MissHezah | Can Cover Letters Be Better?
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Can Cover Letters Be Better?

Can Cover Letters Be Better?

I’ve been thinking about cover letters a lot lately –– probably because I’ve applied to well over a hundred jobs in the past two years. I’ve spent countless hours searching, revising resumes, and writing cover letters. And where has that gotten me? Well, I was ghosted after only one phone interview that went well, and had five rounds of interviews for a job I realized wasn’t a fit. And, it should be noted that the latter only happened because I had a personal connection at the company.


I don’t get it. I’m a professional writer: my cover letters are good. I’ve had several colleagues in leadership positions affirm that my resume is impressive.


It’s demoralizing. It makes me not want to apply to any job ever again. It’s difficult to get excited about even the most perfect job description (which are already so few and far between), because the chances of you hearing back from your plea into the void of LinkedIn are extremely slim.


For two years, I’ve been freelance –– a little bit by choice and a lot by way of circumstance. My last full time role was eliminated while I was six months pregnant. Follow that up with maternity leave and a pandemic, and here I am still hustling my ass off every day to keep clients, get new ones, and apply to full time roles so I can maybe slow down.


I’ll scream it from the rooftops: FREELANCE LIFE IS TOO ROMANTICIZED! (And, it’s not always a lifestyle choice. Sometimes, it’s a necessity.)


Yes, there are clear perks like setting your own hours (never turning off work), and turning down business you don’t want (hardly happens because you never know if/when you’ll get another offer).


To be clear: I am proud of my accomplishments as a freelancer because they are truly all my own. Freelance life is a big empty room with no ceiling. It’s exciting, freeing, and the opportunities are only limited by your own capacity. But, the mental and physical load it takes to maintain success is extraordinary and no one seems to talk about that part. With a toddler and another baby almost here, I am very much at max capacity. So, I keep applying for full time roles because it feels like it might make more sense for this season of life.


This means… I write a lot of cover letters!


As a professional writer, I’ve always been an advocate for cover letters, and used to take a lot of pride in writing them. Out of curiosity about whether or not my cover letter etiquette had evolved, I dug up the oldest one in my inbox, which happened to be for a job I was offered and took.


March 17, 2008

To whom it may concern,

My name is Heather Sundell, and I am contacting you regarding the Marketing and Online Development Coordinator position. I found the opportunity on your posting on Craigslist.com.

I graduated from USC last May with a bachelor’s degree in English, an emphasis in creative writing, and a minor in business administration. I have very strong communication skills, both written verbal. Through my studies, I have learned to be a creative and critical thinker, while retaining a strong sense for business. I feel that both these qualities are essential for success in any business. I was a proud member of Delta Delta Delta for my four years.

I am currently still employed at my first job out of college. I am a Jr. Copywriter at a small Internet company. I am an integral part of the marketing department, with heavy involvement developing marketing strategies. Much of my job entails email marketing, Google AdWords, a monthly newsletter, blogging, writing and updating articles for secondary sites, as well as writing copy for the properties they own. I am heavily involved in SEO strategy and have some affiliate campaign experience. Again, most of what I do is write content, but I am very much involved the creation and implementation of new marketing tactics.

This position couldn’t sound more perfect for me. I feel that my background and interest in online marketing, paired with my years of Greek experience make me an outstanding candidate. I was a member of Delta Delta Delta for all four years of my time at USC, and I even lived in my house for three of them. Along with my own personal Greek experience, I worked at The Greek Escape, a Greek retail store near USC, for a year, exposing me to the entire Greek community from several different schools. I am currently looking for a more interactive job, where I can expand my skills and work in a field I am passionate about. Thank you much for your time.


Heather Sundell


Almost fifteen years later, I gotta say, not bad! Though I take a slightly more personal approach now, later in my career, the structure I typically use is still very similar –– without the sorority references. (To be fair, I was applying for a job where that background was relevant.)


I know I am not alone in my futile-feeling job quest. I know other people also feel like they’re yelling into the void whether it’s by mindlessly hitting “Easy Apply” on LinkedIn or spending an hour tailoring a resume, organizing a portfolio, or crafting a thoughtful and impressive cover letter. So, I decided to get more perspective.


What do YOU guys think about cover letters?


It’s 2022, and even though I’m one of the older ones, I’m still a Millennial so I used Instagram story polls to gather this crude data. Overall, my sample size of roughly 200 respondents ranged between mid-late 20’s to early 40’s. I assume anyone who answered my social media cattle call is currently, or was at one point, a job applicant.



Here are the results:



I have totally not applied to a job because of a cover letter requirement, and this isn’t just because of the time commitment writing one requires. The volume game of applying for jobs has worn me down so that I usually only write cover letters for jobs I am really interested in. I just don’t have the time, energy, or ego to do it over and over again –– with no response.



It’s hard to know what the appropriate amount of time is to spend writing a cover letter, but these stats indicate a half hour is about the median, and that seems right to me. Even still, that feels unsustainable when applying for jobs in today’s climate, which is a complete numbers game.



There is an art to writing a cover letter, but it’s somewhat subjective. When I taught a copywriting class, I even included an in-class exercise on how to write a cover letter because it has become so confusing with no real standardized way to write them. Mine are always pushing two pages, while others write a paragraph. Which is more effective? Does it all depend on who winds up reading it? The even split in this response still indicates confusion to me.



I used to think people read my cover letters –– back in the day, when you’d need to apply to a job with a personal email address. Now, I really have my doubts.



Well, there you have it.


I also spoke with some hiring managers …


Turns out some people are actually reading your cover letters. A handful of friends messaged me in response to my poll to discuss the subject from a hiring manager’s perspective –– mostly in their defense. The overall sentiment was that they were useful … for those who were actually taking the time to read them. The main reason they like receiving them is for screening purposes. They said cover letters were helpful in discerning if a candidate can:


  • Follow directions
  • Read something critically
  • Show personality
  • Take time and care with their work
  • Exhibit a basic understanding of spelling and grammar
  • Prove they’re passionate about the job


As someone who has also been a hiring manager, I don’t disagree with any of this. And, in a hiring environment of 10-15 years ago, I’d even say it was potentially necessary. But the rules of the application road have changed and a cover letter doesn’t always prove to be an accurate binary approval system.


For instance, some people have learning disabilities that make writing long notes a challenge. Others are terrible at selling themselves in writing, but could easily win over a room in an interview. And, based on my own experience and conversations with peers, I don’t necessarily think spending time crafting a cover letter always equates to level of interest in a job. We’re all pretty weary at this point.


What’s the disconnect?


I keep reading about a Great Resignation –– companies in desperation for good talent –– but only anecdotally experience radio silence and repeated rejection for completely qualified roles. So what gives?


It’s clear that when a cover letter does make it into the hands of a hiring manager, it proves to be impactful. I think that’s great. Unfortunately, it seems like the majority of applications don’t ever get seen at all due to two major reasons: an untapped talent pool dubbed as “hidden workers,” and the increased use of automated hiring platforms.


Hidden Workers


The term “hidden workers” refers to applicants who want to work and are actively seeking jobs. They experience distress and discouragement when their regular efforts to seek employment consistently fail due to hiring processes that focus on what they don’t have (such as credentials), rather than the value they can bring (such as capabilities). Hard skills versus soft skills. Credentials versus potentials. These are critical nuances that get lost in the process, and become gatekeepers for great candidates.


Harvard Business School study found that, “hidden workers fall into three broad categories: ‘missing hours’ (working one or more part-time jobs but willing and able to work full-time); ‘missing from work’ (unemployed for a long time but seeking employment); or ‘missing from the workforce’ (not working and not seeking employment but willing and able to work under the right circumstances).


This group could meet this criteria for valid reasons such as taking time away from the workforce because they are caregivers, veterans, immigrants and refugees, have physical disabilities, or relocated for partners and spouses. It also includes people with mental health or developmental/neurodiversity challenges, those from less-advantaged populations, people who were previously incarcerated, and those without traditional qualifications. In the U.S., there are, by estimates, more than 27 million hidden workers.


Aside from discrimination, inadequate training to bolster skill gaps, a big reason this large group of people remain ignored is automated hiring platforms.


Automated Hiring Systems


75 percent of US employers (rising to 99 percent of Fortune 500 companies) use automated hiring software, which was adopted in response to a rise in digital job applications from the ‘90s onwards. Technology has made it easier for people to apply for jobs, but equally convenient for companies to reject them. How automated software reject candidates are varied, but generally stem from the use of overly-simplistic criteria to divide “good” and “bad” applicants without any context (pregnancy, caregiving, recession, etc), whatsoever.


Digital technology was always intended to make it easier for companies to find suitable job candidates, but instead it’s just creating problems. In the early 2010s, the average corporate job posting attracted 120 applicants, but by the end of the decade this figure had risen to 250 applicants per job. Companies have responded to this deluge by applying increasingly rigid filters in their automated software. This has created a vicious cycle of of rejecting completely viable candidates, while increasing a bloated pool of job-seekers.


Is there a solution?


Clearly there are large scale issues at play and, for those problems, the solutions would entail overhauling the entire hiring system, which ain’t gonna happen in my silly little newsletter. So, let’s get back to the question at hand: should companies should require cover letters or not?


In a former hiring world, cover letters were very impactful. Today, not so much. Do I think they need to be completely eliminated? No. As much as my distain for them has grown in the past couple years, I’m not ready to throw them out completely. They just need an overhaul.


Here’s an idea …


I believe the solution lies in short form questions and answers. Hiring managers should decide what exactly they are screening applicants for and craft clear questions that would elicit a satisfying response. For instance, are you looking for?


  • Culture fit
  • Competence
  • Critical thinking
  • Writing skills


Only 1-3 questions should be required with 300 word limits on answers. This sets a clear expectation on how much time should be spent writing a response, and a how much time a hiring manager can expect to spend reviewing. It also levels the playing field for hiring managers, making it faster and easier to compare candidates by looking at apples to apples. An additional advantage would be for people who are not skilled or comfortable with talking about or selling themselves without any direction. This allows them to craft a thoughtful answer with a clear prompt.


If I was asked to respond to one or two questions with short answers, I wouldn’t have a problem taking the time to do it. And, I wouldn’t feel as much like my application was a shot in the dark, or that any rejection was personal. But, that’s just me.


Of course, hiring needs vary depending on industry, seniority, or type of role. (In fact, a friend who is an executive recruiter indicated that a cover letter could make a candidate in her field appear too junior.) But, on the whole, this feels like a more sane and efficient approach, if the responses make it into the hands of humans.

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