5 LinkedIn DM Secrets That Made My Clients Millions
Business coach Matt Essam shares a five-step framework for writing LinkedIn DMs that build relationships and win high-value clients.
Chris Do
Founder, The Futur™ · June 23, 2024
Your LinkedIn DMs Are Being Ignored
Most LinkedIn messages are dead on arrival. They land in an inbox with a thud, reeking of automation and self-interest. They are unsolicited pitches, clumsy compliments, and vague requests that do nothing but drain the recipient’s energy.
Creatives, who master visual communication, often become surprisingly inept when it comes to the written word of outreach. The result is a digital graveyard of ignored messages and missed opportunities.
This is not a personal failing. It is a system failure.
According to business coach Matt Essam, who has helped hundreds of creative entrepreneurs land five- and six-figure deals, the path to winning dream clients on LinkedIn is not through volume or automation. It’s through a deliberate, human-centered process designed to start conversations, not close sales.
Essam tells the stories of his clients, like David, who secured a meeting with a Paramount executive, and Kai, who landed Bentley as a client. These were not lucky breaks. They were the result of a replicable strategy that transforms cold outreach into warm relationships.
The problem is simple: most people treat LinkedIn DMs as a broadcast medium. They talk about themselves, assume the recipient’s problems, and ask for time and attention without earning it. This approach is broken. It is time for a new one.
The Three Principles of Connection
Before ever writing a single message, a fundamental mindset shift is required. Essam outlines three guiding principles that underpin any successful outreach strategy. Without them, even the most cleverly worded script will fail.
The first principle is to give before you get. This is not about altruism; it's about psychology. When you provide something of value upfront, you trigger a sense of reciprocity. “From a psychological perspective, there is some kind of reciprocity which is created when somebody gives you something,” Essam explains. “You feel like you want to give them something back.” This reframes outreach from a selfish act of taking to a generous act of giving, which dismantles the fear of being “salesy” or “spammy.”
The second principle is to message like a millennial. Forget the long, dense paragraphs of a formal letter. Effective digital communication is conversational, short, and interactive. “Whenever I speak to them, it's always a very sort of backwards and forwards conversation,” Essam says of his younger cousins. “It feels conversational… not just huge lengthy paragraphs that are difficult to read.” Most people read DMs on their phones, a context that demands brevity. The goal is a quick exchange, like a text message, not an email that requires significant cognitive load to parse.
The final principle is the most critical: don’t fear the follow-up. This is where most creatives fail. They send one message, receive silence, and retreat, assuming a lack of interest. This is a massive mistake. “Often the opportunity is created in the third or the fourth follow-up,” Essam insists. A non-response is not a definitive “no.” It’s a signal of a million other possibilities: they’re on holiday, they’re busy, they missed the notification. Essam recommends a powerful reframe: “People are interested to have a conversation with you unless they tell you otherwise.” This simple shift in perspective provides the resilience needed to pursue a connection without feeling like a nuisance. In fact, many people will apologize for their late reply, grateful for the reminder.
The 3 C's: Your Daily LinkedIn Ritual
Effective direct messaging doesn't happen in a vacuum. It is one part of a larger, interconnected system that Essam calls The Three C’s of LinkedIn: Connections, Conversations, and Content.
He visualizes it as a continuous, clockwise process. When performed consistently, it makes landing dream clients an inevitability, not a matter of chance. While this article focuses on the conversation piece, understanding the entire ecosystem is crucial.
The three C’s are:
- Connections: This is the foundation. It involves consistently and methodically networking with the right people. Who do you want in your network? Who are the decision-makers, collaborators, and peers in your target industry? This is not about spamming connection requests; it is about curating a professional network with intention.
- Conversations: This is the engine of the system. It’s about actively engaging with your network, primarily through direct messages but also in the comments. “Actually having conversations with people is so underrated,” Essam notes. Instead of just liking a post or leaving a generic comment, ask a question. Show genuine interest. This builds rapport and provides context for deeper interactions. This principle is vital for anyone looking to get clients on demand.
- Content: This is the accelerator. While Essam is clear that his DM strategy works without creating any content yourself, having it makes the process easier. Content provides social proof. It gives people a way to understand who you are, what you stand for, and the value you provide before you ever send a single message. It warms up the relationship. But you do not need to become a full-time content creator; a simple, consistent presence is enough to give context to your conversations.
By thinking of this as a daily practice, you build momentum. Each day, you connect with new people, start new conversations, and share or engage with content. This consistent activity feeds itself, creating a flywheel of opportunity.
The 5-Step Framework for DMs That Get a Response
Sending a message that cuts through the noise requires more than just good intentions. It requires a structure. Essam provides a five-step framework that has been tested with hundreds of his clients, from illustrators to video production studios.
These five elements do not all need to be crammed into the first message. The goal is to start a conversation, so they can be woven in over a series of short, back-and-forth exchanges.
1. The Reason
You must have a clear and immediate answer to the question, “Why are you reaching out to me?” This is non-negotiable. Essam points to a landmark 1978 study by Harvard social psychologist Ellen Langer, which found people are far more likely to comply with a request if you give them a reason, even a flimsy one. In the study, people asking to cut in line at a Xerox machine were nearly twice as successful when they used the word “because.”
Your reason grounds the interaction and removes the suspicion that it's a random, automated message. The reason could be a recent project they launched, a post they shared, or a mutual connection.
2. The Compliment
Everyone appreciates genuine recognition, no matter how successful they are. “I get to hang out with some pretty impressive people like Chris Do and Daniel Priestley,” Essam says. “They're just human. They like compliments.”
The key word is genuine. A vague “love your work” is forgettable and transparent. A specific compliment demonstrates you’ve done your research. Mention a specific project, a particular insight from an article they wrote, or a detail from their portfolio. This shows you’ve invested time and energy, instantly differentiating you from the 99% of low-effort messages they receive.
3. The Anchor
An anchor is a point of commonality that creates an instant bond. It’s the feeling of meeting someone from your hometown while on vacation abroad. Suddenly, a stranger feels like a friend. “Just because you have that thing in common, you feel connected to them,” Essam explains. “That’s what an anchor is. It's something that anchors you together.”
LinkedIn is uniquely designed to help you find these anchors. To make this easier, Essam developed The Anchor Cheat Sheet, a list of common ground to look for on someone’s profile:
- School or University: Search for alumni from your university within your target industry. LinkedIn’s alumni tool makes this incredibly simple.
- Events: Did you both attend the same virtual summit or industry conference? You can connect with attendees after the fact, even if you never met in person. Use the event as your anchor.
- Mutual Connection: The most straightforward anchor. Mentioning a shared acquaintance provides immediate social proof and context.
- Influencer or Thought Leader: Noticing you both follow and admire the work of someone like Brené Brown or, as Essam notes, Chris Do, creates an instant connection over shared values and interests.
- Content: If they create content, this is a goldmine. Referencing a specific point they made in a post or video shows you are paying attention.
- Project: Mentioning a specific piece of work from their portfolio or company website proves you have done your homework and have a genuine interest.
This is a foundational part of building an authentic personal brand through relationships, not just broadcasting.
4. The Value
Everyone is tuned into the same radio station: WIIFM (What’s In It For Me?). Value is not pitching your service. A message that says, “By the way, we build websites, would you like to have a conversation?” is not value; it’s a transaction. That's a mistake many make when trying to attract ideal clients.
True value is given freely, with no expectation of immediate return. It can be an interesting article you found, an introduction to someone in your network, or a free tool you’ve created. “If you can actually offer them something of value upfront for free... you will get a much, much better response,” Essam states. This builds trust and positions you as a helpful resource, not a desperate seller.
5. The Ask
Many messages fizzle out because they fail to propose a clear next step. They dump information on the recipient and leave them wondering, “What do you want me to do now?”
Your ask must be simple, specific, and low-friction. Essam warns against what he calls The Brain Drain, which is any interaction that requires too much mental energy. Avoid open-ended, complex questions like, “What's your biggest business challenge right now?” That’s work.
Instead, use closed or “this or that” questions. “Do you typically work with corporates or SMEs?” is an excellent example. It requires a simple, one-word answer but opens the door to a deeper conversation. The easier you make it for them to respond, the more likely they are to do so. This is a core tenet of effective advanced communication tactics.
How It Looks in Practice: Good vs. Bad DMs
Theory is one thing; execution is another. The difference between a good and bad DM is stark.
Bad messages are almost always about the sender. They make assumptions and immediately try to extract value. Essam shares cringe-worthy examples he has received personally:
- The Assumptive Audit: “I've done audits for your social media profiles... we can help you get more leads.” The sender assumed a problem that Essam doesn’t have. It created guilt and annoyance, not interest.
- The Insulting Pitch: “I noticed your website [is] built on WordPress, which is honestly quite old style... have you considered this?” Not only was the information incorrect (his site is on Webflow), but it opened with a thinly veiled insult.
- The Generic Pitch: “I'm reaching out cuz I can provide you with high-quality appointments and qualified leads.” This is a generic, automated message with no personalization, no reason, and no genuine compliment. It’s pure spam.
In contrast, a good message is personal, respectful, and conversational. Essam offers templates in this style:
A short connection request might read: “Hey John, I just came across your work with Adidas and I see we have a mutual love for retro footwear. Did you manage to score any free shoes?”
This message works because it’s friendly, personal, and includes a reason (Adidas work), an anchor (love for footwear), and a simple, playful question. It feels human.
A slightly longer first message could be: “I just came across your showreel, I was really impressed with your work, especially the project you did with Bobcat. It reminded me of my first role as a runner... Do you typically work with corporates or SMEs?”
Let's break that down. It contains:
- The Reason: “I just came across your showreel.”
- The Compliment: Specific praise for the Bobcat project.
- The Anchor: Mentioning his past role as a “runner” uses industry jargon to show he belongs to the same tribe.
- The Ask: A simple “this or that” question about their client type.
This approach shows you have taken the time and effort to understand who they are. It respects their time and intelligence, creating the foundation for a real relationship. This is the difference between being a pest and being a potential partner.
It's not about finding a magic script. It's about developing the skill of observation and genuine curiosity, a skill that is essential for anyone serious about building a personal brand.
The Consistency Engine
This framework is not a one-time trick. It is a discipline. The real power comes from repetition and consistency. Essam challenges creatives to imagine the compound effect of implementing this strategy daily.
“Imagine what that would be like compounded over a month or two months or three months if you genuinely reached out and connected with five people every single day for the next 30 days,” he posits. “Where would your level of opportunity be compared to where it is now?”
He estimates that once you get into the rhythm, you can follow this process for four or five people in less than 30 minutes a day. That small daily investment builds a pipeline of conversations and relationships. Over time, that pipeline fills with opportunities for projects, collaborations, and referrals.
The goal is not to win a client with a single message. The goal is to build an engine of opportunity that runs consistently in the background, fueled by genuine human connection.
Once you master the process, it can even be delegated. But you must first understand the principles yourself.
This is not about hacking an algorithm. It is about understanding human nature. It's about trading the shotgun blast of generic pitches for the sniper rifle of personalized, value-driven conversation.
The choice is clear. You can continue sending messages into the void, hoping one sticks. Or you can start building relationships, one thoughtful conversation at a time.
Stop pitching. Start connecting.
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“Clarity comes from conversations.”
— Chris Do
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