The rapid innovation and growth across multiple industries, driven by advancements in cloud computing has seen several enterprises racing to the cloud and modernizing their applications and infrastructure in the process. As companies start settling down in these new environments, the next focus is towards optimizing costs, improving efficiency and operational excellence none of which would be possible without a strong observability setup. The complexity of modern distributed systems demands more than the traditional reactive monitoring solutions that have been a norm in the industry for a long time. By using the power of generative AI foundational models and retrieval augmented generation, this talk presents some innovative methods to enhance the observability stack for human-like monitoring.