The difficult email you have been avoiding for three days

Reading time: about 10 minutes

The situation. You need to chase a supplier over terms that were not applied, tell a rep no, or reply to somebody on the team with something they will not like. And you have spent three days opening the email and closing it again.

The block is almost never "I do not know what to say": it is I do not know how to say it without overdoing it or underdoing it. And that is exactly what AI is good at, because the work is tone, not judgement. The judgement — what you are claiming and how far you will go — is yours, which is why the prompt starts there.

What you need to hand: The raw facts, however badly written: what happened, when, what you want to happen now. And the figures, if any. No third-party names if the matter is sensitive.

Step by step

Write the angry draft, for yourself

In your notepad, unfiltered: what you would say if there were no consequences. This is not therapy, it is method: that is where the concrete facts come out — the date, the order number, what they told you on the phone — the ones a polite email always forgets.

That text never gets sent. It is the raw material.

Tell it WHAT RELATIONSHIP you want afterwards

This is the instruction that changes the whole email and the one nobody writes. "Firm but friendly" means nothing. "I want to keep buying from them next year" does, and produces a completely different email from "I am changing supplier and this closes it".

Act as a pharmacy owner writing a professional email.

CONTEXT (this is for you, do not copy it literally):
paste your raw draft here

WHAT I WANT TO HAPPEN: a credit for the difference on the next invoice
THE RELATIONSHIP I WANT AFTERWARDS: to keep working with them normally
WHO RECEIVES IT: the area manager, who is not the one who made the mistake

Write the email with these rules:
- Under 150 words. Subject line separate, specific, no exclamation marks.
- First paragraph: the fact and the date. No preamble.
- One single clear request, with a deadline.
- No sarcasm, no reproach, no "as you well know".
- Do not assume any detail I have not given you.

After the email, tell me in one line what they are most likely to reply
and what I should have ready for that reply.

Take two things out before sending

The same two things are almost always surplus: the opening courtesy paragraph ("hope all is well with you") and an extra adjective somewhere in the complaint. Delete them and the email improves.

And read the last sentence out loud. If it accidentally sounds like a threat, change it: the last sentence is what the reader remembers.
Ask it to read it from the other side

This is the step with the best return in the whole case and the one almost nobody does. Before sending, paste your draft and ask exactly this:

"Read it as if you were <>. Tell me: which sentence would sting most, what would you understand I am asking for, and what would you reply. Do not rewrite it."

The answer usually uncovers two things: a sentence you thought was neutral that reads from outside as a reproach and — more importantly — that what you think you are asking for is not written anywhere. It is the commonest failure of a difficult email: the problem gets explained and nothing concrete gets asked.

And the "do not rewrite it" at the end matters: leave it out and you get another version back and lose the diagnosis, which is what you came for.
Check the facts one by one

This is the serious part. A complaint email with a wrong date or a wrong amount leaves you worse off than before you wrote it: you lose the point you had.

So: date, order number, amount, recipient’s name. All four, against the original document, not against your memory. If the model filled in one you never gave it, it is invented — and that is the most expensive failure in this case.

A full example, and what is wrong with it

The brief: chase a supplier over an order three weeks late, after two unanswered calls, wanting to keep working with them. This is what came out.

What it replies

"Dear [Supplier] team,

I am writing regarding order no. 44718, placed on 2 August, which we have still not received. I have already tried to reach you by telephone on two occasions without response.

I understand that logistical incidents can occur, but the situation is causing stock shortages at our pharmacy and affecting our patients. I would greatly appreciate it if you could review the status of the shipment and inform me at your earliest convenience.

I look forward to your prompt reply. Kind regards."

And now, what is wrong with that reply:

It asks for nothing specific, which is why it cannot be answered. "Review the status" and "inform me at your earliest convenience" are not requests: they are wishes. Whoever receives it does not know what to do to close this email, so they leave it for later. This is the commonest failure of a difficult email — the problem gets explained and nothing executable gets asked for.
"Affecting our patients" is a reproach in disguise. It is true and it sounds professional, but read from the other side it is "because of you, people are without their medication". If your goal is to keep working with them, that sentence buys less than it costs. If your goal were different it would belong — which is why the prompt starts by asking what relationship you want afterwards.
It sounds like a template because it is one. "I am writing regarding", "I would greatly appreciate", "I look forward to your prompt reply". These are the three phrases in every chasing email on earth, and the effect is that yours reads exactly like the other forty that person has unopened.
And it lacks the one thing that moves an email: a date. With no date this sits in the inbox indefinitely and you write again in a fortnight with the same result. "Can you tell me before Friday whether the order is shipping this week or I cancel it?" either gets answered or it does not, and both outcomes are useful to you — which is exactly what this email fails to achieve.

The draft is not badly written: it is badly aimed. And the correction is not stylistic, it is one line — replace the two middle paragraphs with a question that has a date in it.

Try asking: "rewrite it in 5 lines, with ONE specific request and a date, and cut any sentence that could read as a reproach". What comes back is nearly always better than the original and better than what you would have written angry — which was this case’s starting point.

And if your pharmacy is not like that

If the email is to somebody on your team. That changes the brief entirely: in writing, correcting somebody you see every day is nearly always worse than in person. Use it to organise what you are going to say — ask for the three things to cover and in what order — and then talk. The email that does make sense is the one afterwards, summarising what was agreed.

If it is a complaint to a public body. There the formal template is not surplus: it helps. What you add is the specifics a case file needs — dates, reference numbers, which rule you are invoking — and that has to come from you or your professional body, not the model. It drafts; you build the file.

If what blocks you is saying no. It is the commonest case and the easiest to fix: a good "no" is three lines — the no, one reason, and an alternative if there is one — and what makes it longer is guilt, not politeness. Ask for it with that limit stated and do not negotiate with yourself on the reread.

If you are copying other people in. Think twice, because a CC changes the genre of the email: it stops being a request and becomes a minute. Whoever receives it reads it knowing there are witnesses, and that hardens the reply however gentle the text. If somebody genuinely needs to know, a separate email to that person beats a CC on this one.

When it does not work first time

It comes out cold and I sound angry.

Usually the passive voice and the absence of people: "a delay has occurred" instead of "it has not arrived". Say "write it in the first person with short sentences". Paradoxically, direct reads less aggressive than impersonal.

I give it context and it invents details I never mentioned.

Order numbers, dates, people’s names. It is the most expensive failure here, because an email with an invented detail makes you look bad, not the model. Add "invent no details: if one is missing, leave it as [TBC]" and search for those brackets before sending.

I have rewritten it five times and like it less each time.

Stop. By the third iteration you are not improving the email, you are avoiding sending it — which is precisely what you had been doing for three days. Take version 2, rewrite the last line in your own words, and press send.

I want it to sound like me and not like a manual.

Paste two of your own previous emails — ordinary ones, not difficult ones — and say "write in this tone". It works surprisingly well and is the only reliable way: describing your tone in adjectives ("warm but professional") produces the usual template.

Before you use what it gave you

The four hard facts — date, reference, amount, recipient — come from the document, not the model.
There is one request, not three.
No third party is named who did not need to be.
You would not mind receiving it yourself.
You asked it to read the draft from the other side before sending.
There is ONE concrete request and it is clear without re-reading.
It promises no consequence you would not follow through.

It sounds like a template. If the email could be addressed to anyone, it will move no one. The fix is not asking it to "sound more natural": it is giving it one concrete detail only someone who was there would know — the order number, what they said on the phone, the box that arrived open.

It hardens or softens more than you asked. Ask for "firmer" and it can overshoot; ask for "softer" and the complaint disappears. If the tone is off, do not repeat the adjective: name the exact sentence that bothers you and why.

It writes you a threat with good manners. Ask for firmness and it tends to add a consequence — "we will be obliged to…" — that sounds professional and that you had not decided on. Before sending, check it promises nothing you will not follow through. A threat you do not act on costs you more than the original problem.

It adds an apology you did not owe. "Apologies for the inconvenience" at the end of a complaint about something you did not cause. It is automatic — the model tends to soften closings — and it changes who ends up owing whom. Always read the final sentence in full before sending: that is where it creeps in.

Now, with your own. The email you have been avoiding is in your head right now. Do it with that one, not a practice one: the method only sticks when something is at stake. And keep the prompt — the "relationship I want afterwards" part will serve you in all of them.

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The difficult email you have been avoiding for three days

Step by step

Write the angry draft, for yourself

Tell it WHAT RELATIONSHIP you want afterwards

Take two things out before sending

Ask it to read it from the other side

Check the facts one by one

A full example, and what is wrong with it

And if your pharmacy is not like that

When it does not work first time

Before you use what it gave you