SynaBot
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 BarclayLast reviewed July 2026 · Next review October 2026

Before you start

  • A specific email you've been avoiding

Tools you'll use

  • SynaBot
  • ChatGPT

Course modules

  1. 1.Write the raw version first
  2. 2.Give the assistant the goal and the constraints
  3. 3.Ask for the tone check
  4. 4.Rewrite the opening line
  5. 5.Sleep on it if you can

Modules

  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.

    Next: Give the assistant the goal and the constraints →
  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."

    ← Previous: Write the raw version firstNext: Ask for the tone check →
  3. 3

    Ask for the tone check

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

    ← Previous: Give the assistant the goal and the constraintsNext: Rewrite the opening line →
  4. 4

    Rewrite the opening line

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

    ← Previous: Ask for the tone checkNext: Sleep on it if you can →
  5. 5

    Sleep on it if you can

    Not everything sends better in the morning, but hard emails often do.

    ← Previous: Rewrite the opening lineBack to top ↑

What you'll have at the end

A difficult email sent — direct, kind, and clear about the ask.