I Tried Every LinkedIn DM Trick—Here’s the One That Books 5–7 Calls a Month
10 DM Templates That Take You from ‘Thanks for Connecting’ to Invoice Paid
In my last guide, How I Close 5-7 Deals a Month on LinkedIn, we mapped out the entire system for building genuine relationships that convert.
Today, I'm sharing the D.V.D. Method: my DM system that turns new connections into paying clients.
While most people obsess over the perfect first message, the real game is knowing how to guide a conversation from 'Thanks for connecting' all the way to 'Send me the invoice.'
Most people blow it immediately:
Pitch in message #2 → Blocked
Send a generic "thanks for connecting" message → Ignored
Let the conversation die after one exchange → Opportunity lost
Wait for the prospect to magically become interested → Never happens
I made every one of these mistakes. Lost dozens of deals. Watched hot prospects go cold.
Then I started documenting what actually worked in my revenue-generating conversations. Not marketing theory. Not what somebody said should work. What actually moved my conversations from "Accept" to "Let's talk" to "Invoice Paid."
This is exactly what you’ll learn today:
How to discover if they're a fit (without being pushy)
How to stay valuable while they warm up (without being annoying)
How to prove you can help (without working for free)
10 templates I use, word-for-word. Copy, paste, customize. Send.
This isn't about sending more messages. It's about sending the right messages at the right time with the right focus.
Let's break down exactly what happens after they hit "Accept."
The D.V.D. System: My DM System That Books Calls
Most people treat LinkedIn DMs like cold emails. Spray, pray, and watch their reputation die.
I use a different approach: the D.V.D. System:
Discover: Find the right people and start real conversations
Value: Nurture relationships by sharing insights that matter
Demonstrate: Prove you can help by solving real problems
This framework has booked me 200+ calls in the last year while building genuine relationships.
Here's exactly how it works, plus the 10 templates that make it automatic.
Step 1️⃣: Discovery
Not everyone who connects is ready to buy. Most aren't even ready to talk.
Your first job is to figure out if they have a problem you can solve, and in doing so, create a natural opening for a conversation.
These templates help you explore pain points naturally, without sounding like a pushy salesperson fishing for problems.
📄 Template 1A: The “Pain Point Detective”
📅 When to use: After they post about struggling with a specific project or express frustration in comments.
Hey [Name], been following your journey with [specific project/challenge].
Mind if I ask - what's the biggest bottleneck you're hitting right now?
Working with similar [role/company type] and might have some relevant insights to share.
Why this works:
Asks permission (respectful),
Focuses on ONE specific bottleneck (not overwhelming),
Hints at relevant experience without being pushy (generate interest).
📄 Template 1B: The “Goal-Focused Opener”
📅 When to use: Start of quarter, after they announce new initiatives, or when they share ambitious targets. Perfect for forward-thinking prospects.
Hi [Name], curious - what's your main focus for [specific area] over the next quarter?
Been helping [similar companies] accelerate their [relevant outcome] and noticed a few patterns that really move the needle.
Happy to share what's working if it aligns with where you're headed.
Why this works:
Future-focused (goals not problems),
Establishes credibility with similar companies,
Offers value conditional on relevance (not pushy).
📄 Template 1C: The “Shared Struggle ”
📅 When to use: When they share vulnerable content about challenges, post "lessons learned" content, or openly discuss what's not working.
Hey [Name], noticed you've been posting about [specific challenge] lately. That [specific aspect] you mentioned yesterday really resonated.
Been there myself - [brief relatable struggle].
What's been the most frustrating part? The [common pain point] or something else entirely?
Why this works:
Shares vulnerability (builds trust),
Acknowledges their specific situation,
Shows you're actually reading their content,
Gives them options to guide the conversation.
Step 2️⃣: Value
After initial engagement, your job is to stay useful without being annoying.
You achieve that by positioning as a trusted advisor that shares relevant and timely insights. Every touchpoint should make them think "this person gets it."
These templates help you nurture relationships naturally, without sounding desperate or needy. The goal is to deliver consistent value to stay top of mind until they’re ready to move forward.
📄 Template 2A: The “Quick-Tip” Share
📅 When to use: When they post about a specific technical problem, share a work-in-progress, or ask for advice in comments.
Hey [Name], noticed you're working on [specific challenge/goal].
Put together these 3 quick tips that might help:
[Include actual tips]
Hope this saves you some time!
Why this works:
Specific to their situation,
Delivers immediate value,
Genuinely helpful tone.
📄 Template 2B: The “Curated Resource”
📅 When to use: 3-7 days after initial conversation when you find content that directly solves a problem they mentioned. Perfect for maintaining momentum without seeming eager.
Hey [Name], saw your post about [specific challenge] last week - that struggle is real.
Just came across this [resource type] on [related topic] that actually has some solid tips. The part about [specific aspect] is exactly what helped me with [related challenge].
Here's the link: [link]
Let me know if it helps!
Why this works:
References their specific content,
Highlights relevant section,
Casual but professional tone.
📄 Template 2C: The “I Tried This” Share
📅 When to use: When you test something new that solves a problem they mentioned earlier. Best 1-2 weeks after initial conversation to show you've been thinking about their challenge.
Hey [Name], remember you mentioned struggling with [specific challenge]?
I just tried [specific method/tool] last week and it actually worked. Cut my [metric] from [X] to [Y].
The key was [specific technique that made the difference]. Honestly didn't think it would work, but the results speak for themselves.
Happy to share the exact steps if you want to give it a shot.
Why this works:
Personal experience beats theory,
Specific metrics build credibility,
Vulnerability: "didn't think it would work",
Creates connection, soft offer to help.
📄Template 2D: The "Thought of You" Share
📅 When to use: Right after industry news drops, a new tool launches, or you spot a trend that solves their exact problem.
Hey [Name],
Saw this article on [topic] and immediately thought of your [specific goal/project].
They break down [key takeaway] - which is exactly what you were trying to figure out with [their specific situation].
Here's the link: [link]
The part about [specific section] might be especially useful for you.
Why it works:
Shows you remember their specific challenges,
Highlights the most relevant part upfront,
Natural, timing with news,
Saves them research time.
📄 Template 2E: The "Insightful Idea"
📅 When to Use: When you've connected the dots between their challenge and a solution they haven't considered yet. Best for prospects who value strategic thinking.
Hi [Name],
Been thinking about what you said regarding [specific challenge/goal].
What if you [specific idea/approach]? It could help you [specific benefit] without [common pain point they want to avoid].
We did something similar with [brief example/result] and it completely changed how we approach [relevant area].
Worth exploring?
Why it Works:
Shows you've been actively thinking about their problem,
Presents idea as collaborative question, not prescriptive,
Includes proof it works
Step 3️⃣: Demonstrate
Talk is cheap. Everyone has "solutions." But when prospects say "interesting" or "let's stay in touch," they’re just being polite. What they really mean is "show me you can actually help."
This is what a lot of people get wrong. They keep talking instead of proving.
Your job is to find something specific in their work: their GitHub repo, technical blog, published code, demo video or any public work, and make it measurably better.
These templates turn skeptics into believers by solving real problems before asking for anything in return.
📄 Template 3A: The "Quick Win Audit"
📅 When to use: You can demonstrate specific improvements on their public work.
Hey [Name], just reviewed your [specific work] - impressive stuff.
Noticed one thing: your [specific component] is solid, but I spotted a quick optimization that could [specific measurable benefit].
Here's what I'd change:
[Specific before → after example]
This alone should [concrete result]. Want me to walk you through implementing it?
Takes 15 minutes on a quick call.
Why this works:
Opens with a compliment,
Shows you actually reviewed their work,
Provides immediate value,
Low time commitment time commitment
📄 Template 3B: The "Found Your Fix" Message
📅 When to use: After they share specific work output with you (code, designs, processes) that you can actually test and improve. Best when you have concrete before/after results.
Hi [Name],
Remember when you mentioned [specific challenge]? I think I found your bottleneck.
Ran your [specific work/code/process] through my setup and made one change: [specific modification]. Result: [specific measurable improvement].
Here's the before/after: [brief comparison or screenshot]
Want me to show you how to implement this? 15-minute call and you'll have it running.
Why it Works:
Shows you invested real time,
Proves results with evidence,
Makes it tangible (before/after),
Positions call as implementation help, not sales pitch.
Quick Recap: Your 3-Step DM Strategy
Step 1️⃣: Discovery - Find their actual pain points (not what you assume)
Template 1A: The "Pain Point Detective": Uncover real challenges through thoughtful questions
Template 1B: The "Goal-Focused Opener": Explore future objectives and ambitions
Template 1C: The "Shared Struggle": Bond over common problems you've both faced
Step 2️⃣: Value - Stay valuable without being annoying
Template 2A: The "Quick Tip"- Solve their immediate problem with actionable advice
Template 2B: The "Curated Resource"- Send curated content that addresses their challenges
Template 2C: The “I Tried This” - Share personal results from solving similar problems
Template 2D: The "Thought of You" - Leverage industry news for natural touchpoints
Template 2E: The "Insightful Idea" Suggestion- Offer fresh perspectives they haven't considered
Step 3️⃣: Demonstrate - Prove your worth with specific improvements
Template 3A: The "Quick Win Audit"- Show concrete improvements to their public work
Template 3B: The "Found Your Fix" - Test their shared work and deliver measurable improvements
Think of it like texting a friend: casual, low-key, straight to the point. Respect their time, skip the fluff, and focus on being actually helpful. That's how real relationships (and deals) happen.
Ready to Start Converting?
I've loaded all 10 templates into your personal message vault. Everything's formatted, ready to copy, and with dynamic placeholders so you can personalize them instantly without extra work.
Here's how you get started:
Get Kondo free for a month
Pick the template that fits your situation
Fill in the [brackets] with specific details (names auto-populate)
Send it (no overthinking, these messages have already worked for me)
Watch real conversations start happening 👏
Here’s a live example to get you started:
Keep nurturing those connections, and the opportunities will continue to unfold.
That’s it for now—more soon!
Catch you next time,
Creator of LinkedIn Audience Building for AI/ML Engineers
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