The Art of the Cover Letter

There are very few ultimate truths in the world, but this one is pretty close: at some point in your career you are going to have to write a cover letter. No matter what field you pursue, and in what capacity, you are going to be asked to sell yourself, your company, or your project on one page of paper (yes, one page, no exceptions). Some try to claim the cover letter is an outdated relic from the days when a handshake could buy a new car and martinis were oddly available in the workplace. But I disagree. Admittedly, this is largely because I am a professional writer and one page of text hardly makes me tremble in my underoos. Many young professionals, however, are intimidated by the cover letter and miss countless opportunities because of their reluctance or misunderstanding of the concept. As per usual, I’m here to help. Follow along at home.

Establish Understanding
The key to any passable writing is a complete knowledge of your audience. That doesn’t mean you have to know every sordid detail of their browsing history, it just means that you need to be able to build context for your writing that is informed by facts. If you are writing a cover letter to apply for a position, you better damn sure know the mission, history, and values of the company. What is their product? Do they have a philosophy? Who are their employees? Where do they show up in the community? These are the types of questions that facilitate persuasive writing at a level beyond listing your personal achievements. Familiarity with your audience should be completely established before you write a single word. It may seem counterintuitive to put off writing your letter to do some Googling, but it pays untold dividends in the long run.

Abandon the ‘Process’
Sometime toward the end of the last millennium, the educational system rolled out a standardized writing process that went something like this: Make a web, group your ideas into three body paragraphs, write an introduction and conclusion, and hit print. The Five Paragraph Essay was revolutionary in its ease of understanding for young children just getting the hang of expressing their thoughts. It’s also the bane of my goddamn existence because nobody ever made it clear that it was a starting point – not the ultimate formula for writing. You are not limited to five paragraphs, nor are you obligated to have five paragraphs! Write in such a way that it feels natural and compelling.

Draft with Reckless Abandon
Full disclosure: I am not much for planning. When presented with a piece of writing, I prefer to just jump right in without making a web or an outline of any kind. This works for me because it is my style. However, if you more comfortable arranging your thoughts first, do it. In either case, write your first draft without stopping to second guess sentences, toil over the perfect word choice, or scan for perfect grammar. Get all of your thoughts out of your head and onto paper. I cannot stress this enough. Giving yourself permission to just word vomit on your first pass ensures two things. First, you are less likely to lose those initial thoughts and emotional appeals which breathe life into your writing. Also, it eliminates all but the most severe forms of writer’s block. Nine times out of ten, what we call writer’s block is not a lack of ideas, it is a lack of the perfect idea. Those rarely come on the first pass, and can often be found when sorting through the wrong ideas in your first draft. Don’t be afraid of a bad draft – it’s part of the process.

Something to consider when writing your first draft is the purpose behind your cover letter. If you are applying for a new job, chances are you are also sending a resume – do not simply regurgitate your resume! The reason cover letters exist is because they provide a platform for interpersonal communication. If I want to know the raw data of your project, I can look that up. If I wanted to know what products your company makes, I can read your brochure. This is your best – and sometimes only – opportunity to sell the ‘why’ of your proposition. In many cases, this involves making an emotional appeal, or providing information above and beyond that which is contained in the body of your work. Be compelling and make a case for yourself that supports the facts and doesn’t just parrot them.

Polish and Add Value
When you have something substantial to work with (i.e. a first draft), the real fun begins. I like to compare the review process to carving marble – you start with a sledgehammer and end with the tiniest chisel. Start by honing your ideas at a macro level. Your first pass is not the time to dwell on individual word choice. Reorganize, add, and delete until your ideas are represented well. Then review for flow, syntax, word choice, and the stylistic elements you believe make you stand out. It is at this point that you can reference your initial research and add value to your writing. Maybe there are some keywords you saw in the company’s mission statement that you can plug into your letter? Or perhaps you got a little to0 wordy recounting the endless lessons you learned while studying abroad in Europe (side note: nobody but your mother cares about your time abroad) and there is an opportunity to replace that section with more relevant information.

Review, Review, Outsource
If you ever let a piece of professional writing leave your possession without reviewing it, you are a much braver person than I am. You are your own brand, and you need to own it to the best of your abilities. Review your work, dammit! Read through it again and again until you are confident it is your best work. Some recommend reading aloud when reviewing, but I’ll leave that up to your discretion. You will get tired of this step, and the siren’s call of “good enough” will always be in your ear. But trust in the process. Finally, right before you pull the trigger and send in your letter to be considered for the next season of The Bachelor, phone a friend. Fresh eyes are never a bad thing, and you’d be surprised what you miss even after multiple read-throughs. If the option exists, have someone else proofread your letter.

This is a pretty simple guide to something a lot of seasoned professionals still struggle with. Like most things in life, writing a great cover letter takes practice. Put in the work to ensure your first impression on paper is as sharp as your first impression in person.

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