Why do we hate writing cover letters?

It’s no surprise. Job seekers hate writing cover letters. In fact, it’s arguably the most dreaded step in the job application process. But why? It’s a relatively short document (unless you’re applying for an academic job) with fairly clear expectations. And, aside from the odd employer here and there who no longer requires a cover letter, it’s a document that every job seeker is familiar with and has likely written several times over in their career.

Yet, the hatred persists, and perhaps for good reason. As reported by the New York Times in 2017, three-quarters of high school 12th graders in the United States lack proficiency in writing, and 40% of ACT test takers lacked the writing skills to successfully complete a college-level writing course. What do these grim statistics have to do with adults who are on the job market and writing cover letters? Writing is, after all, a learned skill, not an innate or natural talent, as many would imagine it. If a job seeker does not have a solid background in writing, including good instruction and years of practice, they will naturally feel insecure and unprepared when faced with the blank page, leading to a sense of dread, anxiety, and even hatred of the task. As The Write Foundation puts it, “Insufficient groundwork manifests insecurity and frustration.”      

But, aside from this generalized anxiety and lack of confidence around writing, what exactly is it about the cover letter itself that inspires such apprehension? Here are a few of the top reasons job seekers curse this precursor to the interview, along with some suggestions for ways to make the process a whole lot less painful:  

It’s formulaic

While a formula (anyone remember the 5-paragraph essay from grade school?) can be comforting by setting clear “rules” and expectations for the writer, it can also be a crutch that constrains and takes the fun (yes, I said fun) out of writing. This is especially true if you’re applying for multiple jobs and writing multiple cover letters using a strict formula. After a while, the writing process can become boring and tedious… not something a job seeker would look forward to.

What to do instead?

First of all, remember that the purpose of the cover letter is not to simply restate your resume or CV in long form. This is boring to write, and, even worse, it’s boring for potential employers to read because you’re not actually saying anything new. The cover letter should give employers a glimpse into your personality, your character, and all those brilliant “soft” skills you have that don’t belong on a resume.

It also provides you with a platform to reference specific examples of times in your life and career when you bore these skills out. It’s a place where you can fill in any gaps or answer questions that the resume might prompt. To express your interest in and passion for your field or the job. In short, to give a sense in a few paragraphs of who you are and, as much as you can, what you’re all about. So, while it’s fine to have an overall organizing principle (or formula), don’t let yourself be hemmed in by topic sentences and bullet points. Focus on substance rather than format.

It’s too much pressure

If the cover letter is, as I said in the previous paragraph, a space where you can give a sense “of who you are and what you’re all about,” that can be pretty overwhelming to articulate in three paragraphs. Relax, you don’t have to boil down your entire life’s history into one document. No employer is expecting this, and job seekers who try to do too much in the cover letter actually end up coming across as a little inexperienced or immature professionally.

What to do instead?

There are two good ways to take the fear and stress out of writing: first of all, don’t try to be “perfect” or worry about saying the “wrong” thing. Instead, focus on being authentic and giving as much quality, substantive detail as you can.

Secondly, and most importantly, remove some of the pressure by breaking the cover letter up into bite-sized pieces. The best way to do this is – before you write one word – make a quick outline. Jot down the main ideas you want to get across in each paragraph and a bullet point examples that you’ll use to demonstrate each idea. For example, in one paragraph you may want to emphasize your leadership and problem-solving skills, so in your outline, you’ll write down a few examples of situations where you’ve demonstrated these skills and had positive outcomes or results (and anytime you can quantify these outcomes in concrete, measurable terms, the better). At this point, don’t worry about how your sentences sound. Remember, you’re not writing yet, just making a plan for how you’re going to organize your points in the cover letter.

In fact, I believe so strongly in the power of an outline to make the writing process easier and faster and also to result in a much better, more organized final document, that I’d even go so far as to say you may want to spend as much time on this step as the actual writing of the cover letter. Basically, the better your outline is and the more organized your thoughts are before you start writing, the cover letter almost writes itself. Really.

It’s time consuming

If you’ve ever spent hours in front of your computer screen trying to put this document together, well, you’re not alone. Because it’s usually perceived as the most difficult job application material to prepare, writing the cover letter usually takes up the most time. Simply put, it stumps a lot of applicants and can, therefore, be pretty slow-going.

What to do instead?

The outline recommended above should take care of this as well. If you spend the bulk of your time in the planning and ideation phase –not actually writing – then once you are ready to put your thoughts down, the whole process will go much faster because you won’t be trying to figure what to say and simultaneously how to say it. Instead, you can just focus here on crafting clear, concise sentences that get your already-prepared points across in a professional way.

You don’t know what to say

This is a big one. You can’t write a good outline or a good cover letter if you’re unsure about what to talk about.

What to do instead?

First of all, when you’re preparing to write your outline or letter, it’s a good idea to have the job description right in front of you. I recommend actually physically printing it out and having it next to your computer. Use a highlighter to point out the most important skills or experiences that the role requires. Then, give some thought to your own past experiences and see if you can brainstorm moments or situations when you demonstrated these skills. Write down as many of these as you can think of – don’t worry about the cover letter yet.

After you have a fairly good list going, take a second look and pick out two or three of the most relevant ones, or situations where you had the best results. Then, add these to your outline. Keep doing lists like this and editing them down until you’ve come up with a few of your strongest skills and examples. Again, your efforts here should be concentrated on the planning phase of what you’re going to say – the substance of your letter – not your writing, which should be the last step in this process (followed only by a good proofreading session right before you submit).

“I’m just not a good writer.”

Good writing is often seen as a talent rather than a skill. This perception sets most of us up for failure, because if we don’t feel we have the “talent,” we’re not going to have a good attitude about any task, cover letter writing included, that involves writing.

What to do instead?

While the whole “talent” thing may be true for some fiction or poetry writers – true artists – learning how to be a good communicator on the page is a learned skill just like any other. There’s no mystery in it. No special “gift” that we either have or don’t have. It’s simply not that glamorous. It all boils down to training, education, and, most importantly, practice. The more you write (and read, for that matter), the better you’ll get at it. So, if you fall into the category of one of the many people who hate writing because they feel they’re just not naturally good at it, remember, that no one is naturally good at it. So, embrace each opportunity you have to express yourself in written form, because with each document you put together, from cover letters and resumes to emails or research proposals, you’ll be that much closer to becoming a better, more confident writer.