Cover Letter Strategy Checklist


Do you understand the strategic importance of cover letters? They are intended to complement the job seeker perspective of your resume with a focus on employer needs. The cover letter’s job is to prove you are what the employer is looking for.

This checklist focuses on the strategic elements of cover letter content. If you’re planning a cover letter or have one ready to send, take a stroll through this list to ensure strategic optimization.

  • Do you know what kind of cover letter to send – invited/job-posting response, uninvited/cold-contact/prospecting, referral/networking, or recruiter letter?
  • Are you planning to send employers any cover letters via email, as part of your electronic job search? (You’ll want to determine the best way to send it electronically – as an attachment or in the body of an email.)
  • Do you have a basic understanding of how a cover letter should be written? Learn more.
  • Does your letter’s opening paragraph command attention and avoid boring, clichéd cover letter openers?
  • Is the letter sharply focused? Have you avoided needless detail and autobiographical ramblings?
  • Have you avoided such phrases as “I feel” and “I believe,” which tend to weaken and dilute the statements you make about yourself? (use instead: “I am confident…” “I am convinced…”).
  • Is it confident without being boastful? Is it interesting? Does it project the image of a person the hiring manager would like to get to know better – or as a boring dullard or arrogant blowhard? Have you read it from the employer’s perspective?
  • Is it addressed to a named individual?
  • Have you left out everything negative?
  • Is it specific? Have you spelled out the job or type of job you’re targeting?
  • If it’s in response to a job posting, does the letter speak to the requirements of the position?
  • Have you explicitly connected the dots for the employer to ensure understanding of how your experiences, skills, and accomplishments fit the employer’s needs and contribute to the company?
  • Have you shown that you comprehensively grasp what the employer is looking for?
  • Have you told the employer what you can do for the company rather than what the company can do for you? A “me-focused” letter is one of the most significant cover-letter mistakes.
  • Have you used caution with “willing to learn” statements so the employer isn’t reminded of training time and expenses?
  • Have you avoided pleading for favors or sounding desperate and “willing to do anything?”
  • If a college student or new grad, have you made the most of your college experience? Have you avoided over-reliance on an academic frame of reference and instead explained how your academic and extracurricular experiences relate to the job you’re targeting?
  • Have you avoided rewriting/rehashing your resume in your cover letter?
  • Have you eschewed discussing hobbies or interests unless relevant to the position?
  • Have you added more credibility to the value judgments you make about yourself by attributing them to a former employer(s) or professor? For example, “My former employers can attest that I am a motivated hard worker.”
  • Have you further substantiated the claims you make about yourself by giving examples that amplify and prove your assertions?
  • Have you demonstrated your knowledge of the company you’re writing to? This kind of company knowledge is often cited as a wow factor by hiring managers.
  • Have you ensured that your letter is not too skimpy and doesn’t depend too much on your resume to do the work for you? Have you elaborated on your qualifications, transferable skills, and your fit with the position?  
  • Have you presented your Unique Selling Proposition (USP)? What truly sets you apart as a candidate? You USP is often the answer to the question, “Why should I hire this person over all other candidates?”
  • Have you quantified and given examples of accomplishments that demonstrate your skills wherever possible? Have you, for example, told the employer how many employers you supervised, how many customers you handled, how much money you saved the company, and most importantly, by what percentage you increased sales or profits?
  • Have you included a “call to action” (request for interview) in the final paragraph and told the employer you’ll call for an appointment? Have you avoided leaving the ball in the employer’s court with a weak statement such as, “If you are interested in my qualifications, please call me”?

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