This paper examines intergenerational cooperation in the Systems Thinking and Society website development project, an initiative aimed at creating a digital platform for collaboration, dissemination, and knowledge exchange in the field of systems thinking in Slovenia and beyond. The platform is designed to connect stakeholders from education, public administration, civil society, and business, while supporting the visibility of good practices, research, and collaborative initiatives. The study focuses on a project team composed of two senior members over the age of 50, including the coordinator and project owner, and six students aged between 20 and 24. It explores how generational differences influence communication patterns, role distribution, decision making, evaluation, and mutual learning during the development process. Methodologically, the study applies a qualitative approach based on structured group discussions. Team members discussed and assessed the work of other groups, and these discussions were recorded, transcribed, and analysed thematically. This phase was followed by a joint discussion aimed at identifying recurring tensions, strengthening synergies, and proposing ways to overcome emerging issues. The findings indicate that intergenerational diversity created both coordination challenges and important learning opportunities. Differences in expectations, pace of work, and communication style occasionally produced misunderstandings, yet they also enabled the combination of strategic oversight, contextual experience, digital fluency, and creative problem solving. The paper suggests that structured reflection, reciprocal feedback, and facilitated dialogue can improve collaboration across age groups. The study contributes practical implications for the design and management of collaborative digital projects that rely on mixed-age teams.