The emergence of generative AI (GenAI) in observability tools is seen as a natural progression, promising to transform how organizations handle monitoring and incident response in IT environments. While past experiences with AIOps, which aimed to address operational complexities but fell short due to unmet expectations and organizational reluctance to adapt, serve as a cautionary tale, GenAI offers new opportunities. AI-powered observability tools have the potential to democratize access to system insights by allowing nontechnical users to interact with telemetry data using natural language, enhancing productivity, and optimizing system performance. By integrating AI for tasks like anomaly detection and root cause analysis, these tools can streamline operations and reduce manual intervention, though success depends on organizations' willingness to embrace necessary changes. The successful implementation of GenAI-driven observability solutions requires learning from previous technological shifts to meet the evolving demands of cloud-native architectures and IT operations.