Never Send a Naked Executive Resume, or, Why Write Cover Letters?
Never Send a Naked Executive Resume
or, Why Write Cover Letters?
Cover letters are those documents that typically accompany the executive resume you send out to prospective hiring teams. If we assume that the audience for your executive resume are humans (feel free to ask me about why applying online is 100% time wasted), then cover letters have two audiences: one is people who read cover letters, and one is people who don’t read cover letters. Read on to learn how to write a cover letter that gets your resume noticed.
What does this principle of having two audiences for your cover letter really mean? It means you have to have a cover letter, because you should never send a naked resume. But the truth is, you don’t know if your audience is going to read it, so if there is even a small chance they might read your cover letter, then you should have a good one.

What makes a good cover letter? First, a good cover letter to start out is not a generic “here I am, and I’m ready to apply for this job. I read it in an online job that there’s this job available and you could consider me.” That message is impersonal and bland. To get more personal and to ensure that your cover letter resonates with your audience, you have to start thinking about what the job specifically is asking for and infuse some of your background with respect to your audience’s expectations in this cover letter.
As you mention relevant points from your executive career history, highlight the key achievements that you think are going to be relevant to this particular audience — in the context of what this company is expecting. So don’t even start to put pen to paper until you have done some research on the company and the role as well as have thought about culture fit, language choice, and all the factors that are going to appeal to your audience.
Quite recently, I was writing a cover letter for an outside sales leader. The job posting was truly revealing. The language was something like this: “Have tattoos? Great! Show off your ink. Like to come in with pink hair? Great! We love color.” Clearly, this audience is a little bit looser, friendlier, less buttoned-up than say a company that merely says “Please submit your salary requirements.” You can learn more about the company culture, beyond how the job posting reads, on the company website, specifically the “about us” section.
One other key element you need to include in your cover letter, typically after you describe your expertise, is the two “asks.” In other words, your cover letter is meant to introduce your resume so you want to invite your reader a) to look at your resume for additional information, and b) to ask for the interview. You don’t ask for the interview because it’s expected; you asked for it because it matters to you, and you want your audience to connect with the fact that you care about getting this interview.
In conclusion, you have to have a cover letter because you don’t know if your audience is going to read it or not, you know not to send a naked resume. As you prepare your letter, always let them know you are passionate about what you are asking for, because your enthusiasm for the role will be critical to their interpretation of your candidacy.