AI Boss newsletter
Edition
Ask a better first question.
By Adrian Dunkley & the AI Boss team
From the 19 October 2026 edition. News, event dates and tool details reflect that edition.
Before your next client meeting, turn a public announcement into a useful question. Your opening should do more work than the office air-conditioning.
01 / TOOL TIP · PERPLEXITY
Research before you pitch
In Perplexity’s search box, enter the prompt below with a company name, country and website. Open each citation and check its date and supporting passage. Keep public facts separate from your sales hunches; use no confidential client material.
Free search includes citations with usage limits. Check access locally; this exercise needs no paid research mode.
Search guide · Plans and limits
| Public facts | → | Possible relevance | → | Ask the client |
02 / PROMPT OF THE DAY · KEEP THIS Prepare a pre-meeting brief. |
03 / REDDIT PICK
A 14 October discussion questions trust in AI search citations. The thread’s claims and comments are not independently verified here. Our adaptation: Caribbean suppliers researching prospects should trace claims to dated official pages before turning them into meeting questions.
Live ranking unavailable; retrieved discussion was cached.
04 / TWO AI DEVELOPMENTS
CARIBBEAN · REPORTED 18 OCT 2026
UWI calls for a Caribbean voice in AI
CBC reports that UWI Chancellor Dodridge Miller urged graduates to help shape technology around the region’s voices, culture and values. Our takeaway: involve local staff and customers when testing an AI service’s language and assumptions.
GLOBAL · RELEASED 17 OCT 2026
DeepSeek updates its Flash model
DeepSeek announced V4.1-Flash-1017, saying it is live on its website, app and API. Our takeaway: Caribbean developers should trial a non-confidential task and count corrections before changing tools.
Sponsored · Our training
AI Officer — Board level training
Ask StarApple AI about training for boards and executive teams. Bring an AI investment proposal to discuss oversight, accountability and measuring value after human checking and correction costs.
| Define value | → | Name the owner | → | Review evidence |
| Enquire about board training → |
05 / AI BOSS SHOW & TELL · RECENT BUILD
Did your follow-up reflect their priorities?
On 15 October, Adrian shared that he had built a Board Meter with AI to assess documents against specific stakeholders.
Try the Stakeholder Meter approach on an approved follow-up: supply priorities the client explicitly confirms, then request priority | supporting passage | gap | proposed edit. Never infer private preferences. Any qualitative rating is an editorial judgment, not a prediction of approval.
06 / RELATED READS · FROM OUR SITES
Why board AI literacy matters · StarApple’s argument (29 Jul).
AI agents for Caribbean small firms · Workflow and local-data considerations (Jun).
Your move: verify one public fact, then bring one question to your next client conversation.
Adrian Dunkley & the AI Boss team
Be the boss of AI