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Winston
Howes
Member of Technical Staff
OpenAI
Winston is a Member of Technical Staff at OpenAI, with a background in computer security and web systems. He designs and builds technical solutions that improve system security and resilience, working across teams to address risks that emerge as AI systems move from development into real-world use.
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26 August 2026 11:00 - 11:30
Is it really the model or systems problem?
A single prompt is manageable. Add tools, memory, and multi-step workflows, and the system starts behaving differently under real conditions. Small inconsistencies compound, dependencies become harder to track, and issues surface in places you weren’t looking. This session focuses on where orchestration starts to break down in practice, how complexity builds across systems, why it’s difficult to debug, and what teams are doing to make these workflows more stable. Key takeaways: → Where orchestration introduces failure points as systems become more interconnected → Why multi-step workflows are harder to reason about than they appear → What teams are doing to reduce fragility across complex systems