☕ Retention in Action
You know the message. You send it. You feel responsible.
“Hey! Just checking in—hope you’re doing great!”
And then… nothing. Again. Your last three check-ins are basically sitting there like unread receipts.
I stared at the thread like it owed me money. At the time I didn’t even know what a mistake I was making.
Three “check-in” messages over the last few months.
All friendly. All polite. All… completely ignored.
And you know what makes it worse? The messages weren’t even bad.
They were the kind of thing any sane Realtor would send:
“Hey! Hope you’re settling in.”
“Just checking in—how’s the new place?”
“Hope all is well!”
Which is exactly the problem.
They read like closing credits. Not a conversation starter.
So I did what every Realtor does when their follow-up isn’t working:
I blamed the client for five seconds. (“People are busy.”)
Then I blamed myself for five seconds. (“I’m annoying.”)
Then I did the only productive thing left…
I changed one sentence.
Instead of sending another “hope you’re doing great” message that gives them nothing to grab onto, I sent a question that practically hands them a reply:
“What’s changed since you moved in lately?”
I hit send and immediately felt that little wave of regret like:
“Cool. Now I’m officially bothering them with a question.”
But here’s what happened.
Replies started coming back—fast. Not long essays. Just easy, human answers:
“Finally finished the basement.”
“We’ve got a weird crack in the ceiling… should we worry?”
“Thinking about upsizing this summer.”
“Our neighbor might list—what’s the neighborhood doing?”
That’s when it clicked:
My old messages were nice.
This one was answerable.
And answerable beats nice every time.
Lesson/Takeaway:
Polite check-ins get ignored because they don’t give clients a reason to respond. One specific, easy-to-answer question turns silence into a real conversation.
⚡ Action Tip
Swap Your “Check-In” For A “Change Question”
What it is: Replace your next “hope you’re doing well” message with a simple question about what’s changed.
Why it works: People ignore updates… but they answer prompts (especially ones that don’t feel salesy).
How to do it: Text/email 10 past clients today with the exact 7-word question.
Example message:
“Hey [Name]—quick one: what’s changed since you moved in lately?”
(If they reply with anything—you win. Your job is simply to keep the conversation going like a normal human.)
📚 Worth a Look
Resource of the Week: The Mom Test (book) — Rob Fitzpatrick
The insight: The quality of your answers depends on the quality of your questions. Vague questions get polite, useless replies. Specific questions get real information.
Why it matters: Your follow-up isn’t failing because your clients don’t like you—it’s failing because your message doesn’t give them a “next word.”
Put it into practice: Create a mini list of 5 “easy answer” questions you rotate all year (home, family, neighborhood, work, plans). Keep them simple. Keep them specific.
🔮 Coming Next Week..
Most follow-up fails for a quieter reason than “no time”: your database is full of people who will never reply again… and you’re treating them like they will.
Next week: The “Last 10” List — the dead-simple way to revive cold contacts without mass emailing, awkward nudges, or “just checking in” messages that go nowhere.
You’re reading The Grind Works — free weekly strategies to get more repeat clients and referrals.
Questions? Hit reply or send an email to [email protected]
Disclaimer:
The Grind Works newsletter is for educational and informational purposes only. The strategies, tools, and resources shared are general in nature and may not be suitable for every business or situation. Nothing in this newsletter should be interpreted as legal, financial, or professional advice. Results from client retention and referral strategies will vary based on market conditions, execution, and other factors outside our control. Before implementing any tactic, you should evaluate it in light of your own business circumstances and, where appropriate, consult with qualified professionals. The Grind Works makes no guarantees regarding outcomes, income, or results.