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.

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