Compelling Cover Letters: Why They Still Matter

Get peer input when crafting your cover letter. An objective reader can help you determine if your story captures the key traits you wish to demonstrate in the letter.

By Jill O’Mahony Stewart

Are cover letters still necessary? This question comes up a lot. As bots screen our resumes, we wonder if we really need an accompanying cover letter.

A resounding “yes” comes from the online world supporting job seekers:

  • “… far too often, job seekers treat the cover letter as an afterthought to writing a resume. Or they don’t bother to write one at all.” Robert Half Blog, January 2020
  • Yahoo Finance says, “A stellar cover letter is still a job search must-have.”
  • com notes, “For starters, it’s basic manners to send one.”
  • And Business Insider advises, “…you should always have an excellent cover letter ready to go because you never know how much weight your hiring manager will put on it.”

Compelling cover letters set us apart.

Danny Rubin, author of “Wait, How Do I Write This Email?” quotes a former CEO who says employers “hire character, and train skill.” Your resume summarizes your experience, skills and education. The cover letter is your chance to demonstrate character traits.

The value of storytelling

While internship experiences count, recent grads can also tell stories of earlier jobs they’ve held. And it doesn’t matter if you were “just” a lifeguard, a server or a retail clerk. A succinct story about saving a life or making someone’s day better – whether at a restaurant or a store – tells a lot about you, your personality and your character.

The best stories have drama and details. Here are a couple of good examples of grabber opening lines:

“It was a retail nightmare.”

Though exhausted from closing the night before, this retail clerk told a story that showed he was patient, kind, and friendly to his two older lady customers while selling them each two pairs of shoes. Let’s interview this guy!

Or here’s another:

“56,754 videos…It was overwhelming to see, but I immediately got down to business.”

This video screener sounds persistent, not easily scared off, and focused. His approach to the ever-mounting video challenge earned him an office and a promotion within weeks of starting his first internship.

In each instance, I wanted more details. What happened? How did it turn out? Is everything OK? And in the course of reading on, I learned a bit about each applicant’s personality and character.

A well-told, succinct story draws us in. In a few sentences, you can describe the situation confronting you, your response to it, and the results achieved. From the brief but revelatory story, the letter can then pivot to how you would use those traits to the job you are seeking.

In the final paragraph, you ask to follow-up, then pleasantly sign off. All on one page. All mechanically sound, and all well formatted to look like a professional business letter.

Rely on your resume to capture your skills, work experience and education. Complement your resume with a letter that touts your character and personality to set you apart and open the door to an interview, and maybe even an offer. 

Jill O’Mahony Stewart teaches writing workshops for professionals to help them sharpen their style and communications effectiveness. At Career Transitions Center of Chicago  she conducts a workshop called “Compelling [and Creative] Cover Letters.” She also teaches writing for public relations at DePaul University’s College of Communication. @jillostewart


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