Our article introduces an exploratory process study of successful plural leadership configuration in searching for alternative solutions to wicked problems. The study was executed within four educational organisations that solved challenging wicked problems arising from today’s changing contexts. We argue that plural leadership configuration is a dynamic process when people in diverse organisational positions, roles, and levels design profitable endeavours through their ideas and activities, bring about desirable outcomes within diverse conditions and outline the future. We searched for potential systemic patterns, characteristics, and structure within this dynamic process. To find these properties, we exploited the theoretical concept of an event that corresponds to organisational experiences in terms of people, ideas, activities, conditions, and outcomes. We presumed that the systemic properties could be found through events’ interaction that is proved to be dynamic. Consequently, we exploited dynamic system theories and studied chains of succeeding events and their agglomerations. As a result, we determined properties that were generalisable across the four organisations. The main results indicated that to find alternative solutions to wicked problems, a strong connection between activities and ideas was crucial. However, committed people were needed as moderators between them. Focusing only on conditions such as plans or new programmes, did not bring about successful solutions.