The hardest emails are rarely hard because of grammar. They are hard because of tone, stakes, and relationship.
AI is useful here because it can help you create a first draft that sounds calm, clear, and firm when you are annoyed, anxious, or stuck.
Important: in this lesson, you are not writing the final email yourself.
You are practicing how to write a strong prompt that tells AI how to draft the email.
The Difficult Email Formula
A weak prompt says:
Write an email about this.
A strong prompt gives AI the ingredients it needs:
- Situation — what happened?
- Goal — what do you want the email to accomplish?
- Relationship — who are you writing to?
- Tone — how should the email sound?
- Constraints — length, deadline, phrases to avoid, or specific details to include
That turns "write me an email" into something actually usable.
Strong Email Prompt Template
Use this structure:
Write an email to [person] about [situation].
The goal is to [goal].
The relationship is [relationship/context].
Use a [tone] tone.
Include [important details].
Keep it [length/format constraint].
Avoid [anything to avoid].
Example:
Write an email to my freelance client about an overdue invoice. The goal is to get payment without sounding emotional or hostile. This is a client relationship I want to preserve if possible, but two reminders have already been ignored. Use a firm, professional tone. Mention the overdue invoice, the two prior reminders, a 5-day payment deadline, and that I may need to escalate if payment is not received. Keep it under 200 words.
Useful Scenarios
AI can help you draft prompts for emails like:
- asking for a raise
- following up on a proposal
- declining a request politely
- giving critical feedback
- escalating a complaint
- chasing an overdue invoice
- asking for clarification
- apologizing professionally
- setting a boundary
- negotiating a deadline
Practice: What Should the Prompt Include?
Multiple Choice
You want AI to draft a difficult email. Which prompt gives AI the best instructions?
True or False: The Prompt Is the Assignment
Multiple Choice
In this lesson, the goal is to write the final email yourself, not to write a prompt that tells AI how to draft it.
Prompt Challenge: The Awkward Ask
You are not writing the final email.
Your job is to write the prompt you would give AI so it can draft the email correctly.
Rate my prompt — how many rubric items can you hit?
Your Mission
Your freelance client owes you payment for work delivered 3 weeks ago. Two previous reminder emails have been ignored. You need AI to draft a firm but professional third reminder email that makes it clear this is the last reminder before you take further action. Write the exact prompt you would give the AI.
Do not write the final email yourself. Write the prompt you would give AI. Include the situation, tone, deadline, and consequence.
Prompt Challenge: Follow-Up Email
You are not writing the final follow-up email.
Your job is to write the prompt you would give AI so it can draft the follow-up.
Rate my prompt — how many rubric items can you hit?
Your Mission
You need AI to draft a short follow-up email to Marcus after you sent a proposal to Acme Corp last Tuesday. The email should be polite, clear, and easy to answer. Write the exact prompt you would give the AI.
Do not write the email itself. Write the prompt that tells AI who the email is for, what happened, what tone to use, and what response you want.
Prompt Challenge: Declining Without Burning the Bridge
You are not writing the final email.
Your job is to write the prompt you would give AI.
Rate my prompt — how many rubric items can you hit?
Your Mission
A colleague asked you to take on extra work this week, but you are already overloaded. You want AI to draft a polite email that says no without damaging the relationship. Write the exact prompt you would give the AI.
A good difficult-email prompt gives AI the emotional goal, not just the information. Tell it you want to say no while keeping the relationship intact.
Common Mistakes
Mistake 1: Writing the email instead of the prompt
Wrong for this exercise:
Hi Marcus, just checking in on the proposal...
Better:
Write a short polite follow-up email to Marcus about the proposal I sent last Tuesday...
The course is testing whether you can direct AI, not whether you can manually write the email.
Mistake 2: Forgetting the tone
Weak:
Write an invoice reminder.
Better:
Write a firm but professional invoice reminder that is clear without sounding hostile.
Mistake 3: Forgetting the relationship
Weak:
Tell them no.
Better:
Write a polite email to a colleague declining extra work while preserving the relationship.
Mistake 4: Forgetting the desired outcome
Weak:
Follow up on this proposal.
Better:
Write a short follow-up email asking whether they reviewed the proposal and whether a 20-minute call next week makes sense.
Copy/Paste Prompt Pack
Overdue Invoice
Write a firm but professional reminder email to my client about an overdue invoice. Mention that payment is overdue, include the original due date if provided, ask for payment by [deadline], and explain the next step if payment is not received. Keep it calm and under 200 words.
Proposal Follow-Up
Write a short polite follow-up email to [name] about the proposal I sent on [date]. Ask whether they had a chance to review it and make the next step easy by asking for a yes/no reply or a short call. Include a clear subject line and clean sign-off.
Declining a Request
Write a polite professional email declining [request]. Explain that I cannot take it on because [reason]. Keep the tone respectful, preserve the relationship, and offer [alternative] if appropriate.
Giving Critical Feedback
Write a constructive feedback email to [person] about [issue]. Keep the tone respectful and specific. Focus on the behavior or outcome, not personal criticism. Include what needs to change and offer a clear next step.
Escalating a Complaint
Write a firm professional escalation email about [problem]. Mention what has already happened, previous attempts to resolve it, the impact of the issue, and the specific resolution I am requesting. Keep the tone calm and factual.
Key takeaway: For difficult emails, do not just ask AI to "write an email." Give it the situation, goal, relationship, tone, constraints, and desired next step.
Up next: Lesson 6 - Summarizing massive documents