Promote Yo Self: The Lost Art of the Cover Letter

Harmony
8 min readMar 7, 2022

--

My dearest job-seeking Marketers,

If you can’t effectively market yourself for the position to which you are applying, I reserve the right to question if you can effectively market my organization’s brand and services. Too harsh? Maybe. But after having recently interacted with applications from over 600 candidates across a variety of roles, I am baffled by the decline of the cover letter as an essential tool for promoting one’s value to a potential employer — especially among individuals who are professional communicators and marketers by trade.

In October 2021, I began a new role as the head of marketing for a non-profit working to define and address barriers to accessing educational resources. In today’s post-pandemic landscape, that’s an environment rife with transition.

From the earliest stages of interviewing for my own role, I knew the person in this position would be leading the Marketing organization through large-scale, long-term change — developing and expanding the team, assessing and enhancing our technology, introducing new go-to-market strategies, and retooling operational processes.(🎵 “these are a few of my favorite things” 🎵)

As part of this process, our team is quickly growing! In my brief tenure, we’ve already hired four new employees, are recruiting for four others, and have plans for more to come in the future.

It is not uncommon for a hiring manager to sort and categorize dozens, or even hundreds of resumes per position. At this volume of openings, that requires a lot of fast decision-making using a complex series of inputs as we seek to build and sustain a diverse, equitable, and inclusive workplace. One of the best tools a candidate can use to help a hiring manager sort and categorize their application is a cover letter.

Yet I’d (generously) estimate that fewer than 25% of the applicants to my recent roles have submitted one. I’m not so hardcore that a lack of cover letter is an immediate disqualification, but I know other Marketing leaders for whom this is an absolute deal-breaker, and I get why. Minimally, by offering a cover letter of any quality, you increase the amount of time the hiring manager will spend engaging with your application. Ideally, you’ve provided a relevant and compelling message that jumps you to the top of the list.

TL;DR: if you write a cover letter, I will read it. And let’s be very clear, that can work for or against you depending on the quality of that cover letter. So if you’re going to write one, and please please please do consider it, make sure it’s good.

Google “how to write a good cover letter” if you have to. The Internet already offers a trove of advice and services to help. Here are some less conventional nuggets of wisdom I’d like to add to the noise.

  1. Write a cover letter.
    Hear this in the voice of Tom and Donna…PRA MOTE YO SELF. You know more about yourself than anything! Do justice to highlighting your own unique strengths and what differentiates you from other candidates as a way of giving me confidence that you can do the same for our brand and services.
  2. Spell check and proofread it.
    Then do it again. Read it backwards and aloud. Have someone else spell check and proofread it. As a marketer, you’re often the last set of eyes on a piece of content before it’s published or promoted to the masses. This is a sample of the quality of work you are capable of — your attention to detail and accuracy is paramount.
  3. Format it properly with legibility and accessibility in mind.
    I’m a sucker for good packaging and appreciate people who use these documents to demonstrate their design skills. The robots (AI) ingesting your content into applicant tracking software might not care, but I do. Formatting can make or break how your text, as data, is imported. That means it also impacts the amount of time you might spend rekeying information and uploading PDFs. For that reason, it is totally fine, even for marketers, to put forward conventionally formatted documents. It is not fine for that document to be written in a size 8pt, serif and italicized font. I’ve seen all of these used separately and *shudder* together. Consistently format your headings, align your indents, check your bullets, use a legible font size, and adopt an easily readable font style. The robots might not care, but humans do.
  4. Customize it a lot. Option A.
    Look, I get it. Searching for new employment is time consuming and customizing cover letters is hard. For certain roles, the core content of your cover letter may not need to flex much. You don’t need to reinvent the entire wheel for each company, but you should show that you can tailor your message to the audience. Use your intro, conclusion and a phrase or two to connect some dots between your skills and experience, the mission of the organization, and the core responsibilities outlined in the job description.
  5. Customize it a little. Option B.
    If you decide not to listen to #4 and do a more substantive customization, at the very least, and I can’t stress this enough, fill in the blanks in your template. It’s somewhat shocking how often a generic template either hasn’t been filled in at all, or is still populated with the title and company of the last job you applied for.
  6. Vary your sentence structure.
    Just because you’re writing about yourself, doesn’t mean every sentence should start with an “I.” Again, this is an opportunity to show you know what a good marketing message looks like. “I believe my experience as a senior marketing manager makes me an excellent fit,” could easily become “Experiences such as ______, ______, and ______, make me uniquely qualified for the [Title of Position] role.” Or better yet, “You’ve indicated that experience with X, Y, and Z is essential to success at Company. In my role as Sr. Marketing Manager at Other Company, I…(describe an effort that showcases your experience doing those exact things).”
  7. Take risks. Be human. Be bold.
    But not too bold. It’s a balance. Humor? Great. Sarcasm? It isn’t for everyone. Vulnerability? Love it. Connect your story to the value it brings to the role or how it shapes your perspective in a way that makes you a unique candidate. If the personal anecdotes aren’t well-grounded, they can come across as pandering. Challenge assumptions and offer insights. In doing so, be careful not to presume or insult. It’s too easy to pass judgment from the outside without understanding the context in which decisions were made, or by whom. Use your authentic voice. Unless you swear a lot. Don’t swear in your cover letter.
  8. Balance being current with being relevant.
    A great cover letter connects your experiences and style to the work and culture described in the job description and on the company website. Your most current examples won’t always be the most relevant, and that’s okay. The cover letter gives you an opportunity to shine a light on an amazing accomplishment that would otherwise be buried in a chronological resume. In certain roles, like technology-oriented positions, having recent and relevant experience or training is what gives you the edge. In other roles, having a steady progression of increasing experience over time is what does the trick. Feel free to provide a mix of your greatest hits alongside what you’re most excited to be working on now.
  9. If you can, preemptively answer the obvious questions.
    Not everyone has a career that progresses in a traditional, linear, or otherwise logical path. Gaps in employment exist for all sorts of reasons. Sometimes job titles don’t reflect the skills you developed. Maybe you dabbled outside of your industry or area of expertise and it was a great learning experience. Perhaps you have a series of short stints across a number of organizations and it’s because contract-based work offered the flexibility you needed to manage a personal circumstance. You don’t need to tell your life story in the cover letter, but if there is a clear and succinct way to address what otherwise might look like a red flag, you should try.
  10. Testimonials are great-ish.
    This one might be a total outlier, but it stood out so much I’m using it to round out a list that would otherwise only have 9 items and haunt me forever as seeming incomplete. A candidate once uploaded a letter of recommendation from a former employer in lieu of their cover letter, and it was nearly a decade old. That was an odd choice. Uploading references or accolades in addition to your other documents is great. I don’t mind unsolicited references as long as they’re relevant. Better yet, link to your LinkedIn profile as part of the conclusion of your cover letter and invite the hiring manager to peruse your recommendations section and any other extras your cover letter and resume don’t naturally accommodate.
ITHAKA’S value is expressed as “Everyone belongs. We value diversity and actively seek different perspectives.
We work to help every employee participate and succeed.”

It’s worth noting that cover letters are not without controversy. There is legitimate concern that a longer-form written piece risks introducing bias into the hiring process. This is a real issue, particularly in the context of gender, so we use software to flag potentially biased language within every job description we post. Obviously, we do not expect applicants to have access to the same tools.

That’s why every employee, and especially our people leaders, is trained ongoing on topics related to diversity, equity, and inclusion, like how to recognize and overcome implicit bias.

If fear of bias is what’s holding you back from submitting a cover letter with your application, I’d encourage you to try. One of our core values is belonging. We want to hire people who can be their authentic self at every step of every day, starting with the application process.

Yes, you are seeking new employment in a candidate-driven market. But the fact that candidates can be more discerning than ever does not mean hiring managers are being less so.

We can and do adapt our processes to keep up, but we can’t compromise the quality of people we hire, or the rigor with which we vet candidates to ensure we onboard a diverse group of employees passionate about our mission, eager to embody our values, and who will be thoughtful stewards of our carefully crafted brand.

Use everything you were taught in Marketing 101 to promote yourself. I guarantee a well-written cover letter is an outstanding way for you to stand out.

Best of luck to you in your search.

--

--

Harmony

I inconsistently publish essays on a variety of topics. My name is Harmony. My life is often chaos. The writing process helps bring order.