Your AI doesn't

know you yet.

Here's how to fix that.

Presented by Natalia Rosa | Big Ambitions

natalia@bigambitions.co.za

01

Be honest.

How many AI-drafted client emails

have you started this month, and then

rewritten the whole thing from scratch anyway?

Your AI doesn't know you yet | Big Ambitions

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It's not the tool.

Your AI assistant has no idea who you are.

Your AI doesn't know you yet | Big Ambitions

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ACT ONE

The diagnosis

Why your AI keeps sounding generic.

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The shift that changes everything

AS A TOOL

• Starts from zero every time
• Generic output, every output
• Used a few times a week
• Replaced when the next one launches

AS A CO-WORKER

• Knows your voice, clients, style
• Tailored output, getting sharper
• Used every day, across the work
• Compounds in value over time

Your AI doesn't know you yet | Big Ambitions

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You already know how to do this.

Every skill you need is one you use already.

1

Remembering preferences

The Smiths don't like seafood. The Joneses always upgrade.

2

Adjusting tone by audience

Family enquiry sounds different from a corporate booking.

3

Building a client file

Past trips, contacts, supplier history, what they loved.

4

Briefing new colleagues

How we write, what we avoid, who our clients are.

Your AI doesn't know you yet | Big Ambitions

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ACT TWO

The four

foundational moves

Set up once. Compounds forever.

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01

MOVE 1

Tell it who you are

The single biggest lever you have, and the one nearly everyone ignores. Custom instructions tell your AI who's asking and what they expect.

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Better, still… Give it a name!

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What goes in your custom instructions

Treat it like the brief you'd give a new senior team member on day one.

• Who you are: your name, your role, what your business does
• Who your clients typically are: their profile, what they care about, their budget bracket
• Your destinations: where you specialise, where you don't go, your strongest supplier relationships
• Your voice: how you write, what you avoid, the tone your clients expect
• What it should do automatically: ask before assuming, flag uncertainty, suggest verification
• What it should never do: invent supplier names, fabricate reviews, pretend to know live availability

DO IT FIRST

Five minutes here saves you hours every week for the rest of your AI life.

Your AI doesn't know you yet | Big Ambitions

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02

MOVE 2

Give it a place to work

A single AI conversation is a sticky note. A Project is a desk. Give your assistant somewhere to keep your context.

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How to use Projects, properly

One Project per relationship or workstream. Don't dump everything in one place.

• One Project per active client. Include: the brief, preferences, past trips, supplier preferences
• One Project per destination you specialise in. Include: your best operators, briefing notes, things you say in every itinerary for that place
• One Project for your business voice. Include: your tone of voice document, sample sign-offs, sample proposals, things you'd never say
• Each Project: minimum two reference documents, ideally five or six. Add more as you go
• Available in: Claude (Projects), ChatGPT (Projects/Custom GPTs), NotebookLM, Copilot

MENTAL MODEL

Same idea as a client file in your CRM. The assistant is the one reading it.

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03

MOVE 3

Build a prompt library

Every task you do every week deserves a prompt that already works. Stop typing the brief from scratch.

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The prompts that compound

Start with the five tasks you do most often.

• The itinerary draft prompt: built around your standard structure and your tone
• The supplier follow-up prompt: chase, with context on what was promised and when
• The destination paragraph prompt: for the proposal, with your house phrases and supplier mentions baked in
• The proposal opener: the first three sentences of every client proposal, tailored to enquiry type
• The 'I need to think about this' prompt: an internal sense-check before responding to a tricky enquiry

GROW IT

Add one new prompt a week. By Indaba next year, you've got a library worth its weight in gold.

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04

MOVE 4

Document your voice

Until your AI knows how you sound, every output will sound like everyone else. One page fixes this.

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What goes in your tone of voice document

One page. Specific. Refined over time as you notice what AI gets wrong.

• Three to five words that describe how you sound (warm, specific, never effusive, honest, dry)
• Sentence length and rhythm: short, punchy, long flowing? Mix it how?
• Words and phrases you use often: your verbal tics, the bits clients quote back to you
• Words and phrases you never use: industry cliches, hype words, anything you cringe at
• How you open: do you greet, do you get straight into it, do you use first names
• How you close: sign-off, call to action, your standard final line
• Three to five sample paragraphs of your actual writing for the AI to study

REFINE IT

Tweak this every fortnight as you notice what your AI gets wrong about your voice.

Your AI doesn't know you yet | Big Ambitions

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ACT THREE

Where it gets interesting

Connectors, integrations, and the new AI browsers.

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Travel connectors: live data, where it works

Plug your AI into the booking platforms you already use. Mature today, but uneven.

BOOKING.COM

Available, useful

Search hotels by destination, dates, guest mix, filters. Best for property research, less reliable for live pricing.

EXPEDIA

Available, mixed

Flight and hotel search via partnership integrations. Quality depends heavily on the AI tool you're using.

TRIPADVISOR

Available, useful

Reviews and destination context. Better for inspiration and verification than booking decisions.

WHAT'S COMING

Direct supplier connectors

The next wave: AI plugged directly into your preferred operator and DMC systems. Watch this space in 2026-27.

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Microsoft 365 and Google Workspace

AI inside the tools you're already in all day. This is the integration that matters most.

INBOX

Drafting and triage

Copilot in Outlook or Gemini in Gmail can draft replies in your voice, summarise threads, surface what needs your attention first.

WORD / DOCS

Proposals and itineraries

First-draft proposals, restructure existing text, edit for tone. The Tone of Voice document does the heavy lifting here.

EXCEL / SHEETS

Costing and analysis

Build cost sheets from a brief. Analyse a season's bookings. Find patterns in supplier performance you didn't have time to look for.

TEAMS / MEET

Meeting notes that work

Real-time transcripts, post-meeting summaries, action items. The biggest unlock for client calls and supplier meetings.

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Project management integrations

Your AI as a project chaser, status updater, and silent project manager.

ASANA

AI summaries baked in

Project status, who's late on what, weekly digests written in plain English. Stops the Friday afternoon project chase.

CLICKUP

ClickUp Brain

Generates updates, drafts replies in tasks, summarises threads. Best for teams already living in ClickUp.

MONDAY

Monday AI

Forecasts, anomaly spotting, status writeups. Solid for sales-pipeline-style workflows.

TRELLO

Atlassian Intelligence

Lighter touch. Good for solo operators or small teams. Better integrated since the Atlassian platform consolidation.

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AI browsers: the new frontier

Early days, but moving fast. The research workflow happens in the browser. So now does the AI.

CHATGPT ATLAS

OpenAI's browser

ChatGPT lives in the sidebar of every web page. Ask it questions about what you're reading, get summaries, draft from page content.

PERPLEXITY COMET

Search-first browser

Built around answer-first browsing. Strong for travel research where you need fast comparison across sources.

CLAUDE IN CHROME

Browser agent

Anthropic's extension turns Claude into a browsing agent. Can navigate sites and pull information together for you.

DIA

The new entrant

From the Arc team. Built around AI from the ground up. Worth watching, particularly for research-heavy workflows.

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The features almost nobody uses

These are quiet superpowers, especially for our industry.

VOICE MODE

Talk, don't type

Between meetings, in the car, between flights. Think out loud, get a useful answer. Massively under-used by mobile professionals.

IMAGE GENERATION

Mood boards in seconds

Quick visual roughs for proposal mood, destination atmosphere, hotel vibe. Don't replace photography. Replace the search for stock.

MEMORY

Cross-session recall

Some tools (ChatGPT, Claude) remember things you've told them in past chats. Useful, but check the privacy settings before you turn it on.

DICTATION

Speak the prompt

Even where there's no full voice mode, dictating your prompt is twice as fast as typing it. Phone or laptop. Few people remember they can.

Your AI doesn't know you yet | Big Ambitions

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ACT FOUR

The grown-up conversation

Privacy, hallucinations, and judgement.

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What stays out of AI, full stop

If you wouldn't send it to a competitor, don't paste it into a free-tier AI.

Client passport details

Identity documents. Out, always.

Financial information

Credit cards, bank details, payment data. Out, always.

Personal contact data

Mobile numbers, home addresses, anything that identifies a private individual.

Supplier pricing under NDA

Confidential commercial terms. Out unless you're on an enterprise tier with data protection.

Anything covered by an NDA you've signed

Read the NDA. Most predate AI. If in doubt, ask the supplier.

Anything you wouldn't put on a competitor's whiteboard

That's the gut test. If the answer is yes, don't paste it in.

Your AI doesn't know you yet | Big Ambitions

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Travel AI lies more than most realise

Confident, plausible, sometimes completely fabricated.

WATCH FOR

• Hotels that don't exist
• Reviewer names invented to sound credible
• Prices and availability that look right but aren't
• Operating hours, opening seasons, route frequencies
• Visa requirements (these change, AI doesn't always know)

VERIFY LIKE THIS

• The two-AI test: run the same prompt through Claude and Copilot. Note where they disagree.
• The 'show your working' prompt: ask the AI to list its sources and flag where it's uncertain.
• The 'I'd sign my name to this' test: would you put it in front of a paying client as-is?

Your AI doesn't know you yet | Big Ambitions

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ACT FIVE

Making it stick

What you do this week, and the week after that.

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The 30-day practice

Five small habits. Compound massively.

MONDAY

Open your AI. Five minutes. Brief it on the three things you most need help with this week. That's your weekly briefing meeting with your new team member.

WEEKLY

Add one new prompt to your library. Keep what works. Refine what doesn't. By month three you've got 12 prompts doing serious work.

FORTNIGHTLY

Refine your tone of voice document. Notice where AI gets you wrong. Add an example. Cut a phrase that's not landing.

BEFORE A CLIENT SEES IT

Run the two-AI test. Use the 'show your working' prompt. Sanity-check before sending to a client.

PERMANENTLY

Give yourself permission to play. Not every interaction needs to produce something. Curiosity is what compounds.

Your AI doesn't know you yet | Big Ambitions

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Your takeaway

The Ultimate AI Personalisation Checklist

Twenty practical actions. Ten to set up this week. Ten to build into your weekly practice.

INSIDE

• Custom instructions: what to put where
• Project setup for your active clients
• The starter prompts for your library
• Tone of voice document template
• The verification habits and privacy lines

HOW TO GET IT

Sent to your inbox after the session.

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Questions?

Let's hear them.

CONTINUE THE CONVERSATION

Natalia Rosa | Big Ambitions | bigambitions.co.za

Find me on LinkedIn or drop a line through the Big Ambitions site.

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