The Message That Ruined Everything
You've seen it. Maybe you've even sent it: "Hi {{FirstName}}, I noticed we're both in the marketing space. I'd love to connect and explore potential synergies."
It lands in someone's inbox like a cold fish. The placeholder text screams "mass outreach." The vague "synergies" reeks of a sales pitch. The recipient deletes it without a second thought—and you wonder why LinkedIn "doesn't work."
Here's the uncomfortable truth: LinkedIn doesn't have a connection problem. It has a relationship problem.
Most professionals treat LinkedIn like a transactional marketplace—send enough connection requests, pitch enough people, and eventually someone will bite. But the people who consistently generate real opportunities on LinkedIn? They're playing a completely different game. They're not chasing connections. They're cultivating relationships.
Why Most LinkedIn Outreach Feels Salesy (And How to Fix It)
Let's start with the obvious: people can smell a sales pitch from a mile away. And on LinkedIn, where everyone's guard is up, your outreach needs to clear an exceptionally high bar.
The problem isn't that you're selling—it's that you're leading with selling. You're asking for something (time, attention, a meeting) before you've earned the right to ask. That's not networking. That's just noise.
Transactional vs. Relational Mindset
Here's the fundamental shift you need to make:
- Transactional thinking: "How can I get this person to help me?"
- Relational thinking: "How can I add value to this person's world?"
When you approach LinkedIn with a relational mindset, everything changes. Your connection requests become invitations to genuine dialogue. Your comments become opportunities to add insight. Your DMs become the start of real conversations—not pitches disguised as pleasantries.
This shift is at the core of building authentic connections where opportunities come to you because you've built trust and provided value consistently. And it starts with ensuring your profile is optimized—learn how LinkedIn profile SEO makes you more discoverable to the right people.
Step 1: Build Familiarity Before You Ever Send a DM
The biggest mistake professionals make? Going straight for the DM without any prior interaction. You wouldn't walk up to a stranger at a conference and immediately ask for a meeting—so why do it on LinkedIn?
Before you reach out to someone, invest in micro-interactions that build recognition and trust. Here's how:
Engage With Their Content First
- Like their posts consistently: Don't just heart everything—be selective. React to posts that genuinely resonate with you.
- Leave thoughtful comments: Skip the "Great post!" responses. Instead, add a perspective, ask a clarifying question, or share a related experience. This is where commenting becomes your most powerful networking tool.
- Show up regularly: One comment isn't enough. Show up in their feed multiple times over a few weeks. Familiarity builds trust.
When you finally send that connection request or DM, you're not a stranger—you're the person who's been adding value in their comments section. That changes everything.
Track Your Touchpoints
It's easy to forget who you've engaged with and when. That's why tracking matters. Use a simple system—a spreadsheet, a CRM, or a tool like ANDI—to log:
- Who you've commented on and when
- What posts resonated with them
- When it's time to move from comments to DMs
This isn't about being manipulative—it's about being intentional. Relationships require attention, and attention requires systems. Understanding the hidden power of micro-interactions will amplify your results.
Step 2: Personalize Your Outreach (For Real)
Let's be honest: most "personalized" outreach isn't personal at all. It's just mail merge with someone's name and company plugged in. Real personalization requires actual effort—and that's exactly why it works.
Go Beyond the Surface Details
Don't just mention their job title or company. Reference something specific about their work:
- A recent post they shared and why it resonated with you
- A project they worked on that you admire
- A challenge they've mentioned that you've also faced
- A perspective they have that's different from the mainstream
Example of bad personalization: "Hi Sarah, I see you work at XYZ Corp. I'd love to connect."
Example of real personalization: "Hi Sarah, your post last week about scaling customer success without burning out your team really stuck with me. We're facing the same tension right now—balancing automation with the human touch. Would love to hear more about how you're thinking through it."
See the difference? The second message shows you've actually paid attention. It invites dialogue instead of demanding time. It's not salesy—it's curious. And when people visit your profile after receiving such thoughtful outreach, make sure your About section tells your story in a way that reinforces the authentic impression you've created.
Lead With Value, Not Asks
If your first message includes a request (a meeting, a demo, a coffee chat), you're doing it wrong. Instead, lead with value:
- Share an article or resource relevant to a challenge they've mentioned
- Offer a genuine compliment on their work (without expecting anything in return)
- Ask a thoughtful question that shows you're engaged with their ideas
Value-first outreach disarms people. It signals that you're not just another person trying to extract something from them. You're someone who might actually be worth knowing.
Step 3: Nurture the Relationship Over Time (Not Just When You Need Something)
Here's where most LinkedIn relationships die: someone connects, has one conversation, and then disappears until they need something six months later.
Sound familiar?
Real relationships require ongoing nurture. That doesn't mean you need to message everyone weekly—it just means you need to stay visible and relevant in their world. Understanding why consistency beats charisma on LinkedIn will help you maintain momentum.
Stay Top of Mind Without Being Annoying
Here are low-effort, high-impact ways to stay connected:
- React to their updates: When they share a win, a new role, or a milestone, be there to celebrate it.
- Send periodic check-ins: Every few months, reach out with no agenda. "Hey, been thinking about that challenge you mentioned—how's it going?"
- Tag them in relevant content: If you see an article, post, or resource that would genuinely help them, send it their way.
- Amplify their voice: Share their content with your network (with thoughtful commentary, not just a repost).
The key word here is genuine. Don't do these things as tactics—do them because you actually care about the people in your network. Authenticity can't be faked, and people can always tell when you're just checking boxes.
Give Before You Ask
When you do eventually need something—a referral, an intro, advice—you'll have earned the right to ask. But even then, frame it as a two-way relationship:
"Hey [Name], I'm working on [specific project] and I know you have experience in this area. Would you be open to a quick chat? And if there's anything I can help you with on my end, I'm happy to return the favor."
Notice the reciprocity. You're not just taking—you're offering to give. That's how professional relationships are supposed to work.
Step 4: Avoid the Common Relationship-Killers
Even with the best intentions, it's easy to sabotage your own efforts. Here are the most common mistakes that make you come across as salesy—and how to avoid them:
Mistake #1: Pitching Too Soon
If your second message is a pitch, you've lost. Give the relationship time to breathe. Aim for at least 3–5 meaningful interactions before you ever introduce what you do (unless they ask first).
Mistake #2: Making It All About You
Nobody cares about your credentials, your awards, or your impressive client list—at least not initially. They care about what's in it for them. Frame every interaction around their needs, challenges, and interests.
Mistake #3: Disappearing After Connecting
Don't be the person who connects and then ghosts. If you're going to build a network, actually nurture it. Consistency beats intensity every time.
Mistake #4: Being Transactional
If you only reach out when you need something, people will notice. Build relationships when you don't need anything, so when you do, it feels natural—not opportunistic.
Success Story: From Stranger to Client in 90 Days
Emma, a freelance brand strategist, wanted to work with mid-sized tech companies. Instead of cold pitching founders, she took a relational approach:
- Weeks 1–4: She identified 20 founders in her target market and spent 10 minutes daily commenting thoughtfully on their posts.
- Weeks 5–8: After building familiarity, she sent personalized connection requests referencing specific posts. 15 accepted.
- Weeks 9–12: She continued engaging, occasionally sharing helpful resources via DM—never pitching.
In Week 10, one founder reached out: "I keep seeing your name pop up and love your insights. We're actually looking for help with our brand positioning—would you be open to a chat?"
Emma closed a $25,000 project. She never sent a single pitch. She just showed up consistently, added value, and let the relationship unfold naturally.
That's the power of building real relationships. You stop chasing opportunities and start attracting them. Learn more about building digital rapport that feels natural, not forced.
Your 30-Day Action Plan
Ready to build real relationships on LinkedIn? Here's your roadmap:
Week 1: Identify and Observe
- Identify 10–20 people you want to connect with (clients, collaborators, mentors)
- Follow them and spend time reading their content
- Take notes on their challenges, interests, and communication style
Week 2: Start Engaging
- Comment thoughtfully on 3–5 posts per day from your target list
- Focus on adding value, not promoting yourself
- Track who engages back with your comments
Week 3: Send Connection Requests
- Send personalized connection requests to people you've engaged with multiple times
- Reference a specific post or comment in your note
- Keep it short, genuine, and agenda-free
Week 4: Deepen the Relationships
- Continue engaging with their content regularly
- Send occasional DMs to continue conversations started in comments
- Share resources, celebrate their wins, and stay visible—without asking for anything
After 30 days, you'll have built genuine familiarity with dozens of people in your network. Some will become clients. Some will become collaborators. Some will simply become people you respect and enjoy engaging with. All of it is valuable.
Frequently Asked Questions
How long should I engage with someone before reaching out directly?
There's no magic number, but aim for 3–5 meaningful interactions (thoughtful comments, likes, or shares) over 2–3 weeks. The goal is to become a familiar name before you ever send a DM or connection request.
What if I don't have time to engage with dozens of people every day?
Start small. Focus on 10–15 key people and spend just 15 minutes a day engaging with their content. Quality beats quantity. Consistent, thoughtful engagement with a smaller group will yield better results than superficial interactions with hundreds.
How do I avoid sounding fake when personalizing my outreach?
Don't force it. Only reach out to people whose work genuinely interests you. If you have to manufacture a reason to connect, it's probably not the right connection. Authenticity comes through when you're actually curious about the other person.
Is it okay to connect with competitors or people in the same industry?
Absolutely. Some of the best relationships come from peers and competitors. They understand your challenges, can offer insights, and often become collaborators or referral sources. Don't silo yourself—expand your network horizontally as well as vertically.
Next step: Take control of your LinkedIn relationships — Try ANDI Free.
