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AI decisions, examined in depth

Longer takes on the topics that matter for AI leadership. Each article builds on a LinkedIn post with added context, evidence, and frameworks.

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Hand-drawn illustration on a warm cream background. A small metal keyring with a round loop hangs centered in the frame, seen from above. Three items hang from it: a gold-toned key with cut teeth on the left, a silver-toned key with cut teeth in the middle, and a small pale blue-white rectangular blank tag with a hole and no markings on the right. A soft blue-grey shadow spreads beneath the keyring on the cream ground.
Real World 7 min read

It Checked Its Own Work

Anthropic's Claude caught its own analysis error in a lab test, then an outside lab confirmed it was right. Here's why that matters more than speed.

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Hand-drawn ink and crayon editorial illustration on a warm cream background. Four identical steel-blue mechanical levers stand upright in a row, each a tall cylindrical rod topped with a round ball handle and mounted on its own round bolted base, all four fixed along a plain wooden shelf seen from slightly below. A small amber price-tag-shaped label hangs by a thin cord from the neck of the leftmost lever, the only warm amber accent anywhere in the image. A soft grey-blue shadow spreads across the ground beneath the shelf.
Building 6 min read

Four Levers, Not One Dial

AI autonomy isn't one dial. Anthropic's own team breaks it into four separate handoffs, and only one of them decides whether the rest are safe to hand off.

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A lone figure in a dark coat, seen from behind, stands at the foot of an empty judge's bench in a vast stone hall. A single gavel rests on the bench, the only warm accent in a cool blue-gray palette.
Governance 4 min read

The Silent Exit Clause

A safety check the builder can veto isn't a check. Anthropic's own policy confirms the gap, and METR's audit shows what real independence looks like.

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Hand-drawn ink and crayon editorial illustration on a warm cream background. A shallow rectangular office letter tray sits centred on plain cream ground, seen from slightly above and a little to the left, its moulded plastic drawn in flat mid steel blue with heavy charcoal outlines and a wide scooped curve cut into the centre of its low front wall. The tray is heaped well above its walls with a thick untidy pile of loose white paper sheets, drawn as ragged overlapping edges that spill out past the tray on both sides, with one larger sheet laid flat across the top of the pile. Resting on that top sheet, just left of centre, is a small pair of reading glasses with warm amber tortoiseshell frames, closed, its arms folded in across the lenses. A loose charcoal shadow falls to the right of the tray and scattered charcoal dashes suggest the surface to its left. No text and no people.
Strategy & ROI 4 min read

The Check That Left With the Afternoon

A McKinsey case describes a distributor whose system reads public building permits and drafts the sales outreach. The work it removed was somebody's afternoon, and an afternoon is never only one job: while a person was assembling the material, they were also reading it. That reading was a control nobody had written down, and it leaves with the work.

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Hand-drawn ink and crayon editorial illustration on a warm cream background. A small wooden rowing boat painted pale steel blue rests right way up on two plain wooden sawhorses, seen from the side and slightly above, filling most of the frame, its planked hull outlined in charcoal with a thwart and a stern seat visible inside. On the ground by the right-hand trestle stands a small open tin of amber paint with a brush leaning in it, a patch of amber on the stern seat and two amber spills on the ground beside the tin. Loose blue wash and charcoal hatching suggest the ground. No people, no water, no text.
Building 9 min read

Don't Build What You Can't Keep

McKinsey's 2026 survey found 32% of respondents saying their organization decided against buying at least one software product or feature because it could be built with coding agents. The companion post argued that the buy rule grew a second half. This article does the three things the post could not: reads the survey's size gap honestly, sorts builds into the three kinds that need different rules, and shows how to price what keeping a built tool costs every month.

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Hand-drawn ink and crayon editorial illustration on a warm cream background. A steel blue metal office filing cabinet with three closed drawers stands in three-quarter view, filling most of the frame, each drawer fitted with a small recessed label holder and a tubular handle. More than a dozen small yellow paper notes are taped flat across its front and left side at slight angles, several curling at the corners, and every one of them is blank. A loosely hatched grey shadow spreads across the ground beneath the cabinet.
Building 7 min read

Cheap to Write, Expensive to Keep

A system that remembers across more than one layer has a stratum you can delete with no consequence and a stratum that takes everything with it. Cost asymmetry moves important knowledge into the cheap one without anyone deciding it. This is the evidence for why that happens, and why better writing tools do not fix it.

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