Uploaded August 2026 | Updated September 2026, 2 weeks ago
Why do AI systems silently fail? How can you set up a system that produces results while also reviewing and validating the work? This week on the show, Calvin Hendryx-Parker returns to discuss his recent talk "Orchestrate Agentic AI: Context, Checklists, and No-Miss Reviews."
👉 Links from the show: realpython.com/podcasts/rpp/308
Calvin describes how silent failures can occur when handing a large document to an LLM for parsing. He describes it as the tragedy of context, where the LLM is confident, but you have no idea what it didn't read. We discuss issues with file formats, dropped attachments, and silent truncation.
Calvin shares the example project from his talk, which includes Markdown files for the agents, hooks, skills, and scripts. He also discusses a variety of coding agents, skill frameworks, and CLI tools.
Topics:
- 00:00:00 -- Introduction
- 00:02:19 -- Co-hosting Python Bytes
- 00:03:43 -- Why AI Fails Silently talk
- 00:11:07 -- Digging into silent failures and an audit trail
- 00:18:44 -- How would you define hooks?
- 00:20:48 -- Document extraction, embeddings, and Cowork
- 00:30:38 -- Stripping the noise from file formats
- 00:34:43 -- Things that are now baked into models
- 00:45:53 -- Video Course Spotlight
- 00:47:23 -- Leveraging agents to pick models
- 00:51:44 -- GitHub repo for the project
- 00:54:57 -- The current market around tokens
- 01:00:12 -- What are you excited about in the world of Python?
- 01:03:02 -- What do you want to learn next?
- 01:04:21 -- The content the LLMs are trained on
- 01:07:36 -- Upcoming events
- 01:08:38 -- Thanks and goodbye
👉 Links from the show: realpython.com/podcasts/rpp/308
Download your free Python Cheat Sheet here: realpython.com/cheatsheet
Free Python Skill Test with instant level + learning plan: realpython.com/skill-test
Want to learn faster? Become a Python Expert with unlimited access to 5,000+ tutorials, videos, and exercises: realpython.com/start
🐍 Become a Python expert with real-world tutorials, on-demand courses, interactive quizzes, and 24/7 access to a community of experts at realpython.com
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🐍 Start Here → realpython.com/start
🗺️ Guided Learning Paths → realpython.com/learning-paths
🎧 Real Python Podcast → realpython.com/podcast
📚 Python Books → realpython.com/books
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🧑💻 Quizzes & Exercises → realpython.com/quizzes
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⭐️ Reviews & Learner Stories: realpython.com/learner-stories
▰▰▰▰▰▰▰▰▰▰▰▰▰▰▰▰▰▰▰▰
Why do AI systems silently fail? How can you set up a system that produces results while also reviewing and validating the work? This week on the show, Calvin Hendryx-Parker returns to discuss his recent talk "Orchestrate Agentic AI: Context, Checklists, and No-Miss Reviews."
👉 Links from the show: realpython.com/podcasts/rpp/308
Calvin describes how silent failures can occur when handing a large document to an LLM for parsing. He describes it as the tragedy of context, where the LLM is confident, but you have no idea what it didn't read. We discuss issues with file formats, dropped attachments, and silent truncation.
Calvin shares the example project from his talk, which includes Markdown files for the agents, hooks, skills, and scripts. He also discusses a variety of coding agents, skill frameworks, and CLI tools.
Topics:
- 00:00:00 -- Introduction
- 00:02:19 -- Co-hosting Python Bytes
- 00:03:43 -- Why AI Fails Silently talk
- 00:11:07 -- Digging into silent failures and an audit trail
- 00:18:44 -- How would you define hooks?
- 00:20:48 -- Document extraction, embeddings, and Cowork
- 00:30:38 -- Stripping the noise from file formats
- 00:34:43 -- Things that are now baked into models
- 00:45:53 -- Video Course Spotlight
- 00:47:23 -- Leveraging agents to pick models
- 00:51:44 -- GitHub repo for the project
- 00:54:57 -- The current market around tokens
- 01:00:12 -- What are you excited about in the world of Python?
- 01:03:02 -- What do you want to learn next?
- 01:04:21 -- The content the LLMs are trained on
- 01:07:36 -- Upcoming events
- 01:08:38 -- Thanks and goodbye
👉 Links from the show: realpython.com/podcasts/rpp/308
Download your free Python Cheat Sheet here: realpython.com/cheatsheet
Free Python Skill Test with instant level + learning plan: realpython.com/skill-test
Want to learn faster? Become a Python Expert with unlimited access to 5,000+ tutorials, videos, and exercises: realpython.com/start
🐍 Become a Python expert with real-world tutorials, on-demand courses, interactive quizzes, and 24/7 access to a community of experts at realpython.com
▰▰▰▰▰▰▰▰▰▰▰▰▰▰▰▰▰▰▰▰
🐍 Start Here → realpython.com/start
🗺️ Guided Learning Paths → realpython.com/learning-paths
🎧 Real Python Podcast → realpython.com/podcast
📚 Python Books → realpython.com/books
📖 Python Reference → realpython.com/ref
🧑💻 Quizzes & Exercises → realpython.com/quizzes
🎓 Live Courses: realpython.com/live
⭐️ Reviews & Learner Stories: realpython.com/learner-stories
▰▰▰▰▰▰▰▰▰▰▰▰▰▰▰▰▰▰▰▰
