John Cutler · 3 min read · Design

TBM 406: Seeing Everything, Understanding Nothing (The Context Trap)

Read the original on cutlefish.substack.com →

AI hype treats context as something to transmit and merge, but real understanding emerges from interaction. The article argues that leadership is design work—refining intent through dialogue, scenario exploration, and continuous adjustment so context is enacted within shared situations rather than assembled as background.

Key Takeaways

Excerpt

AI is supercharging legacy leadership assumptions about context and control. In AI discourse, “context” is increasingly framed as the new source of truth. It’s a familiar and seductive idea that if only enough information can be assembled and surfaced, clarity and control will follow. Context engineering frequently treats context as a package that can be handed over or merged. I’ll share—or my prompt or retrieval system will share — what I know; you’ll share what you know (the receiver’s context); and we’ll both have our needs met. This assumes that shared context can be constructed by combining individual contexts and…

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