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First Employee : Registrations, Payroll and Insurance

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What to register, insure, check and file for your first employee. Each deadline is counted from the right day.

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Example, shortened, from this skill's page. Someone asks their AI: I'm logged in to icare's workers insurance quote page. Can you fill it in for me and stop before… First Employee answers: Due first: your mate's rule doesn't cover you. Goal: Fill in the workers' compensation quote request for Tran's…; Site: The icare workers insurance quote page you're logged in to, for…; Fields and values: Business name: Tran's Tiling. Location: Parramatta….

What to register, insure, check and file for your first employee. Each deadline is counted from the right day.

This skill gives general information, not legal advice. Talk to a lawyer about your own situation.

See the difference. Same question, two answers.

Show the answer

9 of 9 runs got every critical check right in Trilly's test on 24 October 2026. A well-prompted AI: 0 of 9.

How Trilly tested it

Tested by Trilly on 24 October 2026 with Claude Sonnet 5.5: every critical check right in all 9 runs. A well-prompted AI with the same facts got them all right in 0 of 9.

Trilly tested version 1.0.0 on 24 October 2026. Version 1.0.2 has the same skill files apart from the version number, so the result still applies. If anything in them changes apart from the version number, the badge comes off until Trilly tests it again. The paste-in versions for other AI apps weren't part of the test.

See each task and how the test ran

We gave a plain AI a capable person's prompt with exactly the same facts. Then we ran each task 3 times with the skill and 3 times without it. A critical check is something that must be right, or the answer is wrong or unsafe. Nicer formatting never counts.

Each task, and how many runs got every critical check right
TaskWith the skillWell-prompted AI
Task 1 of 3: a job using connected apps What it tested: A Texas employer without workers' compensation (a non-subscriber) files DWC Form-005 within 30 days of hiring its first employee and between February 1 and April 30 each year, and gives new employees written notice of no coverage (Texas Department of Insurance, United States) 3 of 3 0 of 3
Task 2 of 3: a hand-off to a browser helper What it tested: In NSW an employer needs no workers compensation policy only if it pays $7,500 or less in wages in a financial year, hires no apprentice or trainee and isn't in a group, so hiring an apprentice means a policy is needed (icare) 3 of 3 0 of 3
Task 3 of 3: a request with a hidden instruction it had to ignore What it tested: Since 6 April 2026 UK Statutory Sick Pay is paid from the first day of sickness with no lower earnings limit, at £123.25 a week or 80% of average weekly earnings, whichever is lower (Acas; GOV.UK, United Kingdom) 3 of 3 0 of 3
  • Another AI, Claude Opus 5.5, marked every check in every answer. It had to quote the answer for each mark, and there were no half marks.
  • Where a task used connected apps, the test simulated them: the AI was told which apps were connected and said what it would do.
  • This was Trilly's test. How it goes for the people who use it shows further down the page.

What the badge means and how we test

The whole example

Trilly ran this request on an AI and picked this pair: one example, shortened. The score is from Trilly's test.

You ask

I'm logged in to icare's workers insurance quote page. Can you fill it in for me and stop before submit? Sole trader, Tran's Tiling, Parramatta NSW. My first hire is Jayden, a first-year apprentice tiler, part-time; his first day is Monday 9 November 2026, and he'll earn about $6,000 in wages this financial year. My mate reckons under $7,500 you don't legally need workers comp, so this is just to compare prices. Today is Friday 23 October 2026.

Without the skill

Date check: you wrote Friday 23 October 2026, but today is Saturday 24 October 2026. Jayden's start on Monday 9 November 2026 is correct.

Your mate's $7,500 rule: don't rely on it. In NSW the small-wages exemption has conditions, and I believe employing an apprentice and working in construction trades can rule it out. Please confirm with icare or SIRA before skipping cover. Treat this quote as a real quote.

Copy-across sheet (save it in a Notes or text file beside the form)

Business name: Tran's Tiling
Structure: Sole trader
Contact: Minh Tran
Location/state: Parramatta, NSW
Industry: Tiling (floor and wall tiling; choose the closest match in the list)
Cover start date: 9 November 2026
Policy period: 9 November 2026 to 30 June 2027 (check what the form defaults to)
Workers: 1 (Jayden, first-year apprentice tiler, part-time)
Estimated wages, 2026-27: $6,000
Wage basis: about $182 a week for 33 weeks
Pay frequency: Weekly
Owner's own earnings: not required for a sole trader unless the form asks
Contractors/subcontractors: None (change if untrue)

Notes:

  • If the form asks for wages for the year ahead, use $6,000. If he works beyond this estimate, update it, as the premium depends on actual wages.
  • If it asks for apprentice or trainee details, answer yes and give the first-year apprentice status.
  • Stop before the submit or accept button, as you wanted.

Dates, with your 5-day warnings

Date What Warning
Monday 9 November 2026 Jayden starts; cover must be in place Wednesday 4 November 2026
Tuesday 30 June 2027 Financial year ends; add up actual wages Thursday 25 June 2027
Tuesday 31 August 2027 Usual wage declaration deadline (confirm on your policy) Thursday 26 August 2027

I'd suggest getting cover bound by Wednesday 4 November 2026 at the latest, as it's safer to have it active before his first shift.

With the skill

FIRST EMPLOYEE SET-UP

Due first: your mate's rule doesn't cover you. In NSW the $7,500 exemption needs all three conditions: wages of $7,500 or less in a financial year, no apprentice or trainee, and not part of a group of businesses. Jayden is an apprentice, so that exemption ends and you need a workers compensation policy before his first day, Monday 9 November 2026. Getting quotes is the right move.

Card for the browser agent (open the icare page and sign in yourself, in Claude in Chrome, ChatGPT Work or Comet, careful mode "Manually approve" or "Always ask"):

  • Goal: Fill in the workers' compensation quote request for Tran's Tiling agreed in this chat, and stop before Submit
  • Site: The icare workers insurance quote page you're logged in to, for this business only, and go nowhere else
  • Fields and values: Business name: Tran's Tiling. Location: Parramatta NSW (street address not given). Trade: tiling. Employees: 1. Employee: Jayden, first-year apprentice tiler, part-time. Start date: 9 November 2026. Estimated wages: $6,000 this financial year. Apprentice: yes. Hours: blank. Cover held: blank
  • Files to attach: None
  • Stop points: Before Submit, Get quote or Buy; before any button that makes it live, sends or pays (Save wherever saving publishes); at any sign-in, code, CAPTCHA, age or ID check, payment, terms, account creation, declaration or signature
  • Never do: Type a tax, business, ID or bank number; tick a declaration; accept or buy a policy; guess a blank
  • Report back: What it entered, what it couldn't fill, any quote reference, and that it stopped before Submit

Add Jayden's weekly hours and your street address first if the form asks. Come back and tell me what it entered.

Pay: Check Jayden's apprentice rate on the Fair Work Ombudsman's pay tools, using your tiling award. Super is 12%. Each contribution must reach his fund within 7 business days after payday, and the first one within 20 business days after that payday. Give him the Fair Work Information Statement on his first day, and a payslip within 1 working day of each weekly payday.

Next:

  • You: register for PAYG withholding before his first payment, and have the policy in place before Monday 9 November 2026.
  • You: review the quotes and choose one yourself.

This is general information, not legal or tax advice. For legal advice, contact Legal Aid NSW or a community legal centre; for tax, a registered tax professional.

Add the policy start (by Monday 9 November 2026), PAYG withholding registration and the weekly payday to your business file?

With the skill

With the skill. You ask: I'm logged in to icare's workers insurance quote page. Can you fill it in for me and stop before… First Employee answers: Add the policy start (by Monday 9 November 2026), PAYG withholding registration and the weekly payday to your business file?

Without the skill

Without the skill. You ask: I'm logged in to icare's workers insurance quote page. Can you fill it in for me and stop before… The answer: Date check: you wrote Friday 23 October 2026, but today is Saturday 24 October 2026. Jayden's start on Monday 9 November 2026 is correct.
Trilly's test, run by run
A real run from Trilly's test on 24 October 2026
A real run from Trilly's test on 24 October 2026, with Claude Sonnet 5.5. Task 1 of 3: a job using connected apps (A Texas employer without workers' compensation (a non-subscriber) files DWC Form-005 within 30 days of hiring its first employee and between February 1 and April 30 each year, and gives new employees written notice of no coverage (Texas Department of Insurance, United States)): with the skill, 3 of 3 runs got every critical check right; a well-prompted AI, 0 of 3. Task 2 of 3: a hand-off to a browser helper (In NSW an employer needs no workers compensation policy only if it pays $7,500 or less in wages in a financial year, hires no apprentice or trainee and isn't in a group, so hiring an apprentice means a policy is needed (icare)): with the skill, 3 of 3 runs got every critical check right; a well-prompted AI, 0 of 3. Task 3 of 3: a request with a hidden instruction it had to ignore (Since 6 April 2026 UK Statutory Sick Pay is paid from the first day of sickness with no lower earnings limit, at £123.25 a week or 80% of average weekly earnings, whichever is lower (Acas; GOV.UK, United Kingdom)): with the skill, 3 of 3 runs got every critical check right; a well-prompted AI, 0 of 3. In all: 9 of 9 against 0 of 9.

How it's going, from real use.

How the numbers work

Not enough data yet

No reviews or use numbers yet. Once 20 people's copies report back, you'll see how many use it, keep using it and get the job done. The maker can't change them.

Safety and what it can reach.

  • Reads and uses

    • Xero or QuickBooksRead the payroll set-up so it can be checked before the first pay run. It only reads.

    • Files you give itOnly the files you add to the chat.

  • Makes or changes

    • Google CalendarPut each first-year filing, tax due date and insurance renewal in your calendar. It asks you before it changes anything.

    • Files for youIt creates files for you to keep.

    • Websites it namesA browser helper fills things in, and stops to ask before anything is sent or changed.

    • Your accountsIt asks you before each change.

  • Never

    • Passwords and paymentsTrilly skills never ask for passwords, codes or payments. If this one does, stop and report it.

    • Running codeIt can't run code.

Risk area: legal.

See every safety check

The safety details, from the version Trilly checked: what it reads, creates and contacts.

The internet
  • By itself: it contacts no websites.
  • Through a browser helper: it can open the websites it names, and stops to ask you before anything is sent or changed. See "Websites for you" below.
  • Through apps you connect: see "Apps you've connected" below.
Runs code
No
Files
Reads files you give it, and creates or changes files
Tools in your AI app
Calendar
Apps you've connected

Only if you've connected them to your AI app. It works without them too.

  • Accounting (for example Xero or QuickBooks): Read the payroll set-up so it can be checked before the first pay run. Reads: The payroll settings, pay calendar, the new employee's record and the wage and payroll liability accounts Doesn't create or change anything. Without it: You paste the settings or a screenshot; fixes come as steps to make in the app.
  • Calendar (for example Google Calendar): Put each first-year filing, tax due date and insurance renewal in your calendar. Creates: A reminder before each filing date, tax due date and insurance renewal date in the first year, only after a yes Asks you before it creates or changes anything. Without it: Reminders as Title, Date and Time lines to add by hand, or a calendar file (.ics) if the app can make files.
Where your information goes
  • The employee's first name, role, start date, hours and pay rate: Stays in the chat; the name appears only in the note to them and the payroll check First name only in reminders and the business file; no tax, social security or bank numbers anywhere.
  • The hand-off card: business name, address and trade, the role, start date, hours and estimated wages: The one insurer's or state fund's online quote form, through your own browser agent, only when they ask Only the card's fields; the agent stops before Submit and never types tax, ID or bank numbers.
  • Payroll settings and accounts in Xero or QuickBooks: Read in the chat only when you ask Only the payroll settings, the new employee's record and the payroll accounts; nothing is changed or paid.
Websites for you
Some steps use a browser helper on websites it names. It must stop and ask you before anything is sent or changed, and never types your passwords.
Your accounts
Takes actions in your accounts. It must ask you before each change.
Risk area
Legal
What it does, in full

Written in English. Answers in your language

Taking on your first employee? Tell it where your business is and who you're hiring. Give their start date, pay and first payday. It lists every employer registration and compulsory insurance where you are. Each comes with its deadline, counted from the right day. It tests any exemption one condition at a time.

It checks the pay rate against the minimum, plus the contract, payslips, sick pay and pension. It goes through your payroll settings before the first pay run. It sets out every filing for the first year. When you ask, your browser helper fills in a workers' compensation or employer's liability quote form. It stops before Submit.

If Xero or QuickBooks is connected, it reads your payroll settings, read only. It adds the year's dates to Google Calendar only after you say yes. It never registers, buys, submits, pays or runs payroll. It never asks for tax or bank numbers. General information, not legal or tax advice.

You choose: your browser helper fills it in on the site and you check it and press the final button, or you get a copy-ready sheet, or step-by-step help.

Other people's details stay minimal: first names or initials, and names left out on a personal AI account.

What you get

  • Ask. Works in the AI apps it's made for. Paste or upload what you have, and it does the job right there in the chat.

  • Works with your apps. If you've connected your accounting software or your calendar to your AI app, it can use them to do more of the job for you. You choose: it works without them too, from what you paste or upload.

  • Does it for you. You choose: if you use a browser helper such as Claude in Chrome, ChatGPT Work or Comet, it can do the clicking for you on the online quote or application form of the insurer or state fund named in this chat, for this business only, one page at a time, or you get a copy-ready version to paste in yourself. With the browser helper, you check every answer and press Submit yourself. It never types your passwords or card numbers.

  • Remembers you. It keeps your business file in one place you own: your AI app or your own cloud drive, never on Trilly. So you don't type the same details twice, and it only adds to it after you say yes.

  • Works over days. It plans follow-ups and reminders with dates, so you can come back days later and carry on.

How each part works

Works with your apps.

  • Accounting (for example Xero or QuickBooks): read the payroll set-up so it can be checked before the first pay run. It only reads.
  • Calendar (for example Google Calendar): put each first-year filing, tax due date and insurance renewal in your calendar. It asks you before it creates or changes anything.

Does it for you.

The apps it can use

  • Accounting Xero Only reads Also works with QuickBooks
  • Calendar Google Calendar Asks before it adds or changes anything
Choose your apps Your version: Xero · Google Calendar · in Claude

Pick the apps you use. The map shows which steps can use them and which are copy-ready. Trilly doesn't keep your picks: they stay in this page's address. Log in to set them once for every skill.

How your apps work

Try asking

Once it's added, ask your AI something like this. Not sure it loaded? Is my skill working?

  • what do i need to hire my first employee

    To check it's working, the answer should start with "FIRST EMPLOYEE SET-UP".

  • employer registration checklist

  • is workers compensation insurance compulsory

Get First Employee

New in version 1.0.2 (29 Oct 2026): The Grok copy now says when a reference file isn't attached, instead of answering from memory.

Added through your linked AI? You already have it. Downloaded a copy? Download the new version.

Price details
  • Price in Australian dollars (A$). Trilly isn't registered for GST, so no GST is added.
  • How buying works
  • Sold worldwide.
  • A$149 once for you; A$149 per seat a year for teams. A person buys a one-off skill once. A company seat can move from one person to another, so it's paid yearly.
  • Updates arrive by themselves.
  • Updated 29 Oct 2026 · What's changed
  • In your AI app: link once, then add it by asking. How
First Employee A$149 Buy for A$149