Do Cover Letters Still Matter in 2025? Here's the Real Answer

Out of everything I’ve been asked over the last 15+ years as a career Coach, this is hands down one of the most common questions—especially from professionals over 40 who are applying after some time away or trying to pivot.

So let me give it to you straight:

Yes, cover letters still matter.

Not for every job, not in every situation—but when they do, they really do.

Let Me Tell You About Erin

Erin hadn’t applied for a job in five years. She stepped away from her career to care for her father, who had been diagnosed with long-haul COVID. It wasn’t something she planned—but it changed everything.

She became the point of contact for multiple specialists. Managed care plans. Scheduled appointments. Advocated during hospital visits. Coordinated everything from home health services to insurance follow-ups.

And as she moved through it all, something clicked.

She realized what she was doing wasn’t all that different from the project management roles she held earlier in her career. She was leading a process, solving problems, juggling timelines, and keeping the big picture in mind—all while communicating with clarity and compassion.

When her father’s health stabilized (he’s doing well, I’m happy to share), Erin was ready to return to work. But not in the same way she left.

This time, she wanted to take the skills she built through caregiving—and combine them with her project management background—to pursue program manager roles in healthcare or mission-driven organizations.

Did she put this in her cover letter? Absolutely.

I helped her write it.

She shared how caregiving helped her grow—not just personally, but professionally. She connected her past leadership experience with her renewed sense of purpose and interest in improving systems that support people.

And we didn’t stop there. We coached her on how to talk about it in interviews—with honesty, focus, and confidence.

That’s when things changed.

Same résumé.

Same qualifications.

But now her story was front and center—and that made all the difference.

You’ve Heard About Storytelling, Right?

Storytelling isn’t just for interviews or branding.

It belongs in your cover letter too.

It’s how you connect the dots for someone reading your application.

It’s where you show them:

• Why this job matters to you
• Why you chose this company
• Why now is the right time for you to step in and contribute

Your résumé tells them what you’ve done.

The cover letter tells them why it matters—and that can be the difference.

Why This Still Matters in 2025

There’s no shortage of job seekers right now.

In 2025, this is just one way to stand out among a sea of applicants.

And I say one because this is what I help people with every day—especially professionals over 40. I teach them how to stand out in a job market that’s fast, digital, and often overwhelming.

A cover letter might not always be the thing that gets you hired.

But it could be the thing that gets you noticed.

When Cover Letters Help Most

Here’s when I recommend including one:

• You’ve been out of the workforce and need to explain a gap
• You’re making a career change
• You want to challenge age-related assumptions without saying it outright
• You’re applying to a company that really matters to you
• You’ve applied before and want to reintroduce yourself with intention

This is your space to speak. And for some of my clients, it’s been the only thing that got their foot in the door.

When It’s Okay to Skip It

Now, there are times when I tell people to skip it:

• If a recruiter says don’t send one
• If the system won’t accept attachments
• If it’s a fast-fill or high-volume role with hundreds of applicants

But when that field says optional—to me, that’s an open door. And most people walk right past it.

Here’s What I Tell My Clients

You don’t need a perfect letter. You need a real one.

Answer three things:

1.  Why this job?

2.  Why this company?

3.  Why now?

Keep it short—just one page. And make it sound like you. Not robotic. Not overly formal. Just honest and clear.

If you’ve ever said, “I wish I could explain what happened,” or “If they just knew why I’m applying,”—this is where you do that.

Here’s the Bottom Line

Cover letters aren’t old-school—they’re overlooked.

And in a time where so much feels automated, human connection still matters.

Writing one won’t guarantee a job.

But skipping it might cost you the one you really wanted.

Because at the end of the day, it’s not always the most experienced person who gets chosen—

It’s the one who made the clearest connection.

P.S.

If you’re over 40 and putting yourself out there but not getting the response you hoped for, it might not be your résumé—it might be the way your story is showing up.

That’s what I help with inside Career360. And you don’t have to figure it out alone.