When Your Cover Letter Can Hurt You

Albert Tawil Headshot


Albert Tawil, Founder & CEO of Lateral Hub

In our last blog post, we covered when you should include a cover letter in your application.  If there is one takeaway, it is this: if the firm would be wondering why you are applying or qualified for the job, then you should include a cover letter.  If it is obvious from your resume and other materials, then a cover letter is less important.
Now, you might say – well, certainly, a cover letter can’t hurt, right?
My answer is: a *good* cover letter can’t hurt.  Others can.
Here are a few things to keep in mind to make sure your cover letter doesn’t hurt your application:
1/ Customize for each firm
The most important thing in a cover letter is to make it specific to the firm to which you are applying.
This may seem obvious, but many candidates don’t do it.  Cover letters can be time-consuming, and it is easy and tempting to use a generic cover letter.  Or, copy and paste the body of the cover letter and switch the firm name and address.
Of course, you don’t need to re-write a new cover letter from scratch for every application, but you should describe why you are a good fit for that firm specifically.  Do some research about the firm’s practice before drafting the cover letter, and try to incorporate tidbits of information that you find.  If you are retooling to a new practice, or looking to do a different subset of work within the same overall category (for example, middle market private equity M&A instead of public company M&A), then understand what the practice would entail and explain why your experience and skills transfer well to the new role.
Including a cover letter that doesn’t include the firm’s name or job posting at all is a clear signal to the firm that you are not willing to spend time on the application.  Including those items is basically a minimum requirement.
2/ Keep it concise. 
Cover letters should be 3-4 paragraphs and limited to one page.  The first paragraph can be a short introduction about yourself and the role in which you are interested.  The next two paragraphs can be used to explain your experience and why are you interested and a good fit for the position.  The cover letter can wrap up with a short conclusion and how the firm can get in touch with you.
3/ Make sure it’s well-written without typos.
Typos are low-hanging fruit.  They are an unfortunate way to hurt your chances but an easy thing to fix.  Because of how important attention to detail is as a law firm associate, an error in your cover letter can signal to the recruiting team or partner reviewing your application that your attention to detail is lacking and can come through in your legal work as well. First impressions matter.
After writing your cover letter, let it sit for a bit.   Go back and re-read it with fresh eyes later in the day and edit accordingly.  An easy way to catch obvious mistakes is to first run a Word spell and grammar check.  Then, if you want an extra pair of eyes to be safe, you can have a friend, family member, or significant other proofread it.  Some law school career services offices can help review your cover letter generally as well, for substance (not just for typos!).
Having it proofread can also help with writing quality, aside from just typos.  In addition to explaining why you are a good fit, the cover letter is also a signal to the firm about your attention to detail and writing quality.  A poorly written cover letter may explain well what your experience is, but the partners or recruiting team may feel that your work product doesn’t meet the firm’s standards.
One of the most common mistakes in cover letters is including the wrong firm’s name within the body of the cover letter.  The reason for this is obvious – when you use the same cover letter template and change only a few things, like the firm name and a couple of details, you can forget to make all the changes and leave another firm’s name accidentally.
There is no other way to say this — for God’s sake, please don’t make this mistake.  Nothing is more of a ding in your cover letter than saying how great of a fit you are to work at Firm A and submitting it to Firm B.  When you are creating multiple cover letters with the same template, here a couple of easy ways to prevent this:  
–Create a checklist of the things you need to change for each separate cover letter, and check off every box for every draft.  If changing the firm’s name is on that checklist, then it won’t get missed.  
–Another idea is to keep the firm name in brackets (“[firm name]”) and then, as a matter of course each time, do a ctrl+F for any brackets in the document before finalizing.  Similarly to what you might do as an associate preparing a draft memo or contract markup and searching for stray placeholders before finalizing.  Create a system to follow each time and stick by it.
4/ Write it yourself
With all the buzz around AI, it is very tempting to have ChatGPT write your cover letter for you.  Please don’t do this.  
ChatGPT can be helpful as a first draft to get over your writer’s block getting started – if you choose do to that, you should be sure to edit it accordingly for accuracy, grammar, typos, length, and to match your writing style.   Simply asking ChatGPT to write a cover letter and copying and pasting with no editing is a risky move with little upside.  Believe it or not, it is usually pretty obvious when something was written by ChatGPT without edits, and cover letters are no exception.
Cover letters can be helpful in many situations to add color to your application and show why you are a good fit.  But don’t let your cover letter harm your chances when applying for lateral openings.

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