how to read your DM like a stranger
(the 30-second test that catches what you can't see)
It was a Saturday brunch with you and three work friends. Your partner came along.
The mimosas hit the table. The eggs hit the table. Somebody started telling the story about Marcus and the coffee machine. The wrong pods. Janet’s reaction. The thing Derek said in the all-hands.
The table erupted.
Deep belly laughing. Eyes-watering laughing. The kind where someone has to put their fork down for a second.
Your partner sat there with a fork halfway to their mouth. Smiling. Waiting. Polite.
You caught it.
You leaned over and tried to explain. “So Marcus, he’s the one who orders supplies, and there’s this thing with the wrong pods, and Janet, she’s like…”
Your partner nodded. Took a bite. Smiled at the table when the next round of laughing started.
You realized something on your second mimosa.
You weren’t telling a funny story. You were replaying a memory that only works if you were there.
Your partner wasn’t there.
Neither was your prospect.
We’ve been talking about my friend Reid and the DM sequence he recently paid an agency $2K.
For five days now we’ve been diagnosing what’s broken IN those messages.
Today’s mistake isn’t a thing inside the message. It’s all the things inside Reid’s head.
When read goes over his messages, he thinks:
- the proof is impressive
- the offer is direct
- the next step is clear
He’s not wrong, from where he’s sitting. But that’s not where the prospect is sitting.
Here’s Reid’s second message again:
“Forgot to mention, we just helped Catalyst Cloud generate an extra $1.2M in 90 days by adding 200 outbound touches per week.
If we were able to help you do something similar, would that be worth a conversation?“
Read that with Reid’s eyes.
He knows Catalyst Cloud. He worked on the project.
He saw the dashboard. He knows what 200 outbound touches looks like inside that account. He knows the $1.2M is real because he watched it happen.
Now read it with the prospect’s eyes.
Catalyst Cloud is a name. It might as well be made up.
$1.2M is a number on a screen. The prospect has no way to verify it.
200 outbound touches per week is a process detail. The prospect has no idea if that’s a lot or a little.
The whole message works inside Reid’s head, but falls apart inside the prospect’s head.
Today, I’m talking about why you can’t see what’s wrong with your own messages:
→ The three context gaps every DM has, and how to spot them in your own writing
→ The “stranger test” that strips your context out of any message in 30 seconds
→ Why proof that feels obvious to you reads like noise to your prospect
Let’s start with the gap that costs the most replies…
The Context Mistake: You’re writing for someone who already knows what you know.
Reid’s message has a name in it: Catalyst Cloud.
When Reid writes “Catalyst Cloud,” he’s seeing a logo. A Slack channel. A specific contact. A specific dashboard. A specific quarter where the numbers turned around.
When the prospect reads “Catalyst Cloud,” they’re seeing… nothing. It’s just a word. It could be a real client. It could be a hypothetical. It could be a typo.
And the prospect doesn’t stop to figure out which. They just keep scrolling.
1️⃣ This is the first context gap. Call it the name recognition gap.
Every proper noun/name in your message that the prospect doesn’t already recognize is a tiny shrug.
The reader’s eyes pass over it without stopping. They don’t look it up. They don’t ask. They just keep reading, slightly less interested than they were before.
2️⃣ The second context gap is the proof gap.
Reid wrote “$1.2M in 90 days.” Reid knows that number is real. The prospect has no way to know that.
They’ve seen a thousand DMs with a number in them. They’ve seen six this week from agencies pitching them.
When you cite a number a stranger can’t verify, the number doesn’t land as proof. It lands as a claim. And claims from strangers don’t build trust. They build skepticism.
3️⃣ The third gap is the relevance transfer gap.
Reid wrote “200 outbound touches per week.” To Reid, that’s a flex. It’s a hard number. It signals capacity, system, scale.
To the prospect, it’s a process detail.
The prospect doesn’t run a sales team. They don’t think in outbound touches.
They think in revenue, hires, runway, customer churn. “200 outbound touches per week” doesn’t connect to anything they’re worried about. It’s just… noise.
Three gaps. All three running at once. Every line in Reid’s second message lands inside one of them.
That’s why his sequence has been silent for three months.
❌ Before: “Forgot to mention, we just helped Catalyst Cloud generate an extra $1.2M in 90 days by adding 200 outbound touches per week. If we were able to help you do something similar, would that be worth a conversation?”
✅ After: “Most B2B sales teams I talk to are running at 60-70% of the outbound volume they think they’re running at. Reps log activity loosely, the dashboard shows what got logged, and the gap shows up as a slow pipeline a quarter later. Easy to fix once you see it. Want me to send you the 5-minute version of how to spot it in your own data?”
The After doesn’t have a name in it.
It doesn’t have a number that needs verification.
It doesn’t have a process detail.
It has a description of a problem the prospect can recognize from inside their own head.
Here’s how to fix it in your own DMs:
1️⃣ Run the stranger test. Read your message back as if you’ve never met yourself.
Mark every proper noun/name, every number, and every process detail.
For each one, ask: would a stranger know what this means? If no, it’s a context gap.
Cut it or replace it with something the stranger would recognize.
2️⃣ Trade names for descriptions. Instead of “we worked with Catalyst Cloud,” write “we worked with a B2B SaaS company in your space.”
The description carries the same signal without asking the prospect to recognize a name they don’t know.
You can name names later, when there’s trust.
3️⃣ Trade claims for observations. Instead of “we generated $1.2M in 90 days,” write “the pattern we keep seeing is X.”
Observations are easier to trust than claims because they’re framed as something the prospect can verify in their own data, not something the prospect has to take your word for.
The pattern across all three: stop asking the prospect to take your context as given.
Build your message out of things they can recognize from where they’re standing.
That’s it.
Here’s what you learned today:
→ Every message has three context gaps: name recognition, proof, relevance transfer
→ The stranger test catches all three in 30 seconds
→ Descriptions and observations travel. Names and claims don’t.
The hardest part is that you can’t see the gaps in your own messages while you’re writing them.
You’re inside your own head. You know the names. You know the numbers. You know what the process detail means.
Pull up the last DM you sent that didn’t get a reply. Read it as if you’ve never met yourself.
Mark every proper noun/name and every number. Then put a check by how many of them a stranger would recognize.
Over the next 31 days, I’m walking you through:
→ The “same question, three different ways” pattern that signals a script
→ The Calendly link drop that gets sent before you’ve earned the booking
→ The single-word “[FIRST NAME]?” desperation message
→ The 7-day anatomy of a DM sequence that’s actually working
→ The follow-up rhythm that doesn’t read as needy
→ The breakup message that gets more replies than the booking ask
→ Why “circling back” is the most expensive two words in your DMs
→ The objection-handling line that ends 80% of “not right now” replies
→ The booking question that turns DM conversations into calendar holds
What we’ve already covered:
→ Day 1: she knew by the appetizers. The 5-word test that decides whether your prospect reads your DM.
→ Day 2: he said your name 14 times. The anchor line test for performance vs. presence.
→ Day 3: you up?. The eye roll filter for desperate openers.
→ Day 4: one job. or no reply.. The IKEA test for cognitive load across every message in your sequence.
→ Day 5: she didn’t almost forget. The gift test for re-openers that promise something they don’t deliver.
I packaged today’s diagnostic as a standalone tool: The Context Gap Diagnostic.
A diagnostic that strips your context out of any DM message and scores what’s left across three dimensions: name recognition, claim verifiability, and relevance transfer.
You’ll see exactly which lines in your message only work inside your head, and which ones actually travel to the prospect’s:
→ Score any DM message across three dimensions in 30 seconds
→ See the specific lines that don’t travel and why
→ Use the worked-example library to see what context-stripped rewrites look like across SaaS, agency, and coaching DMs
→ Run the diagnostic on your full sequence using Cowork as your diagnostic partner
Paid 8am In Atlanta subscribers: use code included with today’s mega-prompt at checkout for $20 off.
Not a paid subscriber yet? Upgrade your subscription to get $20 off this diagnostic (and every tool I drop in the May Series).
