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Demystifying the Cover Letter

One topic that continually vexes job seekers is the cover letter. It’s not as well-known as the resume and it’s less public than a LinkedIn profile...as a result job searchers are often intimidated by cover letters.

By Kendell Brown

Kendell Brown is a member of the iRelaunch Career Coaching team. Founder of Ascension Careers and a relauncher herself, She works with clients with to ascertain and achieve their career goals via strategic planning, positioning and branding assessments, identifying transferrable skills and providing counsel for working through challenging work situations. Kendell is an iRelaunch professional resume writer and offers discounts to the relauncher community. Learn more about this service here.


I’ve been a career coach for quite some time and I’ve worked with clients on a wide variety of topics ranging from the mundane (How should I format my resume?) to the exotic (What skills did I gain from my breast-feeding consultancy?). However, one topic that continually vexes clients is the cover letter. It’s not as well-known as the resume and it’s less public than a LinkedIn profile, as a result job searchers are often intimidated by cover letters. Consequently, they have many questions. Here are three common cover letter questions with answers (Spoiler - #3 is just for relaunchers).

Q: Should I write a cover letter?

This is far and away the most common question I get. So many employers create job postings and require a resume, but make a cover letter optional. When a cover letter is optional, is it really optional? And if it’s really optional, should I write one?

A: Yes – Write a cover letter when:

  • A cover letter is explicitly requested
  • A cover letter is not requested, but also not expressly prohibited

Taking the time to write a cover letter shows interest in the position and a willingness to take the extra step. When a manager is deciding between candidates, the one that gets the offer is the one that’s already gone above and beyond.

A: No – There are times when a cover letter won’t help your candidacy.

  • Don’t write a cover letter when the posting says not to do so.
  • Don’t write a cover letter when the application site doesn’t provide opportunity to submit one.

If the posting either explicitly or implicitly says not to include a cover letter, don’t do it. If you submit a cover letter in this scenario - at best, your effort gets ignored; at worst, you piss off someone in the hiring chain.

Q: What’s the difference between a resume, a LinkedIn profile and a cover letter?

Each of these job searching tools plays a different role while cumulatively shaping your candidacy. While the information you convey in each will likely overlap, the language used and the details presented should not be copied verbatim.

  • Resume – Resumes are backward-looking. They highlight your tasks and responsibilities, skills and competencies and notable achievements all in the context of prior experiences. Due to space constraints, your resume is forced to provide a high-level view.
  • LinkedIn profile – If your resume is a self-portrait, your LinkedIn profile is a three-dimensional sculpture. You can show your many sides – your prior accomplishments, your future ambitions and your side hustle interests. The public nature of LinkedIn plus the lack of a length restriction means you can fully show all facets of your brand.
  • Cover letter – The beauty of a cover letter is that it is the ultimate customization tool. The content doesn’t follow strict guidelines like a resume. Meaning, a short-lived project that may not be appropriate for a resume can appropriately be highlighted in a cover letter. Additionally, your LinkedIn profile will include all of your skills, whereas you can use a cover letter to focus attention on your most relevant skills for a particular position.

Do I mention my career break in a cover letter?

Yes, you should mention your career break. The cover letter is your best opportunity to both discuss the break and show how it relates to your candidacy for a specific role. Perhaps it was during the break that you decided to go in a new career direction. Or maybe you discovered new talents that broaden your skill set. Often, the break can be positioned as a time of reflection which lead to an understanding that this is the right role.

In talking with clients, I’ve learned, this question actually underscores two concerns:

  • Overwhelming employers
    • Q: “It’s on my resume and it’s in my LI profile, is there anything to be gained from including my break in a cover letter? A: Your break is a part of your brand. To exclude it from your cover letter would invite confusion amongst those assessing your candidacy.
  • Striking an appropriate balance
    • Q: “What do I prioritize – explaining my break or sharing pertinent skills and experiences?” A: Your cover letter is a bespoke document that is written to tell your story for a specific job. The priority should be amplifying whatever best shows you as a perfect fit.


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