AI Boss newsletter
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By Adrian Dunkley & the AI Boss team
From the 15 October 2026 edition. News, event dates and tool details reflect that edition.
YOUR DAILY AI WORK BREAK · ~3 MIN
A polished proposal can still miss the questions your stakeholders care about. Today: try the Stakeholder Meter on one draft before you share it.
| Your draft | → | Priority check | → | Your edits |
Review one stakeholder at a time. Link each edit to a stated priority.
01 / TOOL TIP · CLAUDE
Stop repeating your editing rules
In a Claude Project, select Set project instructions. Save: “Use plain language. Check my draft against supplied stakeholder priorities. Flag assumptions.” Claude applies these instructions to chats inside that project. Add an approved writing sample to project knowledge for context.
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02 / PROMPT OF THE DAY · COPY THIS Review my draft against the stakeholder priorities below. For each priority, return a table: stakeholder | priority | supporting passage | clear, partial or missing | suggested edit. Flag assumptions. Preserve my meaning and voice. Invent no facts or private preferences. Finish with the most useful change to make first. |
03 / FROM REDDIT’S HOT FEED
A useful idea hiding between the memes
A Reddit user described organising a parent’s recorded stories while preserving his phrases. Their first AI edit sounded too polished. Clearer editing limits helped, according to the post.
Try our work version: turn a sales rep’s approved voice-note transcript into a follow-up draft, or a supervisor’s shift notes into a handover. Have the speaker check the meaning before sharing.
User anecdote, not a tested productivity claim. Read the post ↗
04 / TWO STORIES WORTH YOUR TIME
CARIBBEAN · NOTICE PUBLISHED 8 OCT
CARICOM puts AI music on the agenda
CARICOM and IFPI announced an October 15 webinar on AI tools, digital music, and legal and policy developments. Our takeaway: if your team uses AI music in adverts, assign someone to check the usage terms before publication.
MODEL WATCH · RELEASED 7 OCT
Anthropic releases Claude Haiku 5.5
Anthropic says its new small model targets quick, repetitive work such as summaries and classification. Our takeaway for Caribbean teams: test it on a small set of routine enquiry drafts. Compare corrections, response time and total cost with your current setup before switching.
SPONSORED · OUR TRAINING
AI Officer
Board level training
Ask StarApple AI about AI Officer training for your board and executive team. Discuss how to assess AI proposals, question vendors and assign oversight. Bring the decisions your board needs to make.
| Choose a pilot | → | Measure it | → | Decide |
| Ask about board training → |
05 / AI BOSS SHOW & TELL · THIS WEEK
Tired of missing the mark with stakeholders?
This week, the AI Boss used AI to create a Board Meter to assess how well documents align with specific stakeholders. Try the Stakeholder Meter approach on your next pitch.
Your version: list each reader’s stated priorities, then use today’s prompt to find what your draft addresses, skims over or misses. Check the suggested edits yourself. The labels are review judgments; confirm priorities with the people involved.
Want to explore a meter for your team’s documents? Ask us about your use case ↗
06 / FROM OUR SITES
AI agents across Jamaican business sectors ↗
StarApple AI’s sector-by-sector guide.
Can an AI booking agent find your business? ↗
Adrian Dunkley on Jamaica’s tourism data.
Your move: choose one stakeholder and one draft. Run the prompt, check its evidence and keep a before-and-after copy.
Adrian Dunkley & the AI Boss team
Be the boss of AI