beginner 20 min
How to write a difficult email with AI
Get through the emails you've been avoiding — layoffs, refusals, tough feedback — with clarity and empathy.
Guide curated and reviewed byMark Barclay
Before you start
- A specific email you've been avoiding
Tools you'll use
- SynaBot
- ChatGPT
Steps
- 1
Write the raw version first
In your notes app, write the email as you actually feel it. Do not send this. This is context for the AI.
- 2
Give the assistant the goal and the constraints
Prompt: "Rewrite this email to a [recipient] to [goal]. Direct but kind. Under 150 words. No corporate jargon."
- 3
Ask for the tone check
"Read this back. Does it come across as [defensive / vague / cold]? If yes, rewrite that section."
- 4
Rewrite the opening line
AI openings are consistently the weakest part. Say the hard thing in your own words, first.
- 5
Sleep on it if you can
Not everything sends better in the morning, but hard emails often do.
What you'll have at the end
A difficult email sent — direct, kind, and clear about the ask.
