The Monitor — Stephen Boak, Senior Product Designer at Datadog` Stephen Boak, a Senior Product Designer at Datadog, reflects on the evolution of the monitoring industry over seven years and four companies. He notes that despite significant changes in infrastructure, user interaction with monitoring products has remained relatively unchanged. However, he believes that advancements in AI will revolutionize the way users interact with monitoring tools, shifting the focus from tracking metrics to understanding user experience. At Datadog, Boak emphasizes the importance of user experience, using monitoring data to inform how to improve product functionality and user satisfaction. He also highlights the challenges of watching increasingly complex systems, leading to more human effort and complexity in monitoring dashboards, as well as unnecessary alerts and expenses.