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New to AI, Upfront?
I've been writing AI, Upfront for the better part of a year. Thirty-plus briefings. One briefing each week.
If you're arriving for the first time, I won't ask you to read from the beginning. The archive is long and not everything in it reflects where this newsletter is heading. Instead, here are three pieces I'd point any new reader to first. They represent the thinking at the core of what I write about, and they'll tell you quickly whether this is worth your time.
If you want to understand why most AI initiatives fail before they start: Briefing #1: The Great AI Stagnation
Most AI projects don't fail because the technology doesn't work. They fail because organizations design pilots that are built to succeed on the wrong terms: technically sound, strategically hollow. If you've ever watched a promising AI initiative die quietly in a steering committee, this one is for you.
If you want to understand what AI fluency actually requires of a leader: Briefing #4: From AI Literacy to AI Fluency
There's a difference between knowing how to use an AI tool and knowing how to think with one. Most corporate AI training stops at the first. This piece makes that distinction sharply and explains why closing the gap between the two is the single most important thing a leader can do right now.
If you need to make the business case for AI to a skeptical CFO: Briefing #30: How to Talk to Your CFO About AI
This one came directly from a conversation with a senior tech executive whose AI initiative was dead on arrival, not because the idea was bad, but because he was telling the wrong story to the wrong audience. I've been in that room on both sides of the table. This piece walks through how to reframe an AI investment in language that actually moves a CFO from skeptic to ally.
From here, new briefings publish every Monday. Starting now, you’ll see longer pieces, video, and a sharper focus on what leaders in your position can actually do with AI — not just think about.
If there’s a challenge you’re navigating or a topic you’d like me to address, reply to this post. I read everything.
— Barry