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Win Back Customers Who Haven't Called in 6 Months (Free AI Prompts)

By Hometown Bots · Written with June (our AI assistant), reviewed by our founder · · 9 min read

Your old customers already know you. One friendly email can bring some of them back, and tell you exactly why the rest left.

Getting a brand-new customer is hard work. But you probably have a list of people who already paid you once and then went quiet. This post shows you how to reach out to them in one afternoon, with free AI doing the writing.

Never used AI before? That's fine. Every step is spelled out.

Time: about 1 hour the first time.

What you'll need

  • A computer with internet (a phone works too, but a computer is easier)
  • Your business email (we use Gmail in the steps) or your invoices or customer spreadsheet
  • A free ChatGPT account at chatgpt.com (we show you how below)

Two words you'll see

AI chat: a website where you type a question and a computer program types back an answer.

Prompt: the message you type to the AI. You can copy ours and paste it in.

Step 1: Find customers who went quiet

If you use Gmail:

  1. Open Gmail.
  2. Click the search box at the top.
  3. Type this and press Enter: in:sent older_than:6m newer_than:2y
  4. This shows emails you sent between 6 months and 2 years ago. Look for customers you have not heard from since.
  5. Write their names and email addresses on a notepad or in a new spreadsheet (Google Sheets is free at sheets.google.com).

If you use invoices or a spreadsheet:

  1. Open your invoice program (like QuickBooks, Square or Wave) or your customer spreadsheet.
  2. Sort by last job date or last invoice date. Most programs let you click the column title to sort.
  3. Copy everyone whose last job was more than 6 months ago.

Make a simple list with 4 columns: Name, Email, Last job, What we did. Start with 10 to 20 people. You can always do more later.

Step 2: Have AI write a friendly check-in email

First time? Make a free ChatGPT account (you only do this once):

  • Open your web browser (Chrome, Safari or Edge). Click the address bar at the top, type chatgpt.com and press Enter.
  • Click Sign up. Use your email, or "Continue with Google" if you have Gmail.
  • If it asks you to pick a plan, pick the free one. If it asks for a code, check your email for it.

Backups if ChatGPT is busy: Claude (free at claude.ai) or Gemini (free at gemini.google.com). The same prompts work in both.

  1. Go to chatgpt.com and sign in.
  2. Click in the message box at the bottom.
  3. Copy this prompt, paste it in, and fill in the parts in [brackets]:

I run a small [type of business] business. Write a short, friendly check-in email to a past customer I haven't heard from in over 6 months. - Customer name: [name] - Last job: [what we did and roughly when] - Keep it under 100 words, warm, and not salesy. - Thank them for their past business. - Ask one easy question: is there anything we could have done better, or anything they need help with now? - Sign it from [your first name], [business name]. Give me 2 short subject line options too.

  1. Press Enter. Read the answer.
  2. Don't like it? Type: Make it shorter and more casual. and press Enter.

Always read it before sending. Fix anything that isn't true or doesn't sound like you.

Example only (not a real customer):

Subject: Checking in from Main Street Painting

Hi Linda, it's been a while since we painted your living room last spring, and I wanted to say thanks again. Is there anything we could have done better? And if anything new is on your list, I'm happy to help. — Sam, Main Street Painting

Step 3: Send it

  1. In Gmail, click Compose (top left).
  2. Put the customer's email in the To box.
  3. Paste the subject line and the email.
  4. Change the name and job details for each person.
  5. Click Send.

Tip: Send each email one at a time, to one person. Don't put everyone in one email. It feels more personal, and it keeps your customers' emails private.

Step 4: Collect the replies

  1. Each time someone replies, copy their answer.
  2. Paste it into a new column called Reply in your list.
  3. Answer every reply within a day. If someone wants new work, call them.
  4. Wait about a week, then move on to Step 5.

Remove names and phone numbers before pasting replies into AI. Just keep the words of what they said.

Step 5: Ask AI why people left

  1. Open a new chat in ChatGPT.
  2. Copy this prompt and paste it in. Then paste all the replies under it:

``` Here are replies from past customers of my small [type of business] business. I asked why they hadn't called in a while. 1. Group the reasons they gave into themes. 2. For each theme, say how many replies mentioned it. 3. Quote one short line from a reply for each theme. 4. Only use what the replies actually say. Don't guess.

Replies: [paste replies here] ```

  1. Press Enter and read the summary.

Step 6: Build a 5-step plan to fix it

In the same chat, paste this:

Based on these themes, give me a simple 5-step plan to keep more customers coming back. I'm a small business owner with little time and a small budget. For each step, tell me: - what to do - how long it takes - one thing I can do this week Keep it in plain words.

Example only (made-up output to show the shape):

  1. Send a thank-you text the day after every job. (5 minutes per job)
  2. Put a reminder in your calendar to check in 3 months later. ...

Pick one step and do it this week.

Common worries

"Isn't this pushy?" Not if you keep it short, thank them, and ask a real question. You're checking in, not selling.

"What if nobody replies?" That happens. Try again in a few months with a different subject line. Some people will still remember you when they need help.

"Can AI send these for me?" You can set that up later, but start by sending them yourself. You'll learn more from reading the replies.

Your next step

Make your list of 10 customers today. Send the first email tomorrow.

Written by June, the AI helper at Hometown Bots, for a small business owner who wanted to share what works.