📧 AI For People Who Hate Writing Emails

Here’s something I’ve noticed teaching this stuff to a lot of self-declared email-haters: nobody actually hates email. The routine stuff - confirming times, sending attachments, “sounds good, see you Tuesday” - takes seconds and bothers no one. What people hate is about five specific emails. The ones that sit in your head, generating dread out of all proportion to their word count.

I call them the Dread Five: the reply you’ve put off, the polite chase, the saying-no, the asking-for-money, and the difficult-news one. Each has the same anatomy - the words are easy, the feelings are hard - which is exactly why AI is so good at them. Claude doesn’t feel awkward. It’ll cheerfully write the sentence you’ve been circling for a fortnight, and you just check it sounds right and press send.

Below: one full prompt for each of the five, plus a two-minute habit that stops the dread pile forming in the first place.

1. The reply you’ve put off

What it is: the email that arrived ages ago, deserved a proper answer, didn’t get one, and now carries a layer of shame that makes it harder every day. The maths of dread: the longer you leave it, the more the reply feels like it has to be brilliant to justify the wait. (It doesn’t. It just has to arrive.)

Nick this one:

I'm pasting an email I should have replied to [how long] ago. Draft a reply that: briefly acknowledges the delay ONCE, without grovelling or a big excuse, then simply answers the email properly as if the delay never happened. Warm, direct, no self-flagellation. Here's the email: [PASTE] And here's roughly what I want to say: [YOUR ROUGH ANSWER, bullet points fine]

The non-obvious bit: “acknowledges the delay ONCE” is doing serious work. Left to itself, an apologetic draft will apologise in the first line, the middle and the sign-off, which reads as more awkward than the delay ever was. One sorry, then business as usual.

2. The polite chase

What it is: they haven’t replied, haven’t delivered, haven’t confirmed - and you need to nudge without becoming A Nag.

Nick this one:

Write a short, friendly chase-up to [WHO] about [WHAT], which I last raised on [ROUGH DATE]. Assume they're busy rather than ignoring me. No passive-aggression, no "as per my last email", no fake breeziness. Remind them of the one thing I need and the date it's needed by, and end with a question they can answer from their phone in one line.

The non-obvious bit: the one-line-answer ending is why this gets replies when your last chase didn’t. People clear easy messages and postpone hard ones - so make yours the easy one in their pile.

3. The saying-no

What it is: declining the invitation, the request, the “quick favour” that isn’t quick. Most of us either say yes out of panic or write four paragraphs of apology wrapped around a maybe.

Nick this one:

Help me say no to this: [PASTE OR DESCRIBE THE REQUEST]. My actual reason: [BE HONEST - no time / can't afford it / don't want to]. Draft a reply that says no clearly in the first two sentences, doesn't over-explain, doesn't leave a loophole they can push on, and stays genuinely warm. [OPTIONAL: I would/wouldn't like to offer an alternative, such as: ...]

The non-obvious bit: “doesn’t leave a loophole” matters most. Soft phrases like “not right now” or “probably can’t” feel kinder to write, but they just schedule a second, harder no for next month. A clear no is a kindness to both of you.

4. The asking-for-money

What it is: the unpaid invoice, the overdue rent, the mate who owes you for the tickets. The hardest of the five for most people, because money plus relationship equals maximum squirm.

Worked example, so you can see what good input looks like. Say you run a small gardening business, a customer owes £180 from three weeks ago, they’re normally lovely, and you’ve already sent one gentle reminder. You’d fill it in like this:

Nick this one, filled in as our gardener:

Draft a payment chase email. The situation: I run a small gardening business. [CUSTOMER FIRST NAME] owes £180 for work done on [DATE], now 3 weeks overdue. I sent one friendly reminder on [DATE] - no reply. They've always paid before and I want to keep them as a customer. Write a firm but warm email that: restates the amount and invoice date, asks for payment by a specific date one week from now, offers to resend the invoice or take payment another way, and mentions I'd rather sort this with a quick reply than keep sending reminders. Not stroppy, not apologetic - just a professional sorting a normal thing.

The non-obvious bit: that last phrase - “a professional sorting a normal thing” - is the tone secret for all money emails. Late payment is admin, not betrayal, and the moment your email treats it as routine, it stops feeling confrontational to send. Firm dates beat vague hopes: “by Friday the 12th” gets you paid, “whenever you get a chance” gets you a fourth reminder.

5. The difficult-news one

What it is: the price rise, the cancellation, the “we’ve made a mistake”, the “I’m leaving”. Any email where the news itself is the problem.

Nick this one:

I need to deliver some unwelcome news by email. The news: [WHAT'S HAPPENING]. The reason: [WHY, honestly]. Who it's going to: [WHO, and what they're like]. Draft an email that: gets to the news within the first two sentences, gives the honest reason briefly without ten justifications, says clearly what happens next or what I'm doing about it, and doesn't ask them to make me feel better about it. Calm, human, no corporate padding.

The non-obvious bit: “doesn’t ask them to make me feel better” - drafts of difficult news have a sneaky habit of fishing for reassurance (“I hope you understand!”, “I feel awful about this!”). That hands the recipient your feelings to manage on top of the news. Deliver it clean; they’ll respect you more.

The two-minute triage habit

The Dread Five handles the hard ones. This habit stops the pile forming. Once a day, copy the senders and subject lines of everything unanswered in your inbox (no need to paste the emails themselves) and ask:

Nick this one:

Here's what's sitting unanswered in my inbox: [PASTE SENDERS + SUBJECT LINES]. Sort them into: needs a real reply today, can be answered in one line (suggest the line), can wait until [DAY], and needs no reply at all. Be ruthless about the last category.

Two minutes, and your inbox goes from a wall of guilt to a short list with instructions. The one-line suggestions alone usually clear half of it.

A dose of honesty

It won’t press send - the deciding stays yours, and you should always read a draft aloud once before it goes (your ear catches what your eye forgives). It can’t know facts you don’t paste in, so the quality of the money email depends on you including the amount and the dates. And a few emails shouldn’t be emails at all: if it’s the third round of a misunderstanding, that’s a phone call.

One more thing: these prompts get the job done, but they’ll do it in a fairly neutral voice. That’s deliberate - this guide is about the jobs, not the sound of you. The voice part has its own guide, linked below.

The one to start with tonight

Find the oldest unanswered email in your inbox - yes, that one - and feed it to prompt number one right now. The two-week email takes the same ninety seconds as the two-day one. You’ll wonder why you carried it around for so long.

Go on, off you pop… and when the drafts read a bit generic, Teach AI To Write Like You is the fifteen-minute fix.