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,’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.

Contact a recruiter button

Melissa Ripp

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.