The Great Disconnect: Why Employers and Job Seekers Keep Missing Each Other

After years of working on both sides of the hiring table, I keep seeing the same frustrating pattern: employers say they can’t find the right people, and job seekers feel like they’re shouting into the void. Both sides are trying, and yet—somehow—they keep missing each other.

This disconnect isn’t just annoying. It’s costly, on so many levels. Great candidates are getting passed over, and businesses are losing out on the kind of talent that could really make a difference.

Small business owners especially feel the strain. They’re overwhelmed with applications but still can’t seem to find “the one.” I hear things like:

🔸 “They looked great on paper, but they just didn’t have the real-world skills.”

🔸 “They knew the tech but didn’t mesh with the team.”

🔸 “They interviewed well but fizzled out once they started.”

🔸 “They want flexibility but don’t seem all that dependable.”

One client told me they reviewed 75 applications for a single operations role and still came up empty. “I just need someone who can hit the ground running,” they said. “Is that too much to ask?”

Meanwhile, I’m working with job seekers who are just as frustrated. They’re applying to roles that seem like a perfect fit, only to be ghostedor rejected with no idea why. They tell me:

• “I’m not even sure what this job actually is—they’re so vague.”
• “They want five years of experience but are offering entry-level pay.”
• “I’ve used similar tools, but because it’s not the exact one, I’m out.”
• “They keep saying ‘culture fit,’ but what does that even mean?”

One of my clients, who has over eight years of project management experience, applied to 42 jobs before landing a single interview. “I know I can do this work,” she said. “I just can’t seem to get through the front door.”

Let’s stop sugarcoating it: hiring today feels like a broken game—and both sides are losing.

Employers are flooded with applications but still say, “We just can’t find the right people.” Candidates are pouring hours into tailoring resumes, rewriting cover letters, and learning how to “beat the algorithm,” only to hear nothing in return. Everyone’s tired, frustrated, and starting to question whether the system is even working.

It’s not that people aren’t trying. It’s that the system is no longer designed for actual connection. Here's what's really going wrong:

1. Job Descriptions Have Become Fantasy Projections

Too many job postings read like a wish list written by a committee—crammed with buzzwords, vague jargon, and a laundry list of qualifications that no single person could possibly meet. What was once a tool to attract the right candidate has become a barrier to entry.

Instead of clearly outlining what the job *actually* requires, many descriptions present an idealized version of the role. And in doing so, they eliminate people who could absolutely succeed with a little support and learning.

2. Resumes Have Turned Into Buzzword Bingo Cards

Candidates know the odds are against them. So they spend hours—sometimes days—tweaking every bullet point, agonizing over keywords, and crafting phrases designed to get through automated systems and in front of a real human. And still? Crickets.

The focus has shifted from telling a compelling, authentic story to fitting a machine-readable mold. And the result? We lose the nuance. The context. The real person behind the paper.

3. Automation Is Efficient—but It’s Missing the Point

I’m not anti-technology. AI and automation can be incredibly useful tools—when they support the process, not replace it. But right now, we’ve gone too far in the other direction.

Applicant tracking systems and AI screeners are built to filter *out*, not invite in. They prioritize exact matches, overlook transferable skills, and flag great candidates as “not a fit” simply because a single phrase didn’t match up. It's efficient, sure. But we’ve traded speed for substance. And connection is getting lost in the process.

4. Everyone's Playing It Safe—And Playing Too Small

Employers want someone who’s done the job before. Candidates only apply for roles where they check every single box. No one wants to take a risk—even when that’s exactly what’s needed.

But hiring isn’t about checking boxes. It’s about potential. Some of the best hires come from unexpected places. But when both sides are stuck in this “perfect match or bust” mindset, we leave no room for creativity, possibility, or growth.

5. We've Forgotten There's a Human on the Other Side

This might be the biggest one: we’ve lost the human side of hiring.

We’re so deep into automation, optimization, and efficiency that we’ve forgotten what this process is really about—people. A job search isn’t just a transaction. For a candidate, it’s their livelihood, their confidence, and often their identity on the line. For employers, it’s not just about filling a role—it’s about finding someone who will contribute to the culture, grow with the company, and do meaningful work.

That kind of connection doesn’t show up on a keyword scan. It shows up in stories. Conversations. Chemistry. And right now, we’re not creating enough space for any of that.

The good news? This is fixable. But not with another template or another tool. We need a shift in mindset—on both sides of the table. Less optimization. More intention. Less perfection-seeking. More potential-spotting.

For Employers:

🟣 Be honest about what you actually need.

What will this person do, day to day? What will success look like in the first few months? Strip the job description down to the essentials. Say what you mean.

🟣 Stop searching for perfection—look for potential.

If someone has 75% of what you need and a proven ability to learn, that’s gold. You don’t need a clone—you need a contributor.

🟣 Let people show you who they are.

Ask better questions. Invite real conversations. Let them walk you through how they solve problems or think on their feet. That’s where the good stuff lives.

🟣 Bring humanity back into the process.

Every resume belongs to a real person. A little care and communication goes a long way—especially when you're saying no.

For Job Seekers:

🔸 Don’t just say what you did—show what changed because of you.

Make it easy for hiring managers to see the impact you made, not just the tasks you handled.

🔸 Spell it out.

If your background isn’t an obvious match, connect the dots for them. Show them *why* your experience is still highly relevant.

🔸 Lead with adaptability.

In a changing world, your ability to learn, shift, and figure things out is more valuable than ever. Share those stories.

🔸 Don’t wait for the perfect title.

Look past labels. If the work excites you and you have the skills to succeed, go for it—and make your case.

🔸 Don’t wait for the perfect title.

Look past labels. If the work excites you and you have the skills to succeed, go for it—and make your case.

🔸 Remember: you’re not a checklist.

You’re a full, capable, dynamic person—not just a string of keywords or titles. Own that.

You’re a full, capable, dynamic person—not just a string of keywords or titles. Own that.

The hiring process shouldn’t feel like a never-ending series of rejections, red flags, and resume rewrites. It shouldn’t take 30 applications to get a conversation. And it shouldn’t leave anyone—employer or job seeker—burned out and discouraged.

But right now, it does.

We can fix that. And it starts by remembering what this is really about: people trying to find the right fit so they can do meaningful work together.

If we want better results, we need better conversations. More listening. More imagination. And a willingness to see past the surface.

So let’s talk about it—

Where have you seen this disconnect show up in your own experience? And what do you think would make the biggest difference in closing the gap—for real?

Leave a comment below, I'd love to hear your thoughts. 👇