I am often asked to proofread my friends' cover letters before they are sent to the presses. It helps that I enjoy editing, but letting another set of eyeballs read your work before you send it is highly highly HIGHLY recommended. Not only will they check for basic grammar, spelling, and readability (all very important), they will also give useful feedback about what seems to be missing, what could use more detail, or what is really unnecessary.

All of that is well and good, but where do you START when you don't know what to say?

There are many, many articles already in existence about how to write a cover letter. Please Google "cover letter" and find a basic template, which will lead you very well when you don't know where to start.

My area of expertise is the actual writing, so let me weigh in on two example cover letters that I read recently, and share my thoughts.

This student is applying for a job as a security guard for Amazon:

Dear Hiring Manager

I am seeking the position of Law Enforcement Response Specialist. I am skilled in Microsoft Word, PowerPoint, and Excel. My most recent employer is Rite Aid, where I am a Shift Supervisor and manage the other associates. While working, I attend Eastern Washington University, through Bellevue College, and I will receive my Bachelor’s of Psychology in June. My interest is in the criminal justice system. I have been on a few ride-alongs with the King County Sheriff’s Department, Bellevue, Redmond, and State Patrol. Thank you for your consideration.

Not only is this cover letter too short, it also repeats much of the content that will be included in their resume (like work experience and specific skills). No where does this cover letter mention what this student will be bringing to the job that is outside the scope of the position. This letter is also missing any information on why this job is a good fit for the student. What does ride-alongs have to do with being a security guard? What do they mean "my interest is in the criminal justice system"?

It is also worth noting that this student attends Eastern Washington University AT Bellevue College. It's a university satellite campus, not a university program run by a community college. Knowing how to talk about your own education and previous work experience matters.

The second cover letter I read was much better to begin, but still has a long way to go to be most effective.

Dear [name]: I am a goal oriented professional who specializes in relationship management, creative marketing strategy, and logistics. Your Sr. Marketing Programs Manager position popped out as one that would be incredibly fulfilling and fits seamlessly with my skill set and experience. I understand that you are looking for someone with a background in marketing and time line management, who has a proven track record of executing on creative initiatives, and is accustomed to wearing multiple hats and managing a wide range of personalities. As the CMO and subsequently the VP of ABC Start Up, I developed skills in all of these areas. I believe in building and maintaining strong relationships, and having clear expectations and measurable goals. Enclosed is my resume that more fully details my background and work experience, and how they relate to your position. I firmly believe that I can be a valuable asset to your team. I welcome the opportunity to speak with you about this position and how my experience could help XX Company achieve its goals. Thank you in advance for your consideration. Best,

This is a much better cover letter and would likely do well as it is. However, I happen to know that this person has a ton of experience but that her experience is much greater than her years. As someone reaching for a senior management position, it is important that her cover letter communicate her experience and not her age.

I recommended that she remove the phrase "this position popped out" and replace it with "this position stood out." She has done a good job of answering the main points in the position description, but I think she could go further to explain the details of her experience. I recommended that she be specific about times when she competed in pitching competitions for ABC Start Up, that she was a manager and leader of a team that included engineers, photographers, marketers, full-time staff, interns, and hired consultants. I recommended that she describe the managerial methods she implemented while managing that team.

I also believe in reducing words whenever possible. Remember: the cover letter is attached to your resume. To say that your resume is enclosed, and will demonstrate how your skills fit the job description, is redundant. You wouldn't be attaching your resume (nor sending a cover letter) if your work experience did not demonstrate your fitness for the job for which you are applying. Try "Please find my resume attached."

I also recommend drawing boundaries for the preferred method of communication with the hiring manager. Especially if you are still working (and are thus unavailable during certain times of day), let the hiring manager know. Consider something like "I work from 9 - 5 daily, but I am available after regular business hours for a phone call, and am always available via email."

A personal side note: I hate when people finish a letter with 'best.' It's dumb. It means nothing. Say thank you, or sincerely, or regards, but please God, don't just say 'best'. (It's also not business kosher.)

A Few Other Notes

Bookend your letter with thank yous. "Thank you for taking the time to read my cover letter.... Thank you, [name]"
Avoid overly explaining what is already clear. If you don't have a second sentence with another example, do not repeat it again for bulk.
Find the name of the person who you are addressing. To Whom It May Concern is extremely outdated, but Dear Hiring Manager is weak if you can find the hiring manager on the company website but you didn't.
Reference the position for which you are applying.
Speak specifically to the main job responsibilities you will be performing.
Demonstrate how your goals and values are correctly aligned with the values of the company and the responsibilities of the job.
Especially with internships, but with many regular jobs, it is expected that at some point you will move on. Mention how this job is a good fit for you, but remember that the hiring manager is not here to fulfill your life's dreams; they want to know that you will do the job well.
Explain any details about your story that need explaining. If you have been away from work for a long time, or recently changed from one job to another, it is worth stringing those events together for the hiring manager.

Remember: this is an introduction of your personality before you have walked through the door. You want to convey yourself as yourself, not some super buttoned up awkward business person.

However, very few of us are truly so unique that we can pull off breaking the mold completely in our cover letters. When I was in college, one of my teachers shared the extremely ridiculous photo collage cover letter that a student sent to a sports news show and still got the internship. That's great, but that's not most of us. Most of us will be best off by writing a normal cover letter, but doing it very, very well.

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CRAFTING YOUR COVER LETTER