Escaping the Prompt Debt Trap: Drew Breunig Live with Tim O’Reilly
Published by O'Reilly Media, Inc.
How to evolve your engineering practices and stop fighting the weights
The clearest sign you're overinvesting in a prompt is “fighting the weights.” This happens when the model won't do what you ask because you're working against its training. It’s a common failure mode Drew Breunig saw everywhere when he and coauthor Srihari Sriraman examined how different labs write system prompts for their applications. And as labs train their harnesses into their models (which they already appear to be doing), this problem will only become more pronounced, as the systems applied AI engineers are building no longer behave like Claude Code or ChatGPT do.
Drew, writer, technology leader, and CEO and cofounder of cmpnd.ai, has been exploring the challenges of AI and context engineering on his blog and soon to come, in The Context Engineering Handbook from O’Reilly. He’ll join Tim O'Reilly to discuss the prompt debt that developers accumulate and share actionable strategies that will help you shed it, drawn from the work of agentic software developers, who are, as Drew notes, “likely years ahead of everyone else when it comes to experimenting with and evolving their culture and practices to accommodate AI tools.” As always, the conversation will be guided by your questions and comments, but Drew and Tim will likely touch on how to specify system behavior through rigorous measurements, evaluations, and tests, the merits of automated systems and tooling such as DSPy for optimization, and maybe even the coding agent “golf pro tips" Drew has been collecting from top-tier agentic developers.
Recommended prep or follow-up:
- Read The Problem is Prompt Debt (blog post)
- Read The Context Engineering Handbook (early release)
Schedule
The time frames are only estimates and may vary according to how the class is progressing.
Monday, August 3, 2026, at 9:00am PT / 12:00pm ET
- Interactive discussion and Q&A (60 minutes)
Your Hosts and Guests
Tim O'Reilly
Tim O’Reilly is the founder and CEO of O'Reilly Media, Inc. His original business plan was simply "interesting work for interesting people," and that's worked out pretty well. He publishes books, runs online conferences, invests in early-stage startups, urges companies to create more value than they capture, and tries to change the world by spreading and amplifying the knowledge of innovators. He’s perhaps best known for his role in shaping big ideas like open source software, unconferences (Foo Camp), Web 2.0, and government as a platform. His 2017 book WTF? What’s the Future and Why It’s Up to Us explored the role of human agency in shaping the future in the face of the coming AI wave. These days, he’s focused on mechanism design for the human-AI economy. Mechanism design is sometimes described as “reverse game theory”, whereby you start with the outcome you want and then figure out what rules of the game will produce that outcome. He explores these ideas at the non-profit AI Disclosures Project, which he co-founded with Ilan Strauss. He writes frequently on Substack at the O’Reilly Radar, the AI Disclosures Project’s Asimov’s Addendum, and his own Conversations with AI.
Drew Breunig
Drew Breunig is a writer and technology leader, currently assembling The Context Engineering Handbook for O’Reilly. He is the CEO and cofounder of cmpnd.ai, previously ran strategy and data science at PlaceIQ (acquired by Precisely) and cofounded Reporter, an award-winning quantified self app. He writes about AI, data, and geospatial technology at dbreunig.com.