Discussion - Topic: Context Engineering

This week's topic: Context Engineering

Discussion resources to help guide the conversation will be posted below a few days before the meetup.

Zoom link will be added about 5 min before the event starts.

As described in Thoughtworks Technology Radar Vol. #34.

Context engineering has evolved from an optimization tactic into a foundational architectural concern for modern AI systems. Unlike prompt engineering, which focuses on wording, context engineering treats the context window as a design surface and intentionally constructs the AI’s information environment.

As agents tackle more complex tasks, dumping raw data into large context windows leads to “context rot” and degraded reasoning. To combat this, teams are shifting from static, monolithic prompts to progressive context disclosure. Instead of front-loading every instruction and reference an agent might need, these systems start with a lightweight index of what’s available. The agent determines what prompts or contexts are relevant and pulls in only what’s needed, keeping the signal-to-noise ratio sharp at every step.

We’re seeing several techniques mature in this space: Context setup leverages prompt caching to front-load static instructions, reducing costs and improving time to first token. Dynamic retrieval goes beyond basic RAG by selecting tools and loading only the necessary MCP servers, avoiding unnecessary context expansion. Context graphs model institutional reasoning — such as policies, exceptions and precedents — as structured, queryable data. Context management techniques use stateful compression and sub-agents to summarize intermediate outputs in long-running workflows.

Treating AI context as a static text box is a fast track to hallucinations. To build resilient enterprise agents, teams must engineer context as a dynamic, precisely managed pipeline.

Discussion Resources :

Will be added a few days before the event.