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The Dos and Don'ts of Cover Letter Writing

The Dos and Don'ts of Cover Letter Writing
By Morgan Brazil, Esq.

Cover letters are a necessary evil in all job searches-a necessary and critical evil. While many job searchers think a solid resume should speak for itself, the reality is it often does not. In fact, a poorly written or sloppy cover letter can detract from even the most impeccable of resumes. The first step in writing a cover letter is to appreciate the potential effect it can have on the decision maker and that it may be the only tool you have to separate yourself from all the other applicants. While there is no standard formula to follow, there are some things you should be sure to do, and there are some things you should never do when crafting your cover letter.

Top-Five Dos
  1. Organize your letter in a reader-friendly and easily digestible format. The reader is most likely a very busy professional, and you have to capture his/her attention quickly. Also, the easier it is for the reader to get through the information, the more likely he/she will not just skim over the letter and miss your biggest selling points. For example, bullet points can be used to list important matters you have recently worked on, whether they are cases on which you have had significant case-management responsibility or transactions on which you played a large role. If you are a junior attorney who may not have had primary responsibility on cases or transactions, be sure to summarize the issues involved in the litigation or the details of the deal and your specific role in the matter in one or two short sentences. Similar to resume writing, there is no bright-line rule in length; however, in general, you should aim to limit your letter to one page, unless there are specific circumstances that warrant a longer letter.

  2. Write in a confident, purposeful tone, and highlight your strengths. This is your chance to sell yourself, but temper your enthusiasm with a healthy dose of modesty. State clearly what you believe to be your strongest assets and those skills you have been complimented on by prior employers. Also, consider mentioning significant obstacles you have overcome or additional responsibilities you took on in your academic career, such as working to put yourself through law school or choosing to attend a particular school because of scholarship monies received. This is your chance to separate yourself from other applicants, and no detail may be too small. Also, back up your assertions with specific illustrations. For example, many young associates make the claim that they have great research and writing skills. While this is probably true, you should be able to back up such claim by citing either an example of a brief you wrote that garnered compliments or a successful dispositive motion you drafted.

  3. Individualize each letter. Address it by name to the hiring person. You may want to also consider sending your resume to an attorney at the company with whom you have something in common, such as the same law school or undergrad institution. More important, show that you have done your research on the company. A mass-produced cover letter will not impress your audience; targeting a company specifically in your cover letter adds sincerity to your application and will demonstrate to the reader your desire to work for that particular company.

  4. Put your fate in your hands. End the letter with the responsibility for further action on your shoulders. Unless the job posting or company website states otherwise (be sure to do your research, as some companies specifically request no phone calls from applicants), state in your letter that you will follow up to discuss a possible meeting regarding the position. While it may take some companies a few weeks to review resumes after they are received, follow up nonetheless about a week after you have sent in your resume to inquire about the status of the review, state that you are excited about discussing the position further, and ask if any additional information is needed to assist the decision maker in processing your application.

  5. Proofread, Proofread, Proofread.

This is arguably the most important thing you can do when drafting a cover letter. No matter how persuasive the information contained within the letter, if the reader is distracted by misspellings, improper word usage, or sloppy punctuation, you will not be seriously considered for a position. As a funny example of how distracting sloppy work can be, a friend recently forwarded me a Motion for Continuance filed in a case in Florida. The plaintiff's counsel sought to continue the beginning of trial because he was recovering from painful disc surgery. However, in his request for the continuance, either he or his assistant confused disc, as in the spinal kind, with disk, as in the computer kind. To make matters much worse, he had misspelled "disk" in the motion by using a c instead of an s. Can you imagine the judge's face when he read the request? Obviously, this is a lesson that is particularly important throughout this profession; you will never get in the door if you send in shoddy and careless work. From the example above, you can see that using spell-check is not enough, so read the letter aloud or have a friend look it over to spot anything you may have missed.

Top-Five Don'ts

  1. Don't be negative about anything. If you are seeking to leave your current position because of a personality conflict or because it is simply not a good fit, put a positive spin on your motivations for looking for a new position. Maybe you are seeking to join a company with greater opportunity for future advancement or seeking an opportunity to get more hands-on experience than your current position allows. However you choose to phrase it, make sure your motivations focus on your desire to grow as an attorney and develop your skills and practice. Just as when you are interviewing, a company is trying to get a sense for your personality and enthusiasm for the job. If the reader senses negativity in your cover letter, he/she will be turned off right away.

  2. Avoid fluff. As the opposite of #2 above, fluff is a list of qualities you possess without supplying supporting evidence. Again, specific illustrations are imperative. For example, instead of just stating "I believe you will find me to be smart, hardworking, and capable of effectively managing a number of matters at one time." Try "I graduated in the top 20% of a top-tier law school while also serving as a member of the Business Journal. In addition, I am no stranger to hard work, as I am on track to bill 2,200 hours for my law firm this year. Also, my current position has allowed me to hone my time-management skills, as I have consistently been able to effectively manage a heavy docket of more than 10 cases at any given time." Proving to a company that you possess specific attributes will go a lot further than just advancing unsubstantiated claims.

  3. Avoid repeated use of I. While the cover letter focuses on what you bring to the table, you want to avoid sounding totally self-absorbed and want to be able to show the company how your strengths will better its legal department. Also, vary sentence construction and length to keep the reader engaged in your message.

  4. Don't just regurgitate your resume. The cover letter should be used as a vehicle to provide additional information or to elaborate on or highlight the details in your resume. Take the most interesting or impressive parts of your resume and summarize them. Discuss individual matters you have worked on in more detail. Do not, however, just reiterate the firms or companies you have worked at and the schools you have attended. That should already be clearly noted in the resume.

  5. Don't use wordy or overly complicated phrases. Speak English! It should not read "I am clearly focused on the minutiae involved in composing court documents," but rather "I am detail-oriented." Such complicated language only distracts the reader. The fewer words you use to get your message across and the more direct you are in making your point, the better off you will be.
Of course, these dos and don'ts are not exhaustive and only represent a few important considerations. Overall, however, it is very important to always do your research first and to remember the specific audience when writing the letter. Keep your formatting, including font choice, and tone professional. In addition, think about the size of the company and what it may value the most in its employees. Also, check out the company's website to review the credentials of the other attorneys. If your academics do not appear to be on par with their current attorneys, think of reasons why they should consider you nonetheless. Did you put yourself through law school while working full time? Have you published articles in prominent journals? Ask yourself this: Why would this company want to hire me? Persuasively answering this question will lead to a first-rate cover letter!

Or is the actual area of practice not intrinsically interesting to you?

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