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
• Download Visionaries, Rebels and Machines
• Download Follow the Money
• Visit the website.

Learn more about our people:

• Jamie Dobson: LinkedIn
• Join Jamie’s Substack 
• Ian Miell: LinkedIn | Website
• Tom Stockton: LinkedIn | Website

If you enjoyed this episode then please either:

• Follow, rate, and review on Apple Podcasts
• Follow and rate on Spotify
• Watch our videos on our YouTube Channel!

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Jamie Dobson and Ian Miell explore how “following the money” explains why software architecture mirrors funding models, incentives, and organizational structure, extending Conway’s Law into “Miell’s Law.” Jamie then interviews Sam Newman on why Conway’s Law resonates, why the Inverse Conway Maneuver is often misunderstood, and how architects should navigate uncertainty, AI, resilience, and basic financial curiosity.

Question of the week:   

Is architecture your problem or is it your financial model?

Horror Story of the week:   

Ian Miell describes a bank Kubernetes platform whose users multiplied rapidly while funding stayed flat, leaving the same team unable to meet escalating operational demands.

Interview of the week:   

Sam Newman – Conway’s Law’s limits, the flawed Inverse Conway Maneuver, and architecting for uncertainty and resilience.

Find out more about Container Solutions:

• Download the Cloud Native Attitude
• Download Visionaries, Rebels and Machines
• Download Follow the Money
• Visit the website.

Learn more about our people:

• Jamie Dobson: LinkedIn
• Join Jamie’s Substack 
• Ian Miell: LinkedIn | Website
• Sam Newman: LinkedIn | Website

If you enjoyed this episode then please either:

• Follow, rate, and review on Apple Podcasts
• Follow and rate on Spotify
• Watch our videos on our YouTube Channel!

Hosted on Acast. See acast.com/privacy for more information.

Jamie Dobson, Ian Miell, and James O’ Donovan explore whether AI can genuinely improve leadership judgment—or simply accelerate bad decisions—before Jamie interviews Barry O’Reilly on combining human instincts with machine intelligence to increase decision velocity and decision advantage. They also unpack a “vibe coding” horror story that threatens tools like Salesforce and warn that AI investments will fail without solid cloud, data, and governance foundations.

Question of the week: 

How can AI serve not as a replacement or as an intern, but as an actual thinking partner for you in your day-to-day jobs to improve your judgment and specific decisions?

Horror Story of the week: 

CarboNet abandoned a Salesforce implementation to “vibe code” a bespoke replacement—risking a future mess of ungoverned systems that eventually costs more to untangle than doing it right initially.

Interview of the week: 

Barry O’Reilly – How leaders can augment judgment by matching traits, tasks, and AI tools.

Find out more about Container Solutions:

• Download the Cloud Native Attitude
• Download Visionaries, Rebels and Machines
• Download Follow the Money
• Visit the website.

Learn more about our people:

• Jamie Dobson: LinkedIn
• Join Jamie’s Substack 
• Ian Miell: LinkedIn | Website
• James O’Donovan: LinkedIn | Website
• Barry O’Reilly: LinkedIn | Website

If you enjoyed this episode then please either:

• Follow, rate, and review on Apple Podcasts
• Follow and rate on Spotify
• Watch our videos on our YouTube Channel!

Hosted on Acast. See acast.com/privacy for more information.

Jamie Dobson and Ian Miell debate whether ChatGPT/OpenAI is “the new Netscape,” exploring how generative AI may mark a true industry inflection point while rapidly commoditizing amid fierce competition and uncertain economics. Jamie then interviews RedMonk founder James Governor (author of *Progressive Delivery*) on token economics, hyperscaler advantages, China’s model momentum, and closes with practical guidance on winning with commodity tech through late-mover confidence, amplification of existing moats, and cheap experimentation that scales smartly.

Question of the week:   

Is OpenAI or ChatGPT the new Netscape?

Consulting Advice of the Week: 

Ian and Jamie discuss the criteria that OpenAI needs to fit to be considered the “new Netscape” and hone down on a conclusion.

Interview of the week: 

James Governor – Explains why ChatGPT may be a “Netscape moment,” focusing on token economics and progressive delivery.

Find out more about Container Solutions:

• Download the Cloud Native Attitude
• Download Visionaries, Rebels and Machines
• Download Follow the Money
• Visit the website.

Learn more about our people:

• Jamie Dobson: LinkedIn
• Join Jamie’s Substack 
• Ian Miell: LinkedIn | Website
• James Governor: LinkedIn | Website

If you enjoyed this episode then please either:

• Follow, rate, and review on Apple Podcasts
• Follow and rate on Spotify
• Watch our videos on our YouTube Channel!

Hosted on Acast. See acast.com/privacy for more information.

Jamie Dobson, Ian, Angus, and Gustavo unpack how AI is (and isn’t) changing tech hiring—arguing that interviews should assess real working practices with modern tools, not memory tests or “code from scratch” machismo. They also share a Netflix-inspired talent-management horror story and hear from talent acquisition futurist Matt Alder on AI-driven application volume, fraud, bias, and what skills will matter most for the next generation.

Question of the week:   

How has AI affected tech hiring?

Horror Story of the week:   

Jamie Dobson recounts how companies copy Netflix’s tech but ignore talent density and leadership practices—then fail their “cloud transformation” while clinging to magical thinking and refusing to address workforce and management realities.

Interview of the week:   

Matt Alder – AI is breaking traditional recruiting, forcing new assessment methods, clearer policies, and a focus on flexibility.

Find out more about Container Solutions:

• Download the Cloud Native Attitude
• Download Visionaries, Rebels and Machines
• Download Follow the Money
• Visit the website.

Learn more about our people:

• Jamie Dobson: LinkedIn
• Join Jamie’s Substack 
• Angus Pointer: LinkedIn | Website
• Gustavo Carvalho: LinkedIn | Website
• Ian Miell: LinkedIn | Website
• Matt Alder: LinkedIn | Website

If you enjoyed this episode then please either:

• Follow, rate, and review on Apple Podcasts
• Follow and rate on Spotify
• Watch our videos on our YouTube Channel!

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Jamie Dobson, Chris Vermeulen, and Önsel Akin debate whether AI agents should act autonomously in organizations—arguing for conditional autonomy with strong human-in-the-loop controls, security, observability, and “read-only/shadow mode” rollouts. Jamie then interviews Adrian Cockcroft on “developers on demand,” how agentic coding changes product/platform work, and why an AI bubble may burst—making capability cheaper and more widespread.

Question of the week:   

Do we allow AI agents to act autonomously inside organizations?

Horror Story of the week:   

Customers often have an outdated, overly simplistic view of AI (chat/coding/research), missing newer agentic capabilities and therefore failing to design strong, scalable use cases.

Interview of the week:   

Adrian Cockcroft – How agentic AI enables “developer capacity on demand” and accelerates prototyping.

Find out more about Container Solutions:

• Download the Cloud Native Attitude
• Download Visionaries, Rebels and Machines
• Download Follow the Money
• Visit the website.

Learn more about our people:

• Jamie Dobson: LinkedIn
• Join Jamie’s Substack 
• Christiaan Vermeulen: LinkedIn | Website
• Önsel Akin: LinkedIn | Website
• Adrian Cockcroft: LinkedIn | Website

If you enjoyed this episode then please either:

• Follow, rate, and review on Apple Podcasts
• Follow and rate on Spotify
• Watch our videos on our YouTube Channel!

Hosted on Acast. See acast.com/privacy for more information.

Thanks for watching Container Solutions TV.

If you enjoyed this episode, subscribe on YouTube and follow Container Solutions on LinkedIn for the cut-down parts and weekly clips.

If you want help with platform engineering, cloud native transformation, or operating model change, visit our website via the link below and get in touch.

See you in the next episode.

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