Why Your Cover Letter Isn't Working as Hard as it Should be

Frequently, I'll have candidates tell me that they're going to send me their cover letter and resume and that I should use that as a starting point. I tell them not to bother because I won't use it anyway. Usually they look angry at my comment, and I need to clarify. I ask them what does their cover letter say. Usually something along lines of 'Well, it describes my resume'. Or, if they've done a lot of research online about how to write a cover letter, they say 'It's a generic template about myself where I can punch in key words and phrases from the job description to show I'm qualified for the job, as well as the company's mission statement somewhere in there'. To both of them, I tell them we're starting from scratch, and to come back with a cup of coffee so we can talk and start over. If I haven't offended

them, they come back, and sometimes even with a cup of coffee for me (not very often, though. Extra points when they do!).

I know, candidate two in the description above is how most websites describe writing cover letters. Go do a Google search and check; I'll wait. It's wrong, though. Yes, you check off their boxes in a very literal sense. However, if you've been on the other side of the curtain, you likely know that those boxes are essentially filler. Sure, the candidate shows that they are not blasting out their resume to anything that they are remotely qualified for without showing that they've done some research. So they can jump through hoops; big deal. Just like I've said before regarding interviewing, they are not looking for a robot who knows how to play the game. Yes, you need to know the rules, but that doesn't mean you want to do what everyone else is doing. So you wrote that you're a hard worker with excellent skills; do you think you're the only one saying that?

So what do you do, then? Tell a story about yourself, and explain where this company fits in. Just like with an interview, it's an opportunity to not only showcase and contextualize your successes in your career (which should be reinforced and complimented by your resume, not just a repetition), but also why you are uniquely the best candidate for the position.

For example, I've spoken about career pivoting as a necessary skill in the modern world, one which is particularly important for folks who've gotten degrees in less desirable majors such as the liberal arts. We need to do this, but with a nuanced approach. I will use an old cover letter of mine as an example:

Thank you for taking the time to review my resume regarding this position. I believe that my unique background not only fills the need your company has presented while also meeting my own career goals, but will create new opportunities for significant growth within your firm.

So here's your cover letter entry. A bit formal, and can be quite universal. Not much deviation, except to include the position.

We continue:

My work & education history, at first glance, seems illogical. Graduating college with a degree in English & education in 2009 meant staying put in my first white-collar position— a real estate law firm. It was here that I realized I had a talent for finance & accounting, as I quickly moved within the firm to manage my own caseload and to develop new client relationships which ultimately became the primary source of income for the firm. 

This is where it gets interesting. Here I've started talking about the lack of linearity in my resume head on. I'm contextualizing my resume and highlighting my successes. This can be tailored to the specifics of the job you're applying for. Focus on the successes that they can relate to and is meaningful to them. Instead of spitting back bullet points from the job post, answer them as if they were questions at an interview through example.


However, my interests in teaching & education led me back to school for my Masters in English, during which time I found employment for a small non-profit which valued my education background as well as my hands-on experience in finance. I quickly oversaw all of the book-keeping, grant-writing, annual federal audits, and public relations development, and negotiated robust contracts with three different school systems in order to cement the financial stability of the non-profit over the long-term. My successes led to my recruitment as the director of the continuing education programs in the high school for all summer programs. Throughout this time, I continued to teach part-time at nights while growing the non-profit, and my growing enjoyment of managing finances pushed me back into school once again for accounting.

Again, this is contextualizing my evolving career path and how I ended up where I was at this point in time. I'm pointing out skills through examples, and reinforcing some of the key aspects of my resume, as well as the specifics of what they're looking for. I've including the part-time teaching at night to show my work ethic, because this experience on my resume is somewhat buried, and to reinforce the duality of my backgrounds (education and English versus accounting and finance). I try to highlight parts of the position that are significant for the job I'm applying for and to give a sense of continued growth in responsibility as my career progresses.

Continuing, let other people show your success:

I have succeeded above and beyond in all of my career paths. This is evidenced not only in my work, but in my philanthropic involvement—I have been recruited as a board director for another non-profit I had worked with in the past, and managed the CSR annual report for HANAC New York, a multi-million dollar non-profit in New York City.

Here I can go into detail about my extracurricular experiences. Things that may not stand out on my resume but say a lot about my quality of work can come to the forefront here, and reinforce that my work experience isn't a full reflection of my capabilities. When the people that work around you recruit you, it's a telling sign for a future employer.

Lastly, wrap it up with your goals, and how they coincide with the company's.

My passions in accounting focus in a few specialty areas; taxation & wealth management. Having spent significant time overseas, I am open and eager to travel, and my E.U. Dual Citizenship affords me the unique qualification to travel as needed without lengthy paperwork. My teaching background has aided me in successful project & staff management, as I am skilled in identifying key ways to motivate my staff using behavioral controls. As my career path has shown, I am not set on a specific vision of my career, and this opportunity maximizes each of my specific background skills, where I am able to both teach, train, and work in a financial capacity, making every day an exciting challenge which will further push me towards success. Thank you for your time.

After reading the cover letter cohesively, it makes sense, and it's a reflection of myself. It frames my resume, which shows my varied experience which otherwise would seem contradicting and as though I was simply jumping from one job to the next, without any rhyme or reason. Further I align my values and interests with the company's which is backed up by evidence, which also touches upon their goals in their job description.

That's all there is to it. Don't worry so much about mission statements and how great of a company they are, focus on showing how you are the right fit for them, and have the evidence to back it up. You're not going to stand out if you respond to their job posting by copy/pasting their bullet points in your cover letter- tell them the story of why they would be stupid not to interview you.