Do Cover Letters Really Matter in Executive Job Search?

Opinions vary on whether or not cover letters matter. Do people even read them? Do you really need to use them in your job search?

It’s true that not everyone will read your cover letter.

But just the fact that you’ve included one gives a good impression of you. Not sending one can make you appear lazy and unprofessional.

The reality is that plenty of people will be expecting a cover letter (or covering email message). And, if it’s a good one that captures and holds attention, it will more than likely be read.

Those who DO read them favor candidates with well-written cover letters that convey personality.

Why cover letters are important

My research and 25+ years’ experience in the careers industry revealed that NOT having a cover letter may ruin your chances, but HAVING a strong cover letter will never hurt your chances.

Many people read them religiously and judge candidates by them as strongly as they do their resumes and online presence.

Are you willing to risk skipping the cover letter and take the chance that the people you’ve sent your resume to won’t care?

My advice? It just makes sense to include one. Take the time to write customized cover letters each time you send out your resume. And make sure they’re memorable, further support your personal brand and market your potential value, beyond your resume.

Consider this

The vast majority of executive jobs, especially at the top executive level (VP, EVP, C-suite, President, General Manager, etc.), are often not advertised anywhere. They don’t come through job boards. They come through networking into “hidden” jobs at the companies and organizations you’re targeting.

Assuming that your main job search strategy is networking – NOT hitting job boards hard – you’ll be sending your targeted resume to various select people. You’ll need to introduce it with some kind of cover letter – whether you snail-mail it or email it.

At the very least, a covering letter or email message is an expected courtesy to the reader, and clarifies why you’re writing to them.

Something to keep in mind

Although your resume needs to be targeted towards specific employers and kinds of jobs, your cover letter should be even more specifically targeted.

Because it will be focused on just that one employer, you can name-drop, include more specific skills relevant to that employer, and include other smaller details you may not want to put in your resume.

So you can see that it’s wise to always include a cover letter with your resume.

But there is one exception: When you respond to a job posting that specifies NOT to include one.

Do’s and Don’ts for a Great Cover Letter

Sara McCord, an experienced hiring manager, discussed what things about cover letters turned her off and what captured her attention:

With the initial read-through, she’d put people in the “no” pile if their cover letter:

Included typos, an impersonal salutation (“Dear Sir or Madam”), or a non-specific vibe that indicated find-replace.
Had an over-effusive tone that reeked of desperation, thanking the reader profusely for taking the time to read it.

If the opening sentence drew her in with something that made the candidate memorable, she’d keep reading. And that applicant made it into the “yes” pile.

If the first line consisted solely of the anemic “I am writing to apply for [job] at [company],” she’d probably knock that person out of the running.

When providing examples of skill and expertise, instead of just including a laundry list, she suggests adding in splashes of personality:

“Make the case that you’re more qualified than all the other applicants. You want to make clear what distinguishes you, so the hiring manager can see why you’re worth following up with to learn more.”

How To Write a Cover Letter That Gets Read . . . and Positions You as a Good Hiring Choice

Personalize each letter.

Send them to actual people, putting their name in the salutation.

“Dear Sir”, “Dear Madam”, or “To Whom It May Concern” won’t do. Search online to find their name, or call the company if you have to. If you can’t take the initiative to find a person’s name, and you resort to “To Whom It May Concern”, you’ll appear to be not very interested in the company or the job.

Customize the content for the job and company you’re targeting.

One sure way to have your letters overlooked is to use a template, sending generic content to each employer. Remember I said earlier that your cover letter needs to be even more specific than your resume?

A cover letter is an opportunity to zero in on your ability to solve that company’s problems even more specifically than you can in your targeted resume. For added oomph, mention each company by name within the body of the letter once or twice.

And make sure the thrust of your letters takes the readers themselves into account. For instance, a cold-call letter may have a different focus and read a bit differently than a referral letter. [More on the different types of cover letters below.]

Don’t just copy and paste parts of your resume.

Simply rehashing your resume in cover letters can have a negative impact.

Cover letters should be regarded and written as one more stand-alone personal marketing piece in your brand communications plan, supporting your brand and good-fit qualities for the company.

Mine the information found in well-written job descriptions.

Since you’ll be networking into the companies you’re targeting, you probably won’t have designated job postings to work from. But you may be able to find job openings that look like a good mutual fit. They can be valuable resources for composing cover letters that will hit home. Use the same keywords in your cover letters.

But remember what I wrote earlier. Job boards are a very ineffective way to land jobs. Please don’t spend a lot of time responding to online job postings. But DO use the information for research purposes.

Be specific about your potential value.

Instead of just claiming you’ve mastered a certain skill or have an area of expertise, provide a specific example of how you used that skill to benefit a past employer.

Don’t be afraid to show your personality and passions.

Generate chemistry with personal branding! This is one way to differentiate your unique combination of skills, motivating strengths and personal attributes over those you’re competing against.

Use cover letters to state certain things you wouldn’t say in your resume.

Cover letters are the place to include sensitive information you wouldn’t put on your resume, such as relocation or returning to work plans.

Write in an informal but professional tone.

According to a FastCompany article:

“Avoid overly formal language and long, complicated sentences that may disinterest the reader. Aim to make the letter friendly, clear, and professional. A good best practice is to research the company’s brand and tailor the wording in a way that speaks their language.”

You don’t need to reinvent the wheel with each cover letter.

Because you’re focusing your search towards one kind of job, you may be able to re-use some of your cover letter content from one letter to the next, customizing the introductory paragraph and elsewhere as needed.

Try the “old is new again” approach with cover letters.

Snail-mail your resume flat, in a 9 x 12 inch envelope, with cover letter paper-clipped on top.

How To Send Your Cover Letter: Email Message vs. Email Attachment

Some people advise sending the cover letter as a separate attachment in the email (along with the resume attachment) and including a short e-note as the email message itself.

The e-note should have a compelling subject line with relevant keywords to capture attention. And the content of the e-note should be a quick sell that gets right to the point.

I prefer the second option: using the cover letter as the email message itself.

Think about it. Recipients of your email are already getting two versions of your resume as attachments: a highly-formatted version and a stripped down, ATS-friendly version.

I think adding the cover letter as a third attachment is too much. As with every aspect of your job search, be empathetic.

Put yourself in the shoes of the recruiters and other hiring professionals assessing you. Make it as easy as possible for these people to get right to the information about you they need to see.

Cover Letter Length and Formatting

Remember that since your cover letter is an email message, it will often be viewed on the recipient’s phone or other small screen.

And, along with your resume, your cover letter will probably be sent through their ATS.

Make it easy to read and with plenty of white space.
Break up the content into 3-4 paragraphs of no more than 4-5 lines.
Keep it to around 200-250 words. Many ATS can only accommodate 250 words in a cover letter.
Don’t use odd fonts, graphics, tables or columns. They may become corrupted through emailing and ATS may not be able to scan them.

Although how you set up the cover letter is not set in stone, here’s a typical breakdown:

Subject line

As you would with any email, state the purpose of this email message, including the job you’re interested in.

First paragraph

Don’t start with a tired phrase like “I’m writing to express my interest in x position.” You’ve already stated this in the subject line.

Get right to the point in the opening paragraph. Let them know why you’re writing to them. I often frame this as a compelling question: “Are you looking for a [job title] who …”

If someone at the company referred you, by all means mention them once you okay it with the referrer.

The same FastCompany article as above suggests dynamic introductions like these 4 opening lines:

“While you won’t find the title “Community Manager” listed on my résumé, I’ve actually been bringing people together online and off for three years while running my own blog and series of meetups.”
“I’ve wanted to work in education ever since my third-grade teacher, Ms. Dorchester, helped me discover a love of reading.”
“My approach to management is simple: I strive to be the kind of leader I’d want to work for.”
“In my three years at [prior company], I increased our average quarterly sales by [percentage].”

Main body of the letter

Differentiate and position yourself as a problem solver for that employer.

Here are some things you can do or include:

Add a specific example or two of relevant projects you were involved with. For instance, instead of saying “I’m a problem solver”, provide an example.
Add a list of 4-5 short bullet points to highlight top relevant contributions to past employers and top skills.
Add a strong testimonial or accolade from someone you work with.
Use storytelling to help them see how you accomplish things and to envision you on the job with them.
Use headings to break up the content, such as “Game-Changing Initiatives I Introduced at [current or past employer].
Refer to recent news about the company, such as what drew you to them. Make a connection to something about them.
If your resume contains any red flags like employment gaps, address them here.

Closing paragraph

Something like the following is appropriate:

“I am confident that my background in ABC combined with my skills in XYZ will have an immediate impact as your next [name of position]. Thank you for your consideration and I welcome the opportunity to speak with you to discuss my potential contributions to [company name].”

Before you hit send!

Proofread your cover letter very carefully more than once. If possible, have someone else proofread it, too.

Up Your Odds with the Right Cover Letter

You’ll need various kinds of cover letters, customizing them for the various kinds of people you’ll send them to.

Here are some of the types of job search cover letters:

Letters to recruiters in your niche – let them know what kinds of jobs and companies you’re interested in.

Letters to HR professionals at your target companies.

Prospecting or cold contact letters, or letters of interest to top-level decision makers (not HR) at your target companies – to suss out unadvertised openings (or “hidden” jobs)

Requests for letters of introduction – typically to people working at your target companies, asking them to write you a letter of introduction to someone in authority at their own company or another company they have an in with.

Referral letters – when someone has already referred you.

Networking letters to various people you know – requesting job search advice and possibly assistance.

Requests for informational interviews with people you may not know – letters to various employees at your target companies and successful people in your field to request a bit of time to get information about working at the company, or job search advice. This type of letter may or may not be accompanied by your resume.

And of course, letters in response to job postings. Don’t spend much time doing this but, when you do, tailor each cover letter based on the job description and include plenty of the keywords noted in the description.

Where To Find the Right Information To Help You Write a Cover Letter

It all comes back to step one in launching any successful executive job search campaign – targeting your search to specific employers and knowing what it is about you that they need.

Research your list of target companies to determine their needs and problems, and how you are uniquely qualified to help them problem-solve and meet those needs.

Identify their pain points, and build your cover letter around what makes you a good fit for them.