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Writers Block Cover Letter

I've written other posts about writing challenges connected to the job search: how writing anxiety can affect the job search and how writing samples add another layer of challenge to the job seeker. But of all the writing-related activities of the job search, the one task most universally hated is the cover letter.  It seems to cause anxiety for many otherwise well-qualified job seekers.  And there's a reason for that: it's not an easy document to write. You have to find a way to appeal to the employer, summarize your key strengths relevant to the position, convey your personality, express your interest, and differentiate yourself from every other candidate- and all in one page.  Oh, that's all?

It's no wonder that many put it off.

Part of the problem seems to be that many people do not view themselves as writers.  Or at least good writers.  They didn't like writing essays in school, and now that they are confronted with a writing assignment that won't result in a grade but rather a job, their anxiety level increases dramatically.  And cover letter writing, like resume writing, is a unique form of writing.  It is essentially a marketing piece or a sales pitch-- not the type of writing even most professional writers do with ease.  It requires a lot of thought.

I've helped thousands of individuals write cover letters, and I find that they struggle with virtually all elements of it: whether it's the opening sentence, targeting it to the position, or finding a way to convey personality without appearing forced. Many people just freeze at the first sentence. Writing blocks and writing anxiety kick in.

So I'm going to spend the next two blog posts on crafting the cover letter.  This post presents 10 guidelines for writing cover letters.  The second post deals with the value of a SWOT analysis to construct your letter. 

So what's the point of a cover letter?  The cover letter, done right, is actually a valuable opportunity for the job seeker to convey information and start a relationship with the employer.  The cover letter is less restrictive than a resume (you can use the word "I", for instance), and it gives you the opportunity to highlight your most important features to an employer.  You can explain aspects of your background that might raise questions  (such as gaps in employment or lack of a specific degree), you can convey personality traits (resumes are notoriously dry and fact-filled), and you can entice the employer to want to meet you. 

As we shift increasingly to social media, email, and other technical approaches to the job search, some experts have questioned whether a cover letter is even needed anymore. While its use or format may be morphing, it's still an important document in the process.  There will always be some employers who say they don't need to see a cover letter-but in general you should assume that you will need to write one.  And, as hard as this may be to digest, consider finding a way to welcome this opportunity to display your talents. 

So... here are 10 basic guidelines for a cover letter.  Violate them at your own risk. 

1. Use proper business letter format.  Make sure you include the date, the name and address of the person/organization you're sending it to, etc.  Use a colon after "Dear Mr. ______:" (commas are for personal correspondence). Here is a great site for proper business correspondence style from Purdue's Online Writing Lab. 

2. Keep it to one page unless you have a very clear reason for going beyond that.  I work in higher education: we're used to reading lots of pages, so I personally am not bothered by a two-page cover letter.  I have even written two page cover letters when applying for jobs myself and have only ever heard one complaint. But, I remind you-- I'm in higher education.  In the business world, keep it to one page. And particularly when your cover letter is written as an email to accompany your attached resume, keep it short and simple. (But not just "Here's my attached resume.  I look forward to hearing from you." You don't get off that easy even in an email.  Sorry.)

3. Write unique content.  The cover letter is a chance to tell your story, to demonstrate some personality, display your communication skills, and highlight your strengths.  It is not the place to simply repeat everything that is in your resume. 

4. Remember how your English teacher always said to "show, don't tell"?  What she meant was: don't just say "I'm a hard worker" (that's telling); show the reader you're a hard worker, as in "Last summer, while working at a full-time job, I successfully completed 6 hours of graduate coursework in accounting, and developed a prospectus for a new business."  See, now you've shown me you're a hard worker.

5. Establish a relationship with your reader. To whom are you writing? As I like to say to students: if you're writing a report on dogs, it's helpful to know if your reader is a veterinarian or in the 3rd grade. Big difference in how you approach the subject. So, who will be reading your cover letter? Someone in the human resources office? (Likely.) Your future boss? (Also likely.) Someone with no understanding of your field? (Possibly.) For this reason, you need to be careful about using jargon or acronyms from your previous or current employer.

6. Write a targeted letter to each position. The failure to personalize it to the job and/or the employer is by far the most common complaint I hear from employers. Employers resent it when they receive what is obviously a generic cover letter where the candidate hasn't taken the time to personalize it to them (as in, "Dear Sir or Madam:").  Almost as bad is the letter which starts out personally addressed to the employer but quickly digresses into an obviously generic letter.

I once posted a position for a career counselor in my office.  I received many applications ranging from a former military officer who spent a paragraph describing his sharpshooting skills (I'm very glad he served in our military, but generally I don't need sharpshooting skills in my office), a person who spent a paragraph describing her religious beliefs and how much she enjoys teaching Sunday School classes (again, I'm glad she enjoys what she does-- but not an issue for my office either), and a high school counselor who described in great detail her client load of pregnant teenagers. 

Here's the mistake they all made: they didn't make the connections for me.  They wasted valuable space on their letters describing details that were irrelevant to the position. And they made no effort to connect their experience to my position or organization.  For instance:  What if the sharpshooter had written something like "In the military, I honed skills which required great patience, accuracy, and focus"; or had the Sunday school teacher written, "I developed lesson plans targeted to the age of my students, and designed to increase knowledge and encourage discussion"; or the high school counselor written "I work with students who are under pressure, and have to make challenging life decisions every day"? Those kinds of statements would show to me that they understand that they are not going to be doing what they've done before in this new job, that they have more deeply analyzed their skills and applied them to the new position-and that they actually know what this new job will entail.  It is not my responsibility as the employer to connect these dots for them-- you must do it yourself in your cover letter (and interview). 

7. Plan to create a letter with three-to-five paragraphs (two-to-four if it's an email).  The first paragraph should explain what you're applying for, how you heard about the opportunity, and why you are particularly qualified.  Try to be subtle about this-- a letter that opens with "I am the most qualified candidate you will find..." usually ends up in the trash.  The employer will judge whether you're the most qualified: you need to convey what talents or experience you have that connect to the position.  The middle paragraphs expand on your connection to the position as well as highlight any research you've done about the opportunities the position and the employer represent to you.  The last paragraph closes with the next action step that will be taken and how you can connect in the future.

8. Try to avoid trite phrases.  I always advise my students NOT to start with the traditional opening, "I am a student at __________ and I am applying for a position as ______________."  Rather, start with something that connects you right away to the position, as in "My three years experience as a bank teller, combined with my economics coursework, have taught me the importance of _____ , a trait needed in your ______ position."

9. Use an active voice, with action verbs. Avoid phrases like "was responsible for", or "reports that were written by me...".  

10. Edit. Proofread. Ruthlessly. 

For more help with your cover letter, check out my blog post on Cover Letter Writing Strategy.

Find me on Facebook.  Follow me on Twitter.  Copyright 2011 Katharine Brooks

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Cover Letters: Why Are They So Hard to Write?

By Melissa Ripp

Marketing Coordinator, Drake & Company Staffing Specialists

If you asked me to rate the top five things that are difficult for me, I’d probably say, in this order:

  1. Writing a cover letter for a job I REALLY want
  2. Writing a cover letter for a job I kind of want
  3. Writing a cover letter for a job that I’m indifferent about
  4. Playing any sport that requires hand-eye coordination
  5. Eating a hard-boiled egg (Ick.)

Over the course of my professional career, I’ve racked my brain trying to figure out why cover letters are so difficult for me. Admittedly, my cover letter anxiety used to get in the way of me applying for positions that I knew I was qualified for. Many a well-meaning friend would say to me, “I don’t get it. You market businesses—and people—for a living. Is it really so hard to write about yourself and your accomplishments?”

In a word…yes. But it’s more than that. In a cover letter, you have to catch the eye of an employer or hiring manager with a detail that will set you apart from other candidates, summarize your key strengths relative to the position, convey your personality, express your interest in the position, and drop in a potential referral – all (preferably) in one page. No matter how great you are at brevity, or how confident you might be as a job seeker, writing a cover letter can still be a struggle. And honestly, it’s not even the writing the cover letter that’s the hard part – it’s simply starting one!

Eventually (with the help of a friend who was willing to pass along her expert knowledge and work with me one-on-one), I was able to gain confidence with cover letter writing. Below are a few bits of wisdom I’ve acquired along the way for getting past the cover letter writer’s block:

Enlist in a friend or mentor for assistance.

When it comes to brainstorming for a cover letter, it might help to talk about it before writing about it. Often, I’d ask a good friend to help me brainstorm. First, we would compile a list of questions to help start the conversation:

What qualities and/or accomplishments do you want to emphasize in your letter?

What exactly are the skills the position is looking for? Do you have those skills? If you don’t, do you have primary skills that somewhat align?

  • What special skills or talents set you apart from the competition?
  • What makes you truly passionate about this particular position?
  • What do you like about the company to which you are applying?
  • What about your letter will be interesting? What will entice the reader to keep reading.

If you can, record this conversation for future use, as you often forget the context of a conversation when you’re looking at scribbled notes a few weeks later. The next time you find a position you’re interested in and need to write a cover letter, you’ll have a bit of pre-recorded inspiration.

Prefer to go it alone? Participate in a one-person “brain dump.”

Preparing for a cover letter doesn’t have to be any different than preparing to write anything else. Set a timer for five minutes and keep your pen flowing, no matter what you write.

If it helps, go through all of the jobs that you’ve had individually and ask yourself what you did at those jobs. What skills did you acquire? What are the accomplishments of which you’re most proud? Do you have any quantitative or qualitative data for those accomplishments? After you’ve done this, take a break—and when you come back to your writing, go ahead and make a note of any piece you think would be a salient point to bring up in your letter. You might be surprised at how much good data exists about yourself that you never would have thought of otherwise.

Blank page anxiety? Find a template that works for you.

You may not realize it, but starting at a blank Microsoft Word document might be what’s giving you anxiety. As a friend of mine once said to me, “Having a template makes me feel like I have some semblance of organization, and it makes me feel like I’ve already done a little work. Believe it or not, that alone makes it much easier to begin.”

This article by Alison Doyle, About.com’s job search writer, includes a link to a variety of cover letter and resume templates that are available for free on Google Docs. These are very simple to personalize with your own information—and they’ll make you feel like you’re actually accomplishing something right away.

Tackle the easy parts first.

“A typical cover letter has three paragraphs—an introductory one, a second paragraph that talks about your accomplishments and your skills, and a final paragraph that wraps it all up,” says Peter Jenkins, Drake’s Office Coordinator and resident resume expert. “So, my advice is to tackle the first and the third paragraph first, and then move on to the one that talks more about yourself and what you bring to the table.” This technique gives a feeling of accomplishment before you tackle what might be a more challenging paragraph.

Take your time—and step away if you need to.

Sometimes, it simply doesn’t work to sit down and rattle off a cover letter in an hour. If you don’t have the time to complete the letter all at once, start the process by working in 15-minute increments.

Now that you have a few tips for how to handle that initial cover letter anxiety, our next blog will talk more about what to include in a cover letter—and what to leave out.

Melissa Ripp is the Marketing Coordinator at Drake & Company, a staffing firm based in Madison, Wisconsin. Drake & Company specializes in temporary, temp-to-hire, and direct hire administrative, clerical, and legal placements. For 36 years, Drake has reached beyond skills and qualifications to match candidate personalities with a company’s culture. You can find Melissa on Google+, and you can find Drake & Company on Facebook, Twitter, LinkedIn, Google+, and Pinterest.

Tags: cover letter, job, jobs, melissa ripp, resume


I wanted to thank you for the wonderful opportunity and your advice and feedback. I will always recommend Drake & Company to anyone who is looking for a job. I appreciate everything and will always remember you. Tweet Share 0 Reddit +1 LinkedIn 0 Email...

- Linda


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