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Advice / Job Search / Cover Letters

3 Quick Tricks to Make Writing a "Conversational" Cover Letter Easy

Cover letter writing is challenging. For a lot of us, it’s really hard. It feels unnatural, unnecessary, and uncomfortable.

Cover letters can also be super confusing. What, even, are you supposed to say in a one? Do reviewers actually read the things? (Yes, we do.) And, an important question: Are you supposed to be all business, or is it OK to use a conversational tone?

I’m going to answer that last question right away: Heck, yes it’s OK. In fact, your best shot at making it strong, engaging, and memorable (ingredients you surely want in this thing) is going to be by making it captivating and conversational.

Always remember there are actual people at the receiving end of this game (unless, of course, you apply online and your materials first channel through an applicant tracking system). And people like to chat. They like to be drawn into the story. They like to be entertained. So why not share who you are, what you specialize in, and why they should stop in their tracks and pay attention to you in a way that sounds like a person wrote it, not a robot.

Have you been conditioned to believe that there’s one “right” way to do these things? Are you afraid that if you don’t speak in high-level business babble that they’ll discount your qualifications, or throw your application into the “no” pile? It’s just not going to happen if you do this in a way that’s relevant, tells them right away what you can walk through their doors and deliver (in that specific role), and holds their attention.

So, how do you pull it off? Here are three quick tricks that’ll help make the process feel more natural:


1. Write it Like You’d Say it

When people who know my professional brand (JobJenny.com) meet me in person for the first time, they often tell me, “Oh my gosh. You’re exactly like your voice on the website.”

This is very complimentary, and most definitely intentional. As a business owner, I work hard to make a serious topic (careers and job search) engaging, enjoyable, and—dare I say—fun. I achieve this in large part by writing just like I’d say it if we were face-to-face in a conversation.

Do that with your cover letter.

Heck, maybe even record your voice first, before you start fumbling around trying to put the words to paper. Based on what you know about this job and this organization’s needs, how would you describe who you are, and why you’re a good fit for this role? In addition, if you can think of any personal stories to share that’ll engage the reader and (at the same time) tie into the story about why you’d be a great fit? By all means.

It’s almost always easier to spill it out vocally—off the top of your head—first, and then fine-tune it on paper after you’ve got your “why you should hire me” speech down.


2. Make Your Lead a Story

Do you have any idea how many cover letters I’ve read that begin with “I am writing to express my interest in the [job title] position advertised on November 14, 2016, on The Muse” (or something equally formulaic and boring)? Probably a thousand or more. Why? Why do we do this? We do this because somewhere along the line, we’ve been led to believe this is “proper.”

But “proper” is very often also “boring,” or “meaningless,” or “just like every other application in the pile.” How about, instead, drawing the reader in right away by kicking off with a story?

Come again? That’s right. Consider leading with a brief example that spells out swiftly, and in a memorable way, why you’re interested in that organization—before heading into the “Here are the specific things I can do for you” section of the letter. (This second part is essential, too.)

How do you pull this off? Here’s an example. Say you’re applying to be a chef at a popular new restaurant. Perhaps your lead looks like this:

“As the son of a chemistry teacher, the kitchen always seemed to be where my family gathered … to watch whatever latest experiment my dad had up his sleeve. This was the room of the house that gave me the most comfort, the most joy and, frankly, the most entertainment. So captivated was I by the kitchen (and my dad’s fearlessness in mixing chemicals), that I decided to build my entire career around it.”

(And then you segue into precisely how your qualifications line up with this role.)


3. Have That Glass of Wine

This is a figure of speech, unless of course you are a wine drinker (in which case, I’m speaking quite literally). To be clear, I am not recklessly suggesting you toss back piles of alcohol in preparation for crafting your masterpiece. Instead, I’m strongly suggesting that you use whatever method you find most useful to get to that relaxed spot before you start toiling away at this thing.

Stress and tension may very well breed stress and tension in your tone. If you can create some space and release your paranoia about saying the wrong things, you’ll likely produce something that’s more conversational, more genuine to you, and more impactful.

Give yourself every possible advantage so that you can work in a relaxed state, and craft something that naturally flows from you. (Just be sure and edit the thing when you’re 100% sober.)



Job seekers seem to get so knotted up about cover letters. And, while they’re definitely not a piece of cake for a lot of people, they surely shouldn’t unravel you.

The more genuine, engaging and on-point you can be, the better.

Strive to be the one they can’t stop talking about, for all the right reasons. Do that, and you’ll be picking out your interview outfit in no time at all.


Photo of person writing courtesy of andresr/Getty Images.