There's a pile. Everybody's got one.
The quote you sent 3 weeks ago that never got answered. The invoice that's 40 days late. The customer who asked a question you didn't know how to answer so you left it. The good client who went quiet and you're not sure why.
None of these are hard emails. They're just uncomfortable, so they sit there, and every day they sit there they get more uncomfortable to send.
Here's how to clear the whole pile in about an hour.
Step 1: Find them, because you don't remember them all
If you've got Claude connected to your email, it can go and look. That's a 90-second setup and it's here.
Go through my sent mail from the last 90 days.
Find every email where I sent a quote, a price, a proposal, or
answered a question about buying something, and where nobody
ever replied.
For each one: who, when, what it was about, and what the last
thing said was.
Sort oldest first.You will find more than you think. Everybody does. These aren't people who said no. They're people who said nothing, which is not the same thing and is worth a lot more money.
If you can't connect your email yet, just export or paste in the threads you already know about. Works the same.
Step 2: The follow-up that doesn't sound desperate
The reason follow-ups don't get sent is that every draft in your head sounds either pushy or pathetic. Here's the frame that avoids both:
Write a follow-up email for this thread.
[paste the original thread]
Rules:
- Under 80 words
- No "just checking in," no "circling back," no "bumping this"
- No apologizing for emailing
- Reference the specific thing we actually talked about
- Give them an easy way to say no without it being awkward
- End with one clear question they can answer in one line
Sound like a person who's busy and fine either way, not
somebody who needs this.That "easy way to say no" instruction is what makes people reply. Somebody who's been ignoring you for 3 weeks feels guilty. Give them the exit and half of them will tell you where things actually stand instead.
Rest of it's yours
Drop your email and the whole thing opens up right here. No waiting on a confirmation, no download, nothing to install.
You'll also get the new ones as I make them. Leave whenever, no hard feelings.
Step 3: The money one
Late invoices are the worst pile because the emotion gets in the way. Take the emotion out:
Write an email chasing an unpaid invoice.
Details: [amount], sent [date], now [X] days overdue.
Relationship: [good customer / new / it's been rocky]
Rules:
- Short, factual, no anger, no groveling
- State the amount and the date plainly
- Assume it's an oversight, because usually it is
- Make it stupidly easy to pay: say exactly how
- One clear next step
Give me 2 versions: friendly nudge, and firmer if that gets
ignored.Ask for both up front. Then in 10 days when nothing's happened, version 2 is already written and you don't have to sit down and get worked up about it again.
Step 4: The awkward one
The one you've genuinely been avoiding. Price increase, a mistake you made, saying no to something, ending a relationship.
I need to send an uncomfortable email and I keep putting it off.
Situation: [what's actually going on, plainly]
What I need them to understand: [the thing]
What I'm worried about: [the actual worry]
Write it. Direct but not cold. Don't over-apologize, don't pad
it with 3 paragraphs of warm-up. Say the thing in the first 2
sentences.
Then tell me the one line most likely to cause a bad reaction,
and give me an alternative for it.That last part is the useful bit. It'll point at the sentence you'd have regretted.
Step 5: The ones you write 40 times a year
Stop rewriting these from scratch. Build them once:
I write roughly the same email over and over for these:
1. [e.g. someone asks for a quote]
2. [e.g. confirming an appointment]
3. [e.g. following up after finishing a job]
4. [e.g. someone asks about pricing before I've seen the work]
For each one write me a template with [BRACKETS] where the
specific details go.
Short. Sound like a person. No corporate filler. Each one
should take me 30 seconds to fill in.Save those somewhere you can grab them. That's an hour of work that gives you back 10 minutes a day forever.
The two rules
Read every one before it sends. Especially anything about money or anything awkward. It doesn't know the history between you and that person, the thing that happened in March, or that they're going through something. You do.
Never let it invent facts. If it wrote a date, an amount, or a promise you didn't give it, that's not real and it's going out under your name. Check the numbers every single time.
Why this one's worth doing first
Most AI stuff pays off eventually. This one pays off this week, because the pile already exists and it's already full of money that's just sitting there waiting for somebody to send a 60-word email.
Start with the oldest unanswered quote. That's the one that's been bothering you longest, and it's probably still open.