24 posts across Directing AI, Judging AI, Supervising Agents
Four separate stories this year — a CEO's warning, a viral study, a blunt writing rule, a $50,000 gap in financial advice — all point at the same three seams. Here's the throughline, and the move that closes each one.
4 min readSimon Willison endorsed a rule blunt enough to actually follow: write it yourself, then use AI only to flag problems, never to supply the fix. Two studies published the same week explain why the line matters more than it sounds.
4 min readGoogle's new Sheets Canvas feature turns a plain-English prompt into a working app on top of your live spreadsheet data. Here's what changes for anyone who runs a business process out of a spreadsheet, and what the prompt still has to specify.
4 min readSubstack launched AI-detection scanning on July 21, powered by Pangram. Any reader can now check any post over 100 words for human vs AI content — one click, no subscription required. Content authenticity is now a visible, reader-facing metric. Here's what to change before you publish again.
5 min readThe useful question isn't whether writers should use AI. It's which stage of writing to hand over — because handing over the wrong one costs you the thing people are paying for.
5 min readOpenAI tripled the custom instructions limit for paid users on July 15. The people who use this well will stop re-explaining themselves every conversation. Here's what a useful briefing document actually contains.
4 min readCursor's July 2026 data shows the top 1% of AI users produce 46 times more than the median. Everyone's using the same tools. The gap is a skill — and it's learnable.
5 min readOpenAI's own safety guidance for ChatGPT Work admits the system can produce 'finished mistakes at a scale that is harder to catch.' The same week, Wharton research killed prompt tricks and Cursor data showed a 46x productivity gap. The differentiator is now verification, not prompting.
6 min readChatGPT Work launched July 9 — an autonomous agent that connects to Slack, Google Drive, and SharePoint and delivers finished documents hours later. Three events this week prove the same principle: it works when you can define what 'done' looks like.
6 min readA study of 18,978 conversations found AI nearly three times more effective at fundraising than trained human canvassers — but only when unconstrained. Match the speed and length, and the advantage disappears. The practical implication for your writing workflow is not what you'd expect.
5 min readFigma's CEO Dylan Field told Stratechery that AI output 'draws from the middle of the distribution' — and that teams become viscerally attached to their first concept. The iterate-and-refine skill is what separates competent AI output from distinctive work.
4 min readThree product shifts in five days — Mollick's 'patron, not wizard' frame, OpenAI's reasoning tiers, and Claude's scheduled agents — prove the professional AI skill stack has moved on from prompting.
6 min readClaude Opus 4.8 shipped with explicit effort controls — users choose whether the model reasons carefully or answers fast, at 3x the cost difference. Here's how to decide which tasks deserve which mode.
4 min readThree AI failure modes got named publicly in the same week — forwarding raw AI answers without reading them, optimising for speed over quality, and letting the model think while you sign off on the result. Each one has a skill that fixes it.
5 min readTwo Hacker News posts hit the front page the same week with a combined 1,374 points. One named the upstream problem — vague briefs going in. One named the downstream problem — raw output going out. The model was fine in both cases.
4 min readGoogle's AI Pointer and Gemini Rambler let you point, speak, and get results without typing a word. The syntax of prompting is being absorbed into the interface. The judgment behind it isn't.
4 min readOpenAI replaced ChatGPT's default model on May 5. It's more accurate and gives 30% shorter answers. That's only useful if your prompts give it enough to work with.
4 min readGoogle's Gemini can now output a finished Word file, spreadsheet, or PDF directly from conversation. Writing prompts that produce share-ready documents is a different skill than writing prompts that produce text.
4 min readAnthropic launched native connectors to 50+ professional creative tools — Adobe Creative Cloud, Blender, Autodesk, Ableton, Canva, and more. Connecting is the easy part. Getting useful output is a constraint problem.
5 min readClaude 4.7 requires surgical specificity. GPT-5.5 demands outcome-focused framing. The same vague prompts that worked last quarter are now producing worse results on both platforms.
4 min readOpenAI shipped image generation that produces up to 8 consistent, text-accurate visuals from a single prompt. It works. The gap between that capability and campaign-ready assets comes down to one thing: the quality of your visual brief.
4 min readAI drafts fast and defaults to generic. For anyone whose job is being heard, that's a real risk. Here's how to use it for speed without your writing converging on everyone else's.
5 min readAnthropic launched Claude Design this week — AI that makes prototypes, pitch decks, and marketing assets through conversation. Whether the output is useful depends entirely on the brief you write.
4 min readPrompt engineering isn't a secret vocabulary or a list of magic phrases. It's the skill of describing a task precisely enough that someone who can't ask you questions could still do it well. Here's what it actually involves.
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