6 Keys to a Killer Cover Letter:
Half-ass this important communication at your own peril

Call me anachronistic, but job seekers who neglect to include optional cover letters miss a huge opportunity to wedge a foot into the corporate door. Artful cover letters enable applicants to stand out, providing narrative color that enhances otherwise drab resumes.

The term “cover letter” is itself anachronistic. In pre-digital days, this letter served as the “cover” of a printed, mailed resume. In the days of mailing resumes in an envelope, specifying the job title in one’s cover letter was mandatory; this is no longer the case. Many of the “rules” about the traditional cover letter no longer apply to today’s digital job applications.

Caveat Emptor: Typically, cover letter advice lacks practical examples. So, I wrote an unusual cover letter to illustrate my points and present a new paradigm for the digital age. The letter captures the voice and personality of the candidate. There is virtually no scenario where copying this letter will serve anyone’s purposes nor should you use it as a template. Instead, take the ideas and use your own brilliance, creativity, and voice to craft a letter that suits your unique situation.

Cover Letter by Author

The following six keys correspond to the red circled numbers in the cover letter above:

1. Skip the personalized salutation

Even if the position description gives the hiring manager’s name, they may not be the one who reads your letter. Instead of spending your time hunting for a name and honorific, focus on writing a strong letter and write a general salutation like “Dear [Company Name] Hiring Team” or the more formal, “To Whom It May Concern.” No one will be offended. On the other hand, it’s easy to screw up an honorific, like mistaking a Ms. for a Mr., and people do take offense at this.

2. Be yourself and forget the formula

Cover letters are concise — they’re not term papers with introductions and conclusions. Traditional cover letters have an introductory paragraph that contains obsequious bullshit like, “I’m honored to apply for your position of Product Manager and believe my qualifications are a superb match for the job.” In the same vein, don’t waste words with anodyne compliments like, “Your terrific mission aligns with my worldview,” unless you have a heartfelt passion for the company.

Ask any blogger, and they’ll say that readers skim, spending a few moments seeking something that captures their interest before moving on. Opening with a confrontational anecdote like the yelling incident is a way to hook the reader. From there, it’s an easy ride through this succinct, sub-350 word letter. The end of this cover letter eliminates the traditional, “Thank you for your consideration. I look forward to hearing from you at your earliest convenience,” because, again, it’s unnecessary blather.

If the company is conservative and you’re not, or vice versa, don’t tone down or punch up your letter to conform. Instead, have the courage to show your true self and let the chips fall. If they don’t want you because you’re sassy, you probably don’t want them either.

3. Don’t beat around the bush

A glance at this candidate’s resume will reveal their lack of qualifications for the position, so there’s no point pretending. Directly call out the qualification discrepancy and use the cover letter to engagingly argue your case. This is the purpose of writing a cover letter! The ability to write a persuasive and straightforward business letter is an asset that prospective employers will view favorably.

4. Bullets should make contact

The reader’s eye goes to bullets, so use ’em and make ’em count. In this letter, the first bullet shows the candidate’s out-of-the-box approach is tolerated because it yields excellent results, quantified by a hard number. The other two bullets show how the candidate’s strengths fit neatly into a Product Manager role. These bullets should reflect some of the important desired qualities specified in the position description.

5. Sell thyself, softly

Remember, you’re trying to land an interview not sell a used car. So, skip the hard sell. In this letter, the candidate humblebrags about patience — a double-edged virtue. In our personal lives, we positively regard having patience with spouses, children, and elderly relatives. For this type of position, potential employers may view having too much patience as a weakness. The candidate makes it clear they will become a Product Manager eventually, but they want it now. In this case, the candidate’s impatience is a virtue disguised as a weakness because it demonstrates ambition and proactiveness.

6. Anticipate red flags and neutralize them

Just about everyone has small bumps in their resume that don’t warrant mentioning in a cover letter. But if you have a big red flag like a significant gap in employment history, it’s advisable to address it since it’s so easy for an unimaginative recruiter to toss out resumes that don’t check all the boxes. In the cover letter, the candidate hints their ambition is borne from a hardscrabble life. Their resume may reflect progressively higher-level jobs with blue-collar roots and possibly a lack of a college degree. By mentioning privilege, the applicant provides context for the recruiter to appreciate the candidate’s challenges and better understand their ambition. This candidate succinctly addresses potential question marks in their resume without belaboring them.

This applicant faces an uphill battle, competing against more experienced candidates. An intriguing cover letter may be enough to win an initial phone interview. From there, it’s up to the job seeker to pull all the stops so interviewers feel this person’s success in the role is less a gamble than a sure thing.

Most online applications make cover letters optional so most applicants probably skip them. Don’t be that applicant, ever. Cover letters are vital because they humanize an often inhumane process. Don’t half-ass it with a two-sentence letter or a boilerplate letter where you change a couple of words. Craft each letter to reflect the job and argue why you’re a fit. Sure, it takes time, but a carefully worded cover letter elevates you from the pack.