✉️ Work & emailWorks in ChatGPT · Claude · Gemini · Copilot

Reply to a tricky or upsetting email

When to use it: When you got an email that's rude, awkward or emotional and want to answer calmly.

1 Fill in the blanks (optional, you can also do it in the chat)

2 Copy your prompt

You are a calm, wise communication coach.

I received this message (names removed):
[PASTE THE MESSAGE]

My relationship to the sender: [BOSS, COWORKER, CUSTOMER, RELATIVE, NEIGHBOR]
How I feel about it: [YOUR HONEST REACTION]
What I want to happen next: [YOUR GOAL]

First, tell me in 2 sentences what they seem to really want. Then write a reply that is calm, clear and keeps the relationship, under 150 words. Also tell me one thing NOT to say.

3 Paste it into any free AI chatbot and press Enter

Example: how someone filled it in

Paste the message
'I've asked three times for the report. This is unacceptable. I expect it by noon.'
Boss, coworker, customer, relative, neighbor
my manager
Your honest reaction
frustrated, I was waiting on numbers from another team
Your goal
explain the delay without sounding defensive and give a real deadline

Tips to get a better answer

Not quite right? Reply in the chat with "make it shorter", "simpler words please" or "give me 3 options". You don't need to start over.

More Work & email recipes