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DennisKennedy.Blog

DennisKennedy.Blog

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Dennis Kennedy on legal tech strategy, innovation, and practical technology for lawyers.

Recent Posts

Building the Stochastic Sandpit for AI
News•Feb 27, 2026

Building the Stochastic Sandpit for AI

The article proposes a "stochastic sandpit" as a thinking workspace where generative AI is used for exploration rather than as a vending‑machine answer engine. It contrasts two usage modes: insurance mode, which enforces tight guardrails for compliance and predictability, and sandpit mode, which encourages productive wrongness to surface hidden assumptions, edge cases, and alternative frames. By deliberately allowing the model to be imperfect, users can generate "impressions"—traces of reasoning that reveal uncertainty and leaps. The sandpit approach is presented as a protocol for high‑stakes fields such as law and policy, ending with a hard rule that only human‑rewritten, source‑anchored output reaches production.

By DennisKennedy.Blog
The End of the Magic Wand: Why 2026 Demands Resilience Prompting
News•Feb 25, 2026

The End of the Magic Wand: Why 2026 Demands Resilience Prompting

Law firms have moved beyond chasing the perfect prompt and now face a deeper challenge: generative AI reasoning systems can produce fluent, persuasive answers that are subtly incorrect. The article argues that lawyers must treat every AI output as a...

By DennisKennedy.Blog