide their informal workplace learning. This research provides a framework for analyzing the complexities of CD process and designing effective interventions, and an example of how such a framework can be used for evaluating CD programs.