Write a difficult work email without the stress
To write a difficult email with AI, give it the situation and the outcome you want, then edit the draft until it sounds like you. You decide what gets sent.
Next step: do Step 1. Copy the box, fill in the blanks, and paste it into the chat.
A prompt is the message you paste. A Director check is a short look before you use the result.
What you'll need
- The facts of the situation (what happened, dates, numbers)
- What you want the reader to do after reading
Step 1: Vent first, privately
It sounds silly, but it works. Tell the AI what's really going on, in your own words. Getting it out helps you see the actual goal.
I need to write a tough email. Here's the situation, unfiltered: [explain]. Before drafting anything, ask me up to 3 questions about my goal, my relationship with the reader, and what I can and can't offer.
Step 2: Answer its questions and get two versions
Thanks. Now write two versions:
A) Warm and collaborative
B) Firm and direct
Each under 150 words, with a clear ask and a specific next step or date. No apologies unless I did something wrong.
Step 3: Make it yours
Pick the version closest to how you'd talk. Swap in your own phrases and check every fact, name and date.
Here's an email I wrote before so you can match my voice: [paste]. Rewrite the version I picked to sound like me.
Ordinary replies, the ones that are slow rather than tense, belong on Reply to work emails. Stay on this page when you are saying no, pushing back, or chasing something owed.
Director check: look before you use it
- Is every fact correct? AI will happily fill in plausible but wrong details.
- What will the reader feel? Ask the AI: "Read this as the recipient. What's your reaction, and what might you misread?"
- Is the ask crystal clear? The reader should know exactly what to do next.
- Would you say this face to face? If not, soften or cut it.
Common questions
Can AI write professional emails for me?
Yes, it's one of the best everyday uses. Give it the facts, your goal and the relationship, then edit the draft so the details and tone are right.
How do I make an AI email not sound like AI?
Paste in one or two emails you've written before and ask it to match your style. Then cut filler phrases like "I hope this email finds you well" and read it out loud before sending.
By Joe Rangel ยท Last updated ยท More Work guides