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 Cowork as a research/personal assistant, but its inconsistent memory and behavior make him less productive and increasingly agitated.  

Interview of the week:   

Tom Stockton – How structured context, guardrails, and Claude Code make AI agents genuinely useful.

Find out more about Container Solutions:

• Download the Cloud Native Attitude
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• Visit the website.

Learn more about our people:

• Jamie Dobson: LinkedIn
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• Ian Miell: LinkedIn | Website
• Tom Stockton: LinkedIn | Website

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