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Time-off request reply prompt: free ChatGPT template

Hiring and HRWorks in ChatGPT, Claude, Gemini and Copilot

Updated · By Robert Breen

Use this when an employee asks for time off and you've made the call: yes, no, or part of it. A good reply states the decision in the first line, explains it with your policy rather than your mood, and offers what you can (a swap, other dates). A rushed reply can sound personal, and an AI-written one can invent policy.

One situation needs extra care: if the request involves the employee's or a family member's health, pregnancy, a disability or military service, leave laws may apply and the decision shouldn't be a quick reply from a manager. The prompt routes those to HR instead of deciding.

Have a professional review it. This prompt helps you draft, not decide. Employment rules vary by state and country, so have HR or an employment attorney review it before you share it.

The prompt

Copy it into ChatGPT (or Claude, Gemini or Copilot) and replace every [BLANK] with your own details. It uses the four parts from Prompt Writing 101: Role, Context, Task and Format.

Role: You are a manager at [BUSINESS], replying to an employee's time-off request.
Context: The request: [REQUEST]. Our time-off policy: [POLICY]. My decision: [DECISION]. Use only the policy and decision above; don't invent rules, deadlines or exceptions. Don't comment on or ask about the reason for the request. If the request mentions the employee's or a family member's health, pregnancy, disability or military service, don't approve or deny anything: say it's being passed to [WHO HANDLES LEAVE] and that they'll be in touch.
Task: Write a reply that gives the decision in the first sentence, explains it in one or two sentences using the policy, offers any alternative in my decision, and says what happens next.
Format: Under 100 words, warm and direct, written as a text or short email. No subject line. Sign with my first name.

Fill in the blanks

[BUSINESS]
Your business name.
[REQUEST]
Who asked, the dates, and the request as they wrote it. Leave out any private details they don't need repeated.
[POLICY]
The relevant rules: notice needed, busy-season limits, how swaps work. Copy them from your handbook if you have one.
[DECISION]
Your answer, including partial approvals and any alternative you're offering. The AI only words it.
[WHO HANDLES LEAVE]
The person or role who handles leave that may be protected by law, such as the owner or your HR provider.

Example, filled in

A made-up example from the free lesson Prompt Writing 101: Role, Context, Task, Format. Summit Lawn Care is the made-up lawn company in Prompt Writing 101, whose fall aeration runs September 29 to October 17. A crew member asked for days that overlap the end of it.

Role: You are a manager at Summit Lawn Care, replying to an employee's time-off request.
Context: The request: Carlos asked on October 1 for Thursday, October 15 through Tuesday, October 20 off. Our time-off policy: requests need two weeks' notice; no time off during aeration season (September 29 to October 17) unless a crew member covers and the owner approves the swap. My decision: approved for Monday, October 19 and Tuesday, October 20; not approved for October 15 and 16 because of aeration; if Carlos finds a crew member to cover those two days, he can ask the owner to approve the swap. Use only the policy and decision above; don't invent rules, deadlines or exceptions. Don't comment on or ask about the reason for the request. If the request mentions the employee's or a family member's health, pregnancy, disability or military service, don't approve or deny anything: say it's being passed to the owner and that they'll be in touch.
Task: Write a reply that gives the decision in the first sentence, explains it in one or two sentences using the policy, offers any alternative in my decision, and says what happens next.
Format: Under 100 words, warm and direct, written as a text or short email. No subject line. Sign with my first name, Mike.

What a good answer looks like

  • The decision first: October 19 and 20 approved, October 15 and 16 not.
  • A reason that points to the aeration season policy, not to Carlos or the crew.
  • The swap option exactly as you set it: he finds cover, the owner approves.
  • No questions or remarks about why he wants the time.

How to check it before you use it

An AI draft can sound right and still say something you never told it. Use the habit from the Reply Faster lesson: check every promise, name, date and number against what you gave it before anything goes out.

  • Check every date against a calendar and against your decision. A wrong day here becomes a no-show or a dispute.
  • Check every rule it mentions against your policy. "Requests must be in writing" or "unpaid" doesn't belong unless it's yours.
  • If the request touches health, family care, pregnancy, disability or military service, don't send a decision; follow your process and loop in HR.
  • Log the decision where you track time off, so the next request is judged the same way.

Why this prompt works

The Decision blank keeps the judgment with you; the AI only words it. The routing rule is a guardrail with a human in the loop: when a request may be protected leave, the right move is a handoff, not a fast answer.

Practice it in the free lesson

Reply Faster: Turn a Messy Customer Email Thread into a Clear, Friendly Reply: Turn a messy customer email thread into a clear, friendly reply: give ChatGPT the thread and your facts, check every promise, fix the tone, and send it from Gmail. You do every step yourself in a practice copy of ChatGPT, and nothing touches your real accounts.

Start the free lesson

Also useful: Prompt Writing 101: Role, Context, Task, Format

Terms used here

GuardrailsHuman in the loopPrompt constraints

All free prompt templates · AI glossary