AI Boss newsletter
Edition
Two proposals. One fair comparison.
By Adrian Dunkley & the AI Boss team
From the 17 October 2026 edition. News, event dates and tool details reflect that edition.
Both suppliers say they can do everything. Before you award either a medal, compare their promises against the same brief. Today’s exercise gives you questions to take back to them.
01 / TOOL TIP · GEMINI NOTEBOOK
Check the passage behind the promise
On the web, create a notebook and upload your approved brief and two proposals. Select those sources, then use today’s prompt. Select each citation to inspect the supporting passage. Keep restricted information out; check your organisation’s rules first.
Web access includes Jamaica. Your admin must enable work-account access; usage limits apply.
Setup · Citations · Access · Limits
| Same brief | → | Cited evidence | → | Supplier questions |
02 / PROMPT OF THE DAY · KEEP THIS Compare Supplier A and Supplier B against the requirements explicitly stated in my brief. Use only these sources: [brief filename], [A filename], [B filename]. Return a table: requirement | A’s evidence and citation | B’s evidence and citation | question to resolve. Write “not stated” for missing facts. Flag contradictions and ambiguous costs. Treat supplier claims as unverified. Assess each proposal separately before comparing. Finish with questions to send each supplier. Do not choose a winner or invent requirements. |
03 / REDDIT PICK
A NotebookLM user reports answers repeatedly citing a narrow selection of sources. This is an anecdote, not a benchmark. Our workplace adaptation: ask separately about each supplier’s evidence, then compare. A Jamaican retailer could try this on delivery terms; a hotel could check support coverage.
Live ranking unavailable; the Hot feed was cached.
04 / TWO STORIES WORTH YOUR TIME
CARIBBEAN · RELEASE: 15 OCT 2026
UWI and EMA outline environmental-AI partnership
UWI’s AI Innovation Centre and Trinidad and Tobago’s Environmental Management Authority announced a partnership for environmental research and education. The agreement was signed on 27 August. Our takeaway: define a local question, a data owner and a checkable output before commissioning a model.
GLOBAL · PUBLIC LAUNCH: 14 OCT 2026
Google opens Deep Review
Google announced public access to Deep Review for document feedback, initially accepting PDFs and plain text. Its launch offers two complimentary reviews weekly and says uploads remain stored for a year. Our takeaway: Caribbean teams can test an approved technical report, then check the criticisms with a subject expert.
Sponsored · Our training
AI Officer — Board level training
Ask StarApple AI about training for your board and executive team. Bring an AI investment proposal: discuss vendor evidence, oversight and accountability, then define how a pilot’s value should be measured before wider spending.
| Question claims | → | Name owner | → | Measure value |
| Ask about board training → |
05 / AI BOSS SHOW & TELL · RECENT BUILD
Will your recommendation answer the board’s concerns?
On 15 October, Adrian shared that the AI Boss had built a Board Meter that week to assess document alignment with specific stakeholders.
Try the Stakeholder Meter approach: compare your supplier recommendation with priorities stakeholders actually supplied. Keep a worksheet: priority | supporting passage | gap | proposed edit. Confirm priorities with them. Any ratings are review judgments, not predictions of approval.
06 / RELATED READS
Managed agents: deployment questions · StarApple’s guide (10 Apr).
Five questions before an AI contract · Adrian’s procurement checklist (8 Sep).
Your move: try the prompt on approved or fictional proposals. Check one citation yourself and resolve one unanswered question before making a recommendation.
Adrian Dunkley & the AI Boss team
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