Cover Letter Writing 101: Paper and Electronic Letters

By Tracy Laswell Williams, CPRW, President, CAREERMagic

When I think of the average job seeker's approach to cover letters, I'm reminded of the Publishers' Clearinghouse Sweepstakes. You know, all those crazy coupons and stickers and NASA-level procedures on how to put it all together correctly. You become excited that you're going to win that $10 million prize because the letter says has your name all over it, just as if they wrote it to you personally, right?

Of course, people whose IQs are higher than their dogs' are quick to realize that the "personalized" letter from the Publishers' Clearinghouse is actually produced by a word processing system with a mail merge feature. My point here is that most hiring executives are waaaaay smarter than your dog. So why insult their intelligence by sending them form letters with their names inserted at various points?

What's that, you say? You don't even bother putting a contact's name on a letter of application? Well, that'll really grab them, won't it? Excuse me, I'd like to have a word with your dog, please.

"Do I ALWAYS need to send a cover letter with my resume?" ask my clients. To which I'd usually reply:

"Why, yes. You need a cover letter to introduce your resume if it's presented without you or your agent to say a few words." Note: an agent can be a colleague employed at your target company, a recruiter, a temporary placement office, even your mother (assuming she has connections...).

These days, my answer is a bit different. When asked if they REALLY have to write a cover letter, I ask them to rank the job lead on a scale of 1-10, with 10 representing "Oh boy, this is the perfect job for me. Oh boy, oh boy, oh boy!"

If the job lead in question is a 7.5 or above, then by all means, do the most outstanding cover letter writing you can muster, or hire someone else to do it. Demonstrate your appreciation of the company's recent strides, current mission, and future direction. Figure out how you fit into their corporate plan, and demonstrate an understanding of what the ideal candidate will contribute to the bottom line. Keep your tone vigorous, businesslike, and positive, without being stilted, overly formal, or lawyer-like.

If the job lead in question is a 7 or below on your interest scale and yet you still have some compulsive need to apply for it, by all means, take the "Slacker Approach." All you have to do is passively mail, fax, or e-mail a resume alone and see what happens. Don't even bother with the pretense of a form letter – in my opinion, it's a waste of time, energy, and resources. If your resume is really sharp, or the company is desperate for someone with your qualifications, you might even get a call anyway.

However, I believe that if you're going to go to the trouble of writing to a prospective employer, you should write a really amazing letter. The first thing you'll need is a contact name. Got one? Great. Call your contact and make sure you understand the nature of the opportunity. DO NOT ask questions about salary – but if you are really unclear, you can ask what "level" of a position it is. Gather the facts you'll need - not only to write a winning letter, but also to follow it up properly.

Once you've sent a letter and a resume, do you smack the toner dust off your hands and congratulate yourself on a job well done? Wait for phone calls? Nooooo. You really do have to follow up within a week or so. Beyond finding out if your application made it safely to the pile (or more likely, the database), you'll get an opportunity to ask other questions, such as the timeframe for interviews, who else might be involved in making the hiring decision, etcetera.

The day of "shotgun" approach – sending 200 form letters and generic resumes to prospective employers by mail -- is over. It may have worked in the 80's, but generally speaking, is not going to be effective in the new millennium. If you're going to take the shotgun approach, by all means, do it electronically and save money. Even better, post your resume to a job-oriented web site like and see what happens. Your probability of success in this type of job search is really dependent on your skill sets, but considering how little effort and money you have to put into it, why not try it?

At a certain point in one's career, it truly does become more effective to narrow your focus to just a few hot leads. The process is simple: do your research, network and build contacts, write great letters, follow-up several times, and repeat with another small batch of leads when necessary. This is the approach that my clients earning $70k+ use, knowing that the power of their network and the "personal touch" leads to the higher-quality positions (including the "dream-up-your-own-position" opportunity).

When sending your letter of application and resume via the U.S.P.S., use a 9" by 12" white envelope. This keeps your documents neat and clean, easy to handle, read, and scan. Don't tri-fold it and stuff it into a cutesy envelope that matches your resume stationery. Don't staple your cover letter to your resume. NEVER use those ostentatious, outdated, ecologically incorrect cardboard presentation folders that say "Confidential Resume Enclosed."

Of course, the advent of online job applications and e-mail has befuddled us job search etiquette experts once again. If a letter is going by e-mail, the conventions are different. The most important thing here is to know what sort of information the company is seeking and how they want it sent (Resume and cover letter? Just a resume? Just a cover letter? Text message in the body of an e-mail? Text message as an attachment? Word document (and watch your fonts) as an attachment ? Cut-and-paste-here?).If you're unclear, call the company and ask!

If you're going to e-mail a cover letter, there are a few modifications to the paper version. Naturally, you don't need to write the date or the company mailing address on your e-mail. You should use the subject line to identify the position sought. And when addressing your contact, add their title and company name. Write a condensed letter (not much more than a screenful of text) that covers the most significant points about why you're excited about the opportunity. If you're sending your resume as an attached file, be sure to note the fact that you did and identify the file format. Ask them if you've sent your resume in the proper way. Attachments may not seem like a big deal to you, but consider this: how long would it take you to open 50 e-mails, download, open, and move the attached files to an appropriate location, assuming they're all virus-free and in a readily usable format?

The advent of the Information Age, what with all its exploding technologies and global impact is wreaking a bit of havoc for the average person, including Joe Jobseeker. It will take some time before we all "get on the same page" technologically. The best thing to do to cope in the meantime is to be patient, strive to communicate clearly, and keep a sense of humor. For all its flashiness, an electronic job search still requires the strong writing skills and proper business etiquette it always has. Sooner or later, you'll be dealing directly with human beings upon whom you'll have to make an impression.

© 1999-2016 Tracy Laswell Williams. All rights reserved.

Tracy Laswell Williams
Tracy Laswell Williams is an accredited resume writer and career consultant who works with a diverse client base nationwide. She built her company CAREERMagic five years ago on the premise that "great minds think differently." Visit the company website at