Think Like a Boss: How Hiring Really Works
by Trevor Calton
Most job seekers believe that hiring starts with a job posting.
It doesn’t.
Hiring managers don’t wake up and say,
“Let me sort through 250 strangers today.”
Instead, they do what most of us would do, they start with who they know.
And that changes everything about how you should approach your job search.
Here’s What Really Happens When a Job Opens Up
First: They Look Inside the Company
Before a manager ever posts a job publicly, they check to see if anyone internally is a good fit:
- Existing employees
- Interns
- Volunteers
Why? Because it’s cheaper, faster, and lower risk. They already know how that person works, and whether they fit the culture.
Then: They Ask Around Their Network
If there’s no one internal, they reach out to:
- Friends and former colleagues
- Vendors and customers
- Industry peers
- People they’ve met at events
Still no posting. Still no resume pile. Just a few texts, emails, or referrals.
Only Then: They Open It to the Public
This is the last resort.
When no one inside or in their network is a fit, then the job gets posted. That’s when the 250 resumes start rolling in. And it becomes a full-time job just to sort through them.
Most hiring managers don’t want to get to this point.
What This Means for You
If you’re applying cold to job postings, you’re putting yourself in the last (and hardest) pool.
Your real goal isn’t to apply better. It’s to stop being a stranger.
How to Get Into the Inner Hiring Circles
Volunteer or Intern
If you want to work somewhere and there’s no opening, find a way in. Volunteer. Intern. Consult. Even a day a month can put you on the radar.
Hiring managers treat volunteers like internal team members. You’re now in the first circle.
Leverage Industry Events
Don’t just attend, volunteer. That gives you a role, a reason to talk to people, and a better chance of connecting with hiring managers directly.
Volunteering = instant context + purpose-driven networking.
Build a Bridge Through Conversation
This is where informational interviews come in.
Even a 20-minute chat gives you an edge over cold applicants. You become a real person. Someone they remember. Someone they might recommend.
The Bottom Line
Most hiring decisions happen before the job is ever posted. And most managers would rather hire someone they know, even indirectly, than gamble on a stranger.
So stop waiting for permission to reach out. Start finding ways to get closer to the decision-makers, before they even know they’re hiring.
Want the Framework That Makes This Easier?
Career Building from the Inside Out teaches you how to:
- Break into the inner circles
- Build trust with hiring managers
- Get noticed before the listing goes live
Want me to teach this at your next event or training? Book a workshop or keynote
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