AI Strategy
Implementation, ROI, adoption, and leadership decisions for AI in business
// ai strategy · jul 28, 2026
Give your AI permission to disagree with you
A year on from Butler and Advisor, the models have hands. Following a bad instruction well no longer costs you a paragraph, so I now ask my assistant to challenge me - with a threshold, and with evidence.
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// ai strategy · jun 21, 2026
Don't bet your strategy on what AI can't do
Here's a bet I see businesses make without realising they're making it. They look at what AI can't do today, they build their plans around those limits, and they treat those limits as fixed. It's an unspoken bet, and it's a losing one. It loses because the thing you're betting against keeps moving. Two forces […]
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// ai strategy · jun 21, 2026
The best AI work is boring
The AI work I trust most is the work that looks boring. There's no clever prompt, no amazing inspiration, no surprises. It does the same boring thing every time, and that is exactly why I trust it. Most people reach for AI's cleverness first and its dependability second. I strongly believe you need it the […]
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// ai strategy · jun 20, 2026
The most useful AI works when you're not watching
The most useful AI works while you're not watching - and the barrier usually isn't a cleverer model, it's permission. A plain-English guide to the Permission Ladder: how much autonomy you give an AI, the access it costs, and why onboarding it like a new hire is the right mental model.
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// ai in practice · apr 18, 2026
AI just came for design
Anthropic just launched Claude Design yesterday. Before I say what I think about the tool, I want to tell you about a story I read earlier in the week from BEFORE the launch. The story came from a designer called Nurkhon, writing on Substack. A product manager walked into a meeting, typed one sentence into […]
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// ai strategy · mar 17, 2026
Reducing AI Risk with Simple Rules
The AI conversation right now is split down the middle, and I think many people on both sides are way off the mark. On one side, you've got people who think AI is the answer to everything - the hype, the...
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// ai in practice · jan 27, 2026
AI Doesn't Care
Four Things AI Still Can't Do The latest AI "reasoning" models are a massive improvement. Gemini 3, ChatGPT 5.x and especially Claude Opus 4.5 - these systems are amazing. But they still have hard limits,...
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// ai strategy · jan 25, 2026
Why "95% of AI Pilots Fail" Is the Wrong Lesson
Why "95% of AI Pilots Fail" Is the Wrong Lesson The headline failures make for good reading. They're just teaching you the wrong things. You've probably seen the stat: 95% of AI pilots fail. The most recent...
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// ai strategy · jan 21, 2026
Why Boring is Interesting
Boring is interesting A couple of weeks ago I published my 'Boring AI' Manifesto. I had a bit of fun with it, but I believe it's important. It's a core idea in my upcoming book, The AI Pilot Handbook. A few...
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// ai strategy · jan 11, 2026
The Boring AI Manifesto
Boring is underrated. I like my elevators to be boring. I like my seatbelt to be boring. The best AI projects are the ones nobody talks about. They just work. I want technology to do the boring work so you...
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