AI Insights for Legal Leaders
Practical analysis on AI adoption for managing partners, COOs, and practice heads. Short, actionable pieces focused on what actually works in legal practice.
Perplexity Has Citations. That's Not the Same as Judgment.
Perplexity is a great research tool. It’s not the best AI tool for attorneys.I was at a seminar recently and heard a lawyer say Perplexity is “the best AI tool for attorneys.”I winced.Not because Perp...
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Gemini's Million-Token Promise? You Get 32,000
created by ChatGPT Image 1.5The Context Window Lie: What You Can Actually Use in Gemini, ChatGPT, and ClaudeI was skiing yesterday when a Reddit post I’d seen that morning kept nagging at me. Someone...
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Your AI Tool Isn't Forgetful. Your Setup Is.
created by ChatGPT Image 1.5Projects in ChatGPT and Claude: the quiet feature that changes how teams workIf you’ve used ChatGPT or Claude at work, you’ve probably had the same experience I have.You op...
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Your Spreadsheet Isn't Broken. Your Process Is.
created by ChatGPT Image 1.5Excel just got a real AI co-workerIf you’ve ever lost an hour to a broken VLOOKUP, a messy export, or a workbook you didn’t build, you know the feeling.Excel isn’t hard bec...
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The Safe Choice Is Now the Risky One
created by ChatGPT Image 1.52026 Is the Year AI Separates Winners from Everyone ElseTL;DR: AI capabilities are accelerating faster than most leaders expected. Models will get smarter, hallucinate less...
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You Don't Need a Computer Science Degree to Learn AI. You Need 90 Days.
Image created by Nano Banana ProZero to Fluent: A 90-Day AI Plan for Business ProfessionalsTL;DR: You don’t need a computer science degree to get good at AI. You need 90 days, one tool, and the discip...
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Your Buyer's AI Is Already Drafting the Counter-Offer. Is Your Revenue Engine Ready?
AI Predictions for RevOps in 2026: The Shift From Dashboards to an Execution EngineEvery RevOps leader knows the moment.It’s Thursday afternoon. You’re in the pipeline meeting. Someone asks, “Is this...
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2026: The Year Legal AI Has to Show Its Work
AI Predictions for 2026 in the Legal IndustryThe shift I’m watchingIn 2024, most legal leaders were still stuck on the first question: “Can we even use this safely?”In 2025, the question got more prac...
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You Turned Off Training. The Feedback Button Didn't Get the Memo.
Training Off Isn’t “Private” in Consumer AIEvery week, someone asks me the same question in a new form. In fact, it came up twice this week in different conversations. h/t to Joseph on Tuesday of thi...
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OpenAI Won the Demo. Google and Anthropic Are Winning the Default.
Why I think OpenAI could lose the next phase to Google and AnthropicThe feeling I can’t shakeFor a while, “OpenAI” and “the frontier” felt basically synonymous.You’d open ChatGPT, do something that fe...
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You Asked How I Keep Up With AI. Here's the Honest Answer.
How I Actually Keep Up with AI (And How You Can Too Without Losing Your Mind)You’ve asked me this question more than any other this year: “How do you keep up with all the AI news?”Here’s the honest an...
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Google Won 2025 by Making AI Boring
Google’s 2025 AI comeback: why they’re now the company to beatA year ago, if you asked me who was winning AI in the real world, I’d have said OpenAI first, Anthropic second, Google third.Not because G...
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Everyone Has AI Now. Almost No One Has AI Advantage. What Actually Changes That.
The 5 AI themes business leaders can’t ignore after 2025If 2025 felt like the year AI went from “interesting” to “everywhere,” you’re not imagining it. In McKinsey’s latest global survey, 88% of respo...
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The Compounding Problem: How AI Leaders Are Pulling Away While Everyone Else Runs Pilots
The AI flywheel is real, and it’s widening the gapYou can feel it in leadership meetings right now.Some teams talk about AI like it’s a set of handy tools. A faster way to draft, search, summarize, an...
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ChatGPT 5.2: The Model That Finally Remembers Page One When It Gets to Page Sixty
ChatGPT 5.2 is out, here’s what’s actually new (in executive English)If you saw “ChatGPT 5.2 launched” and your eyes glazed over, you’re not alone. Model numbers are starting to sound like phone relea...
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Your AI Licenses Aren't the Problem. Your Culture Is.
What OpenAI’s New Enterprise AI Report Really Means For Your BusinessTL;DR:AI at work is no longer a side experiment, usage is exploding and starting to look like core infrastructure.The heaviest user...
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The End of Copy-Paste AI: What Happens When Models Actually Look at Your Work
Why Multimodal Is The Next Big Shift (And Why Gemini Might Be Out In Front)TL;DR: The game is moving from “smart autocomplete for text” to models that can look at your screens, documents, images, and...
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2025: The Year AI Stopped Demoing and Started Delivering
2025: The Year AI Stopped Being a ToyTL;DR: 2025 saw AI shift from impressive demos to real work. DeepSeek proved frontier models don’t require frontier budgets. Reasoning capabilities went mainstream...
Read ArticleGoogle AI Studio: The Free Tool Most Executives Don't Know Exists
If you haven’t used Google’s AI Studio yet to prototype apps, you are missing out on one of the most powerful free AI tools out there. In this quick video, I demonstrate the “Build” feature within Goo...
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The IT Ticket Is Dead: How AI Just Made Every Employee a Developer
The Real AI Pivot Is Happening NowFor the past year, most organizations have treated Generative AI as a content engine - a tool for drafting emails, summarizing reports, or brainstorming marketing cop...
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