How to Use a ChatGPT Prompt to Convert Expired Listing Leads Into Clients
If you've ever called an expired listing lead, you know the feeling. You go through the conversation, you think it went well, you promise to send over a CMA — and then you spend the next 20 minutes staring at a blank email trying to figure out what to say.
That's exactly the problem a well-designed ChatGPT prompt solves.
In this post, Real Estate Digital Marketer and AI Strategist Chris Scott is going to walk you through a complete, step-by-step system for prospecting expired listing leads — from acquiring the list, to the phone call, to the AI-powered follow-up email. This is a practical workflow you can implement today, whether you've used AI before or not.
What Is an Expired Listing and Why Should You Care?
An expired listing is a property that was listed for sale on the MLS but did not sell before the listing agreement ended. The seller is often frustrated, sometimes skeptical of agents, and — if they still want to sell — highly motivated.
That makes expired listings one of the most valuable prospecting opportunities in real estate.
The challenge is standing out. Most expired listing owners get called repeatedly the moment their listing expires. To break through, you need a process that's professional, consultative, and efficient.
Step 1: Acquire Your Expired Listing Leads
Before you can call anyone, you need a list. There are several reliable sources for expired listing leads:
RedX — One of the most widely used tools for prospecting expired listings, FSBOs, and geographic farm leads.
Vulcan7 — Another popular option that provides phone numbers, emails, and other contact data.
Your MLS — In many markets, you can pull expired listings directly from the MLS with your own search filters.
Pro tip: Don't overlook older expired listings. Listings that have been off the market for 30 days or more tend to receive far fewer calls than fresh expired listings. Less competition means a warmer conversation.
Step 2: Call Using a Proven Script
Here's where most agents make their first mistake: they wing the call.
A structured script isn't about sounding robotic. It's about having a conversation that's psychologically designed to lower resistance, uncover motivation, and create a natural next step. Here's the script framework to use:
"Hey [Name], this is [Your Name]. I'm a Realtor. Now, before you hang up, I just wanted to ask a quick question about the home for sale on [Address]. Would that be okay?"
"I saw that it came off the market — did you sell it privately, or is it still available?"
Based on their response:
"You know, I'm kind of surprised it didn't sell. I'm curious — when your agent was giving you weekly updates, did they share feedback or specific strategies to address why it hadn't sold?"
"Do you mind if I ask — if the numbers made sense, would you still be interested in selling?"
There's real psychology embedded in this script. The opening phrase "before you hang up" is a pattern interrupt — it acknowledges the awkward reality of a cold call while buying you a few extra seconds. The questions are consultative, not pushy. And the final question qualifies motivation without pressure.
Step 3: Offer a CMA and Set the Next Step
Once you've had the conversation and identified a motivated seller, the goal is simple: offer to send an updated Comparative Market Analysis (CMA) and set a clear expectation for what comes next.
Here's how to close the call:
"I'd love to pull together an updated market analysis for you so you can see where the numbers actually stand. Can I send that over to your email? What's the best address for you?"
Confirm the email by spelling it back to them. Then set the expectation:
"I'll send that over shortly. Take a look at the numbers, and if they make sense, we can have a quick conversation about a new strategy to get it sold."
This keeps the door open without pressure. The CMA does the selling for you.
Step 4: Pull the CMA from RPR (or Your Preferred Tool)
Once you're off the phone, it's time to pull the CMA. The tool used in this workflow is RPR (Realtors Property Resource) — a free tool available to all NAR members that generates professional, data-rich CMAs.
Other tools that work well for this include:
Cloud CMA — Polished, client-ready reports
MoxiPresent — Strong visual presentation
Your MLS's built-in CMA tool
Once your CMA is ready, download it as a PDF. You're going to use it in the next step.
Step 5: Use ChatGPT to Write a Personalized Follow-Up Email
This is where AI earns its place in your workflow.
Instead of writing the follow-up email from scratch — or sending a generic template — you're going to use a specific ChatGPT prompt that generates a personalized, professional email based on the actual data in your CMA.
Here's how it works:
Open ChatGPT (ChatGPT.com or the ChatGPT app)
Copy and paste the prompt below
Drag and drop your CMA PDF directly into the chat window
Hit send
ChatGPT will read the data in your CMA and generate a fully structured follow-up email — with the prospect's name, property address, pricing snapshot, comparable sales, and a clear call to action.
The ChatGPT Prompt (Copy and Use This)
You are an expert real estate agent. Your job is to draft a personalized follow-up email to an expired listing prospect. The agent already called this prospect, had a conversation, and promised to send an updated CMA.
Use the attached CMA report to extract relevant data for the email. Structure the email as follows:
1. Personalized opening that references the earlier conversation 2. A brief empathetic statement about why homes sometimes don't sell 3. A pricing snapshot section using data from the CMA 4. A property highlights section 5. A comparison table of nearby sold homes 6. A "here's what stood out to me" insight 7. A clear closing that references the CMA being attached and invites a conversation if the numbers make sense
Tone: Professional but warm. Brief and to the point. Do not include unnecessary language. The prospect's time is valuable.
What the Output Looks Like
When you run this prompt with your CMA attached, ChatGPT generates something like this:
Subject: Updated Market Analysis for [Address]
Gary, thank you again for taking the time to speak with me earlier. As promised, I've attached the updated market analysis for [address] so you can review the numbers and see how your property compares to nearby homes.
I understand it can be frustrating when a home doesn't sell the first time around. Often it comes down to a combination of pricing, positioning, and timing in the market.
The email then includes a pricing snapshot, property highlights, a comparison table, and a closing that reinforces the next step — all built from the actual data in your CMA.
No editing required. The output is production-ready because the prompt specifies the structure, tone, and format in advance.
Why the Prompt Structure Matters
Here's the key insight most agents miss when they start using AI: vague prompts produce vague results.
If you ask ChatGPT to "write a follow-up email to an expired listing," you'll get something generic that sounds like every other AI email. That's not useful.
What makes this prompt work is that it specifies:
The role (expert real estate agent)
The context (already spoke with prospect, promised a CMA)
The data source (attached CMA report)
The output structure (every section of the email is defined)
The tone (professional, warm, brief)
The rules (no unnecessary language, respect the prospect's time)
When you constrain the output, you get consistency. And consistency is what allows you to scale this workflow across dozens of expired listing leads without spending hours writing emails.
Putting It All Together: The Full Workflow
Here's the complete system at a glance:
Acquire leads — Use RedX, Vulcan7, or your MLS
Call prospects — Use the script above to lower resistance and qualify motivation
Offer a CMA — Get their email, confirm it, set the next-step expectation
Pull the CMA — Use RPR, Cloud CMA, or your MLS tool
Run the ChatGPT prompt — Upload the CMA and generate the follow-up email
Send the email — Review quickly, attach the CMA PDF, and send
Total time from end of call to email sent: under 10 minutes.
Final Thought
Most agents treat expired listings like a numbers game — call enough people, eventually someone says yes. That's not a system. That's grinding.
What this workflow creates is a repeatable, professional process that gives every expired listing prospect a consistent, high-quality experience. The phone call is structured. The follow-up is personalized. The CMA does the heavy lifting.
AI doesn't replace the human element of this business. It removes the friction so you can show up better.
Frequently Asked Questions
Q: Do I need a paid ChatGPT account to use this? ChatGPT's free tier (GPT-3.5) works for basic prompts, but to upload a PDF like a CMA report, you'll need ChatGPT Plus (GPT-4), which is $20/month. The ability to read and extract data from uploaded documents is a GPT-4 feature.
Q: What if I don't use RPR? Can I still use this prompt? Yes. Any CMA tool that generates a PDF will work — Cloud CMA, MoxiPresent, your MLS's built-in tool, or even a manually formatted report. As long as the PDF contains the property data and comparable sales, ChatGPT can extract the information.
Q: How do I get expired listing leads if I don't want to pay for a service? Check your MLS first. Many MLS systems allow you to search for expired listings directly. You won't always have phone numbers, but you can often find contact info through public records, tax databases, or tools like BeenVerified.
Q: Is it okay to call expired listing owners? Are there legal restrictions? Yes, you can call expired listing owners, but you must comply with the National Do Not Call Registry. Always scrub your list against the DNC registry before calling. Services like RedX and Vulcan7 typically include DNC scrubbing as part of their service.
Q: What if the seller is still frustrated or hostile on the call? That's normal. Expired listing sellers are often disappointed from their previous experience. The script above is designed to acknowledge that frustration rather than ignore it. The question about whether their previous agent shared feedback and strategies validates their experience without criticizing the other agent directly.
Q: How do I know if the numbers "make sense" for the seller? That's what the CMA conversation is for. Your job on the initial call isn't to sell them on a price — it's to create enough curiosity that they're willing to look at the numbers. The CMA and the follow-up email do the work of establishing your credibility and setting realistic expectations.
Q: Can I use this same prompt for other lead types, like FSBOs? Absolutely. With minor adjustments to the context section of the prompt (changing "expired listing prospect" to "FSBO seller" and updating the email structure accordingly), this same approach works for FSBOs, geographic farm prospects, and other lead categories.
