The Awkward Silence After They Accept
Marcus finally got the notification he'd been waiting for: "Jessica Chen accepted your connection request." She was a VP at his dream company, someone he'd been hoping to connect with for months. He was thrilled—for about 30 seconds.
Then the panic set in. What do I say now?
He stared at the message box. Should he pitch his services? Thank her for connecting? Ask for a job? Every option felt either too aggressive or too generic. So he did what most people do: nothing.
Three weeks later, Jessica was just another name in his 500+ connections—someone he'd never actually spoken to. The opportunity was gone before it started.
Sound familiar? The truth is, most LinkedIn connections die in the first DM. Either you send nothing, or you send something that kills the vibe. But when you get that LinkedIn first message after connect right, it sets the tone for everything that follows—real conversations, opportunities, and relationships.
This guide will show you exactly what to say (and what to avoid) so you turn new connections into real relationships.
Why the First Message Matters More Than You Think
Here's the thing: people accept connection requests all the time without thinking much about them. A familiar face, a mutual connection, a decent profile—enough to click "Accept." But accepting doesn't mean they're invested.
Your first message is where you prove that connecting was worth it. It's your chance to:
- Show you're a real person, not a bot or spammer
- Remind them why they connected with you
- Create a reason to keep the conversation going
Get it right, and you move from "random LinkedIn connection" to "someone worth talking to." Get it wrong, and you're just another person who sent a generic pitch.
The Golden Rule of First Messages
Before we get into templates and examples, let's establish the golden rule:
Your first message should feel like the start of a conversation, not the end of one.
That means:
- No pitches
- No favors
- No "pick your brain" requests
- No generic "Thanks for connecting!"
Instead, your message should give them a reason to reply—and make replying feel natural, not obligatory.
What Makes a Good First Message?
The best first messages share three key elements:
1. Personalization
Reference something specific about them—a post they shared, their current role, a shared interest, or mutual connection. This shows you're not copy-pasting the same message to everyone.
2. Value or Relevance
Give them a reason to care. Share a resource, offer a perspective, or ask a thoughtful question related to their work or interests.
3. An Open-Ended Invitation
End with something that invites a response without demanding one. Think "I'd love to hear your take" instead of "Can we schedule a call?"
Good vs. Bad First Message Examples
Let's look at real examples of what works—and what doesn't.
Scenario 1: Connecting After Engaging with Their Content
Bad:
"Hi Jessica, thanks for accepting my request! I'd love to pick your brain about product strategy. Are you free for a quick call?"
Why it fails: Too much, too fast. You're asking for their time before building any rapport.
Good:
"Hey Jessica, I've been following your posts on product positioning—especially your recent thread about messaging clarity. That bit about 'solving the wrong problem with the right words' really hit home. Are you working on any new frameworks around that? Would love to hear where you're taking it."
Why it works: It's specific, shows genuine interest, and asks an open-ended question that relates to their expertise. This approach builds on the psychology of digital rapport—creating familiarity through shared context.
Scenario 2: You Have a Mutual Connection
Bad:
"Hi! I saw we both know Sarah. Small world!"
Why it fails: It's a dead-end statement with nowhere to go.
Good:
"Hey! I noticed we're both connected to Sarah Miller—she's the one who actually suggested I check out your work after I mentioned I was exploring content-led growth strategies. Your background in SaaS content is exactly the kind of perspective I'm trying to learn from. How did you make the transition from traditional marketing to content-first?"
Why it works: It explains the mutual connection context, shows you did your research, and asks a question they'd likely enjoy answering.
Scenario 3: Shared Industry or Interest
Bad:
"Hi! I'm also in marketing. Let's connect and share ideas!"
Why it fails: Too vague and sounds like a copy-paste template.
Good:
"Hey Jessica, I saw you're leading growth at [Company]—I'm in a similar role at a smaller SaaS company and recently hit a wall trying to scale our content distribution. I saw your post about repurposing content across channels and it made me rethink our entire approach. Have you found any unexpected wins in that process?"
Why it works: It's relevant, shows vulnerability (admitting a challenge), and positions the other person as someone who can add value—which most people enjoy doing.
First Message Templates You Can Adapt
Here are plug-and-play templates for different scenarios. Customize them to fit your situation.
Template 1: After Engaging with Their Content
"Hey [Name], I've been seeing your posts on [topic] and really appreciated your take on [specific point]. It got me thinking about [related idea or question]. Have you explored [follow-up angle]? Would love to hear your thoughts."
Template 2: Shared Interest or Challenge
"Hi [Name], I noticed we're both navigating [shared challenge or industry]. I saw on your profile that you [specific accomplishment or role]. I'm currently working on [related project/challenge] and would genuinely love to hear how you approached [specific aspect]. Any lessons you'd be willing to share?"
Template 3: Mutual Connection Introduction
"Hey [Name], [Mutual Connection] mentioned I should connect with you after I brought up [topic]. I checked out your background and was really impressed by [specific detail]. I'm exploring [related area] and would love to learn from your experience. How did you [specific question about their journey]?"
Template 4: Conference or Event Connection
"Hi [Name], great connecting at [event]! I really enjoyed our brief chat about [topic]. I've been thinking more about [something you discussed] and wanted to follow up. Have you had any new thoughts on [related question]?"
These templates work because they follow the principles we covered: personalization, value, and an open invitation to continue the conversation. For more on moving from initial contact to deeper dialogue, check out our guide on turning LinkedIn comments into real conversations.
When to Send Your First Message
Timing matters. Here's when to message:
- Within 24-48 hours of connection: Strike while the context is fresh. Wait too long and they'll forget why they connected.
- Not immediately: Messaging within 5 minutes feels aggressive. Give it a few hours at minimum.
- During business hours (their timezone): Mid-morning or mid-afternoon typically gets the best response rates.
Pro tip: If you connected after engaging with their content, reference that engagement in your message. It reminds them of the context and shows consistency. This is part of the strategic networking funnel that moves people from awareness to conversation.
What NOT to Say in Your First Message
Let's be clear about what kills conversations:
1. The Immediate Pitch
"Hi! Thanks for connecting. I help companies like yours with [service]. Here's a link to book a demo."
Why it fails: You're treating them like a transaction, not a person.
2. The Vague "Thanks for Connecting"
"Thanks for connecting! Looking forward to staying in touch."
Why it fails: It's a dead-end message with no conversation hook.
3. The "Pick Your Brain" Request
"Hey! Can I pick your brain about [topic]? I'd love to grab coffee (virtual or in-person)."
Why it fails: You're asking for their time and expertise without offering anything in return or building rapport first.
4. The Generic Compliment
"I'm impressed by your profile! Let's collaborate."
Why it fails: It's vague, insincere-sounding, and has no clear next step.
What to Do When They Actually Reply
Congrats—they replied! Now what?
Your goal in the second message is to keep the conversation going without forcing it toward an agenda. Here's how:
1. Acknowledge and Expand
Thank them for their response, then add to the conversation with a follow-up thought or question.
"That makes total sense—I hadn't thought about it from that angle. I've been experimenting with [related idea]. Have you seen that work in your experience?"
2. Share Value
Offer a resource, insight, or introduction that relates to what they said.
"That's exactly the challenge we faced last quarter. I found this framework really helpful: [link/resource]. Curious if it aligns with your approach."
3. Suggest a Low-Commitment Next Step (Only if It Feels Natural)
If the conversation is flowing and it makes sense, you can suggest a call or collaboration—but keep it casual and low-pressure.
"This is a great conversation—would you be open to a quick 20-minute chat sometime? I'd love to dig into this more. Totally flexible on timing."
The key is to earn the right to ask by building rapport first. For more on building these relationships strategically, see our post on consistency beating charisma in networking.
What If They Don't Reply?
Not everyone will respond—and that's okay. Here's what to do:
- Wait 5-7 days, then follow up once: Keep it light and add new value. "Hey [Name], just came across this article on [topic we discussed]. Thought you might find it interesting. Hope all is well!"
- If still no reply, move on: Don't take it personally. People are busy, and not every connection will engage. Focus your energy on the ones who do.
- Keep engaging publicly: Continue liking and commenting on their posts. Sometimes a reply comes months later when the timing is better.
Remember: networking is a numbers game with a long timeline. Not every connection will convert immediately, but the ones that do are worth it.
Frequently Asked Questions
How long should my first message be?
Aim for 3-5 sentences. Long enough to add context and personalization, short enough to read quickly. If it looks like a novel, it won't get read.
Should I always message after someone accepts my connection?
Not always. If you don't have a specific reason to reach out, it's okay to wait and engage with their content first. Let a natural conversation opportunity emerge.
Can I send the same message to multiple people?
No. People can tell when you're copying and pasting. Personalization is non-negotiable if you want real responses.
What if I connected with them months ago and never messaged?
It's not too late! Reference something recent they posted or shared, and acknowledge the time gap casually: "I realized we've been connected for a while but never actually chatted..."
Should I mention how I found them or why I connected?
Yes, if it adds context. "I came across your post on [topic]" or "We're both in [industry] and I wanted to connect with more people doing [work]" helps remind them why they accepted.
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