Stop Sending "Just Checking In" Emails.
It’s been three days since you sent the proposal. You haven't heard back.
You start to sweat. You don't want to be annoying, but you need to know if the deal is alive. So, you open your email, take a deep breath, and type the three deadliest words in sales:
"Just checking in..."
You hit send and immediately feel gross. You feel like a pest.
And guess what? Your prospect thinks you're a pest, too.
Why "Checking In" Kills Your Authority
As a solopreneur, you are fighting a constant battle for status. You need to be seen as a peer and an expert, not a desperate vendor begging for a scrap of attention.
When you write "Just checking in" or "Just circling back," you are admitting two things:
You have nothing of value to say.
You are asking for a favor. (You are asking for their time and attention without giving anything in return).
It’s a selfish email. It says, "Pay attention to me because I want you to."
That is low-status behavior. High-status experts don't "check in." They add value.
The "Value-Add" Follow-Up
The KYSS (Keep Your Sales Simple) philosophy dictates that every interaction must move the ball forward. If an email doesn't add value, don't send it.
So, how do you follow up without being annoying? You change the context.
Instead of asking for an update, give them something.
Bad: "Hi Dave, just checking in on that proposal. Let me know if you have questions."
Good: "Hi Dave, I saw this article about [Industry Trend] and thought of our conversation about [Specific Pain Point]. This might help you with X. Let me know what you think."
Good: "Hi Dave, I was thinking about your project and realized we didn't discuss [Specific Detail]. Here is a quick 30-second video on how we usually handle that."
See the difference? The first one takes value. The second one gives value.
When you give value, you earn the right to be in their inbox. You aren't pestering; you're consulting.
Stop Writing Emails from Scratch
The reason you default to "just checking in" is that you are "winging it." You are staring at a blank screen trying to invent a follow-up strategy on the fly.
You need a Cadence.
This is Component 2 of my KYSS system. You need a pre-written sequence of emails and calls (Day 1, Day 3, Day 7) that are already scripted. When you have a script that you know works—one that adds value and maintains your authority—you never have to feel the "follow-up anxiety" again.
Stop typing. Start executing the playbook.
Build Your Full System
Do you stare at your inbox wondering what to say next? You need the Playbook.
I've compiled my exact email scripts, phone cadences, and the entire "no-BS" framework into a 15-minute digital course and manual: KYSS: Keep Your Sales Simple.
[Click here to get the KYSS Course & Manual today.]
Need More Than a Manual? Get Your Team.
Are you ghosted constantly? Let us look at your emails.
In the Selling Pens Community, we review real email scripts. We can tell you exactly why your follow-ups are getting ignored and help you rewrite them to get replies.
Join as a Community Member for peer feedback and live strategy calls.
Join as a Pro Member for me to personally review your email chains and fix your messaging.
[Click here to see the community options and join your new team.]
