The Awkward Email Toolkit: 10 AI Prompts for Messages You Dread Writing

Asking for a raise. Chasing an unpaid invoice. Saying no to your boss. Some messages take an hour to write because the words feel impossible. AI is brilliant at these. You bring the facts and the feeling, it brings the calm, clear wording. Here are 10 prompts for the emails people dread most.

How to use these prompts

1. Copy a prompt and replace the [brackets] with your details.
2. Read the draft and change anything that doesn't sound like you.
3. Ask for tweaks: "warmer", "shorter", "more direct".
4. Never send without reading it out loud once.

1. Following up when nobody replied

Write a short, friendly follow-up to [name] about [topic]. I emailed on [date] and haven't heard back. Don't sound annoyed. Under 80 words.

2. Chasing an unpaid invoice

Write a polite but firm reminder that invoice [number] for [amount] was due on [date]. Include payment details and ask for a payment date. Keep it professional.

Need the invoice itself? Make one with our free Invoice Generator.

3. Saying no without burning bridges

Help me decline [request] from [person]. I want to stay on good terms and suggest [alternative]. Warm, short and clear.

4. Asking for a raise

Draft an email asking my manager for a meeting to discuss my salary. Mention these achievements: [list]. Confident, not demanding.

5. Apologizing for a mistake

Write an apology to [client/colleague] for [mistake]. Take responsibility, explain the fix in one sentence, and don't over-apologize.

6. Pushing back on a deadline

Tell my manager the [project] deadline of [date] isn't realistic because [reason]. Propose [new date] and what I can deliver by the original date.

7. Responding to an angry customer

Reply calmly to this angry message. Acknowledge their frustration, explain what happened in plain words and offer [solution]: [paste message]

8. Asking for a recommendation letter

Write a polite request to [teacher/manager] asking for a recommendation for [program/job]. Mention the deadline [date] and offer to send my CV and key points.

9. Resigning gracefully

Write a short, professional resignation letter. My last day will be [date]. Thank my manager for [specific thing] and offer to help with the handover.

10. Setting a boundary

Help me tell [person] politely that I won't be answering work messages after [time] anymore, and how they can reach me for real emergencies.

Pro tip: check the tone before you hit send

How will this email come across to the reader? Point out anything that sounds rude, passive-aggressive or unclear: [paste draft]

Want your messages to sound natural, not robotic? Run them through our free Writing Checker and grab more templates from the Prompt Library.