I’ve Read 1000+ Cover Letters, and THIS Is What Will Get You the Interview

It's about being specific, sincere, and intentional.

By Madeline Mann
Photo by Steve Halama on Unsplash

​There is a nasty rumor going around that recruiters and hiring managers do not read cover letters. The truth is, many large companies use software to scan resumes for keywords and then forward those candidates deemed qualified to the HR team. In this case, your stunning cover letter would not help you get to the first round.

I get it, this is frustrating because job seekers spend a lot of time applying without much signal or feedback throughout the process. Which leads to LinkedIn posts that encourage job seekers to stop writing cover letters all together.

But for us little guys—the companies who hire dozens instead of hundreds; the start ups looking to change the world with team members who are equal parts talented and passionate; the tribes where each new person immediately sends ripples through the culture—we read every cover letter, and make our interview decisions based on them.

Cover letters are a chance to fill in the “why” behind the resume, especially if the industry, type of company, or role you are applying for isn’t consistent with previous experience. It answers the question: Why the choice to move from the Entertainment to Tech industry? Why go from a massive company to a start up? Why apply for a Marketing position when your previous role was in Sales? Answers to these questions reveal that one is being very deliberate about their career path. The cover letter should show that you match what the company is looking for, and the company matches what you want in an employer.

The other important “why” in the cover letter is “why this company?" It is a huge bonus in the cover letter if there is any mention of geeking out on our technology, cultural tenets, or our mission. These candidates are the ones who understand, at least on a basic level, what we are building and why it is important, and are enthusiastic about it. This gives them an edge because our small start up runs on passion and thirst for knowledge—if you don’t get excited about complex bleeding edge technology then you won’t have nearly as much fun as everyone else.

So below are two cover letters to illustrate how a cover letter can be a total waste of everyone’s time or instantly earn a call from a hiring manager. These are real cover letters submitted for the same role that I have edited to reveal no personal information.

1. The worst (and most common) cover letter
Dear Sir/Madam,
Please find my resume for the position of Executive Assistant. I am experienced in office administration, have excellent problem solving and time management skills. Additionally, I am highly organized and have been successful working in both individual and group settings.
I strongly believe that my educational experience, strong work ethic, customer service experience, communication skills and eagerness to learn will enable me to make a positive contribution to Gem.
I sincerely thank you for taking the time to review my application. I look forward to hearing from you soon.
Sincerely,
[Candidate]

What’s wrong with it?

• It could be for most any job, any company, any industry.
• It shows no personality, gives no context to experience, and does not distinguish this person as an individual.
• It is awfully long for saying nothing of substance.
  
  

How would I fix this cover letter?
When in doubt, always do short and specific instead of long and vague.

My revised version:Hi Gem Team,
I’m an administrative professional for a VP at a large technology company looking to make a big impact in an emerging tech start up. As you can see from my resume, I have held a wide variety roles, and I see this position at Gem as an opportunity for me to embrace my passion for being an assistant while flexing many other muscles by event planning, office management, culture building, and more!
Looking forward to chatting further,
[Candidate]

Why was this version better?

• The “why” they are applying is in the first sentence (looking to make a bigger impact)
• It turns a potential negative (this person’s resume is all over the place with different types of roles…rejected!) into a positive (this person has a ton of skills and interests, perfect for a start up environment…get them on the phone!).
• It references that the company they are applying for is a tech start up. This shows they are being deliberate about (or at least paying attention to) the companies they are applying to. This is a very low bar of expectation but many do not meet it! So many job seekers blast their resume out to dozens of companies without paying attention to where they are actually applying. Break out from the pack! Apply to fewer places and be more specific.
• It shows a touch of eagerness and entrepreneurial spirit that start ups thrive off of.
• It scrapped the formal, “Dear Sir/Madam” and “Sincerely” for a warmer, “Hi Gem Team” and “Looking forward to chatting further.”
• It’s shorter.
  
  

2. The best (and rarest) cover letter
Hi Madeline,
This is the second time I have applied to Gem because I am determined to become a part of your team. While my resume might come across as left-of-center, I have whittled away at it to reveal the pointed yet diverse experiences that make me uniquely qualified to be your Executive Assistant at Gem.

Currently, I assist my Executive Director (ED) as the liaison for a roster of several hundred executive-level contacts, one-fifth of whom work for healthcare institutions you may be familiar with via GemOS, such as [Company Name], [Company Name], and [Company Name]. With my partnership management acumen, I have the balance of left- and right-brain sensibilities to make a professional, personable gatekeeper and liaison for your leadership on a day-to-day basis.

Given my entrepreneurial and curious nature, I am constantly researching start-up technologies and their success stories (and failures) to improve workplace efficiency. Recently I implemented a project management software to assist the production of a statewide symposium. Ultimately, my research and organization system leveraged additional time to help my ED sell out tickets and close $115K in funding for the event ahead of schedule.

Since the last time I applied, I am even more enthusiastic to find that not only is Gem bringing an elegant technology to the fore, you have translated its immense potential into the field of healthcare data management. I am inspired by the opportunity to support Gem in this arena, as well as supply chain management, and bridge my enterprising and administrative capacities with a personal passion for wellness.
Best,
[Candidate]

What stood out about this letter?

• They start out by showing great eagerness by announcing they have applied before. Without a cover letter, this candidate could appear that they are just constantly applying to EA roles, not taking note of which companies they are applying to. Instead, they show that they are deliberate and persistent—excellent!
• They show interest and expertise for the healthcare industry—an industry we work closely with. This suggests they have specialized knowledge and will likely find our work compelling.
• They reference improving workplace efficiency. This shows that they both take initiative to improve their workplace (right in line with our “Make it Happen” company value) and they seek out ways to learn and level up (in line with our “Seek Knowledge” value). Adding this paragraph shows that they understand the kind of person we are looking for.
• The closing paragraph reiterates specific interest in the company and the role (instead of stating something dry and generic).
  
  

The above cover letter is long, which is not essential to making a good impression, but long is good if the relevance of the information is high. Each sentence added something new to the identity of the candidate, whereas in the first example nearly every sentence was a throw away.
​
Conclusion
There is no universal truth when it comes to cover letters—it’s a messy, nuanced, subjective topic. But if I could give you a heuristic to operate by it’s:

• Write a cover letter if it is for a smaller company with a lower volume of hires. BUT…
• Do not write a cover letter unless you have something specific to say about yourself and/or the company.

For lots more specific and actionable advice, check out Self Made Millennial YouTube Channel.

If you are changing jobs or careers, contact one of our coaches in Switzerland for a free introductory coaching session.