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Automate Your Follow-Up and Master Lead Conversion with ChatGPT

You can generate personalized AI text scripts using the RELIC framework and Follow Up Boss to automate real estate lead conversion.

Part 2 of 2 of the AI Masterclass Series. Based on a conversation featuring Ylopo's Head of Growth Aaron 'Kiwi' Franklin, and Realtors-in-Residence Matt Croteau, and Chris Phares from the "AI Masterclass: How Top Ylopo Coaches Use ChatGPT to Work Smarter, Not Harder" Webinar.

Watch it Here.


Part 1 covered how Ylopo coaches use ChatGPT to create listing descriptions and community pages that rank in large language models. This part gets into the automation stuff that'll change how you follow up with leads and convert them.

Matt and Chris (both agents and Ylopo Realtors-in-Residence) walked through their techniques for using AI to handle repetitive tasks, personalize communication when you've got hundreds of people to talk to, and figure out what's working.

The RELIC framework: Your foundation for perfect prompts

Matt introduced the RELIC structure before you start throwing prompts at ChatGPT. It's simple and makes sure you get responses worth using.


R - Role: Tell ChatGPT what it's doing

"You're my copywriter" or "You're my lead conversion coach" or "You're my social media expert."


E - Explicit Instructions: Tell it exactly what you want

Be specific. Don't leave room for interpretation.

The AI is only as good as your instructions.


L - Length: How long should the response be?

400 words for an email. Two sentences for a text.

One paragraph for a summary.


I - Inspiration: Provide examples of style or voice

Show it the vibe you're going for. Reference writing styles or tones.

Give it sample content to match.


C - Context: Tell it who the content's for and why it matters

Who is the audience? What's the goal? Why does this matter?

Matt put it this way:

"Think of it as every time you go to ChatGPT, you want to tell it what role you want it to play. Whenever you're talking to AI, really treat it as it's your assistant, somebody working for you. Give it exact instructions on what you want."


Bonus prompting tips

Two more things make your prompts better.

Add to your prompts: "Ask me questions until you're 95% sure you can complete the task."

This forces ChatGPT to clarify details before it just generates something.

The output ends up way more useful because it's not guessing about what you meant.

You can also tell it "Give me a few versions with different tones" or "Break it down into a simple step-by-step plan" or "That's a lot of info. Tell me what I need to know in one paragraph."

Matt mentioned, "I always just tell it: 'Hey, break it down. Give me a step by step.' And it's really good at doing that."

The reflection part matters because sometimes ChatGPT gives you way too much.

You need to be able to say "simplify this" and get something you can actually use.

Matt started doing exactly that with his weekly deal emails. He needed the AI to take a complex task and break it down into something he could send out every Monday without thinking about it.


Strategy 3: Automated "Deal of the Week" emails using Zillow integration

A lot of agents who do well send weekly "Deal of the Week" or "Hot Properties" emails to their database. It works, but creating these emails manually eats up 1-2 hours every week.

You're searching through MLS listings, finding properties in different categories, writing descriptions, formatting the email. By the time you're done, you're exhausted and probably behind on something else.

Matt said, "What used to take me an hour or two to figure out every week, now it works in just seconds."

ChatGPT has a native Zillow integration. You don't need to set anything up.

Just tell it to search Zillow and it will.

Matt showed his complete prompt that runs automatically every Monday at 9:00 AM:

You are my copywriter and property researcher on Zillow. Each Monday at 9:00 AM, find me the top 5 listings in Orange County, CA:

  1. One pool home

  2. One golf course property

  3. One high-end single family home

  4. One standard single family home

  5. One condo

For each property, provide:

  • City

  • List price

  • Bed/bath count

  • A short, catchy 1-2 sentence description

Write a clean, professional email titled "Orange County Deals of the Week" with my brand. Format in text without any property links (no addresses or URLs in the email body).

Keep it around 400 words with two short sentences per property. Use a conversational, friendly tone that makes people want to reach out for more info.

You can tell ChatGPT: "Do this task for me every week at this time or every day at this time" and it'll do it. Matt explained that when you're not at your computer, you still get the results.

"I have it on my phone, the app. The app pops up and gives me a notification that says, 'Hey, your thing is ready.'"

You just get a push notification like, "This thing you asked me to do is done."

Each Monday morning, Matt gets an email formatted like this:

Orange County Deals of the Week

Pool Home Paradise

Lake Forest | $1,175,000 | 4 bed / 2 bath

Stunning resort-style pool home perfect for entertaining. Beautifully updated kitchen and spacious backyard oasis.

Golfer's Dream

Mission Viejo | $1,450,000 | 3 bed / 3 bath

Wake up to fairway views in this immaculate golf course property. Highly sought-after location with premium upgrades throughout.

[And so on for all 5 properties...]

The email is written in text format with no Zillow links. That's on purpose.

It forces recipients to reply if they want more information, which creates engagement and conversation opportunities.

Matt was clear: "I'm not sending out Zillow links in the email. I'm basically saying, 'Here are the deals. If you want to know more, reply back.'"

This keeps leads out of Zillow's ecosystem, creates reply opportunities, positions you as the source of information, generates actual conversations with your database.

Strategy 4: Daily automated market updates

Matt also uses scheduled ChatGPT tasks for daily mortgage rate updates:

Every day at 9:00 AM, look at Mortgage News Daily.

Give me a summary of the mortgage rates with market sentiment.

Include whether rates are up or down from yesterday and any notable trends.

"Literally every day, my ChatGPT pops up, gives me what the rates are looking like, if they're up or down from yesterday, a little bit of details on the market sentiment, and I can click into Mortgage News Daily and see what's going on," Matt explained.

You stay informed without manually checking websites every morning.

Matt mentioned using similar scheduled prompts for rental property comp tracking, new listing alerts in specific neighborhoods, price reduction notifications. Market trend summaries.

Local news digests.

He said, "I have a bunch of things where I tell it to do things at certain times a day. It's super exciting."

The scheduled tasks handle the research part. But sometimes you need more than just information.

You need the right thing to say when a lead throws an objection at you in the middle of a call.

Strategy 5: Custom GPTs for lead objection handling

You're on a call with a lead when they throw an objection at you. "We're waiting until we save more money." Or "We're not sure about the market right now."

Maybe "We need to sell our current home first."

You need to acknowledge their concern, ask discovery questions, provide education, handle the objection professionally, move toward next steps. 

Even if you've been doing this for years, you can freeze or respond poorly under pressure.

Matt built a custom GPT specifically programmed to help with objection handling.

In ChatGPT, click "Explore" under GPTs. Click the "+" button to "Create."

Name it (like "Lead Conversion Coach"). Write your instructions prompt.

Upload reference files. Save and use anytime.

Matt's Lead Conversion Coach Prompt:

You are my lead conversion coach.

For every lead objection I give you, provide:

  • A soft-touch opening line that acknowledges the objection

  • 3-5 discovery questions to understand their situation better

  • A brief educational nugget I can share with the client

  • A scripted close that moves toward next steps

  • Follow-up text and email suggestions

Try not to use fair housing sensitive language.

Base your responses on the uploaded scripting documents.

The custom GPT references documents that Matt uploaded. The Ylopo Delete Version Handbook (created by coaches Kiwi, Chris, Barry, Gabe, and Jim).

His team's internal scripting documents. Proven objection handling frameworks from conversations that led to closed deals.

Matt explained, "It explicitly looks at those files when I ask it a question and gives me lead conversion tips."

During the webinar, Matt typed a simple objection: "I have a buyer. They are waiting because they need to save money."

Within seconds, the Lead Conversion Coach responded:


Opening Line:

"I totally understand you're waiting to be ready to make a move. Smart thinking. Let me ask you a few questions..."


Discovery Questions:

  1. What does perfect timing look like for you?

  2. How long have you been thinking about buying?

  3. Have you met with a lender to see where you stand today?

  4. What if I could show you options that require less down payment than you think?

  5. Are you concerned about missing out on the right home while you're saving?

Educational Nugget:

"Most buyers assume 20% down is standard. But many qualified buyers purchase with just 3-5% down, especially first-time buyers. The real question isn't how much you have saved but whether the monthly payment works for your budget."

Scripted Close:

"Why don't we set up a quick strategy session with my preferred lender? They can show you exactly what you qualify for today and create a savings plan to help you hit your goals. What does your schedule look like this week?"


Follow-Up:

Text: "Hey [Name], just wanted to circle back on our chat about your home search timeline. Would a lender strategy session be helpful? I can intro you to someone who specializes in first-time buyers."

Email: Draft with more details about down payment assistance programs

Matt noted, "If you have no idea where to go on a lead objection, you can literally type it into a custom GPT like this and it'll help you out. This has been super useful for me and my team.

My ISAs use it a lot just to help them with objection handling."

Having scripts ready is one thing. But when you've got 265 text messages with Fred and you're staring at your phone thinking "I really should follow up but I have no idea what to say," that's where Follow Up Boss's AI becomes useful.

Strategy 6: Follow Up Boss embedded AI for personalized communication

Chris emphasized how Follow Up Boss's embedded AI messaging becomes exponentially more valuable when combined with Ylopo's platform. "This is looking at the properties they looked at, any conversations, literally going through the whole API and looking at the full details of that lead."

Because Ylopo's AI² technology, IDX feed, and Dynamic Ads (DARE) all push data into Follow Up Boss, the AI has access to every property a lead viewed on your Ylopo website. Every listing they favorited or shared.

Their search criteria and preferences. All text message conversations.

Email open and click data. Priority alert triggers from Ylopo AI.

Behavioral scoring and engagement history.

This creates a rich data profile that the AI can reference. It's not just looking at one or two data points, it's looking at everything.

Chris developed a simple but powerful prompt structure for Follow Up Boss's custom AI messaging.

The Template:

Write a [TONE DESCRIPTORS] text that [PURPOSE] and [STRUCTURE].

Keep it [DESCRIPTORS].

Example Chris Used:

Write a warm and conversational text that references something we previously discussed

and checks in on the home search progress. Shows genuine interest in their situation

and includes a simple question to encourage a response. Keep it brief and natural.

Tone Descriptors: Warm, Conversational, Professional, Friendly, Casual

Purpose: References something we discussed, Checks in on home search progress, Offers help with a specific need, Celebrates a milestone, Provides market updates

Structure: Shows genuine interest, Includes a simple question, Encourages a response, References specific property, Mentions timeline or next steps

Descriptors: Brief, Natural, Conversational, Authentic, Personal

Example 1 - Antonio (Monthly Payment Conversation):

Prompt + Antonio's lead profile

AI Output: "Hey Antonio, I hope you're doing well. I wanted to check in and see how your home search is going. Have you had a chance to discuss monthly payments with your loan officer yet?

Let me know if there's anything specific you're looking for or if you'd like to explore options together."

Example 2 - Chuck (Scheduled Showing):

Same prompt + Chuck's lead profile

AI Output: "Hey Chuck, just checking in to see how everything's going with your home search. I remember you were interested in 22 Dow Street and had a walkthrough scheduled for Saturday at 11:00 AM.

Are you feeling good about it? Let me know if you have any questions or if there's anything else I can do to help."

Chris got real about why this matters. "You know those days where you're like, 'Ah, I really should have texted Fred and I just, I'm overloaded.

I've hit that decision fatigue limit. I have 265 text messages with Fred.

I just don't know what to say'?"

"I can just go here, drop my prompt in, and let it go through all of that API. Let it go through all that information."

The Follow Up Boss AI reviews the entire conversation history. Checks recent IDX activity.

References scheduled showings. Knows the last topic discussed.

Crafts a personalized message. Takes 10 seconds instead of 10 minutes.

Chris observed, "It definitely has picked up on my tone. It kind of knows what questions I like to ask, what things I like to talk about."

Over time, the AI learns your communication style and gets better at matching your voice. The more you use it, the less editing you have to do on the outputs.

The AI's getting better at keeping conversations going. But what it can't tell you is why certain conversations turn into closings while others don't.

Strategy 7: Analyzing closed deals to replicate success

Most agents close deals but never analyze what actually worked. They move on to the next lead without understanding what created the initial engagement, which touchpoints were critical, what could have killed the deal, how they can replicate this again.

Chris emphasized, "This is the real application example of everything that we learned."

Chris created an extensive prompt (available in the Ylopo Success Community) that analyzes closed deals to extract replicable lessons. Not just celebrating the win but understanding why you won so you can do it again.

Go to the closed lead in Follow Up Boss. Use Command+P (Mac) or Control+P (PC).

Save as PDF. This captures the complete conversation history, property views, timeline, notes.

Open a new ChatGPT conversation. Attach the PDF file.

Paste in Chris's analysis prompt.

The AI provides: What You Did Well (specific actions that moved the deal forward), What Would Have Killed the Deal (moments that could have gone wrong), Timeline Overview (journey from lead to close), Behavioral Signals (key moments of high intent), Communication Patterns (which messages got responses). Critical Touchpoints (the make-or-break interactions).

Technology Impact (how Ylopo features contributed). Objections Handled (how concerns were addressed).

Speed and Timing (response time impact). Replicable Lessons (exact actions to repeat).

Chris demonstrated with his recent closing. The AI analyzed the entire lead journey and identified these replicable lessons:

  1. Reply within 15 minutes when a priority alert fires from Ylopo AI

  2. Don't just say "Can I help?" Ask: "That property is vacant. Want to see it at 4:00 PM today?"

  3. Use Ylopo's dynamic listing alert links from your site

  4. Capitalize on high-intent moments with same-day appointments

  5. Acknowledge pre-approval, down payment savings, etc.

The AI's analysis revealed the exact sequence. Marilyn viewed a house 4 times on Chris's Ylopo IDX website.

Ylopo Priority Alert fired (the property received multiple views). Ylopo AI² sent an automated text: "I see you're interested in this property..."

Chris received the alert and knew exactly when to jump in.

Chris offered same-day showing: "That property is vacant. Want to pop over at 4?"

Marilyn said yes. Showed the home that Sunday afternoon.

Wrote an offer. Closed the deal.

Chris explained, "All the communication up to this point led us to really dialing in that search alert. The search alert goes out.

The Ylopo Priority tag hits. AI Squared primed me to jump in on the conversation.

All I had to do was jump in and say, 'Hey, that property is vacant. You want to go look at it?'"

Chris noted, "After five or six closings, you can take all of these outputs and kind of put them together and have a conversation with ChatGPT about it."

Imagine having data from 5-10 closed deals showing which Ylopo features contributed most often, optimal response time windows, most effective messages. Objection handling approaches that work for you specifically.

Common patterns in your wins.

You can then ask ChatGPT to create a personalized playbook based on your actual results. Not someone else's theory but your results.

Chris shared one more thing about using ChatGPT effectively: "When you start with a well-engineered prompt, after your output is done, you can switch into this conversational tone."

If the AI gives you too much information, just say "That's a lot of info. Tell me what I need to know in one paragraph" or "Break this down into 5 bullet points" or "Give me the three most important actions" or "Explain this like I'm teaching it to my ISA."

Chris emphasized, "We want to be realtors who are partnered with AI to understand what's working and what's not working so we can pivot quickly."

Though honestly, pivoting quickly only works if ChatGPT actually understands how you communicate in the first place.

Customizing ChatGPT for success

Both Kiwi and Matt shared some personalization tips that make using ChatGPT feel less robotic and more like working with an actual assistant.

Settings > Personalization > Name. Matt's ChatGPT calls him "Kiwi."

Makes interactions feel more natural. Creates a friendlier experience.

Small thing, but it changes the dynamic.

Settings > Personalization > Custom Instructions. Add this power prompt: "If I give a brief description or answer that limits your ability to give the best answer, always ask a follow-up question so you can get what you need."

Or this one: "Ask me clarifying questions until you're 95% confident you can complete the task successfully."

You can tell ChatGPT to be chatty, witty, sarcastic, professional, conversational, direct and brief.

Matt noted, "Just a little bit of personalization options available to you guys. So take advantage of those if you'd like."

The personalization stuff matters more than you'd think because once ChatGPT knows your style, everything else (the deal emails, the objection handling, the follow-ups, the deal analysis) becomes way more useful.


Key takeaways from Part 2

Use ChatGPT's Zillow integration for automated deal emails. Schedule tasks to run daily or weekly while you sleep.

Create morning briefings for market updates and rates. Let AI handle repetitive research tasks.

The stuff that drains your energy but has to get done anyway, automate it.

Build custom GPTs loaded with your team's best scripts. Upload the Ylopo Delete Version Handbook for objection handling.

Use the RELIC structure for better prompts. Treat ChatGPT as your assistant and give explicit instructions.

The clearer you are, the better the output.

Use Follow Up Boss's embedded AI with your Ylopo data. Use Chris's template: Tone + Purpose + Structure + Descriptors.

Let AI review entire lead histories to craft personalized messages. Combat decision fatigue with AI-generated communication.

Those days when you just can't think of what to say, let the AI handle it.

Analyze closed deals to identify replicable patterns. Look for Ylopo feature contributions (Priority Alerts, AI², DARE).

Build your personalized playbook from actual results. Stay conversational with AI after initial output.

Not just about closing one deal but understanding how to close more deals the same way.

These individual pieces work fine on their own, but they work better when everything connects.


The complete Ylopo + AI ecosystem

  • Content Layer from Part 1: ChatGPT-optimized listing descriptions, SEO-rich community pages, large language model visibility.

  • Automation Layer from Part 2: scheduled market updates, automated deal emails, custom GPT objection handling.

  • Ylopo Platform Integration: AI² Text and Voice engagement, Priority Alert triggers, Dynamic Ads (DARE), IDX website with behavioral tracking, Follow Up Boss CRM sync.

  • Human Touch (which is you): jump in on high-intent moments, close deals AI has warmed up, build relationships, provide expert guidance.

Chris cautioned,

"We don't want to become people who have this AI psychosis as realtors and get out of touch with the real world. But we want to be realtors who are partnered with AI to understand what's working and what's not working so we can pivot quickly."

Join the Ylopo Success Community

All prompts, templates, and frameworks shared in this two-part masterclass are available for free in the Ylopo Success Community on Facebook.

Join the Ylopo Success Community Facebook group. Click on "Files."

Look for "AI Webinar Prompts," "Five Things Every Home Buyer Wants to Know," "RELIC Framework Guide," Deal Analysis Prompt, Follow Up Boss AI Framework.

Want hands-on help putting these into practice?

  • Time: 9:00 AM Pacific, every weekday.

  • Special Focus Fridays: "Follow-Up Friday" typically covers CRM and AI stuff.

  • Format: Live Q&A, prompt writing, problem-solving.

  • Access: Links available in the Ylopo Success Community.

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