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The Relationship Outreach Guide: Exactly What to Do, Step by Step

No theory. No fluff. Just the exact framework to start real conversations at companies you want to work at, even if you know nobody there.

Micah Baird
Micah Baird
Founder, Core Line
February 24, 2026
6 min read

You don't need another article telling you relationships matter in your job search.

You already know that.

What you need is to know exactly what to do Monday morning. This is that.

Step 1: Pick 10 Target Companies

Write down 10 companies you'd genuinely want to work at. Not 50. Not 100. Ten.

You're going deep, not wide. Most people spray applications everywhere and build zero relationships anywhere. You're doing the opposite.

Criteria for your 10:

  • You'd actually be excited to work there
  • Your background is a natural fit
  • They're growing (check LinkedIn headcount trends)
  • Bonus: you have even one weak connection there

Do this now. Literally open a notes app and write the 10 names. Everything else in this guide depends on having a focused list.

Step 2: Find Your People

For each company, find 2 people worth connecting with. Not executives. Peers.

Someone at your level or one above in your target department. They're more approachable, more likely to respond, and when the time comes, more likely to refer you internally.

How to find them:

  1. Go to the company's LinkedIn page
  2. Click "People"
  3. Filter by department and title
  4. Look for people who've been there 1-3 years (long enough to know the culture, not so long they're checked out)
  5. Check mutual connections first - even a second-degree connection changes the dynamic

You're looking for 20 people total across your 10 companies. That's your outreach list.

Step 3: Write the First Message

This is where most people fail. They either don't reach out at all, or they send something like this:

"Hi [Name], I came across your profile and I'm very interested in opportunities at [Company]. Would you have 15 minutes for a quick call?"

That message asks a stranger for a favor before you've given them any reason to say yes. Delete it.

Here's what works instead.

The formula: Specific observation + one genuine question.

That's it. No ask. No mention of jobs. No resume. Just something real you noticed, and one question you actually want the answer to.

Examples that work:

"I saw you made the move from [previous company] to [current company] about two years ago. I'm at a similar crossroads right now and that transition is exactly what I'm thinking about. What surprised you most about the shift?"

"I was reading about [specific initiative, product launch, or news at their company] and it caught my attention because I worked on something similar at [your company]. How has that been going from the inside?"

"Your background in [specific thing] is almost identical to mine. I'm trying to figure out the best next move for someone with this kind of profile. What would you do differently if you were starting over?"

Notice what these have in common. They're specific. They're about the other person. They invite a real answer, not a yes or no. And they're short, three or four sentences max.

The goal of the first message is one thing: get a response.

Step 4: Have the Actual Conversation

When they respond, don't pitch yourself. Not yet.

Ask a follow-up question based on what they said. Share something relevant from your own experience. Be a real person having a real conversation.

Two or three exchanges in, you've built enough rapport to be honest:

"I've really appreciated this conversation. I'm actually exploring some transitions myself and [Company] is one I'm genuinely excited about. I don't want to be presumptuous, but if there's ever a role that fits my background, I'd love to be on your radar. No pressure at all."

Low pressure. Genuine. And because you've earned some goodwill first, it lands completely differently than a cold ask.

Step 5: Follow Up Without Being Annoying

Most relationships die because nobody follows up. Not because of rejection, just silence and forgetfulness on both sides.

The rule: follow up once, lightly, if you don't hear back after 5-7 days.

"Hey [Name], just wanted to bump this up in case it got buried. No worries if timing isn't right."

That's it. One sentence. If they don't respond after that, move on. No third message.

For active conversations, check back in every 2-3 weeks with something useful. An article they'd find relevant. A quick update on something you discussed. Not "just checking in", that's lazy. Give them a reason to reply.

Step 6: Track Everything

This is the part that separates people who get results from people who stay busy.

You have 20 conversations in progress across 10 companies. You cannot keep this in your head.

For each person, you need to know:

  • When you last talked
  • What you talked about
  • What you said you'd follow up on
  • What your next move is

If you lose track of a conversation for more than two weeks, the relationship goes cold. The opportunity disappears. And you did all that work for nothing.

This is exactly what Core Line is built for. Track people, conversations, and follow-ups. Not just companies and application dates.

The 30-Day Timeline

Week 1: Finalize your 10 companies. Find 20 people. Send your first 20 messages.

Week 2: Follow up on non-responses (once). Deepen conversations that started.

Week 3: You should have 5-8 real conversations going. Start being honest about your search with the warmest ones.

Week 4: At least one of these will have gone somewhere a job portal never would have. Someone referring you internally. A role you heard about before it posted. An intro to the actual hiring manager.

That's the pipeline. It's slower to start than clicking Apply. It's dramatically more effective at the end.

The One Thing

If you take nothing else from this guide, take this:

Send one message today. Not tomorrow. Not after you perfect your LinkedIn profile. Today.

Pick one person from one company on your list. Write three sentences. Send it.

That's how this starts.


Core Line tracks your relationships, not just your applications. The CRM built for job seekers who know that people get people hired. coreline.app

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Micah Baird
Micah Baird

Founder, Core Line

Micah is the founder of Core Line. After years of helping friends navigate job searches and seeing the same patterns repeat, he built Core Line to help everyone manage their career relationships like a pro.

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