How I Write the Client Email I've Been Avoiding for Three Days
There is always one email sitting in my head. Not in drafts — in my head, which is worse. A client has quietly added a third round of revisions to a two-round contract. An invoice went out five weeks ago and nothing came back. Someone I like working with is paying me what I charged eighteen months ago and I need to fix that.
None of these are hard to write. I've written versions of all of them. What makes them sit there for three days is that I haven't decided what I actually want, and you cannot write a clear email about an unclear position. So I open the reply box, feel the fog, and go do something billable instead.
For a long time I thought the AI use case here was *drafting* — hand it the situation, get an email. It isn't. When you ask a model for the email directly you get something that reads like a template from a freelancing course: professional, spineless, full of "I wanted to circle back regarding." You paste it, hate it, close the tab, and now the email has been sitting there four days.
The use case is the part before the email. Getting the position clear enough that the writing becomes trivial — because it genuinely is trivial, once you know what you're asking for.
First: make it tell me what I'm actually negotiating
The scope creep case is the clearest example. The literal problem is "they asked for a third round." The real problem is one of about four different things — an underspecified contract, a client who doesn't know they're over, a project that changed underneath us, or me being bad at saying no early. Each of those gets a completely different email, and if I don't know which one I'm in, I write the mushy email that covers all four.
Here is a client situation I've been avoiding dealing with: [DESCRIBE IT PLAINLY, INCLUDING WHAT WAS AGREED AND WHAT'S HAPPENING NOW]. Do not write an email. Before any writing happens I need the situation clear. 1. What is the actual disagreement here — state it in one sentence, as neutrally as you can, the way a third party would describe it. 2. What are the two or three plausible readings of the client's behaviour? Include at least one where they're acting in good faith and genuinely don't see a problem. 3. What did I leave ambiguous that made this possible? 4. What are my realistic options, including the ones I probably don't want to hear — absorbing it, charging for it, renegotiating the whole engagement, walking? 5. For each option, what does it cost me beyond money — relationship, precedent, future work?
Point 2 is the one that changes my emails. Left to myself, three days into avoidance, I have quietly built a story where the client is taking advantage of me. Usually they aren't. Usually they're a marketing manager who has never bought this kind of work before and has no idea that "can we just try one more version" is a budget question. The good-faith reading is almost always closer to true, and an email written from it lands completely differently than one written from a grievance I've been marinating in since Tuesday.
Point 5 catches the opposite failure. Absorbing one extra revision costs an afternoon. It also sets the precedent that rounds are free, which costs every project after this one. I know that. I forget it precisely when I'm tired and want the discomfort to go away.
Then: draft against a position, not a feeling
Once I know what I want, I ask for the email — but the prompt carries the position, the tone ceiling, and the specific ways this kind of message goes wrong.
I've decided: [E.G. I'M CHARGING FOR THE THIRD ROUND AT MY DAY RATE, AND I WANT TO KEEP THIS CLIENT]. Write the email. Constraints: - Short. Under 150 words. Nobody softens their way to a clear ask with more paragraphs. - No apology for the existence of the boundary. I can be warm; I'm not sorry that work costs money. - State what was agreed, state what's being asked, name the gap. Once. Do not re-litigate it in the closing paragraph. - End with a specific, easy-to-say-yes-to next step — not "let me know your thoughts." - No "I wanted to reach out", no "just circling back", no "I hope this finds you well." - Do not use the word "unfortunately." Context on the relationship: [HOW LONG, HOW MUCH IT'S WORTH, HOW MUCH I WANT TO KEEP IT].
The "no apology for the existence of the boundary" line is doing most of the work. Models default to a register I'd describe as *apologetic professional* — every clear statement gets wrapped in padding until the actual request is a small hard object buried in a soft one. And a client skimming on their phone reads the padding and misses the object. Then you have a second email to write.
Banning "unfortunately" is not a stylistic tic. That word frames a decision I made as weather that happened to both of us. I'm not unfortunately charging for extra work; I'm charging for extra work.
The pass that actually gets it sent
Draft in hand, I run one more. This is the one that stopped me from sending things I regretted, and — more often — stopped me from sitting on things that were fine.
Read this email as the client receiving it. They are busy, mildly stressed, and reading on a phone between meetings. - What is their first emotional reaction, in three words? - What do they think I'm asking for? Quote the line that tells them. - Where could they reasonably read this as more aggressive than I meant? - Where could they reasonably read it as optional — something they can ignore or defer? - What's the most likely reply, and does that reply move us forward or start a negotiation I don't want? Then tell me: is this email unclear, or is it just uncomfortable? Those are different problems and I only want to fix the first one. Email: [PASTE]
That last question is the whole reason the pass exists. Nine times out of ten the email is clear and I'm stalling because clear feels rude when you're the one who has to send it. Having something read it back and say *this is fine, you just don't want to send it* is, embarrassingly, enough to make me hit send.
The tenth time it catches something real — usually an ask that reads as optional. "Let me know if you'd like to proceed" is not an ask, it's an invitation to do nothing, and I write it constantly when I'm nervous.
What I don't hand over
I don't let it invent facts about the agreement. Every number, date and clause in the final email is one I put in the prompt myself, because a model will confidently produce a plausible "as we agreed in our initial scope" that I then have to defend in front of someone holding the actual contract.
And I don't send anything in a voice that isn't mine. Clients I've worked with for years would notice immediately if I suddenly wrote like a support macro. The draft gets me a clear structure and a spine; the phrasing gets rewritten in my own words in about ninety seconds, which is a fair trade for not having spent three days not writing it.
Why these are saved and not improvised
The moment I need these prompts is the exact moment I'm least likely to write them well: annoyed, avoiding, on my fourth cup of coffee. Improvising a careful clarify-then-draft-then-stress-test sequence while irritated is not a thing that happens. What happens is I type "write a polite email about the extra revisions," get the spineless template, and put it off another day.
So they live in Super Prompts, one click from the reply box. That's most of what the library is for — not clever prompts, but the good version of a prompt I'd otherwise write badly under pressure.
If there's an email you've been carrying around for a few days, don't draft it. Run the first prompt and find out what you're actually negotiating. Mine is usually not what I thought at the top of the week.