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The Real Legal AI Risk is in the Handoffs

By Dennis Kennedy on March 18, 2026

Most legal AI talk is still focused on whether the engine starts, while the real danger is that no one knows who’s actually steering the car once it hits the highway. It turns out the human in the loop isn’t a safety feature if the human doesn’t know which loop they’re currently standing in.

We…

Posted in #blogfirst, AI, Law Department Innovation, LegalAI, Uncategorized

Organization Innovation Risk Tolerance Quiz

By Dennis Kennedy on November 1, 2021

For many years, modern portfolio theory and its adaptation to technology and innovation in law has been one of my recurring big themes. As in your financial portfolio, risk and reward must be assessed and your tech and innovation efforts must be seen as a portfolio to increase your chances of good longterm returns.

You…

Posted in Gumroad, Innovation, Legal Technology, Products
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