The Three LinkedIn Messages I Almost Didn’t Send

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I’ve been applying for roles lately. Like many of you, I spend hours tailoring resumes, writing cover letters, and hoping my application stands out in a sea of others.

This week, I decided to try something different.

Instead of just submitting and waiting, I reached out to three people at a company I’m genuinely interested in. Not with a transactional ask. Not name-dropping mutual connections. Just a simple, honest note.

One had written a blog post about involving IT early in deployments. I referenced his actual insight—not generic flattery.

Another hadn’t published anything, so I referenced the company’s stated philosophy from their job description—accurately, in quotes.

The third was an IC who’d noted she was “open to connect.” I asked a genuine question about her craft—what she’s found most rewarding delivering implementations across different industries.

None of my messages mentioned that I’d applied. None asked for a referral.

I almost didn’t send them. Imposter syndrome kicked in: What if they think I’m networking for access? What if they decline and it hurts my chances? What if it feels forced?

But here’s what I realized:

People don’t mind being approached respectfully. They do mind being used.

A thoughtful connection request that shows you actually read their content, absorbed their philosophy, or care about their craft—that’s the opposite of blind networking. It’s professional curiosity. It’s peer respect. It’s human.

Will all three accept? Probably not. And that’s okay. A declined request doesn’t reflect on my candidacy—it reflects their inbox, their policy, their context.

So what are the potential outcomes?

  1. Accept + No Reply (most likely)
    • Neutral-positive: You’re now on their radar as a thoughtful peer who did homework. If they’re on the hiring team, this may quietly elevate your application when they review it.
  2. Accept + Brief Reply (possible)
    • They might answer your question or acknowledge the connection. No need to push further—just thank them and let it rest.
  3. Declined/Ignored (possible)
    • Declined LinkedIn requests don’t flag your application negatively. Hiring systems don’t track this. Your resume stands on its own merits.
  4. They ask why you are connecting (unlikely – they will probably default to 3)
    • When someone asks why you’re connecting, keep it simple: mention your relevant role, reference something specific about their company or work that genuinely resonated with you, and clarify there’s no hidden agenda. Suggested reply: “I’m in [your field/role] and resonated with [company’s] approach to [specific philosophy/value]. No ask—just appreciated connecting with peers in the space.”
    • You are following this template:

      The 3-part connection response:
      • Who you are: “I’m in [your field/role]…”
      • Why them specifically: “…and resonated with [company’s philosophy / their content]”
      • No pressure: “…No ask—just appreciated connecting with peers in the space.”

But the ones who do? We’ve already started a conversation before my resume even lands on their desk. Not as a supplicant. As a peer.

If you’re in the job search trenches right now: you don’t need to be transactional to be strategic. You don’t need to flatter to stand out. You just need to be genuinely interested in the people behind the company.

That’s not networking. That’s connecting.

Have you reached out to people at companies you’re applying to? How did it go? I’d love to hear what’s worked (or hasn’t) for you in the comments.

Keywords: job search networking, authentic LinkedIn outreach, non-transactional networking, connecting before applying, peer-to-peer professional connections

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