AI Document Consolidation: Hidden Risks Lawyers Must Know
I have written before about how I use AI tools to assemble PowerPoint decks. For lawyers, this can be incredibly efficient. I can take multiple slide decks, articles, ethics opinions, and outlines and ask a generative AI system to consolidate them into a single, coherent presentation. Such a tactic also minimizes hallucinations, because I make […]
Checking the Law Still Means Reading the Cases
How to Deal with Artificial Intelligence When Conducting Legal Research Over the past year, courts have had to confront an uncomfortable and increasingly common problem involving artificial intelligence and misinformation. Briefs have been filed citing cases that do not exist or inaccurately describing holdings. Judicial opinions have been issued and later withdrawn after it became […]
AI Operating Instructions for Legal Practice
Did you know that you can give standing orders to many AIs? Once you provide these orders and tell them to remember them, many AIs will remember the orders and always follow them. I use standing orders to decrease (but not eliminate) the risk of hallucinations and reassurance loops, as well as controlling the output […]
Reassurance Loops and Why AI Can Quietly Undermine Judgment
One of the most subtle risks in working with AI has nothing to do with hallucinations, data breaches, or outright errors. It has to do with reassurance. People often describe AI as persuasive or authoritative, but that is not quite right. What AI does exceptionally well is friction reduction. It smooths uncertainty. It makes a […]
The Quiet Automation of Healthcare
I recently went to Jefferson to see my doctor. It was a doctor I don’t need to see very often, and I had not visited her for several years. When I spoke to the person to set up the appointment, she told me that the office had moved. When I arrived, I was immediately impressed […]
What the AIs Said About Themselves: A Lawyer’s Guide to AI “Self-Reporting” on Privacy
Over the past several weeks, I have been writing about each of the major AIs. I asked each of them the same thing: I am writing a blog post for attorneys on what they should know about what attorneys should know about you, that is [name of ai] so they can be aware of what […]
Copilot Is Not One Tool: It Is Four Distinct Environments

Lawyers often talk about “Copilot” as if it is a single tool. It is not. Microsoft uses the same name across multiple products that behave very differently from a confidentiality and governance standpoint. For lawyers, the meaningful dividing line is whether Copilot is operating inside your organization’s Microsoft 365 tenant or outside it. Everything else […]
Perplexity and Privacy: What Its “Low Footprint” Model Really Means
Perplexity AI often presents itself as a more privacy-respectful alternative to large platform AI tools. And in some respects, that is true. But as with every AI platform, the real answer is not “private” or “not private.” The answer is “it depends.” This post explains what Perplexity’s privacy posture actually looks like in practice and […]