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By: Pilot & Rutter

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Andy James

Latest from Soundings | Pilot & Rutter

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Limited Time Smart: Run a Deliberate AI Inversion
A single light bulb glowing bright white, held up by a hand against a dark background: a sudden burst of intelligence switched on.
Anthropic’s Fable 5 is now rolled out to most plans, but when it was first introduced, it set in motion an exercise I am now doing routinely. If you remember from a month ago (eons in AI time), Fable 5 was introduced as free for a

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Everything Is Permissible
A residential street completely submerged by muddy brown floodwater, with a thin red-and-white barrier tape strung across it as the only marker: a sign standing in for the fence that was needed.
Nothing is true, everything is permitted. That line from the Assassin’s Creed games is also the operating philosophy of the AI you just put to work. To the model, everything is permitted. Not because it is reckless, but because it has no rules and only priorities.
Old software followed rules, and

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Rise of the Technical Product Manager
A chef at the pass under warm kitchen lamps at night, line cooks working behind and plates stacked for service.
For as long as I have built things, engineering took time, and everything else waited on it. The build sat on the critical path: the longest step, so it set the pace for everyone. AI just collapsed that step. And in collapsing it, AI surfaced where the real

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AI Is Not a New Business Problem. It’s an Old One.
View from behind in a small-plane cockpit: an experienced pilot and a newcomer sit side by side at the controls, flying forward over open country.
Last year you hired a guy named AJ.
Brand new, came in off the street. You did not check many references, but he was sharp, said the right things, and you needed help in finance. So that is where you put him.
AJ

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Alignment Is Not a State. It’s a Fight Against Entropy.
A conductor with baton raised leads a full orchestra mid-performance, the players holding to his direction.
Leave a hot cup of coffee on your desk and walk away. It does not stay hot. It does not get hotter. It cools toward the temperature of the room, every time, without exception, because the universe has a quiet, relentless bias toward disorder.

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Congrats on Becoming a CAIO! Now What?
Tugboat steering a large container ship, a metaphor for leading through influence rather than authority.
You got the title. The C-suite seat, the announcement, the LinkedIn flood of congratulations. Here is the part nobody put in the offer letter: you do not actually have a department, and you do not actually have authority.
The Chief AI Officer is the fastest-growing seat in

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AI Is Not a Tool. It’s a Culture.
Aerial night view of a city with its grid of buildings and streets fully lit, power reaching every block.
Walk into most companies right now and you can find AI in exactly one place: the technology department. It has a budget line, a steering committee, and a corner of the org chart down in IT, where it sits like another server to be maintained. That

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