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Ask for Flexible Work and Get an Answer in Time

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Your flexible work request made properly under the law where you work, with the employer's deadline dated and a clear next step if it's refused or ignored.

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Example, shortened, from this skill's page. Someone asks their AI: Today is Wed Oct 21, 2026. I'm a claims analyst in Bayline Insurance's San Francisco office… Ask for Flexible Work and Get an Answer in Time answers: You'll use Bayline's Workday request page. Sign in yourself, in Claude in Chrome, ChatGPT Work or Comet, on Careful mode (Manually approve or Always ask). The letter, Flexible work request: 10 am start Tuesdays and Thursdays: Please reply in writing by November 11, 2026.

Your flexible work request made properly under the law where you work, with the employer's deadline dated and a clear next step if it's refused or ignored.

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

It writes the letter. Same question, two answers.

Show the answer

9 of 9 runs got every critical check right in Trilly's test on 25 October 2026. A well-prompted AI: 0 of 9.

How Trilly tested it

Tested by Trilly on 25 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 1.0.3 on 25 October 2026. Version 1.0.5 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 hand-off to a browser helper What it tested: San Francisco's Family Friendly Workplace Ordinance: an employer with 20 or more employees must respond to a caregiver's written request within 21 days, and must meet to discuss alternatives before it can deny for undue hardship (Office of Labor Standards Enforcement) 3 of 3 0 of 3
Task 2 of 3: a request with a hidden instruction it had to ignore 3 of 3 0 of 3
Task 3 of 3: a job using connected apps 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

Today is Wed Oct 21, 2026. I'm a claims analyst in Bayline Insurance's San Francisco office (about 400 staff), 3 years full time. I need to start at 10 am instead of 8:30 on Tuesdays and Thursdays to take my son (7) to his therapy. Bayline takes these requests on a form in Workday. Can you fill it in for me? I'll sign in. My manager is Rachel Kim.

Without the skill

I can't access Workday, so here's wording for each section. Edit anything in [brackets].

Request type Flexible work schedule / modified start time

Days affected Tuesdays and Thursdays

Requested schedule Start at 10:00 am (instead of 8:30 am) on Tuesdays and Thursdays. I'll end at 6:30 pm on those days so I still work my full hours. All other days stay the same.

Proposed start date [Enter date, e.g., the first Tuesday after approval]

Trial period I'd like to begin with a [6]-week trial, ending [date]. At the end, Rachel and I can decide whether to make the schedule permanent, adjust it, or stop.

Check-ins I'll schedule three check-ins with Rachel before the trial ends (for example, around weeks 2, 4, and 5) to review how it's going and make adjustments.

Reason for request My 7-year-old son has a recurring appointment on Tuesday and Thursday mornings, and I need to take him. This schedule lets me do that while meeting my work responsibilities.

Business impact / coverage plan I've been a full-time claims analyst at Bayline for three years. I'll keep my current workload and deadlines. Before 10:00 am on Tuesdays and Thursdays, I'll make sure urgent items are handed off or flagged the day before. I'll be reachable by [phone/Teams] if something time-sensitive comes up. My later end time on those days keeps full coverage of my hours.

Comments to manager (Rachel Kim) Hi Rachel, I'm submitting a request to start at 10:00 am on Tuesdays and Thursdays so I can take my son to a standing appointment. I'm proposing a trial period with three check-ins so we can confirm it works for you and the team. I'm happy to discuss any adjustments. Thank you, Marcus

(answer cut for length)

With the skill

FLEXIBLE WORK REQUEST

You'll use Bayline's Workday request page. Sign in yourself, in Claude in Chrome, ChatGPT Work or Comet, on Careful mode (Manually approve or Always ask).

Hand-off card Goal: Fill in Marcus's flexible work request on Bayline Insurance's Workday form, stopping before Submit Site: Bayline Insurance's Workday flexible work request page, and go nowhere else Fields and values: Arrangement: 10:00 am start (not 8:30) on Tuesdays and Thursdays; start date: [your date]; length: ongoing, with an 8-week trial reviewed on [date]; reason: take my son (7) to therapy; manager: Rachel Kim; request text below Files to attach: None unless the form takes one Stop points: Before Submit; at any sign-in, code, CAPTCHA, age or ID check, payment, terms or account creation; at any declaration, statement of truth or signature; before any button that makes it live, sends or pays (Save wherever saving publishes) Never do: Type an employee or tax number (you type it); add health or family details beyond the card Report back: Fields entered, anything not found, any reference shown

San Francisco's Family Friendly Workplace Ordinance covers you. Bayline must respond within 21 days of your written request: by Wednesday, November 11, 2026 if it goes in today. If it won't agree as asked, it must meet you to discuss alternatives, and can deny only for undue hardship, in writing. This is general information, not legal advice.

Request text Subject: Flexible work request: 10 am start Tuesdays and Thursdays

Dear Rachel,

This is a request under San Francisco's Family Friendly Workplace Ordinance, made on October 21, 2026. I'm asking to start at 10:00 am instead of 8:30 am on Tuesdays and Thursdays from [start date], because I'm the main carer for my son, who attends therapy those mornings. I'll make up the time, hand over any early claims the evening before, and be reachable by phone and Teams. I'm happy to try this for 8 weeks and review it on [date]. I haven't made an earlier request. Please reply in writing by November 11, 2026.

Marcus Webb Claims analyst

Date What Who
Oct 21, 2026 Request goes in You
Nov 6, 2026 Check-in if no reply You
Nov 11, 2026 Written reply due Bayline

Please give me your start date and trial review date. Press Submit yourself, then tell me any reference number.

Add the October 21, 2026 request date, the November 11, 2026 deadline and the Workday request to your career file?

With the skill

With the skill. You ask: Today is Wed Oct 21, 2026. I'm a claims analyst in Bayline Insurance's San Francisco office… Ask for Flexible Work and Get an Answer in Time answers: Flexible work request: 10 am start Tuesdays and Thursdays Add the October 21, 2026 request date, the November 11, 2026 deadline and the Workday request to your career file?

Without the skill

Without the skill. You ask: Today is Wed Oct 21, 2026. I'm a claims analyst in Bayline Insurance's San Francisco office… The answer: Request type Flexible work schedule / modified start time Days affected Tuesdays and Thursdays
Trilly's test, run by run
A real run from Trilly's test on 25 October 2026
A real run from Trilly's test on 25 October 2026, with Claude Sonnet 5.5. Task 1 of 3: a hand-off to a browser helper (San Francisco's Family Friendly Workplace Ordinance: an employer with 20 or more employees must respond to a caregiver's written request within 21 days, and must meet to discuss alternatives before it can deny for undue hardship (Office of Labor Standards Enforcement)): with the skill, 3 of 3 runs got every critical check right; a well-prompted AI, 0 of 3. Task 2 of 3: a request with a hidden instruction it had to ignore: with the skill, 3 of 3 runs got every critical check right; a well-prompted AI, 0 of 3. Task 3 of 3: a job using connected apps: 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

    • GmailIt only reads.

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

  • Makes or changes

    • OutlookFind the earlier request and any reply you pick, and save the request as a draft in a work Outlook account. It asks you before it changes anything.

    • Google CalendarAdd the employer's deadline, the meeting and any trial review to your own calendar. It asks first here too.

    • 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
Email, Calendar
Apps you've connected

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

  • Email (for example Outlook; Gmail only reads): Find the earlier request and any reply you pick, and save the request as a draft in a work Outlook account. Reads: The emails you pick from a search by the manager's name or the word flexible Creates: Outlook, on a work account where the admin allows it: the request or covering email as a draft, only after a yes. Never sends. Asks you before it creates or changes anything. Without it: You paste the emails; the request is written in the chat for them to send.
  • Calendar (for example Google Calendar): Add the employer's deadline, the meeting and any trial review to your own calendar. Creates: One event per deadline, meeting or review, only after a yes. Never invites anyone. Asks you before it creates or changes anything. Without it: Each date 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 change asked for, the reason, length of service, the manager's name and the employer's replies: Stays in the chat. It reaches the employer or a dispute body only when you send it. Only the reason the law needs; no medical or family detail beyond it.
  • The hand-off card: the arrangement, start date, reason, request text and manager: The employer's own online flexible work request form, through your own browser agent The agent enters only what's on the card, types no employee or tax number, and stops before Submit and at any sign-in or declaration.
  • Deadlines, meetings and review dates: Your own Google Calendar, after a yes Titles name the step, not the reason for the request.
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

Tell it the change you need, such as a later start for school pick-up, fewer days or working from home. It checks whether the law where you work gives you a right to ask and what your request must say, then writes it in your own voice, ready to send.

It dates the employer's deadline to reply, prepares answers to the likely objections from your own role and roster, and checks any refusal against the grounds the law allows. If the answer is no, or never comes, it sets out the next step and its time limit and prepares the form's answers. Your browser helper can fill your employer's online request form and stop before Submit.

It gives general information, not legal advice, and never sends anything for you. If your email or calendar is connected, it can find earlier messages, save the request as a draft and add the dates, and it asks first.

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 email 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 website it names, 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 career 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.

  • Email (for example Outlook; Gmail only reads): find the earlier request and any reply you pick, and save the request as a draft in a work Outlook account. It asks you before it creates or changes anything.
  • Calendar (for example Google Calendar): add the employer's deadline, the meeting and any trial review to your own calendar. It asks you before it creates or changes anything.

Does it for you.

The apps it can use

  • Email Gmail Only reads Also works with Outlook
  • Calendar Google Calendar Asks before it adds or changes anything
Choose your apps Your version: Gmail · 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?

  • I need to start later two days a week for school pick-up. How do I ask so it can't just be waved away?

    To check it's working, the answer should start with "FLEXIBLE WORK REQUEST".

  • flexible working request letter

  • flexible work request response deadline

Get Ask for Flexible Work and Get an Answer in Time

New in version 1.0.5 (28 Oct 2026): Grok copy: says what to do when the country or reference file isn't attached, so Grok doesn't give its rules 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$29 once for you; A$29 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 28 Oct 2026 · What's changed
  • In your AI app: link once, then add it by asking. How
Ask for Flexible Work and Get an Answer in Time A$29 Buy for A$29