SuperHi on Cover Letters: How Do I Address It, How Long Should it Be and How Do I Talk About My Experience?

How do you address a cover letter? How about if you don’t know who’s going to read it?

At some point it seems we were all told that “to whom it may concern” was an appropriate and polite way to address formal correspondence when we don’t know exactly who it’s for, in a case like, say, a cover letter. As it turns out the business of getting hired has changed a bit and that just doesn’t cut it these days. At this point “to whom it may concern” just comes off as detached and impersonal rather than the formal and respectful that it seems to be aiming for. So, what do we do?

In a perfect world all listings would tell you who they should be addressed to. It takes the pressure off you, ensures that they’ll be receiving correctly addressed letters and opens the possibility of applications being slightly more personal and specific. Understandably for a variety of reasons this can’t always be the case so we’re left in a bit of a pickle. Do we leave it unaddressed? Do write “Dear Hiring Manager?” Do we guess? Or do we just say hi? Well, like so many of these answers it’s going to depend.

The one reliable rule is that you should absolutely be researching. The ideal solution is that you can narrow down the possible people enough that you can actually identify the reader. Between LinkedIn, company sites and other freely available info online you actually have a pretty good shot! Especially when it comes to smaller companies, a little digging can go a long way — we all live on the internet, find it out! If there’s only one or two people in an HR department it’ll likely be them, if the company or organization is smaller you might be best of guessing the lead of the team or department you’re applying for and if it’s even smaller than that you may want to put the CEO, COO or director. Sure, it’s a bit of a guessing game, but it’s not as risky as it might seem.

Think about your own life, what’s more impersonal, receiving mail that’s correctly addressed to the “Resident of 111 Doop Street” or a piece of mail accidentally addressed to a roommate or a family member? Between spam, advertising and social media we all receive tons and tons of anonymous and impersonal communication all the time — it doesn’t even register. When it comes to a job application that’s about the worst case scenario. At this point, a “To Whom it May Concern” or a “Dear Hiring Manager” just comes off the wrong way and the perceived lack of effort might even strike the reader as a red flag, disqualifying you in your first few sentences. Take the time, look around, make a good guess. If you absolutely can’t bear the uncertainty you can always grit your teeth, wince and write “Hello [This Company] Team.”

How long should a cover letter be?

A cover letter should be around three or four short paragraphs. Usually each of these paragraphs should only be a few sentences that are well edited to clearly and densely carry your point. In the first paragraph you should introduce yourself briefly with just a little bit of color and repeat what position you’re applying for. In the second and third you should have the content of your letter either expanding on the experience in your resume or otherwise giving context to your work and application. And then you should close things with a nice sign off and a kind word to the reader.

Ok yes, it’s not that simple, but that’s how it should feel to the reader. Snappy, quick and containing only what it needs. If you’re writing or proofing your cover letter and you find yourself meandering or, god forbid, drifting onto a second page, you know you need to take a step back and reel things in. Character and color are great, but they need to be integrated into this tight format, not tacked on with a long story about this or that project.

It’s not always easy to cut out a story that feels important to you, but a thoughtful, well-edited two or three hundred words will go much father than a sprawling essay on the first project you led. The process of writing a cover letter is all about editing, reducing and condensing.

How do I convey my experience & nod towards the money I want?

Ideally a listing should be pretty explicit about the experience required and the pay range, but there certainly are times where that isn’t the case. When it comes to your experience your resume should pretty much have things covered, but if a listing is particularly vague you can talk about projects and roles you’ve had in more detail to give a clearer picture of where you are in your career and what the employer should know about your level of experience going in. This is definitely a situation where you’ll need to tread carefully.

Where this becomes more important is when you’re applying for a job that’s explicitly and clearly more senior than your past experience. In this case you may want to gently outline the ways in which you’re ready for more responsibility or are otherwise well prepared to move on in your career. You can put more emphasis on the leadership or organizational roles you’ve taken on in your work and how those have made you ready for the role you’re applying for. But you should keep the discussion to the qualities that make you ready to step up rather than putting it in terms of salary or benefits.

Yes this is a chance to explain where you are in your career, but you shouldn’t be trying to negotiate before you’re even in the door. At the absolute earliest you can politely ask about the salary range before accepting the interview but in 99% of situations you should wait until you’ve made it through the first few interview steps before trying to iron our the details of your potential employment.