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How should I go about preparing a cover letter?

As I've applying to different internships, I've found that not all internships require a cover letter. Nevertheless, everyone keeps telling me I should still submit one with my resume, but I've never written one. What should I make sure to include in my cover letter?
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Megan’s Answer

Hi Ethan,
A cover letter should be written with the intention of showing the hiring manager what unique skills and what value you would bring to a job. For example, at one point I had applied to be the CIO for North Idaho College as we had just moved to Idaho and I wanted a life change. The challenge for me is that I don't have a college degree but I have many years of experience in software engineering. The letter I wrote instead focused on the fact that the lack of a degree had never hindered me. I had originally worked in Hollywood and become successful in a job where we got 10,000 resumes a week for positions. All of my computer knowledge is self taught yet I rose to the top 20% in a Fortune 100 company that has a work force of ~17% women. The letter didn't get me the job but did get me a great response from the HR person and a new connection. Which I have to say, when you are sending in resumes without network connections, it is extremely difficult to do. I can honestly say that there are cover letters that I have struggled with in trying to find the uniqueness and in the end if I was honest, the job likely wasn't right for me. Whatever you do, please remember that the cover letter shouldn't be a regurgitation of your resume.

Things always have a way of working out the way they are supposed to so just keep at it and you'll find an internship that is right for you.

Good luck!
Megan

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April’s Answer

There are a few principles that I like to keep in mind when writing my cover letters:

1) Make it unique to the company... Imagine that you're reading lots of letters from a big pool of candidates. Many people will submit a generic cover letter, without making it specific to each job they're applying for. The company ends up with a pile of cover letters that basically say, "You should hire me because I'm a very hard worker, and I really like your company." If you're the person who has to read through them all, that's going to be very boring. Plus, it's not going to help you learn what makes each of these applicants unique. Try to keep that in mind when submitting your own cover letters: a) do some research about each company, b) make each letter unique to that company, c) and try to keep it interesting (but still professional) for your reader. Reading through the company's values on their website is often a great place to find something special about them that resonates with you.

2) Make it unique to YOU... One way to make things more interesting for your reader is to turn your letter into a story. Now that you've done your research and found something unique about the company, connect it to something unique about yourself -- maybe a story from a sports team, a trip you took, your family, a book that make you think differently, a class you took... it can be anything! Just try to show that you understand and share the values of the place you're applying to. (Example further below.)

3) Keep it short, sweet, and spell-checked... Because so many hiring managers do end up with large pools of applicants, the truth is that many will not take much time to read through every word of a cover letter. They'll probably only skim through, and may rule out certain candidates quickly just based on spelling and grammar errors alone. So, be sure to use spell-check and grammar-check, but also try reading the letter out loud to yourself, to help catch areas that don't sound quite right or drone on for too long. It's also great to find the strongest writer among your friends and family and ask them to proof read. In terms of length, try to target between 1/2 and 3/4 of one page, single-spaced, in a standard professional font (like Times New Roman). Never make a cover letter longer than one page!

As an example, here's a letter that I wrote for a previous employer (Guild Education) -- a company that makes online education accessible to working adults. Because education was obviously important to this company (which I knew because I had done my research), I tied that value to the role that education (and specifically adult education) had played in my own life. I addressed the letter directly to the hiring manager. And, after researching the hiring manager on LinkedIn, I saw that he was a big fan of dad jokes. So I threw one in at the end, just to make things more interesting for him.

Dear Bob,

I spent nine years at several universities, both as a student and as an instructor, before I became a project manager. I always thought I would stay in higher education forever, and in fact, the role that pulled me out of academia was the chance to manage projects for a small technical training school that catered to veterans and working adults. Unexpectedly, that move turned my path toward technology itself, and I spent the next decade guiding software teams toward efficient methodologies and managing tight resources.

Last year, I left my job at SendGrid to dive more deeply into code at the Turing School of Software & Design—a move that has calcified my previous experience into something even more useful to a company like Guild. For example, I know that some Guild teams work with AWS. At SendGrid I managed the program to move our datacenters to Amazon. I’m now able to combine that experience with hands-on exposure to cloud providers, database systems, frontend libraries, MVC structures, API best practices, and microservices architecture to contribute to your team as a more well-rounded employee.

I left project management for Turing because I was feeling stagnant in my own growth and development. I ended up falling in love with code, but that only happened because I had the chance to pursue continued education as an adult. Like Guild, I have a deep respect for the life-changing opportunities afforded by education, and the chance to make it more universally available while writing code feels like a dream job.

I’d love the chance to talk further about what contributions I could make to your team.

Thank you,
April

P.S. I heard you like dad jokes. When does a joke become a dad joke? When it becomes apparent….

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Emily’s Answer

Hi Ethan,

I like to leverage my cover letter as a means to express my personality, demonstrate my skills, and highlight accomplishments that may not be on my resume, but maybe important for my candidacy.

To get started, I would ask your friends and coworkers what their cover letters sound like to get your own creative juices flowing, ask for feedback from recruiters when they call, and get curious with interviewers about your application. You might be surprised to find what is working and once you know you can begin nailing down your secret sauce.


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Simeon’s Answer

Usually, your cover letter is supposed to be brief and mostly explain your interest in the opening and in the company itself. Try to keep your cover letter to five sentences or less. Also, try not to be super dramatic about how much you'd love the position and how it'll fulfill your wildest ambitions. Instead, keep it pretty contained and professional. The cover letter is more of a warm-up/opener to the resume and isn't supposed to be the focal point of your application.

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