On Tuesday I shared a stat from Leonard Steinberg that landed hard: 67% of online inquiries to agents go unanswered. Average response time is over 8 hours.
I called it the Capacity Paradox. Agents are using AI. They're saving time. But they're still dropping the ball on what generates the most revenue: staying in touch with the people who already know and trust them.
Today I'm giving you a repeatable 15-minute workflow you can run every week for the rest of the year.
Step 1: Pull Your 2023 Deal List
Go into your transaction records and pull every person you closed a deal with in 2023. Buyers and sellers. Why 2023? These clients are two to three years out from their transaction. Far enough that most agents have completely lost touch. Close enough that the relationship is still real. And right in the window where life changes start happening: new jobs, growing families, relocations, downsizing parents.
If you don't have a clean list of your 2023 closings, that's its own problem worth fixing this weekend (AI can help). If you don’t, pick the first 5 and move to Step 2.
Step 2. Let AI do the research
Open your AI tool of choice and paste this. I tested this exact prompt in Claude Opus 4.6, ChatGPT 5.2, and Gemini this week and all three delivered impressive research results. Use whichever you're most comfortable with, though enabling web search will get you the sharpest neighborhood intel:
I'm reconnecting with clients in this list that I closed deals with in 2023. For each person research what they've been up to professionally and personally. Then look up what's happening right now in their neighborhood: recent sales, new developments, price shifts, local news. Give me a short summary for each person and one specific thing I could mention in a check-in that would show I'm paying attention.
The neighborhood research is what separates this from a generic check-in. You're not reaching out because you want something. You're reaching out because you noticed something and thought of them.
Step 3. Draft the messages
Take the research from Step 2 and paste it back in with this:
Write a short personal check-in email for each of these past clients. Open warmly. Mention something specific I’m genuinely impressed by or happy for them about. Keep it conversational, like a friend who's been paying attention. At the very end, drop one casual line about something happening in their neighborhood right now. Make it feel like a passing thought, not a pitch. No sales angle. No 'let me know if you're thinking about selling.' Just a human being who’s grateful for them.
Everything you need to reconnect in under a minute. Read each one. Edit anything that doesn't sound like you. Send the ones that feel right. Bonus if you’re using Claude and have connected your gmail you can ask it to prep the email and leave them in your Gmail drafts folder.
Step 4. Make it a weekly habit
Today you start with 2023. Next you pull 2022 closings. As far back as you have the data - you get the idea. Within a few weeks you'll have personally reconnected with every client you've closed in the last ten years. Three ways to make it stick:
Calendar block. 15-minute recurring event every Friday morning. Call it "Closed deal reconnect" When it fires, run Steps 1 through 3.
ChatGPT Scheduled Task. If you're on ChatGPT Plus, set a scheduled task for every Friday at 8 am: "Remind me to pull my past clients I haven't contacted recently, research what they've been up to, and draft personal check-in sms and emails." It pings you with the communication already ready to go.
The method doesn't matter. The consistency does.
AI doesn't replace the relationship. It removes the friction that keeps you from maintaining it. One agent in a survey of 400 from last year put it plainly: "Simplifying follow-up would be amazing. That is my biggest issue. Not following up and letting the next agent across town take my leads because they did."
The research takes 5 minutes instead of 45. The drafts take 1 minute instead of 20. And the message that gets a reply isn't the one with market data. It's the one that makes someone feel seen.
-Matt
This is an example of the core workflows we build together in my AI Marketing Accelerator. The next cohort starts March 23 and runs through April 3. Five 90-minute sessions where you build listing content workflows, world-class communication programs, and the 12-month sphere automation that was the number one request from 400 agents I surveyed last year.
