Tuesdays are 3 AI updates, one hot take, one action. Weekends are 1 practical real estate agent workflow.

Most of your next year of business is sitting in people you already know. The trick is reaching out without it eating a Saturday, especially when there is World Cup soccer to watch!

Last weekend you built a Voice Guide so AI writes like you. Today you put that to work on your sphere and get Claude Cowork to write the emails straight into your Gmail every two weeks. This was the part of my recent workshop that made people’s eyes light up.

AI won't email your clients for you, and it shouldn't. What it does is kill the blank screen: it creates drafts that sound like you ready for you to just push send while it’s halftime in the latest game.

Before Cowork can write anything personal, it needs to know who these people are. Open a spreadsheet and give each past client and sphere contact a row with a few basics: name, email, neighborhood, what you worked on together and roughly when, and one line about the relationship ("bought the Tudor on Elm in 2022, two kids and a golden retriever"). Pull it from your CRM or your closed-deal records if you have them, or work from memory. Rough is fine. Even five lines of context per person is enough for AI to write something that sounds like you actually know them, because you do.

Open Cowork, connect your Gmail, and start a new task. Point it at the spreadsheet you just made and at your Voice Guide (if you saved the Voice Guide as a skill, it's already loaded). Then paste this:

"Using my contact list, find the past clients and sphere contacts I haven't emailed in 90 days. For each one, write a short, warm, personal check-in email and save it as a draft in my Gmail. No sales pitch, no 'let me know if you know anyone buying or selling.' Just a real note from someone who remembers them. Use the relationship notes for who they are and my Voice Guide for how I write."

The first batch may not be exactly how you want them to sound. Push back with this:

"These are too safe. Make each one reference something specific to that person or that deal. If someone bought a fixer-upper, ask how the renovation turned out. If someone relocated for a job, ask how the new city is treating them. I'd rather send 10 that feel real than 30 that feel like a mail merge."

An email that mentions the kitchen they were going to redo lands completely differently than "Hope you're doing well!" The detail is what makes someone write back, and your Voice Guide is what keeps it in your phrasing instead of a customer-service tone.

This is the move from the workshop. Tell Cowork: "Run this every two weeks and surface only the contacts I haven't emailed in 90 days, so I'm never writing the same person too often." Now the task wakes up on its own, pulls the next slice of your sphere, and leaves a fresh batch of drafts sitting in your Gmail. You open five at a time, change a word so it sounds like today's version of you, and send them between showings or while you wait on a buyer who's running late. Over a time period, your whole database gets a real, personal note, and you never once sat down for a "marketing afternoon" you weren’t gonna schedule anyway.

When someone writes back, that's your cue to do the one thing AI can't: be a person. Call them, grab a coffee. The email reopens the door, and you walk through it.

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This was one of the exercises that got the biggest reaction at my June 6 Claude Cowork training. Here was one of my favorite quotes that drove home the difference between my trainings and the other random videos out there teaching you AI:

“This class blew me away. I tried learning piece by piece from online creators and other cheap online classes. This was so specific to my business and thats what I wanted. I once I see how it can help here, I can then be more creative. THANK YOU MATT!! You are an Great Instructor!!

— Karen Hurst, Compass

I'm doing a live version of this workshop at the Compass SoCal Luxury Summit in Orange County, August 10–12. If you're going to be there and want more information about the session, just reply directly to this email with SUMMIT and I’ll send you the details.

-Matt