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Pick one task you already repeat, and set AI up to do that one well. A first attempt that starts with "build my marketing strategy" comes back generic, and the generic answer is what convinces people AI is overhyped.

A good first task

Comes round at least once a month

You have put it off more than once

There is a document you would have to read

You can say what the answer should contain

A bad first task

Happens once a year

You would have to invent the material

Nothing is written down to work from

"Make it better" is the whole instruction

The supplier agreement you signed in a hurry answers all four lines on the left. It comes round every renewal, reading it properly is a job you keep moving to tomorrow, and every answer you want is already on its pages.

Pick one answer

You do all three of these most months. Which one is the best first task to give AI?

Read the supplier quotes in your inbox and pull out prices and delivery dates

Decide which of your two suppliers to drop next quarter

Write next week's staff rota from memory

The quotes arrive as documents, so there is something to read, and the answer is facts already on the page. Which supplier to drop needs judgement you have never written down, and the rota lives in your head, so AI would invent both.

35:T21f9,

The file is what makes this work in an hour. Hand AI a document and it reads for you; ask without one and it fills the gap with whatever is average.

Anything with deadlines, money, obligations or risk in it counts: a supplier agreement, a client scope of work, a lease, the year-end statement your accountant just sent, a discovery-call transcript. The shape is the same across trades, so one brief covers all of them.

The task the rest of this course walks through is this one.

Read this contract and tell me the deadlines, what I owe, what they owe, and anything unclear or risky.

Every answer it asks for is already written somewhere in the file. No strategy, no opinion, no judgement call.

Use your own file if you have one, and name the task in one sentence before you go further.

Write your answer

My one task, in one sentence

Name the file, then what you want pulled out of it. For the sample: the Cedar Lane Bakery agreement.

Your answers are only visible to you

If the only document you have feels too sensitive to start with, use the sample: a fictional marketing agreement between a bakery and a studio, with real deadlines, real money and one renewal clause worth finding.

Cedar Lane Bakery — Marketing Services Agreement.pdf

4.96 KB · PDF Document

Download it now and keep it open.

Pick one answer

A client asks you to AI your pricing page. Why is that a weaker first task than reading a contract?

Pricing is too commercially sensitive to paste into an AI tool

Nothing written down holds the answer, so the model works from averages

Pricing pages need a longer, more carefully worded prompt

There is no document holding the answer, so the model writes from averages instead of from your material. A contract already contains every fact the brief asks for, which is also what makes the answer checkable.

36:Teae,

Six tasks people pick when they first try AI. For each one, say whether it is a good first task, and what you would change.

Respond to each line

Sort six tasks

Each line is somebody's first task. Say whether it works, and name the fix.

6 lines · about 7 minThe task

The hard lines come at you one at a time. Answer the way you would in the room, and see straight away which answers would land.

Start drillOnly you see what you write here

37:T2614,

Four questions on choosing the task and the file behind it.

Pick one answer

Two tasks come round every month and both annoy you. One works from an emailed PDF, the other from what you remember of the week. Which do you give AI first?

The one that works from the PDF

The one you remember, because you can correct the model as it goes

Whichever takes longer by hand

True or false?

A task with no document behind it is still fine for a first AI setup, as long as the prompt is detailed enough.

Match the pairs

Match each trade to the document it would start with.

Fill in the blanks

Complete the test for a first task.

A good first task repeats, you have put it off, and the answer is already inside a ________.

38:T1636,

Pick one tool and stop there. Three tabs open and nothing finished is how the hour disappears.

All three do the same move, and the move is putting your document where the model can read it.

Tool	How the file gets in
Claude	The plus sign in the chat, then Add from Google Drive, or attach the file
ChatGPT	Attach the file, or connect the Google Drive app under Settings, then Plugins
Gemini	Add files, then Add from Drive

Attaching the file from your computer works everywhere and is enough for this task. Claude's Google connectors are open on every plan, including the free one, and that is the reason the walkthrough uses it. On a work account an administrator may have to switch connectors on first.

Before asking for anything serious, make the AI prove it can see the document. Paste this in.

Prompt

What file have I just given you? Tell me its title, its date, and one sentence on what it is for. Don't summarise the contents yet.

If it guesses, or says it cannot see a file, the attachment never arrived. Re-attach it and run the check again before you ask for anything else.

Pick one answer

The AI answers your check prompt with a confident description of a contract you did not attach. What happened?

The file was too long, so it summarised the first part

It never received the file and answered from the wording of your question

The file needs converting to plain text first

It never got the file, so it answered from the shape of the request. Re-attach and run the check again; a model that is guessing at this point will guess about your deadlines too.

39:T11c1,

A free plan takes in less of your document than a paid one, and what the model never read it cannot flag. That is most of the reason first attempts come back vague.

ChatGPT states the ceiling in pages of text.

ChatGPT plan	Text it takes in one go
Free	about 12 pages
Go and Plus	about 40 pages, or about 320 on the reasoning models
Pro	about 250 pages, or about 680 on the reasoning models

A twelve-page agreement fits anywhere. A sixty-page lease on a free plan does not, so the answer will be confident about the start and silent about the clauses further in. Free plans also cap how many files you can upload in a day.

Staying free is workable. Split the long document into sections, run the same brief on each one, and keep the paid plan in mind for the day a sixty-page agreement lands.

Pick one answer

Your forty-page supplier agreement comes back summarised on a free plan, and the renewal clause on page thirty-one is missing. What is the most likely cause?

The prompt did not mention renewal clauses

PDFs lose their later pages when uploaded

The document is longer than the plan takes in, so the later pages were never read

Forty pages is past what a free plan takes in one go, so the clause was never in front of the model. Splitting the document into sections, or running it on a paid plan, puts page thirty-one where it can be read.

3a:T192d,

Connecting Drive lets the AI open files in that one account, and only on request. It does not copy your Drive anywhere, it does not show your files to other users, and it cannot reach anything you could not already open yourself.

Tick off as you go

Connect the account the document actually lives in

Turn the training switch off if you would rather not share chats

Attach one file at a time when the document is sensitive

Ask your administrator first if the account belongs to work

Two details are worth knowing before you approve it. The AI reads the text of a document and not the pictures inside it, so a scanned page can come back empty. And on a personal plan your chats can be used to train the model unless you turn that off; in ChatGPT the switch sits under Settings, then Data controls, then Improve the model for everyone.

In Claude, material pulled in through a connector stays out of model training either way. Text you paste into the chat yourself does not get that treatment, which is an argument for connecting the file rather than copying it.

Pick one answer

Your partner says connecting Drive means handing the whole company's files to an AI company. What is the accurate correction?

It reads one file in one account when asked, inside the permissions you already have

Nothing leaves your computer at any point

Files are fully private on every plan, so there is nothing to check

A connector is a request you make each time, inside the permissions you already have. The honest caveat is the training switch on personal plans, which is why it is worth checking rather than denying.

3b:Tca5,

The person who has to agree to this is rarely the person who read the help page.

Explain it in your words

Explain what connecting Google Drive to an AI tool does and does not do

A business partner who thinks it means handing over every file the company owns

Type or record your explanation

Check my explanationOnly you see what you write here

3c:T260a,

Four questions on getting your document in front of the model, and on what that costs you.

Put them in order

Put the steps in the order you would run them.

Get the document in front of it

Pick one tool

Ask it to name the file it can see

Ask it to do the real work

Pick one answer

A fifty-page lease has to be read today and you are on a free plan. What gets you the most reliable answer?

Send the whole lease and ask for a thorough reading

Split it into sections and run the same brief on each one

Shorten the prompt so more of the plan's capacity goes to the file

True or false?

Connecting Google Drive gives the AI access to files you yourself cannot open.

Fill in the blanks

Complete the check you run before asking for real work.

Ask the AI for the file's title, its date and one sentence on what it is for, and do not go on until it can ________ the document.

3d:T1738,

A brief has four parts: role, goal, context and format. Typing "summarise this" supplies one of them, which is why the summary comes back fine and useless.

The model reads your contract faster than you do and catches things you would miss at the end of a long day. It also knows nothing about your business, your suppliers, or what you would call a good answer. A brief closes that gap, the same way it would for somebody on their first morning.

Role

Who is reading this, and with what eyes. A careful owner. A bookkeeper double-checking the numbers. A sceptical lawyer.

Goal

What you want at the end, named. Every deadline. The risks. A shorter draft.

Context

What is true that the document does not say. New supplier. Two-person team, no legal staff. Worried about getting locked in.

Format

What the answer should look like. A bulleted list under each heading, with the section number beside every item.

Four lines, two minutes, and the same four lines work on every document of that kind from here on.

Pick one answer

A brief reads: 'You are a careful owner with no legal staff. Tell me the deadlines and the risks in the attached contract.' Which part is missing?

Role

Context

Format

Role and context are both there, and the goal is named. Nothing says what the answer should look like, so you get a shape chosen by the model rather than a list you can scan and check.

3e:T13b7,

The walkthrough task, with all four parts filled in. Copy it into the chat that already holds your file and send it.

Prompt

You are a careful, slightly sceptical business owner reading this contract before signing.
Pull four things out of the attached file:
Every date that matters, and what is due on or by it.
What I owe: payments, deliverables, time commitments.
What they owe me.
Anything unclear, risky or easy to miss, with one sentence on why.
Format: a short bulleted list under each heading, and name the section every bullet came from, like (Section 3), so I can check it.
Context: I run a small business with no legal staff. I would rather you flag something harmless than miss something expensive.

What comes back should be four headed lists, with a section named beside every line. On the sample agreement the item worth finding is the renewal: give no written notice thirty days before the term ends and it renews for another twelve months.

Pick one answer

Why does the brief ask for the section number next to every bullet?

It gives every claim a place in the document you can check it against

It makes the model read the later pages rather than the first few

It keeps the answer short

The section number is what turns an answer into something you can verify in under a minute. Without it you are left trusting the summary or re-reading the whole document, which is the work you were trying to avoid.

3f:T1960,

AI can state something your document does not say, in the same even tone as everything it got right. So check the claims that would cost you money, and leave the rest.

A short list of answers beside a longer document, with a line running from one bullet back to the single clause it came from

Pick one or two: the renewal date, the early-termination figure. The answer named a section, so open it, read the sentence, and compare. On the sample agreement the renewal notice window is thirty days and the early-exit fee is half the remaining monthly fees, both of which take seconds to confirm.

Tick off as you go

Pick a claim that would cost you something if it were wrong

Open the section the answer named and read the sentence

If it does not match, quote the section back and ask which is right

When a claim and the clause disagree, the clause wins, and one more message is usually enough to get the figure recalculated.

Pick one answer

The answer says your notice deadline is 30 June. The section it cites says notice is due thirty days before the term ends, and the term ends 31 July. What do you do?

Use 30 June, since the model read the clause and you did not

Quote the clause back, say the term ends 31 July, and ask it to recalculate

Discard the answer and read the contract yourself

The model did the arithmetic and the clause is what settles it, so put the discrepancy in front of the model and let it count the days again. Dropping the whole answer throws away four correct lists, and taking either date on trust is how the deadline gets missed.

40:T124e,

Keep the brief and the file together in a project, and the next run starts from both instead of from a blank box.

A project is a space whose instructions and files apply to every chat inside it. Write the brief in once, drop in a past document you were happy with, and the next contract is a single attachment away.

Tool	Where the brief goes	Where the files go
Claude	Set project instructions	Project knowledge
ChatGPT	Project settings, under the ••• menu	Project files

Claude's free plan allows five projects. ChatGPT takes five files per project on Free, twenty-five on Go and Plus, forty on Pro.

If you already keep a prompt like this in a custom GPT, move it. Custom GPTs stop working on 11 December 2026, and OpenAI converts them from My GPTs with Migrate to plugin. Personal accounts can no longer create new ones, and workspaces are planned to stop on 26 October 2026. Both dates are OpenAI's and can move, so follow the notice in your own account.

Pick one answer

You were about to build a custom GPT to hold this brief. What is the better move today?

Put the brief in a project, which both tools support today

Build the custom GPT and migrate it before the retirement date

Keep the brief in a note and paste it in each time

A project does the same job for one person, on free plans in both tools, and nothing about it stops working in December. Building the GPT first means doing the work twice, and copying the brief in by hand is the step people stop doing in week two.

41:Tae7,

The sample was the rehearsal. The win is on a document you actually signed.

Do this for real

Run your saved brief on a real document from your own work

Find something you have signed, or are about to sign, in the last twelve months: a supplier agreement, a client scope of work, an insurance renewal, a software contract that renews by itself. Attach it in your project and run the saved brief unchanged. Then check two claims against the sections it named. Write one line in the project notes: the next document you will point it at.

After you do it, you'll check in on

Which claim did you check, and did it hold up?
What did it flag that you had not noticed?
What is the next document you will run it on?

I'm in

42:T31c3,

Five questions on briefing, checking and keeping the setup.

Match the pairs

Match each line of a brief to the part it supplies.

Pick one answer

The answer cites sections for every claim except the two about money. What does that tell you?

The money terms are probably in an appendix you did not attach

Those two are the lines to check first, so ask it which sections they came from

The format instruction failed, so the brief needs rewriting

True or false?

A setup saved as a custom GPT will keep working after 11 December 2026.

Pick one answer

A month later the same brief returns a weak answer on a new supplier contract. What do you change first?

The brief, by adding the line about the thing it missed

The tool, since another model may read it better

The wording, by asking the model more politely

Fill in the blanks

Complete the reason the saved setup matters.

A project keeps the brief and the files in one place, so the second run starts from ________.

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