[reply worthy | day 8] someone pulled this on me yesterday
(didn't recognize the setup in my own DMs)
Your neighbor invited you over for a cookout.
Fourth of July. Beers in the cooler. Kids running around in the yard.
Somebody’s playing music too loud and nobody’s complaining because the burgers smell good.
Your neighbor walks up to you, beer in hand. His usual friendly smile.
“How’s everything going?”
You start to answer. The job. The kid’s soccer team. The trip you’re planning for the fall.
He nods along.
Then: “That’s awesome. So my buddy and I just opened a financial planning practice and we’re looking for a few good families to work with…”
Awwwwwww crap. He didn’t want to know about the fam. It was a setup.
The cookout was the prospecting event. The question was the lead-in for potential clients.
I had someone pull this exact move on me in my DMs yesterday. ME 😳
We’re gonna call him … Spencer.
Spencer isn’t Reid. Reid paid an agency $2K and they write his sequence for him because he knows he’s not very good at this.
But Spencer is. Or at least - he thinks so.
So what had happened was…
I sent Spencer a connection request. He accepted within seconds and sent the first message right after:
“Glad we’re connected. Really enjoy your content on messaging strategy. Would love to hear how you think about it.”
Warm opener. Specific reference to my content. A question that signals genuine interest.
That’s a strong M1. Played correctly, that earns a reply.
I replied later that day. Acknowledged him by name. Asked him a question to figure out where he was operating from so I knew where he was starting from in his understanding of selling through DMs:
“Appreciate that. Noticed you’ve got a nice size following across platforms and looks like you have an offer teaching people about camera presence. When someone sees your content here, what’s the typical path they take before they chat with you on Zoom? That’ll help me outline the framework better.”
By evening, Spencer replied:
“Here’s a talk I gave on building camera presence you might want to watch: [Vimeo link]. And here’s my calendar to book a time: [bit.ly link]. Check out the video, grab a slot, and we can dig into it.”
I read it twice. Then I started writing this newsletter.
Today, I’m walking you through the first mistake in Spencer’s two-message sequence:
→ Why a curiosity question can read as engagement but function as bait
→ The 3 fingerprints that separate genuine curiosity from a baited question
→ The one-line mirror test that catches it before you send
Let’s start with what Spencer actually did when he asked his question…
Spencer’s Mistake: He killed the goodwill he’d built from the original question when it became clear it was bait
Read Spencer’s M1 again:
“Glad we’re connected. Really enjoy your content on camera presence. Would love to hear how you think about it.”
On the surface, that’s a strong opener. Specific. Warm. Curious.
Now read his M2:
“Here’s a talk I gave on building camera presence you might want to watch. And here’s my calendar to book a time. Check out the video, grab a slot, and we can dig into it.”
There is nothing being followed up on. There’s no engagement with the question I asked. There’s a video drop, a calendar drop, and a stacked CTA.
Spencer’s M1 wasn’t a question. It was a bait.
He asked it knowing my answer would be the setup for his ask. The “would love to hear how you think about it” wasn’t there because he wanted the answer. It was there because the answer was the doorway.
That’s why Spencer’s mistake is harder to catch than Reid’s.
Reid’s M4 was loud. A Calendly link into silence. You can flag it in 5 seconds.
Spencer’s M1 is quiet. A Calendly link into a conversation he asked for. It slips past most operators because it has the shape of engagement.
But it isn’t engagement. It’s bait
The 3 fingerprints of a Bait Question
Now let’s be clear. In a DM funnel, every question asked has a dual purpose.
Yes. You want to know the answer. But you’re also asking questions that lead to a conversion event for your offer.
But, as we talked about yesterday, every conversation has a permission ladder.
And Spencer didn’t just skip rungs. He pulled the entire ladder away from the roof.
Every Bait Question like Spencer’s has the same three tells. Once you see them, you can’t unsee them. They show up in your inbox every week. They might be showing up in your sent folder too.
1️⃣ Fingerprint 1: The Setup.
Before Spencer’s M2 ever landed, his M1 was already built as bait.
Here’s the test. Could my answer have changed what Spencer sent next?
I didn’t even give him an answer. I asked him a question back. I didn’t know his level of knowledge on DM strategy, so I needed to figure out where he was operating from before I could help him with the right information. That’s what my reply was doing.
It didn’t matter.
His M2 came back the same way it would have come back if I’d said “thanks” or “cool” or written him three paragraphs.
The Vimeo link. The calendar. The stacked CTA. My question didn’t change his next move because his next move was already loaded before my reply came in.
That’s the setup. The question sounds open. But the sender already has the next message drafted in their head. Your reply is just the green light to send it.
2️⃣ Fingerprint 2: The Pace.
Real curiosity asks two or three follow-up questions before either party offers anything. The conversation builds. Each message earns the next one.
A Bait Question goes from “would love to hear more” to “here’s my stuff” in one message.
Spencer asked. I answered. Spencer pitched.
Three messages. One question. Zero conversation.
The speed is the tell. When someone goes from curiosity to calendar link in a single exchange, the curiosity was a costume.
3️⃣ Fingerprint 3: The Non-Echo.
This is the loudest one.
A real question, answered honestly, gets a follow-up that engages with the answer. The reply echoes what was said. It picks up a thread, asks a clarifying question, names what stood out.
Spencer’s M2 doesn’t acknowledge a single thing I said. Not the question I asked about how his prospects move through his content. Not the thing I said about his following.
To be honest with you, I don’t even know if he actually read it, based on his response.
The reply could have been pasted into any DM thread on his phone and it would have made the same amount of sense.
That’s the non-echo. When the follow-up doesn’t reference a single specific thing from your reply, the question wasn’t asked to hear the answer. It was asked to open the door.
❌ Bait: “I love your content on DM strategy. Would love to hear how you think about it.”
✅ Real: “I love your content on DM strategy. The piece on the permission ladder stuck with me because I’ve been wondering whether my calendar link drops too early. Is there a way for me to know while I’m actively in conversation?”
The difference isn’t in the warmth. Both messages are warm.
Bait sounds like he read my headline and pieced together something to sound interested.
Real sounds like someone who’s actually interested based on engaging with my content.
The mirror test you run on your own DMs.
Open your sent folder. Find the last DM where you asked the prospect a question.
Now read your next message in that thread.
Did your next message echo what they said? Did it pick up a thread, ask a clarifying question, name what stood out about their reply?
Or did your next message use their reply as the cue card that signaled “okay, my turn to pitch”?
If you can’t find a single line in your follow-up that responds to a specific thing they wrote, you didn’t ask a question. You put out bait.
Here’s how to fix it:
1️⃣ Before you ask a question, answer this: what would I do if they reply with one word? If your next move would be the same regardless of their answer, you don’t need to ask the question. The question isn’t earning anything. It’s just delaying the pitch.
2️⃣ Make the question impossible to answer generically. “Would love to hear more” can be answered with anything. “What did you think of the part about [specific thing in their content] given that you’re [specific situation in their business]?” can only be answered with thought. The specificity forces real engagement on both sides.
3️⃣ When they answer, echo before you pivot. Pick one specific thing from their reply. Acknowledge it. Ask one follow-up about it. Then, if a pitch is earned, it’s earned. If you skip the echo and go straight to the pivot, you’ve confirmed it was bait.
That’s it.
Here’s what you learned today:
→ A Bait Question has the shape of engagement but the function of a setup
→ The 3 fingerprints (Setup, Pace, Non-Echo) tell you whether a question was asked or scripted
→ The mirror test catches it in your own DMs before you send
Open the last DM where you asked someone a question. Re-read your follow-up.
If your follow-up doesn’t echo something specific they said, rewrite it before you send anything else in that thread.
Over the next 31 days, I’m walking you through:
→ The “same question, three different ways” pattern that signals a script
→ 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.
→ Day 6: the joke died at the table. The context gap diagnostic for messages that only work inside your own head.
→ Day 7: she booked the airbnb. The permission ladder diagnostic for booking asks sent into silence.
I packaged today’s diagnostic as a standalone tool: The Bait Question Diagnostic
The same diagnostic I run on my own sent folder before I send the next reply in any DM thread, now packaged as a 30-second test you can run on the question you’re about to ask before it becomes bait you didn’t know you were putting out.
Inside:
→ The mega-prompt you paste into Claude (scores any DM exchange across all 3 fingerprints in 30 seconds)
→ The drop-in skill file that triggers the diagnostic automatically every time after install
→ The project setup that tunes every repair to your offer, your ICP, your past wins
→ The Cowork workflow that runs the diagnostic across your full DM sent folder in one pass
→ 3 worked examples showing the full diagnostic on Spencer’s M1, plus a real estate agent’s catch-up text and a financial planner’s “quick question” outreach
→ The anonymized screenshot of Spencer’s actual two-message exchange so you can see the full thread I diagnosed
→ 10 pre-tested Real Questions you can swipe to replace any Bait Question in your M1 or M2 today
What it saves you:
The 30 seconds of script-checking on every DM you send (you’ll catch your own bait questions before they leave your phone) + the silent damage of every prospect who flagged you as “running a tactic” in the last six months and never said a word.
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).
