In recent times, both geopolitical challenges and the need to counteract climate change have led to an increase in generated renewable energy as well as an increased demand for clean electrical energy. The resulting variability of electricity production and demand as well as an overall demand increase, put additional stress on the existing grid infrastructure. This leads to strongly increased maintenance demands for distribution system operators (DSOs). Today, condition monitoring is used to address these challenges. Researchers have already explored solutions for monitoring critical assets like switchgear and circuit breakers. However, with a shrinking knowledgeable technical workforce and increasing maintenance requirements, mere monitoring is insufficient. Already today, DSOs ask for actionable recommendations, optimization strategies, and prioritization methods to manage the growing task backlog effectively. In this paper we propose a vision of a grid-level cognitive assistance system that translates the outcome of diagnosis and prognosis systems into actionable work tasks for the grid operator. The solution is highly interdisciplinary and based on empirical studies of real-world requirements. We also describe the related work relevant to the multi-disciplinary aspects and summarize the research gaps that need to be closed over the next years.