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.

Mark Barclay
Guide curated and reviewed byMark Barclay

Before you start

  • A specific email you've been avoiding

Tools you'll use

  • SynaBot
  • ChatGPT

Steps

  1. 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. 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. 3

    Ask for the tone check

    "Read this back. Does it come across as [defensive / vague / cold]? If yes, rewrite that section."

  4. 4

    Rewrite the opening line

    AI openings are consistently the weakest part. Say the hard thing in your own words, first.

  5. 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.