To Whom it May Concern: Your Cover Letter Could Use a Little Work

To Whom it May Concern: Your Cover Letter Could Use a Little Work
Fall 2017 by Emily Anthony

PTO

To whom it may concern: As a frequent recipient of innumerable cover letters, I feel certain that you will agree that I am the ideal candidate to author an article on how to write an excellent cover letter. In my vast experience . . .

Are you bored yet?  I am! And when you read dozens of cover letters in a single week as I often do, it quickly becomes clear that in many cases the writer is just as bored as I am.  True story: I once got a cover letter with a passionate argument for why I should hire this candidate to raise money for the Boy Scouts, due to the impact they’d had on him throughout his life. Trouble was, the job I was hiring for was not with the Boy Scouts. This was not a case of forgetting to change the name in the cover letter, it was a full-on ode to the Boy Scouts, clearly intended for someone else. I called him and said, I think you sent me the wrong cover letter, no worries, it happens! But if you still want to apply for this job, you should send me another letter.  “Do I really need to take the time to write another one?” he asked me. “Don’t you pretty much already know what you need to know about me?” Well, now I do, yes! Call me crazy, but his response gave me an inkling the job I was calling about wasn’t that important to him . . . and as a result, his application was not that important to me.

I’ve read that asking for cover letters is becoming less and less common, and that some large tech firms specifically ask people not to send them for most types of positions. I can only speak for myself and my colleagues at Clover Search Works, but I can tell you that we really are interested in the cover letters we get and we read them all with care.  We hire people to work in small to midsized non-profits, and we’re looking for fit with the missions and the cultures of the organizations we serve. I'll be honest: if someone has a ton of relevant experience and is obviously more than qualified for the job, a perfunctory cover letter probably won't prevent me from following up. But if I'm on the fence about bringing someone in for an interview, a great cover letter may very well tip that person into the yes column. Your cover letter is an opportunity to tell me about parts of yourself that might not be evident from your "just the facts, ma'am" resume-- and most people are a lot more interesting than a bare bones list of where they worked and went to school could possibly represent. Why would you give up that opportunity by sending a super generic, "cut and paste and hit send" kind of letter?

And speaking of cutting and pasting . . . you're not fooling anyone with your recycled letters! I'm not offended to get cover letters that are written in such a way that they could work for any job in your field, but it does suggest to me that you are not interested enough in this job to take the time to write even a sentence or two that is specific to the position.  Case in point: here's an excerpt from a real cover letter I received. I didn't have to redact any identifying characteristics, because honestly, there aren't any:

I have excellent time and project management skills that will directly translate to positive results.  My strong communication skills help create and develop positive, valuable working relationships with a broad range of individuals. As a leader, I work hard to develop a positive environment by encouraging personal and professional respect.  My goal is always to provide the highest quality experience through strong leadership, communication, service and professional development. I enjoy a challenge and work diligently to attain organizational and professional goals.  Please contact me at your earliest convenience regarding this opportunity. 

It doesn't take a genius to figure out that this candidate sent this cover letter to all kinds of organizations to apply for all kinds of jobs, likely in many fields. It's not that reusing most or all of a letter is so terrible, but letters like this provide me with no meaningful information about why that unique candidate would be great for this unique job. And as someone who cares about finding the best fit candidate for every job, that is exactly what I am trying to figure out. I can try to connect the dots myself between your past experience and my open position, but why not give me a hand and spell it out for me? 

Your cover letter should make a case for why you are a good fit for MY organization, not just a case for why you should have any job, anywhere.

In nonprofit hiring, mission fit is important: people who are personally committed to their organization's mission are more likely to go the extra mile, and to stay for many years.  The cover letter is your chance to tell me about how being an avid birdwatcher has influenced your views on protecting wild lands, or how having a sibling with special needs changed your perspective about health care, or whatever your special connection to my issue might be.  If you don't happen to have a strong affinity to the particular issue area, writing about how your values align with the organization's values can still make a powerful connection:   "I am inspired by your mission of providing wilderness experiences for teenagers. When I worked with at-risk youth in theater programs I saw how powerful it was for kids to work together to accomplish something they never thought they could do, and it is clear your programs promote those same values of courage, teamwork, and the joy of realizing your goals." And if your values don’t align either? Then it might be time to rethink submitting the application . . .

In addition to mission fit, writing about how your special skills are a fit with what you know about the job both helps me understand more about you, and shows me that you did your homework about my organization.  Here's another short excerpt from a real cover letter to show you what I mean (although this one I did have to change a little, since there were identifying details, as there should be!):

The varied backgrounds and breadth of experience I see among your staff show me that diverse perspective is a valued commodity in your organization. In addition to my experience managing private sector, non-profit, and entrepreneurial pursuits, I have an MSW as well as an undergraduate degree in economics and a broad business background to draw upon. I should fit right in.

The example I chose is still a little vague about specific skills, but it does demonstrate that this candidate is thinking about how her background will be a match with what she has learned about my organization. In other words, she's making an argument for why she would be an especially good choice. Particularly if you are applying for a job in development, communications, or a leadership position like an Executive Director, I want to see evidence that you know how to make a compelling case in support of something you care about (namely, you!)  since that is a specific skill you will need in those jobs.

Answer my Obvious Questions

Making a case is even more important if there's something about your resume that will make me wonder what’s going on. Why is this candidate who lives in Florida applying for a job in Seattle? Why is someone applying for a job when they just started a new job last month? Why are they applying for a fundraising job if they've been a lawyer for the last 5 years? There is no law that says you have to explain any of these mysteries to me -- and in fact there are laws that say I can't ask you a lot of personal questions to figure them out. But if there is something about your background that raises an obvious question, I think it is very often in your best interest to disclose the answer. 

Moving is a great example: letting me know there is a reason you’re thinking about moving across the country (such as relocating for someone else’s job, or even just that you are ready for a change after living where you have been all your life) helps me know that you are serious about wanting to live here, and that you didn’t just see the job on a national site and fail to notice it is in the Northwest.  If you are trying to make a career change or coming back to work after a long absence, don’t gloss over the fact that you are new to the field and just hope I won’t notice. Instead, write about how what you have been doing has transferable skills to what I am looking for, and any preparation you might have done (such as volunteer work) that will be helpful as you make this change. I know it can feel risky to say too much in this very first document, and in truth there are some things that you probably shouldn’t disclose (“I’m looking for an easy job, because I am so tired of working this hard.”) But there is also some risk I will dismiss your application if I don’t understand why you are applying or how you could be a fit, so it’s worth considering sharing a little bit more.

Here are the other questions about cover letters I get asked all the time, and my answers:

Who do I address it to? Should I really write “to whom it may concern?” I think the short answer is, it doesn’t really matter, we see everything. If you know the name of the person who will read it you can use that, or just go with “Dear Hiring Team” which can cover a lot of bases.

Do you throw out applications when there are typos in the cover letter? I'm not one of those people who will throw your application out because I spotted a typo, and I'm careful to remember that not everyone is or should be a native English speaker who majored in the humanities.  But unfortunately those people are out there, and it is worth remembering that first and foremost, your cover letter is a writing sample. Your cover letter should demonstrate that you took the time to write full sentences and proofread. Like I tell my kids, read it out loud before you hand it in.

How long should it be?  I’m not religious about never going onto the second page if you have something important to say, but trying to get it done in a page is usually a good idea.

Should I do something different to really stand out?   You don't need a personal infographic, a shocking opening line, or a custom designed logo to get my attention (although a quick story never hurts . . .) You just need to show me that you are thoughtful about why you are applying and that you took the assignment seriously.

I hope these thoughts will be helpful the next time you write a cover letter! Share your own cover letter tips, pet peeves, and ideas in the comments below. 

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