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Claude, Context Rot, and Managing AI Like Employees
Jamie Dobson and Ian Miell unpack Jamie’s “Claude CoWork” frustrations, then bring in Tom Stockton to compare real-world agent workflows and what “context rot” means for productivity. Together, Jamie, Ian, and Tom discuss why success with agentic AI depends less on the tools and more on structured management, guardrails, and safe-to-fail experimentation.
Question of the week:
Is success with tools like Claude mostly about managing them like employees—using sensible org practices, context, and guardrails—rather than about the tools themselves?
Horror Story of the week:
Jamie tries using Claude…
The skinny
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