[reply worthy | day 18] why your DMs fail, even when the words are good
(same message, seven strangers)
The restaurant wasn’t bad. Actually some of the best food in the city. That’s what made the experience worse.
The food was fantastic. Plated well. Seasoned perfectly.
The kind of place where the menu has 14 items and someone clearly spent time on each one.
But the waiter kept bringing the same dish to every table.
Couple celebrating an anniversary? Mushroom risotto.
Business lunch, two founders splitting a check? Mushroom risotto.
Woman eating alone, reading a book, clearly in no rush? Mushroom risotto.
Nobody sent it back. Not right away.
They just... didn’t come back.
The kitchen had range. The menu had depth. But the delivery system had one gear, one dish, and one move. For everyone.
Sounds crazy right?!?! You can’t even imagine a restaurant doing such a thing.
But I see something like this all the time in the DM funnels I autopsy.
My friend Reid’s DM sequence... the one he paid an agency $2k for... had this problem.
The sequences 7 messages were largely sent the same way, in the same order, with the same energy, to every single prospect, regardless of what that prospect knows, believes, or cares about when the first message lands.
Some of those prospects barely know they have a problem. Some already know the problem and are comparing solutions. Some have already decided they need help and are just looking for the right person.
Reid’s sequence treated them all the same.
Today, I’m diagnosing why that kills more deals than a bad opener ever will.
→ Why “good messages, wrong prospect” is the most expensive leak in DM outreach
→ How to read which level a prospect is actually at before you send anything
→ The scoring method that tells your team which message to send to which prospect
Let’s start with the dish nobody ordered...
🔼 Mistake 18: Your sequence has one awareness level for every prospect.
The most expensive DM mistake isn’t bad copy… it’s mismatched awareness level.
There are four levels a prospect can be at when your first message arrives:
1️⃣ Level 1: They know the facts of their situation, but they haven’t named the problem yet.
They’ll say things like “I’m using LinkedIn for lead gen” or “my VA handles outbound.” Facts. No emotion. No pain. Just describing what exists.
2️⃣ Level 2: They know their approach and can describe what they’re doing.
“I send 50 connection requests a week and follow up with a pitch.” They can walk you through their process. But they haven’t connected that process to why it’s not working.
3️⃣ Level 3: They know what they want and it’s specific.
“I want to book 4 calls a week from LinkedIn without sounding like every other agency owner in their inbox.” Now there’s a goal. There’s frustration. There’s a gap they can feel.
4️⃣ Level 4: They’ve decided who they want to be.
“I want to be the person prospects reply to because the message was worth reading, not because I followed up 6 times.” Now it’s identity. Values. How they see themselves.
Most DM sequences are written at Level 3 or Level 4 energy...
“Here’s how I can help you hit your goals.”
“Here’s a system aligned with how you want to run outbound.”
But most prospects are at Level 1 or Level 2 when your first message hits their inbox.
They haven’t named their problem yet.
Usually, they’re honestly still trying to fully describe their situation in the first place.
And you’re already pitching a solution they don’t even know they need yet.
Your setter sends the sequence to everybody.
Same 7 messages. Same order. Same energy.
Some prospects are still figuring out they have a problem. Others already know exactly what they need.
The sequence doesn’t care. It treats them all like they’re ready to buy.
🤖 I built a free DM Sequence Grader that scores your sequence (or existing conversations) across 7 dimensions in under 3 minutes.
No “your sequence is great, keep going.” Also no overly critical “everything is awful.”
You get a true score, your weakest dimension, and exactly where to start fixing first:
→ Score your DM sequence or last DM conversation for free here
Stop serving mushroom risotto to every table.
❌ Before (Level 3 pitch to a Level 1 prospect): “Hey Sarah, I help agency founders book 4+ calls a week from LinkedIn without cold calling. Would that be useful?”
✅ After (Level 1 message to a Level 1 prospect): “Hey Sarah, saw your team’s been active on LinkedIn lately. How’s that been going as a lead gen channel for you?”
The first message isn’t wrong. It’s just wrong for Sarah, right now.
She hasn’t told you she wants more calls. She hasn’t told you LinkedIn isn’t working.
You jumped to the prescription before checking the symptoms.
Here’s how to fix it: [quote]
1️⃣ Read the signal before you send.
Look at their last 3 LinkedIn posts, their headline, their recent activity.
Are they describing their situation (Level 1-2) or expressing frustration and goals (Level 3-4)?
Match your first message to where they actually are, not where you want them to be.
2️⃣ Build your sequence as a progression, not a repetition.
Message 1 should meet them at their level. Message 2 should move them one level deeper. Message 3 goes one more. Each message earns the right to go further.
Reid’s sequence stayed at the same awareness level for all 7 messages.
No progression. No deepening.
3️⃣ Train your setter to diagnose before they send.
This isn’t a “you” job forever. Build a one-page cheat sheet your head of growth or VA can use: “If their profile signals Level 1-2, use Opener A. If Level 3-4, use Opener B.”
Two openers. Same sequence after that. But the entry point changes everything.
The fix isn’t [always] writing better messages. Sometimes it’s simply matching the message to the awareness level of person reading it.
That’s it.
Here’s what you learned today:
→ Most DM sequences pitch at Level 3-4 energy to prospects who are at Level 1-2. The message isn’t bad. It’s aimed at someone who isn’t there yet.
→ The four levels (situation, approach, goal, identity) aren’t stages you push people through. They’re where people already ARE when you arrive in their inbox.
→ The fix is matching your opener to the prospect’s actual level, then building each message to move them one level deeper.
Start with just one:
Pull up the last 5 DMs your team sent.
For each one, ask: “Was this message aimed at where the prospect actually was, or where I wished they were?”
If you find even one mismatch, you found revenue sitting on the table.
Over the next 31 days, I’m walking you through:
→ How to audit your DM opener so it earns a reply instead of getting archived
→ The scoring method that tells you if your sequence is a conversation or a monologue
→ Why your “follow-up” messages are actually breakup messages in disguise
→ How to build a 7-step DM sequence from scratch (not copy someone else’s)
→ The diagnostic that finds the silent objection killing your threads
→ How to build a recovery system calibrated to WHERE in the sequence they went silent
→ The full sequence assembly: every piece, scored against every diagnostic from the series
Today’s mega-prompt doesn’t just score your opener.
It maps every message in your sequence to the awareness level it’s aimed at, then compares that to where your prospects actually are when they receive it.
Hand it your sequence. It’ll tell you which messages are aimed too high, which are aimed too low, and what to change.
Paid members get:
✔ The Conversation Spectrum Diagnostic Tool
→ Paste your DM sequence, get every message mapped to the level it targets
→ See the mismatch score: how many messages are aimed at the wrong awareness level.
→ Get rewrite suggestions that match each message to the right level
✔ A one-page setter cheat sheet for diagnosing prospect level from their LinkedIn profile
✔ Two opener variants (Level 1-2 and Level 3-4) your team can deploy today
Run it once. You’ll see exactly where your sequence is serving the same dish to every table.
