Friday, nine in the morning. A homeowner's phone lights up with a text from me, and it opens: "I appreciate you trying to test the system, but I need to clarify what's happening here."
He never asked to test anything. That text was my software's AI refusing to write a follow-up, and a step downstream sent the refusal to him anyway. Twice, to two of his numbers.
I found it the same morning because I read his file. What bothers me is not the bug, which is fixed. It is that for that hour, the most important reader of that message was the seller, and I was the last one to read it.
Here is the check. Ten minutes, today, whatever you use.
Pick three sellers who are still in your follow-up right now. For each one, pull the last ten messages they actually received from you, not the templates, the real sent messages. Then read them out loud, in order, as if you were the seller.
You are listening for three things:
Anything that is not a message. A placeholder, a missing name, a note meant for you.
Anything that ignores what they said. A seller who told you "not until spring" getting a "just checking in" in October.
The gaps. Count the days between messages. If a seller who talked to you has gone longer than ten days without hearing from you, that is a gap, not a strategy.
This works on an AI system, a VA, a dialer with templates, or a spreadsheet and your own thumbs. The failures look the same from the seller's side.
Why it happened to us. The AI had read a messy history: a different number on the same owner had replied "wrong number," and an unsent draft sat in the thread saying we would stop. With no note about which number each text used, it decided it was being asked to break a promise. Then the step that expected a message kept whatever came back. Nothing checked that a message was a message.
That was one of five things that went wrong in our outreach this month. I wrote all five up, with the numbers and the question to ask before any tool texts your sellers: 5 Ways Automated Seller Outreach Fails (We Made Every One This Month)
Reply and tell me: when you read yours out loud, what did you find? A worst text, a longest gap, anything. I read every reply, and the good ones become next week's field notes (without your name unless you want it).
If you would rather not pull the list by hand, the Pipeline Grader shows which leads stalled after the first touch. We never store, sell, or message your list: dealroute.ai/grader
Talk soon,
Jason