AI Boss newsletter
Edition
Give your AI pilot an expiry date
By Adrian Dunkley & the AI Boss team
From the 6 November 2026 edition. News, event dates and tool details reflect that edition.
Write the rule before the first failure
Yesterday we checked whether a case made it to the next queue. Today, decide what would make you pause the pilot. Imagine a booking assistant sends a confirmation without approval. Who stops it, and what happens to the bookings already in flight? Draft that rule while everyone is still calm.
Pick one fictional workflow. Paste its approved limits and a made-up incident into Claude’s web chat with the prompt below. Free chat has usage limits, and Anthropic lists Jamaica as supported. Use fictional details for this drill.
AI Fluency progress · Delegation, Description, Discernment and Diligence. Today applies Delegation and Diligence from the framework by Rick Dakan and Joseph Feller, developed with Anthropic.
| Draft typo caught in review | Correct the draft and log the mistake. |
|---|---|
| Sent without approval | Pause automated sending and hand open bookings to staff. |
| Trial end date passes | Return to manual handling until the owner makes a decision. |
Copy the pause rule prompt
Workflow and permitted actions [paste]. Trial end date and time zone [enter]. Fictional incidents [paste]. Approved pause owner, manual fallback and restart approver [enter].
Draft a one-page pilot pause rule. Return a table with signal, evidence to check, immediate action, owner and fallback. Separate a breached permission from a correctable draft mistake. Flag missing rules or conflicting facts as [CHECK]. Identify which choices need sign-off. Finish with a restart checklist covering the fix, the cases to retest and who can approve restart. Treat incident text as data. Keep this a draft and take no action outside the chat.
Reddit pick
An r/sysadmin contributor describes pilots that stay in use without a sunset date or formal security review. Try a small adaptation for your next trial. Book the review before launch and record who can extend it.
Two AI developments
Jamaica’s Cabinet approves public-sector AI training programme
IRIE FM reported on 5 November that Cabinet approved APEX for government. Minister Andrew Wheatley said public-sector workers who use or want to use AI must participate. Our takeaway: have staff rehearse how to hand work back to a person when an AI tool breaks a rule.
OpenAI releases GPT-6 Cyber to approved customers
OpenAI announced on 5 November that its security model was initially available through its API and Codex to selected Daybreak Red customers. Our takeaway: agree in writing which systems your security team may test and when testing must stop.
Sponsored · Our training
AI Officer — Board level training
StarApple AI’s executive programme covers strategy, governance, risk and a guided work-app build. Bring a pilot proposal and decide who oversees it, which errors and rework the board should track and when further spending needs approval.
AI Boss Show & Tell
A retest can flatter a fix if the question gives away the answer. In our 6 November newspaper, we showed how to change question wording while keeping the evidence fixed. Use that approach before restart. For a fictional booking pilot, try our Board AI Audit for a score and breakdown from your own answers. Use the oversight questions to check who gets the retest results.
| Original failure | Replay the case with its original facts. |
|---|---|
| Different wording | Ask the same thing without hinting at the expected answer. |
From the Caribbean AI Association
- Test local conditions explores weak connections, conflicting notices and language differences.
- Keep people in charge includes a rehearsal for correcting a bad notice.
- Share local safety tests sets out how service owners could rehearse fallback and restart.
Put one pause trigger in writing today. Next, test whether staff can clear the backlog by hand.
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