you automated the wrong parts
and your leads noticed
The laptop sat open on the kitchen table.
Cursor blinking in an empty Google Doc titled “DM System Plan.”
For the fourth Sunday in a row.
You told yourself this would be the weekend.
→ The one where you finally figured out DM automation
→ The one where you’d map out your conversation flow
→ The one where you’d stop losing leads to your own disorganization
Instead, you spent two hours watching YouTube tutorials from people who clearly had teams of developers building their systems.
You bookmarked another “complete DM automation course” you’d never finish.
You screenshot another agency’s pricing page for a system you couldn’t afford.
Then you closed the laptop and told yourself next weekend would be different.
The tools take 3 hours to set up. The strategy takes 1-3 years to master.
Most coaches either wait forever to hire someone, or hire someone without understanding what they’re actually paying for.
Both approaches leave you dependent on people who may or may not know your business.
Today, I’m sharing the 3 fundamental shifts that transform your DM understanding from “I hope this works” into “I know exactly what should happen and why,” including:
→ Why understanding your conversation psychology matters more than finding the right agency
→ What you need to know BEFORE you hire anyone to touch your DM system
→ How a few hours of clarity saves you thousands in wasted retainers and rebuilds
Let’s fix your “I don’t know what I don’t know” problem...
3 Mindset Shifts That Turn “Someday” Into “Done”
Most coaches focus so much on finding the perfect system that they forget...
The imperfect system you actually understand beats the perfect system you can’t evaluate.
Here’s what actually gets results:
1️⃣ Shift 1: From “I need an expert to build my DM system” to “I need to understand my conversion psychology so I can direct whoever builds it”
You’re on a discovery call with a DM automation agency.
They’re throwing around terms like “trigger sequences” and “nurture flows” and “conversion optimization.”
You nod along. You don’t want to look stupid.
They quote $3,500/month.
You have no idea if that’s reasonable because you don’t actually know what a DM system should DO.
You don’t know what questions to ask. You don’t know what success looks like.
So you either say yes and hope for the best... or you say “let me think about it” and go back to your screenshot folder of leads.
❌ Before: “I need to find someone who can build my DM system so I don’t mess it up.”
✅ After: “I need to understand how my conversations actually convert so I can direct anyone I hire, or spot when they’re overcomplicating things.”
Here’s how to make this shift:
1️⃣ Map your own conversion psychology first. Before any agency call, document what happens when a lead actually books. What questions moved them? What objections came up? What made them say yes? This is YOUR intellectual property… not something you should outsource to discover.
2️⃣ Know the three jobs of any DM system. Capture leads. Track conversations. Book calls. That’s it. Everything else is optimization. If someone’s pitching you a 47-step automation sequence, they should be able to explain how each step serves one of these three jobs.
3️⃣ Understand the build vs. strategy distinction. Tools are filing cabinets. Strategy is what goes in them. You can hire someone to set up the filing cabinet. You cannot hire someone to understand your prospects better than you do.
Instead of hoping your hire knows what they’re doing, you can evaluate their work against what you know actually converts.
2️⃣ Shift 2: From “I’ll know a good system when I see it” to “I need to define what success looks like BEFORE I evaluate options”
The agency sends over their “custom DM strategy deck.”
Forty-seven slides. Flowcharts that look like circuit boards. Screenshots of dashboards with numbers you don’t understand.
It looks... impressive? Professional?
You’re not sure. You don’t have anything to compare it to.
They could be showing you genius-level work or overcomplicated nonsense, and you genuinely can’t tell the difference.
So you either trust them blindly or freeze up entirely.
❌ Before: “Once I see a few options, I’ll be able to pick the right one.”
✅ After: “I need to define what a working system looks like for MY business before I evaluate anyone’s proposal.”
Here’s how to make this shift:
1️⃣ Create your success criteria first. Before any agency call, write down: “A successful DM system for my business would capture leads from X, track conversations through Y stages, and book Z calls per week.” Now you have something to measure proposals against.
2️⃣ Know your numbers. What’s your current lead-to-call conversion? How many conversations go cold? Where do people drop off? If you don’t know these numbers, no system can fix what you can’t measure.
3️⃣ Ask the “show me” questions. When someone proposes a solution, ask: “Can you show me exactly where in this system a lead goes from first message to booked call?” If they can’t walk you through it simply, they either don’t understand it or they’re hiding complexity.
Instead of evaluating systems based on how impressive they look, you evaluate them based on whether they solve your actual problems.
3️⃣ Shift 3: From “I’ll let the expert decide what to automate” to “I need to know what should stay human and what can be handed off”
The automation specialist is excited.
“We can automate your entire first three messages! Plus follow-ups! Plus objection handling!”
You’re nodding. More automation means less work, right? That’s the whole point.
Six weeks later, your response rate has tanked.
Leads feel like they’re talking to a bot.
Because they are.
You automated the parts that needed to stay human, and now you’re paying someone to rebuild what you just paid someone else to break.
❌ Before: “The expert will know what to automate. That’s why I’m hiring them.”
✅ After: “I need to understand which parts of MY conversations require human judgment and which are just logistics.”
Here’s how to make this shift:
1️⃣ Categorize your conversation moments. Look at your last 20 DM conversations. Mark each message as either “logistics” (calendar links, FAQ answers, resource delivery) or “judgment” (qualifying questions, objection handling, personal connection). Logistics can be automated. Judgment should stay human.
2️⃣ Know your non-negotiables. Before any automation conversation, decide: “These specific moments in my conversations will NEVER be automated because they require reading the room.” Write them down. Make them boundaries.
3️⃣ Test the assumption. When someone proposes automating a “judgment” moment, ask: “What happens when the prospect responds unexpectedly? Show me the branching logic.” If they can’t, that moment needs a human.
Instead of handing over control and hoping for the best, you direct the automation strategy based on what you know about your own sales conversations.
That’s it.
Here’s what you learned today:
→ You can’t evaluate what you don’t understand. Map your own conversion psychology before any agency call so you know what good looks like.
→ Define success criteria before you evaluate proposals. “Impressive looking” and “actually solves my problem” are different things.
→ Know what should stay human. The most expensive mistake is automating the moments that needed your judgment.
Start with just one...
Before your next agency call or tool purchase, write down exactly what happens in your DM conversations when someone actually books a call.
That’s your North Star.
Ready to understand your DM system before you build it (or hire someone to)?
Flying blind is expensive.
When you don’t understand what your DM system should actually do, you either overpay for complexity you don’t need or under-build and wonder why nothing converts.
Today’s paid member mega-prompt helps you map your entire DM conversion psychology in one session... so you can direct any build with clarity.
Paid members get:
✔ “The Sunday Afternoon DM System Build” - Complete guided prompt
→ Map your actual conversion patterns before touching any tools
→ Define exactly what your system needs to do (and what it doesn’t)
→ Create the brief you’d give any agency or VA
✔ The “what to automate vs. what stays human” decision framework
✔ Evaluation criteria for any proposal or tool you’re considering
Tired of nodding along on agency calls without knowing if you’re being sold something you need?