This dissertation discusses how municipality managers working in or for the social domain within the municipalities of Amsterdam, Rotterdam and The Hague practice leadership and learning when dealing with wicked problems. The study has led to the following key findings: First, the municipal managers in this study have been found to be eager and motivated to create added social value with their partners. Doing meaningful work is thus their primary incentive. At the same time, the way they put this into practice can involve the use of position power, particularly when they ultimately fail to achieve results while cooperating with others. Second, although municipal managers are familiar with the concept of wicked problems, they tend to simplify those problems to more manageable problems, whereby they use an approach they are familiar with, specifically when they experience pressure from the political organization to quickly achieve results. Third, municipal managers know wicked problems require a relational leadership approach. Simultaneously, the leadership skills they envision to be the most essential when dealing with wicked problems, i.e., self-management, vision, and courage, primarily focus on the manager as an individual. This does not necessarily imply that, in dealing with wicked problems, they do not pay attention to relational leadership qualities; it does imply, however, that the primary focus of leadership is on the manager’s own efforts and qualities, and not on those of the collective. Fourth, municipal managers know that learning to deal with wicked problems requires a relational approach. They would like to put this into practice but owing to the many tasks and changes they are confronted with by the political organization, they have little or no time for it. Fifth and finally, the study shows municipal managers consider the learning culture in their organizations to be insufficient in learning to deal with wicked problems. More specifically, they find it important to breed a culture of continuous learning in their organization, allowing them to be an example for others, which provides the safety and trust to (collectively) learn from mistakes and in which learning is embedded in the daily work routine. However, their organization offers little or no support in developing such a learning culture, and as a result of their daily tasks, municipal managers lack the time to be a learning example for others. The main finding of this study is that the examined municipal managers are familiar with the concept of wicked problems and are motivated to use a relational approach of leadership and learning in relation to these problems. To what extent they actually do so depends on several aspects, namely position power, the political organization, leadership qualities, time to learn collectively, and the learning culture. These aspects are of both a contextual (the political organization and learning culture) and individual (positional power, leadership qualities and time to learn collectively) nature, and interact with each other in an unpredictable manner. As a result, the way in which municipal managers implement a relational approach of leadership and learning is divers and depends on the outcomes of the unpredictable and continuously changing relational dynamics between the various contextual and individual aspects.