Cover Letter Tips: When to Write One and What to Say

Cover letters – the age-old formality of writing a letter and explaining why someone should consider you for a job. Cover letter anxiety often prevents applicants from following through and submitting for a role. The thought of putting pen to paper to convince someone to give you a shot can be daunting. What are the right words? Am I coming across authentically? Do I even know how to write a complete sentence?

Applicants aren’t the only ones complaining about cover letters. According to NBC News, as many as 75% of recruiters note that they don’t read cover letters, or at most scan them. But before you stop reading and assume I’m here to tell you to skip the process all together, remember that recruiters are the first in a long line of individuals that will consider your qualifications.

A mini cover letter history lesson

Understanding the cover letter’s purpose can help reframe how, when and why to include one. The intent behind cover letters has changed. Anyone who applied to jobs prior to the digital age will remember when applicants had to physically mail, or hand deliver resumes. Cover letters used to articulate what type of role the candidate was submitting interest in and give some direction as to where their resume fit in with an organization.

Thanks to the technology-first world we now live in, online applications usually do this work for us. The reader has your resume up next to the job description. They know what type of role you are pursuing, otherwise, why would you have clicked submit? Today’s cover letter is more evolved and focused in on how you fill the gaps the employer is trying to bridge.

Do you still need to send a cover letter? The answer is a solid… maybe.

For starters, if the job description asks for a cover letter, you better include one. However, you may run into applications that don’t even offer a space for you to include an attachment or supplementary text (check first before you start drafting). It’s when submitting a cover letter is optional that most applicants start to sweat.

Cover letters will inherently make you appear like a more serious candidate. They can also demonstrate your enthusiasm for the role and show more heart than your resume can on its own.

For those that are looking to move up in their careers or make a big change in the type of role or industry, cover letters are a way to connect dots that aren’t as obvious on your resume.

What to include in your cover letter?

Your cover letter should answer some key basic questions: Who are you? Why are you excited about this job? What makes you the best fit?

This is your chance to breathe a little life into your application. It should not be a regurgitation of your resume.

Start with the job description. Pull out the biggest requirements and needs for the job and focus on how you fill those needs. Make sure that every point in your cover letter addresses the priorities of the job description.

Use the language they use. Accounts vs. Clients, Guests vs. Customers – often interchangeable terms are met with the sentiment of “well, they know what I mean”. But when it comes to cover letter and resume writing it is better assumed otherwise. By aligning your professional narrative with the way the companies you are pursuing describe themselves, you are helping the reader more clearly see you within their organization.

Do your homework. It isn’t enough to just repeat the points on the job description. Let the reader know you understand the industry and the challenges you are being hired to help solve.

Get to know the company culture. Most job descriptions or company websites will try to give you a little insight into the organization’s core values and what they are all about.

Write with a real human in mind. If the job description notes that you will report to the VP of Finance – look that person up on LinkedIn. If it notes that you will be a critical member of the customer success team, do some poking around to find who leads it. There are always clues buried in the job description. Worst case scenario – address is to the recruiting team.

Once you decide who you are writing to, make sure you continue to address that person in your letter. What you say to a recruiter about a role, is likely less technical than what you say to the person you would be reporting to.

Keep it short. Cover letters should be no longer than one page. Remember what we read on a computer screen is different than on paper, and this is a document that is likely going to be pulled up online. You want your paragraphs to be broken out in a way that is easily digestible. It is OK to use headers or bullets that help someone scroll through the letter easily.

Infuse your energy. If you do nothing else with your cover letter, you should be able to explain why you are excited about the role. What made you want to apply in the first place?

At the end of the day, a cover letter for the sake of a cover letter won’t likely win you the job. But a well-crafted cover letter can enhance your first impression and help your application stand out in a competitive marketplace.


Holian Associates provides strategy, resources and coaching for every stage of your career. If you need help with personalized career coaching, job search strategy, career transition, resume creation, LinkedIn development, interview preparation,  professional strengths coaching, salary compensation & benefits coaching, or navigating your job search as a college student or recent college grad, email us at or give us a call at (925) 451-3183.

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