The Undercover Cover Letter

Puzzle PeiceLike so many things related to the job search, cover letters are inconvenient formalities that should be done away with. I predict that someday, a business with enough clout will have the courage to stop asking for them and other businesses will follow suit. But until that day, cover letters must be written, and they will remain clichéd boiler-plate documents that conscientious job applicants will attempt to reinvent while the less conscientious ones poach theirs from friends, making a few necessary alterations.

Business owners and hiring managers that I have spoken with tell me that if they read cover letters, they read the first two or three lines, those lines that tell the prospective employer how the candidate will fit into the organization. Otherwise, the hiring manager will skip the bulky cover letter paragraphs composed by some youthful braggadocio and dive right into the easy-to-read bulleted resume. What hiring manager wouldn’t rather zero in on bullet points and graze over abundant white space, giving their eyes and brain a rest before the lunch hour?

The uselessness of cover letters can be further defended by the idea that nobody of any importance writes letters anymore: not for business, not for friendship, and rarely for love. For business people on the go, making things happen and making money, new ways of communications substitute easily for the old. Texting and short emails with frequent use of bullet points can be used for in-house and client communication. Twitter, Facebook, and LinkedIn for business marketing. And regardless of message, the most effective communications will be those formatted like a tweet, 140 characters or less. The classic business letter, should one ever be required, can be handled by freelance writers hired at the maximum wage of $7.25 per hour, or one dollar per correspondence, whichever the client prefers.

A close and honest evaluation of a single mail sack full of traditional cover letters reveal that most cover letters do exactly what business-writing instructors tell job candidates not to do. They rehash the information already presented in the resume, only this time in paragraph form. Rehashing information in the business environment is a skill used often to drill points into employee’s and client’s heads, but it can also take time away from analysis and innovative thinking.

Still, despite the anachronistic nature of a cover letter in today’s workplace, employers, through hiring managers, feel compelled to do whatever has been done before, and the dated rituals of the job seeking process carry on like useless body parts: I am thinking here of the tailbone, male nipples, tonsils, and the appendix: human body features that should be extracted before they cause harm.

Not only do job candidates waste hours writing cover letters, printing them, taking up computer memory with their bytes, but publishers continue to commission authors to write books about these letters. Such books again rehash the standard list of composition instructions, and libraries that still contain books continue to stack the results. Those who write blogs on the internet also waste time rehashing the cover letter topic. Believe me, type the words “cover letter” into your browser and you’ll soon find, it’s all been covered.

Some covers are clearly better than others.

Some covers are clearly better than others.

In my business writing classes, I have wasted many an hour and student’s time reviewing the standard cover letter criteria. I do so mainly out of sympathy. Students are anxious about getting jobs after graduating, and they know employers want covers. To keep everyone happy, each semester I insist that students purchase a scholastic text such as The Business Writer’s Companion (BWC) and commit the cover letter pages to memory.

The un-invigorating BWC covers all of the elements of the classic cover. It gives advice about format, white space, serif and sans-serif fonts, enthusiastic and plain language, and the avoidance of personally designed logos. While I never promise employment to any student who designs and writes such a letter, I do promise that if students follow BWC instructions, there’s little doubt but they will produce a competent-sounding letter, one highly similar to a thousand and one other covers, and one which gets the job done, if not the job.

To review cover letter composition according to BWC rules, once the desired employer is found, the candidate calls attention to themselves by providing their contact information, although NOT their name, in the top left hand corner of the page. Then follows the date of composition and beneath the date, candidates should have obtained the name and address of “the person who has the power to hire them.” Acquiring employer information shows some initiative on the candidate’s part; however, as most cover letters and resumes are sent via email and the internet, the only address the candidate really needs is the employer’s email. The computer will do the hard work of dating the correspondence.

If I might be allowed a short digression here, I would add that many years ago, in the age of snail mail, resumes and cover letters were typed onto high-quality bond paper and sent to prospective employers in large envelopes left unfolded like slim and semi-sacred Advent calendars. Today the resume is a file attached to an email, and the cover letter copied into the body of the email.

Alternatively, some employers like to take applications over their websites, and here the cover letter takes more of the old-fashioned form. Addresses and dates are retained in the top left corner and the letter is uploaded as an attachment. Meanwhile the candidates’ original resume serves as a reference document. The information contained in the original resume provides a resource while candidates spend several hours attempting to figure out how the company’s online application works. Information must be transferred from the resume to the electronic form. Additionally, the prospective employer will ask several questions concerning military status and sexual and racial identity, the last two questions being illegal to ask in an interview but apparently perfectly fine to ask on an application.

So back to the cover. If we keep with the old-fashioned methods of composition, a salutation should follow the addresses and date. Most job candidates begin with “Dear Sir or Madam” or “Dear Human Resources Manager,” or variations on those themes. “Dear Hiring Manager” works too but the main point is to avoid any suggestion of sexism. The advice most emphasized by the BWC and the many books with titles like “What Color is Your Parachute” or “Getting A Job for Dummies” suggest that you set yourself apart from the competition, meaning that you should do here as you did above the company’s address, write out the “name of the person who has the power to hire you.”

This is an excellent idea and I encourage it. Finding a specific name may also be impossible as companies like Monsanto or government agencies like the NSA prefer to keep secrets and so keep their hiring managers anonymous. Another complication occurs when the candidate finds the given name of the hiring manager but that person has a unisex name like Alex, Jamie, or Blair and Alex, Jamie, or Blair refuse to post photos on LinkedIn or Facebook. Searching for hours on the internet and clicking on the “images” option may not be any more productive. Some brave job candidates may take the extra step and call the business, asking if Cassidy Smith is male or female. The not-so-brave will attempt to fudge the address line with an opening such as “Dear Smith,” but this sounds cold and stilted, and it often helps to warm the oven before inserting the pizza.

After the salutation, the job seeker will often make an attempt to connect to the prospective employer based on their perusal of the job advertisement. Many candidates start their letters as follows: “I saw your advertisement for a Project Manager on Career Builder.com, and I noticed that your company has done many projects that I admire, including X , Y, and Z. In my studies at Impressive University and in my relevant past work experience, I have developed skills necessary to be successful doing similar work, and I would like to be considered for this position.”

With his wicked hook, the Otter (aka Greg Olson) holds the Oriole record with 160 closes. He was a favorite among Baltimore fans until he lost his hook and subsequently his job.

With his wicked hook, the Otter (aka Greg Olson) holds the Oriole record with 160 closes. He was a favorite among Baltimore fans until he lost his hook and subsequently his job.

Following the connection, which might be enhanced by mentioning the name of a mutual acquaintance, the candidate will place the meat of the cover, which is really more ground beef than flank steak or filet mignon. I say ground beef because as I mentioned above, the candidate has already presented the prime cut information in the resume. In the letter, a few of the more select cut bullet points are emphasized in paragraph form, and much emphasis is placed on drawing out the candidate’s hard and soft skills, and distributing these skills among two or three blood-rich paragraphs.

Soft skills may be introduced as follows: “I am a flexible, communicative, driven, hardworking individual who likes to participate in teams and meet deadlines.” Meanwhile, statements that incorporate hard skills take on more concrete characteristics as follows: “Working as an intern in the university’s administrative offices, my knowledge of C++ allowed me to develop a program that streamlined accounting processes, thus saving the university 14 hours per week per employee and giving those employees more time to concentrate on other tasks.” Notice the use of the first person, “I,” in these statements, a luxury not permitted in the resume. In a cover letter you are allowed to be yourself, or I should say, you are allowed to be “me.”

Once the hard and soft skills have been placed in narrative form, the candidate finishes up with a closer. This is the shutdown sales pitch, designed to end the game, seal the deal, and get the call for an interview. There are several approaches to the closer: passive, aggressive, and diplomatic. The passive approach will sound a little like this: “Please contact me if you would like to schedule an interview and further discuss how I might be of value to your company.” The more aggressive tactic is to take the initiative: “I will call you within the next week to see whether you have reviewed my application, and we can schedule a time to discuss your position.” The diplomatic candidate will attempt to finesse the situation as follows: “I look forward to hearing from you, but I understand the many demands on your time, and will call you in a few days to see if you’ve received my resume. And at your convenience, I hope that we might schedule an interview, and I look forward to our conversation.”

Sincerely. Using the word “Sincerely” is a nice way to say goodbye, but a few candidates prefer “Yours Truly” or “Best Regards.” More creative sign-offs like “Cheers,” “So Long,” and “Check You Later” are discouraged. Following the sign-off, your signature is not optional. Sign a paper, scan the signature, and import it into your text and email. Whether or not your signature is decipherable, type your name beneath this signature.


“…type the words “cover letter” into your browser and you’ll soon find, it’s all been covered.”


And so you have a cover letter, one not unlike the cover letters that have gone before and that will be submitted simultaneously with yours. As so many look alike and have similar sounding information, employers will likely set yours aside, toss it in the trashcan, or file it under the categories “Possibly,” “Maybe,” or “How About Later.” Then they will call up their friends at neighboring consulting companies and ask if they know anyone who needs a job or is looking to make a move and would that person be a good fit? Or maybe the employer will strike up a conversation in a bar with a stranger who turns out to have all the right hard and soft skills desired. This candidate will be hired on the spot, on an impulse. People purchase products in this manner all the time, why not choose employees in the same way?

And so, having devolved into something that almost anyone can write if provided proper instruction, the immortality of the cover letter continues unabated like new episodes of The Simpsons. But shouldn’t such covers be put to bed? Or if not put to bed than at least revamped to serve a better purpose. To that end, I would like to suggest a new type of cover that I believe will be far more useful to both candidate and employer. This new letter would expand on the only two lines of the cover’s current incarnation that the employer pays attention to, the first two or three, those in which job candidates state how they will fit into the organization.

We might call this new letter the “undercover cover letter,” as it would require the candidate to do some investigative work and analysis before the writing. It would represent research into the employer’s business and include such items as: 1) The purpose of the company, its goals, and its mission statement. 2) How the company goes about its work, paying attention to processes. And 3) the key players, not only the company clients but also those people who work in the department in which the candidate will be made useful. It should be noted that while the company literature and spokespeople may state explicitly what the leadership believes the company is about, the candidate should not settle for simple answers. What the company says about itself is not always how the public or clients see it, and the candidate should be open to all perspectives.

The ways in which candidates gather this information will be up to them, but their creativity in research technique and how much information they can collect are the main points of the exercise. Some candidates may choose to do simple searches on the internet or in library databases. More innovative applicants may invent other methods. For example, I envision a candidate for an accounting position attempting an in-person investigation. This could involve pasting on a fake beard and mustache, posturing as a plumber or HVAC contractor and gaining access to the business’s facility.

To illustrate: The prospective job applicant and current researcher arrives at the employer’s office door and explains how the monitoring systems in the facilities department are indicating a mechanical failure. The applicant enters the accounting department and sets up a ladder and toolbox near her future coworkers. Then she climbs the ladder, removes ceiling tiles, and makes a show of checking the pipes and ductwork. From such a perch, she will be free to scan the office cubicles below.

At this elevated perspective, careful note could be taken of all elements of the accounting department. What computers and computer programs are used? How does the workflow progress? Who are the key players? Can employee names be found on plaques mounted to desks? Are all work competencies accounted for or does the candidate possess one that will fill a gap? If the candidate hears one of the accounting team shout out in frustration, “I hate Microsoft Access!” this should be scratched on a notepad so the candidate can emphasize having this skill when she writes her cover letter. A word of caution however, any financial information discovered about the company during these investigations should be kept secret. It may come in handy during salary negotiations.

The Boston, not Baltimore, Strangler, played here by Tony Curtis, was once known to make his way into unwelcoming facilities by posing as a maintenance man, a tactic that might be tried by today’s job seekers.

The Boston, not Baltimore, Strangler, played here by Tony Curtis, was once known to make his way into unwelcoming facilities by posing as a maintenance man, a tactic that might be tried by today’s job seekers.

I have an additional suggestion on investigative methods as well. Some investigators might like to work as a team. For instance, the prospective accountant may want to form an alliance with her friend the prospective engineer, and they might accompany one another on office visits. Tag teams of two or three applicants for different positions in different companies can quadruple the amount of information gathered and provide diversions so that informative documents can be scooped up and carried off, the data contained obliquely referenced in the cover letter.

Once all of the information has been gathered, the candidate should synthesize it and produce a cover that presents findings and analysis in clear and simple prose, keeping all of this at less than a page. While this new form of investigative cover letter will begin the same way as the traditional one, with candidates relating how they might fit into the company, the body of the undercover cover letter will be a review and analysis of the current company situation. The letter will cover company goals, processes, culture, and personnel, each element evaluated with attention to their effectiveness.

Throughout the letter, candidates should be careful to use positive language, complimenting effective aspects of the business, but also taking a surgical approach to what the company does wrong. Analysis complete, one final step is critical. After identifying problems, the candidate should hint at possible solutions but not provide any. This will generate employer curiosity and bait the employer to make a pre-interview phone call. Should an interview be won, the candidate can offer solutions to the problems identified, the employer evaluate those solutions, and then the employer can hire the best creative thinker or the dullest worker robot, whichever is preferred.

I can understand that most job candidates and employers will not embrace this new method of cover letter research, analysis, and writing. It’s possible that such a method would make the job search process more time consuming and invade the privacy of companies handling sensitive projects and documentation. But searching for a job or good employee is already as hard as catching a vampire with a mousetrap. Why not at least make it a productive learning experience?

Such an investigative process would be most useful. Job candidates would have to demonstrate perseverance and ingenuity that may later prove valuable once hired. They would sharpen their analytic and synthesizing skills while learning things about company methods, goals, and fellow employees, saving the company time and money in the first weeks of their hire. Most candidates, we all know, spend those first weeks fumbling about anyway, not knowing who is who, let alone being able to perform their job responsibilities. Eliminating this adjustment period would mean that the candidate can get right to work being productive.

Using candidates to do what marketing and management firms usually do would especially benefit small businesses, as mom and pop shops can rarely afford the behemoth fees charged by these firms. Not only do marketing and management consultants charge exorbitant rates, once they depart the businesses they’ve evaluated, nine months later, those businesses are frequently more dysfunctional than ever. I am sure that marketing and management consultants will object to this new hiring practice, but I suggest that those consultants do what we all have to do eventually, get real jobs.

Looking beyond the needs of a small contingent of business consultants, we should not fail to do what our U.S. Constitution demands. As the fourteenth amendment has been interpreted, business life is equivalent to human life, and the investigative process I suggest would contribute to the health, welfare, and fair treatment of all business-hyphen-humans. Therefore, this program should be considered a moral imperative, protecting and securing the sanctity of business-hyphen-human life.

And considering the overall benefits it will provide these business-hyphen-humans, I recommend that a small stipend be paid to job search candidates who conduct these investigations, similar to how unemployment insurance currently works. Yes, many object to entitlements like this, but it all depends on how you look at it. This entitlement would not be so much for the job seeker as for the business, and in general, the good of our capitalist system.

For candidates, of course, the stipend would give them time for the search and investigation. Why should high school and college students be forced to rush around looking for a job, compromising schoolwork and grades, while they continue to attend school? Under the revised undercover cover letter program, the candidate would be able to wait until they’d graduated and then conduct a fully dedicated job search.

In this context, the program would also provide a psychological advantage to American families, as it would help to avoid that awkward time when a young person graduates from school and is forced to return home to live with mom and dad. This extended phase of adolescence can be a traumatic experience for both parent and child, especially when the child starts coming home at all hours of the morning after partying with friends. With such a stipend, the wise and frugal graduate could use the money to get set up in an apartment and pay for groceries. They might also be able to cover costs incurred for the investigations: for example, the price of tools, ladders, and fake beards.

Note: This article was not written with the assistance of Rhonda Serendip, a marketing and management consultant at “Serendip Business Marketing and Management Consulting.”

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One Response to The Undercover Cover Letter

  1. anne rouse says:

    Mark
    Thank you for this article. I am going to save it for future reference-hoping I never need to refer to it for the rest of my working days…!

    Liked by 1 person

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