AI Boss newsletter
Edition
Give your FAQ a difficult customer.
By Adrian Dunkley & the AI Boss team
From the 18 October 2026 edition. News, event dates and tool details reflect that edition.
Your FAQ sounds clear. Then someone asks about a late delivery, a missing receipt and a refund in a different currency. Give AI the awkward questions before your front desk gets them.
01 / TOOL TIP · MICROSOFT COPILOT
Rehearse the questions you missed
Open Copilot’s web chat and paste a short, public or approved FAQ with today’s prompt. Ask it to act as a test customer. Check every suggested answer yourself, then ask the policy owner to resolve gaps. Use fictional scenarios, not real customer records.
Basic Copilot chat has a free option. Features and access vary by account and region; paid Office integrations are separate.
Microsoft’s access and feature guide ↗
| Approved FAQ | → | Awkward questions | → | Owner review |
02 / PROMPT OF THE DAY · KEEP THIS Test this FAQ using six fictional customer questions: two routine, two edge cases and two questions it cannot answer. Use only the supplied FAQ. Return: question | supported answer | exact FAQ passage | missing fact | question for the policy owner. Write “not stated” where evidence is missing. Flag conflicting rules. Preserve currencies and deadlines; invent no refund rights or promises. Finish with proposed FAQ edits, clearly marked for approval. |
03 / REDDIT PICK
In a discussion about practical uses, one commenter describes updating documentation with AI. That is a user anecdote. Our adaptation: test a Jamaican shop’s delivery FAQ or a guesthouse’s check-in instructions with fictional customer questions. Keep unresolved answers for staff review.
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04 / TWO STORIES WORTH YOUR TIME
CARIBBEAN · EARLIER NOTICE: 30 SEP 2026
UNDP puts service delivery on the AI syllabus
UNDP’s Caribbean AI for SIDS series is scheduled on Thursdays from 15 October to 17 December, covering public services, accountability and value. Its application deadline was 11 October. Our takeaway: pair each proposed public-service AI use with an owner and a clear route for correcting mistakes.
GLOBAL · RESEARCH / EARLY ACCESS: 14 OCT 2026
Google expands experimental Earth AI access
Google published a geospatial-agent report and announced expanded experimental access through Ask Google Earth and an agent API. This is limited early access, not a general rollout. Our takeaway: Caribbean environmental teams should test local data coverage and have experts check outputs before relying on them.
Sponsored · Our training
AI Officer — Board level training
Ask StarApple AI about training for boards and executive teams. Bring a proposed AI investment. Discuss who owns mistakes, where human oversight belongs and how to measure useful work after checking and corrections.
| Define value | → | Set oversight | → | Review results |
| Ask about board training → |
05 / AI BOSS SHOW & TELL · RECENT BUILD
Does your internal guide answer the team’s concerns?
On 15 October, Adrian shared that the AI Boss had built a Board Meter to assess documents against specific stakeholders.
Today’s Stakeholder Meter angle: check your staff guide against priorities the team actually supplies. Keep a worksheet: stated priority | supporting passage | gap | proposed edit. Confirm the priorities with them. Qualitative ratings are review judgments, not predictions of approval.
06 / RELATED READS
Jamaica’s fintech AI layer · StarApple’s sector commentary (19 Jun).
The AI Boss Playbook · Adrian’s executive practices, including testing failure (8 Sep).
Your move: run the prompt on one approved FAQ. Resolve one missing answer with its owner, then keep the question as a future test.
Adrian Dunkley & the AI Boss team
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