The Cover Letter Conundrum: When, Why and How to Write and Use Them

In my opinion cover letters are the most controversial aspect of a candidate’s resume portfolio and there is much debate about the pro and con of when, why and how to write and use them effectively.

For me only one cover letter rule is written in stone; if a job posting, recruiter, or the person you are sending it to specifically ask that you include a cover letter you must send one along with your resume! If they also include a special instruction such as salary history etc, you must address the request without being cute or overly evasive.

On the other hand if a cover letter is not requested and you choose not to include one, no harm/no foul.

Something I think job hunters should be aware of is this: when you send both a cover letter and a resume as a package the majority of people in the selection and decision making process will not receive or read your cover letter; unless one is specifically requested.

First off not everyone who first screens your documents will read both; at best 50%-70% of the people will read the cover letter; this figure gets lower depending on how many resumes they have to review. Then at each level of escalation only 25%-50% of the people who got both the resume and cover letter will send the cover letter up the line to the next level of interviewer or decision maker along with your resume.

So if you’re counting on a cover letter being read and influencing the decision to interview or hire you, as we say here in Brooklyn Fuggetaboutit.

The most common cover letter approaches

Sell Yourself Approach
This approach is my least favorite, but for some reason it is the most common. I believe if a resume can stand up to scrutiny a sell yourself oriented cover letter is unnecessary. However if you feel a need to sell yourself in your cover letter to get noticed do it subtly. Focus on how you fit the job, don’t stretch the truth, and by all means don’t be long winded or ramble on. Make your point and stop.

One reason I dislike this type of cover letter is that most people who use this approach tend to reiterate verbatim the words that appear on their resume, especially the accomplishments. Worse yet some cover letters I’ve read include information that contradicts what is written in the resume.

If you are going to sell yourself in a cover letter I suggest rewriting and repackaging the information so it will be fresh not boring when they get around to reading the same information on your resume; and check your facts.

On the creative side I’ve seen people, I being one of them, use charts in cover letters when the goal is to draw comparisons between the candidate and what the company wants, what the competition brings to the table, or to compare industry wide metrics the candidate greatly exceeded.

A sales approach is best used when the resume can not strongly articulate certain critical factors because they may not be current, they are solid but limited in time or scope, or it is felt the competition is stronger. Some use a sales approach because they are lazy or uninformed about tweaking their resume for particular a job, or they feel they have a poor resume but a strong cover letter will compensate for this.

Letter of Introduction Approach

This is the approach I favor most. Again, I am of the belief if your resume can stand up to scrutiny and shows that you fit the desired profile there is no need to pre-sell yourself in a cover letter.

What I prefer is a brief professional letter of introduction expressing your interest in a specific position and telling the reader why you want this particular job and want to work for their company above all others.

I’ve been know to make a strong opening statement and then in the following paragraph/s quote the company’s own words that describe what they are looking for and close the paragraph with a statement such as ‘this is an area in which I excel’, or ‘this is my forte’, or ‘as you will see from my resume and accomplishments, I am a perfect match for the person you seek to interview and hire.’

I also on occasion have suggested including verifiable endorsement/s in this cover letter to validate value.

Closing On Objections approach

Sometimes you are not a perfect fit for a job and your resume taken at face value includes as many deselecting points as qualifiers; and there is a lot of what I call green areas (a term based on my resume writing exercises) that can be misinterpreted. These are areas where you do not have exactly what the company seeks in a hire in the exact way they want it; but you do have closely related skills, experience or had similar responsibilities in a different field or industry.

In these cases I suggest a cover letter that focuses on getting the reader to see you through your eyes and why you feel you can do the job.

If you can anticipate their objections you can overcome them before they become a deselecting factor, or get a reader to give you the benefit of the doubt and bring you in for an interview to see if you are a good match.

This cover letter is the most difficult to write; it needs to be 100% on point, positive, and perfectly worded to get your point across without turning off the screener.

Perry Newman CPC/CSMS is a nationally-recognized career services professional; an executive resume writer and career transition coach, certified social media strategist, AIPC certified recruiter and charter member of the Career Rocketeer team. Passionate about all things related to career management, Perry has been critiquing Career Rocketeer readers' resumes at no cost since 2009. For a complimentary critique, email your resume to

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  1. I disagree with you Perry about not sending a cover letter if one is not specifically requested. Many hiring managers use this as an elimination tool to weed out candidates who are not seriously interested in the position. Since we do not know the cover letter preferences of the individual hiring manager, I recommend that all my clients send a well written cover letter that introduces them as someone worth getting to know. This strategy has been working effectively for them, with a very high interview rate.

  2. Another situation to include a cover letter is when there is something negative in your application: terminations, felonies, job hopping, etc. This “letter of explanation” can help get your foot in the door when otherwise your app would have been disregarded.

  3. Elizabeth Uhlhorn says:

    I always read the cover letters of people I hire. I believe the cover letter gives me a quick synopsis of what the candidate thinks is most important about himself / herself and the job. It gives me a better idea of their personality than the resume does – why do they say they like my company?, why do they want the job? have they researched us well? And when a cover letter is not included (even though many of the University systems we recruit through don’t specifically require them) I reject the candidate outright – if they can’t take the extra time to put together some thoughts on why they’re excited about the job, they’re not the candidate for me.

  4. stephen q shannon says:

    Perry, Your points are compelling. As I work with my boutique clients as a trainer, not a coach, I’ll share your thoughts with them unedited and with attribution.
    Over the past many years I have cautioned against using the cover letter as a not well disguised resume page 3.
    My counsel is to not put promises in the cover letter that are not substantiated in the resume. Done right by the candidate, with some help, I have seen a cover letter produce a paid interview trip and later a job offer. Why? Because when a cover letter includes value propositions that ring true to the doubting hiring official the resume will actually be read for the first time at the interview. We’re talking about a Fortune 50 company seeking land turbine mechanical engineers. Result: Three hires before being laid off elsewhere.

  5. I think this is fairly irresponsible advice. I regularly hear from readers who say they were told that their cover letter got them the interview. While it’s certainly true that some people don’t read cover letters, the job seeker has no way of knowing if they’re dealing with that type of not. Why shouldn’t a job seeker make the effort to do something that might have a real impact on her application, just because there’s some chance that it won’t? Given how frequently job seekers ask about how they can “stand out,” it’s crazy for them not to do this basic step.

  6. John Iekel says:

    I am a Senior Managing Editor, and when I have a staff opening and am reviewing applications, I find the cover letter VERY USEFUL. The cover letter tells me a lot about the following:

    * The ability to write
    * The ability to write a compelling lead
    * The ability to provide a concise summary
    * The ability to proofread
    * The ability to use proper grammar
    * The ability to spell

    If I receive a cover letter that contains mistakes, I will not even read the resume. It would be a waste of time.

  7. Hi Perry,

    I am in total agreement about the use of cover letters being sent unless there is a request for one. I have spoken to many HR Professionals over the years and they without a doubt, say that they do not look at cover letters when resumes are requested especially in large companies. When cover letters are longer than three paragraphs, this also causes their eyes to glaze over so try to lean and mean.

    Smaller companies who looking for more entrepreneurial candidates are probably more open to this because they are looking for people who are creative and have a good network.

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