Do Cover Letters Really Matter in Executive Job Search?

by Meg Guiseppi on June 19, 2017

Opinions vary on whether or not cover letters are even read – or needed – in job search.

Although it’s true that some people won’t even look at them, they probably will notice if you DON’T include one.

The reality is that plenty of people will be expecting a cover letter (or covering email message), and favor candidates with well-written ones 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 for each job. And make sure they’re memorable and further support your personal brand and market your potential value, beyond your resume.

Consider this.

The vast majority of 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 (not just recruiters and HR professionals). 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.

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

Sara McCord, an experienced hiring manager, discussed cover letters, what things about them 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 Cover Letters That Get Read . . . and Position 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 not to be that 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. 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 take 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! 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.

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 messaging from one letter to the next, customizing the introductory paragraph and elsewhere as needed.

Don’t overdo it.

The equivalent of a one-page Word document is long enough. Short intro, 2 or 3 qualifying paragraphs, 3 or four short bullet points (a sentence or two), and a closing paragraph. I also sometimes add a P.S. that includes a compelling quote, because it will capture attention.

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.

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 Build Your Cover Letters Around

It all comes back to step one in launching any successful executive job search campaign – narrowing your search and knowing your target audience.

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

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

More About Executive Job Search

Want a Successful Executive Job Search? Run It Like a Small Business

Are You Executive Job Search-Ready?

5 Ways to Keep Your Executive Job Search Confidential on LinkedIn

7 Ways To Contaminate Your Personal Brand and Doom Your Executive Job Search

How to Land, Brand and Ace Executive Job Interviews

Executive Job Search and Personal Branding Help

Land a GREAT-FIT New Executive GigNeed help with personal branding, your LinkedIn profile, resume and biography, and getting your executive job search on track . . . to land a great-fit new gig?

Take a look at the services I offer, how my process works and what differentiates my value-offer . . . then get in touch with me and we’ll get the ball rolling.

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