Monday, September 6, 2010

Does this Cover Letter Make My Butt Look Big?: Address to Impress

Whether you’re an attorney seeking a change in employment or a “rising” 3L trying to land a job, publication, or clerkship, having a good cover letter can make or break your chances for consideration.

But why stop with “good?” This blog entry will demonstrate the whats and hows of superb cover-letter writing.

Before we plunge into the nuts and bolts of it, it may help you to have an inside look into the mind of the person who will likely receive your cover letter. Chances are that this person is (1) extremely busy, (2) extremely bored with the task of sifting through mountains of applications, and (3) extremely annoyed with all of the terrible cover letters that he/she has already read.

Even when a résumé looks awesome, a crappy cover letter will certainly land you in the circular file. Crappiness can range anywhere from poor format to poor grammar, from too long to too not-paying-enough-attention-to-get-the-job-description-right.

And even when a cover letter is concise, grammar-smart, and correct in stating the proper position sought, it is the rare, RARE cover letter that goes above and beyond “good” by having purpose. Purpose, in addition to the necessaries of good writing, will often draw the distinction among already solid résumés.

So, alas, let’s get down to it, shall we?

First: Bank on the fact that it is highly unlikely that your entire cover letter will be read... that is, until and unless you are selected for an interview. Because of this, you want to show the reader (think: future boss or Zuul to your future boss) that you appreciate his/her time. But you do this with more than a byline at the end of the page; better, you do it with format. Hence, your cover letter should never extend beyond 3 paragraphs.

When Future Boss or Zuul merely glimpses at your cover letter—number 251 in a pile of 400, he/she will greatly appreciate the look of your cover letter at a concise 3 paragraphs. The thought will be something akin to, “Thank god. A short one.” This increases the chance of Zuul actually reading your letter.

Your first and third paragraphs will be very short... about 2 sentences each. Your second paragraph is good stuff is. Think about your second paragraph as the analysis in a memo, brief, or law exam. The analysis, of course, is the most important portion of legal writing, and, likewise, the second paragraph will be the most important portion of your cover letter. But we’ll get to the construction of these paragraphs in a bit.

Second: Each and every sentence should have a purpose. So, when I say that the first and third paragraphs should consist of only about 2 sentences, this is because each of those sentences serve a particular purpose. To arbitrarily add sentences with no purpose is a waste. It’s a waste of your time, and it’s a waste of Zuul’s time.

Third: Your cover letter needs to follow rules of grammar and style that both are accurate and appeal to the legal community. For this, I highly recommend buying, reading, and following the Texas Law Review Manual on Usage & Style (“the manual”).

Do not assume that you know how to use commas. Trust me; most of you don’t. I’m not trying to be a jerk. I’m just telling you that I’ve read many, many, many letters, writing samples, résumés, briefs, memos, blah, blah, blah to lead me to the conclusion that most people simply don’t know how to use commas in every circumstance. And I’m not saying that I know what to do 100% of the time with commas and grammar, but I know a lot more after actually having read the manual. Plus, it’s now in my arsenal in case I get stuck.

Also, refrain from semi-colons, colons, dashes, and so forth until you absolutely understand the rules regarding how and when to use them.

Some helpful rules: (1) Never use conjunctions in a cover letter (or any other professional writing, unless you’re quoting someone). (2) Do not use parentheses; there’s absolutely no need for them in a cover letter.

Some helpful hints: (1) Read your cover letter out loud. Don’t cheat by mumbling through it. Rather, go big or go home: read it out loud as though you were reading it to someone over the phone. Hell, actually read it to someone over the phone.  Find a victim.  Surely somebody out there owes you a favor, right? (2) Release the iron grasp of pride, and—gulp—have somebody else read your cover letter.

Why? I’ll tell you why. I had a student once ask me for help with a cover letter, and she had made a very innocent mistake: she wrote “inter-workings” instead of “inner-workings.” Spell check wouldn’t catch it. Reading it over the phone wouldn’t alert the listener because of our American lack-of-pronunciation of “t”s when they fall in the middle of words. However, another person physically reading the cover letter would likely catch the error. [Note: This student’s original draft of her cover letter was very good, but since Zuuls actively look for reasons to exclude applications, a simple mistake like this could have easily resulted in a quick trip to the circular file.]


Now, we come to the structure of your cover letter. Everything should be block formatted (meaning, justified and flush left; in other words, don’t indent paragraphs).

Header: It must match your résumé precisely.

Date: Don’t forget to update your date if you’re working off of a previous cover letter.

Recipient’s name and address: Make double sure that this information is accurate, which includes that you ensure accurate spelling of everything.

Salutation: Um… “Dear” + title (i.e., “Judge,” “Mr.,” or “Ms.”) + last name. End the salutation with a colon, not a comma.  Be sure to spell any names accurately.

NOTE: If you are in any way uncertain about the gender of the person to whom the letter is supposed to be addressed, never assume one way or the other.  For instance, when I get a letter to "Mr. Zaylia," I never, ever, ever give that person a shot.  I'd rather see someone address a cover letter to my full name than to presume that I am a man.  On the same note, if there is no name for you to use in your salutation, never write "Dear Sirs."  Just... no.  You can write "To Whom It May Concern" or something that is gender-non-specific.  I'd rather see "Dear Sir/Madam" than "Dear Sirs."  If you know that the addressee is a woman, then write "Ms." instead of "Mrs." because it is not professional to assume (1) that women are married, (2) that women want to be defined by their marital status, or (3) that their spouses are men.  I could write a whole separate blog entry about this, but, for now, you'll just have to trust me.

FIRST paragraph:

Sentence #1 should convey two specific things: who you are (i.e., “a third-year law student at X University” or “a third-year attorney”) and what position you are applying for.

Sentence #2 should consist of some blanket statement about believing that you would make a great fit for the position. This is a relatively superficial statement, but don’t worry because the following paragraph will not only relate to this sentence but will, moreover, prove it up.


I am a second-year law student at the University of San Diego School of Law and am interested in a position as an associate with [Your Firm]. I believe that my experiences in criminal law, writing, and advocacy would allow me to successfully contribute to the program.

SECOND paragraph:

Ok. This is it. This is what I call the “prove it” paragraph. This is where you prove the point that you just made in the preceding sentence: namely, that you make a great candidate.

Here, your job is to weave. Just as we weave facts and rules into an analysis as legal writers, in paragraph #2, we weave in our legal experiences with characteristics—the characteristics that employers look for. The point of the second paragraph is not to talk about your qualifications but, instead, to prove them through your experience. No self-proclaimed characteristic should stand by itself; it must be tied to a legal/professional experience so that Zuul can see why you think you have that qualification.

So, just like legal analysis, you will be using the word “because” and its progeny a lot.

Also, if you consider yourself a “diverse” applicant and want to let Zuul know about it, you should do so upfront, but it must, must, MUST speak to a qualification that pertains to the position.  Otherwise, leave it out because it looks like you’re saying, “Hire me because I’m diverse,” and nobody wants to do that.


Because I am the first member in my family not only to attend law school but also to have earned a four-year degree, I am an experienced self-starter, understanding the importance of dedication and follow-through. Using these attributes, I secured two federal externships, hold the chief articles editor position for the San Diego Journal of Climate & Energy Law, am a member of the San Diego International Law Journal, have published six journal articles, and have presented independent research at several national conferences. As a former judicial extern for two federal judges, I have handled and witnessed many criminal matters before the court. Also, as part of my work for the Criminal Division of the California Attorney General, I briefed three criminal cases and, moreover, successfully argued before the California Court of Appeal in three separate criminal matters.

As you can see, I like starting out with the legal/professional experience first before I go into the characteristic/qualification that I garnered or honed from that experience.

Seriously, your second paragraph should consist of—tops—5 sentences. That’s it.

Do not regurgitate your résumé in paragraph #2. Rather, expand on things that are not obvious in your résumé.  For instance, in my paragraph #2, I mentioned my six publications because, frankly, I couldn't fit all six on my single-page résumé, and I wanted Zuul to know that I had six—not two—publications.

THIRD and FINAL paragraph:

Thank Zuul, and, once again, express your interest in discussing your qualifications.


I look forward to discussing with you how my experiences in externing, researching, writing, and publishing would allow me to contribute to [Your Firm]. Thank you for your time and consideration.

Salutation (yes, another one): Something like “Best regards” followed by a comma should do. Note that if your final salutation has more than one word in it, all of them begin with a lower-case letter… except for the first word, that is.

Please note that you should refrain from anything with the word “submit” in it, such as “Respectfully submitted.” This is because you submit things to a court. You submit legal documents. However, this is not a legal document that you’re submitting to a court, so just choose some other salutation. K?

Your name: Press return/enter four times after your salutation, and type your name as it appears in your header. In other words, there should be three blank lines between your salutation and your name.  This is the standard spacing, and it provides enough room for your signature below the salutation.

Enclosure(s): If you are attaching a résumé or something else, like a writing sample, type “Enclosures” immediately below your typed name. If you are only attaching one item, type “Enclosure.”

THAT’S IT!  Whew!

Long entry, but I hope that this will help you along your journey.