Why Are Cover Letters So Hard to Write?

Taunee Besson, career transitions expert and President and Principal Consultant at Dallas-based Career Dimensions, is back today to provide guidance on how to write cover letters that wow hiring authorities.  Armed with the tools she offers below, you can dread writing cover letters no longer! — Maurice Gilbert

hire meCover letters. Along with resumes, they represent probably the most dreaded part of the job search. Even cold calling and committee interviews rarely produce the avoidance behavior these written “soundbites” do. Why are cover letters so hard to write?

They need to be short. People have difficulty summarizing 10- to 20-year careers in a few cogent sentences. As a wise chief financial officer once said when asked for a report forecasting business with Russia, “Give me two days and I’ll give you 30 pages. Give me a month and I’ll condense it to three.” Using words sparingly is hard, intellectual work.

Few people really know what to put in a cover letter. As with so many of life’s practical issues: parenting, supervising, finding the right career, we aren’t taught good cover letter techniques. Hitting on the right formula is a process full of trial and error.

Our egos are on the line. We know the cover letter, in many instances, is the first impression a potential employer will have of us. We want it to be perfect. Since perfection isn’t attainable, we’re defeated before writing the first word.

There’s a nagging feeling that writing the letter is an exercise in futility. We realize relatively very few people get jobs through ads or sending out unsolicited resumes. It’s hard to commit ourselves to a task we think will probably be a waste of time.

Unfortunately, cover letters and their resume partners are an integral part of the job search process. Like any repetitive, distasteful task, they can become a good deal more palatable if reduced to a step-by-step formula. In fact, with a little know-how and practice, some job seekers actually elevate them to an intriguing art form. Here’s how they do it:

First of all, they understand that cover letters are not repetitive. They are custom-tailored “personal summaries” which speak succinctly and directly to their specific target market. Anyone who uses a form letter and simply changes the greeting is guaranteeing themselves a spot in the directory of job search statistics. Companies want to know why the correspondent is interested in them and why they should be interested in him. And they expect to be told in about one minute. Unless the writer can capture their attention in that first moment, her resume will not land in the interview pile.

Good cover letter writers package their product elegantly. Just as they appear at interviews impeccably dressed, when providing printed documents, they put their correspondence on high-quality paper and in simple, easily-read type. They wouldn’t think of using copier paper.  Typos and poor grammar are verboten, so they check every letter carefully before submission.

They know there are four key elements in every good cover letter, whether it responds to an ad, serves as a thank-you note for a networking appointment, provides a self-introduction to potential targeted employers or acts as a follow-up tool for getting in touch with a friend’s important contact. These four components are: the inside address/heading, a section stating why the job seeker is writing, a section saying what he has to offer the employer and a closing indicating what he plans to do next. Let’s take a look at how these key elements work together in a variety of situations.

The Inside Address/Heading

When answering an ad, always put the name and title of the person who will be receiving your resume in the inside address and greeting. This is easy when it’s listed in the ad. Unfortunately, companies often choose to omit this information as a protective device against that individual’s being overwhelmed with phone calls. However, you can show some initiative by calling the receptionist and asking the name of the person in charge of Human Resources or whoever is reviewing resumes for XYZ position. As her job is answering phones, she won’t be offended by your call or refuse to take it.

If there is only a P.O. Box, you can ask the post office if they can release the name of the firm renting it. If so, proceed with the receptionist as mentioned above. If not, you might begin your letter with a cheery “Good Morning,” which has a lot more panache than “To Whom it May Concern.”

If you’ve been researching potential employers for a targeted campaign, you may or may not have found a specific person to whom to write. To uncover the right manager, call the receptionist or do research on LinkedIn, making connections with existing or prior employees of the company who might be able to point you in the right direction.

Fortunately, when you are writing letters to friends’ contacts or networking thank-you notes with an attached resume, you know the name of the person to whom you’re writing. To ensure correct spelling, job title, etc., collect a card at your networking appointment or ask your friend to spell the contact’s name. While this may seem a trivial issue, people get rather testy when their names are misspelled. In fact, they often interpret this as a sign the writer lets important details slip through the cracks.

Why I’m Interested in You

Most people responding to ads begin with, “This letter serves as a response to your May 28 ad for a Chief Financial Officer.” This opening deserves points for brevity, but it certainly won’t stand out from the 200 other responses which start the same way.

To break away from the pack, do a little research in annual reports, trade journals or national business publications to uncover some facts about the organization not known by the general public. Then use them in your opening paragraph.

Example: “Last week I read in the Wall Street Journal that Entegra Technologies has developed a tablet that’s designed for harsh environments and is especially resistant to security breaches, giving your firm a competitive edge against Apple and Samsung in the retail sales and military spaces. When I found your ad on Dice.com for a User Interface Designer, I was intrigued by the opportunity to work for a firm so focused on protecting its consumers from hacking attacks.”

Another good technique is mentioning a personal interest you have in the company or its location, such as family ties, topographical advantages, environmental stewardship, etc.

Example: “As a native Texan and graduate of the University of Texas at Dallas, I would really enjoy moving back home and eating some real Tex-Mex for a change.”

The techniques suggested for responding to ads are useful when the opening is unannounced, as well. As the company hasn’t advertised a job opening, you may want to expand your explanation of why you’re writing to it from a few sentences to a couple of paragraphs. The more positive reasons you can give for contacting it, the better.

Obviously the best way to capture the contact’s attention is mentioning your friend’s name, his suggestion that you meet with Ms. X and why he thinks your getting together would be mutually beneficial. If he’s complemented the contact, it never hurts to give this bit of positive feedback as well.

When attaching a networking thank-you note to a resume, you already know the person receiving your letter. You’ve had the opportunity to form a solid impression and mentally list positive attributes of his personality, company or industry. Pick some of these characteristics to begin your letter.

Example: “I really appreciated your taking the time to get together with me last Friday. Your enthusiasm about Brinker International’s new restaurant concepts and its future growth is contagious. As you gave me a tour of your corporate office, I could see and feel the teamwork and camaraderie which pervades your company. It’s understandable why Brinker is known for its low turnover in an industry plagued by revolving-door employees.”

Why You Should be Interested in Me

When you are answering an ad, your second paragraph should summarize the most important experience, skills and personality traits you have to offer this particular employer. Look carefully at the ad. If it lists specific credentials, experience or job responsibilities that you possess, be sure to highlight these similarities. Quantify as much as you can. Revenue generated, money saved, percent of defects reduced and number of people supervised all give a potential employer a good fix on the scope of your responsibility.

Also, list one or two major achievements that will set you apart from your competition. For instance, if you have recently opened five new offices in Mexico for your current company and the ad is looking to increase international trade, be sure to mention your Mexican contacts and sophisticated understanding of its culture and business law. (Then expand upon the explanation of this qualification in your attached resume.)

In a letter to targeted company, you may not always have an ad to cue your composition of this section. You’ll have to use information from the annual report or trade or business journal articles to suggest possible parallels between your skills and experience and what the firm may need. For instance, if it is introducing a new line of products and you have some background in new product management or sales, emphasize it.

In letters to friends’ contacts, you might mention why your mutual friend thinks you have a useful talent to offer this firm. If Ms. Jones at the Amberton Company has been wrestling with a new management information system and you are great at troubleshooting system problems and motivating disgruntled users, she may really appreciate your friend’s suggesting you get in touch.

When you are writing networking thank-you notes with an attached resume, your information interviewee has already offered her assessment of your most applicable skills and experience. Simply reiterate what she has told you and add a few parallels of your own if some come to mind.

Where Shall We Go From Here?

If you know the name of the company running the ad, say you will call in about a week to confirm receipt of your resume, answer any immediate questions and schedule an interview if warranted. If the company isn’t identified or the ad says “No phone calls,” you will have to resort to a rather wimpy statement about how it seems you are a good match for the position and you look forward to hearing from them soon.

Blind ads can be very frustrating because you lose control of the process once you’ve sent in your resume. And there’s always the unfortunate possibility the advertiser is your own firm. Unless the job sounds really juicy, I suggest you avoid the hassle of anonymous ads.

When you have initiated contact in a letter to targeted company, the next move is your responsibility. Don’t expect your targeted firm to get back to you. You need to follow up in about a week to be sure they have received your letter and suggest a meeting, if it would be mutually beneficial. If you mention your intentions in the letter, they will be expecting your call.

With letters to a friend’s contact, the ball is also in your court. You’ll need to let him know you will be phoning for an appointment in about a week. If he calls you before then, it’s icing on the cake.

The last paragraph of your networking thank-you note with an attached resume will vary according to the results of your information interview. You may:

Confirm an employment interview.

Mention you’ve attached the requested resume and will call to ensure its receipt.

Suggest you have a proposal you would like to discuss and will be calling in a week or two for an appointment.

While writing cover letters may not be high on your list of things you want to do today, if you include the four key elements, you will undoubtedly get better results. Sometimes in life we just have to settle for the end justifying the means.


Taunee Besson headshotTaunee Besson, CMF, is president of Career Dimensions, Inc., a consulting firm founded in 1979, which works with individual and corporate clients in career change; job search; executive, small business and life coaching; college major selection and talent management.

“One of the smartest minds in the career field,” according to Tony Lee (VP of CareerCast Operations at Adicio and former publisher of the Wall Street Journal’s Online Vertical Network), Besson began writing for the Dallas Times Herald in the early 80s. Having read several of her columns, Lee asked her to contribute regular articles to the Journal’s National Business Employment Weekly (NBEW) as well. Since then, she has been a triple award-winning columnist for CareerJournal.com  and Senior Columnist for CareerCast.com, as well as WorkingWoman.com and Oxygen.com. At Lee’s request, Besson authored five editions  of NBEW’s Premier Guide to Resumes and three of its Premier Guide to Cover Letters. She has also written articles and/or been quoted in The Wall Street Journal, The Dallas Morning News, Business Week, Time, Smart Money and Yahoo among others.

Taunee has worked on community nonprofit boards and committees for over 30 years including Girls Inc., Women’s Center of Dallas, Girl Scouts and Dallas Women’s Foundation, The Volunteers of America and Mortarboard, among others. She was a member of the Leadership Dallas in 1987 and Leadership America in 2003.

In 1994, the Dallas Chapter of the American Society for Training and Development chose her as its “Professional of the Year”. Her NBEW columns were selected for the “Ten Best Article Award” in 1990, 1994 and 1997.  
In 1999, Alpha Gamma Delta, a 200,000 member fraternal organization, named her as one of three “Distinguished Citizens” at its biannual international convention.

Published by Conselium Executive Search, the global leader in compliance search.  

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