As systems move from producing outputs to taking actions, the challenge shifts from creation to decision-making. Agents can generate, select, and execute, but without clear judgment, systems drift, over-act, or make decisions that don’t hold up under real conditions. In this keynote, Eden James explores how judgment becomes the limiting factor in agentic systems where decisions are made across prompts, tools, and workflows, often without a single point of control. Drawing on experience across creative systems and applied AI, he looks at how teams can guide behaviour, not just outputs. This session reframes judgment as a system-level problem, how to shape decisions, define boundaries, and maintain direction as autonomy increases. Key takeaways: → Why judgment becomes harder as systems move from generating to acting → Where agent decision-making breaks down without clear constraints → How teams are guiding system behaviour without removing flexibility