I’ve wasted days of my life writing sales emails that went absolutely nowhere.
And not “days” as in “it feels like days.” I mean actual, measurable hours — gone. Poof.
I’ve spent 30 minutes debating if I should open with “Hi John” or “Hey John.”
I’ve rewritten the same subject line 14 times and still hated it.
I’ve rearranged bullet points like they were Jenga pieces holding the whole deal together.
I’ve stared at one sentence so long I started questioning if it was even English anymore.
And for what?
So the prospect could delete it in under 2 seconds without ever reading past the first line.
I’ve obsessed over punctuation like it was the secret key to closing the deal. I’ve swapped out periods for em dashes, replaced exclamation marks with strategic ellipses, and even Googled “best comma placement for sales emails” like a man searching for lost treasure.
And don’t even get me started on the greetings. I’ve tested “Hi,” “Hey,” “Hello,” “Good Morning,” and the ultra-formal “Dear,” just in case I was secretly emailing my grandmother.
Here’s the truth I wish I’d learned years ago: none of that matters if your email never makes it past the buyer’s mental spam filter.
The Mental Spam Filter
Your buyer’s brain is scanning every incoming email in milliseconds, asking:
Do I know this person?
Is this relevant to me right now?
Does this look like work or value?
If your email feels like it’s going to cost them time, mental energy, or risk… it gets deleted, archived, or ignored — even if they have the exact problem you solve.
This can happen when your email:
Takes too long to read — long paragraphs, run-on sentences, and no white space.
Feels like a homework assignment — too many questions or requests packed into one email.
Overloads with details — cramming every feature, benefit, and product fact into the first touch.
Uses jargon or buzzwords — forcing the reader to decode what you mean before they understand why it matters.
Buries the point — making the buyer read six sentences before they know why you’re reaching out.
Most sales emails fail because they're trying to do too much. They're cramming features, benefits, social proof, and a meeting request into one message.
It's like trying to propose marriage on the first date. It's too much.
Here's the thing most sales reps miss: The goal of your first email isn't to book a meeting.
It's to get a reply.
That's it.
Because once someone replies, you can have a conversation. And conversations are where meetings get booked and deals happen.
When you focus on just getting a reply, your emails become shorter, more curious, and way more effective.
I learned this the hard way after sending roughly 47,000 terrible sales emails.
In my next post I'll share the exact framework I use to write sales emails that actually get replies. To learn more about how to write effective sales emails, download my Sales Email Prospecting eBook.