Cover Letter

There is a right way to send a cover letter and a wrong way. Joe Donatelli shares his way.


I once worked a job in which someone gave me the power to interview writers for staff writing positions. Months later the company was sold, and our jobs were eliminated. I’ll leave it to history to decide if this was a coincidence. In my brief tenure at the top, though, I learned that an incredibly large portion of the job-seeking public does not know how to write a proper cover letter.

Misspellings were common. According to many job seekers, their and there and they’re are interchangeable.

Resume templates were quite common as well. You could tell when a candidate was sending the same cover letter to every employer, because it was not tailored to the specific job. “To Whom It May Concern,” they would say, “I am well-qualified for this position, whatever it may be. You are hiring, right? If not, do you know who might be…”

fonzWe interviewed one guy who showed up for his interview in jeans, a white T-shirt and a leather jacket. One minute into the interview he started bad-mouthing his former employer. He then proceeded to drop several f-bombs. I sat across from him and made notes like, “Probably knows how to get cocaine – a plus for the sales team” and “Creative use of swear words” and “Is owning the whole leather jacket persona.” He actually grabbed my notebook to see what I was writing. Needless to say, we canceled the rest of the interviews for the day because we had definitely found our new CFO.

Nowadays I find myself sending the occasional cover letter, because when you’re in the freelance game, the hustle don’t stop. Gigs come and go, and sometimes you have to more or less beg for work. ┬áSo I’ve been reacquainting myself with the best practices of cover letter writing.

This is how it’s done.

Greet the hiring manager by name,

Drop the name of your friend at the company who is recommending you for this position. Casually mention that you taught her everything she knows about her current job. If you don’t know anyone who works at the company, use an attention-grabber here. Something bold like, “You’ve seen the rest, now see the best.” Or: “I once saved a busload of people from plunging off a cliff in Belize. Do I have your attention now? Good. Because I want to be your next regional sales manager, and if given this opportunity I will keep your Midwestern sales staff from plunging off the cliff of our Belize-like economy.” You get the picture. Come out guns-a-blazing.

Scan the job ad and jam as many of the skills required into the second paragraph. “I have the leadership and organizational skills to quantify online solutions for a 21st century marketplace thanks to my self-starter attitude, college degree, professionalism, American citizenship, database skills, ability to be a team player, knowledge of light HTML and California driver’s license.”

Recap all relevant jobs you have had. If you have not had any relevant jobs, get one. If there isn’t that kind of time, provide parallel examples of how work you have done crosses over to the work you will do. Add numbers to highlight success stories, regardless of context. Include an example of you taking initiative and getting results. “I thought I had pulled everyone out of the building, and that’s when the rafters cracked and the room caved in from the heat of the fire, and I heard the baby cry, and I knew I had to go back in, even though I was scheduled to give the Zimmerman presentation in half an hour.”

Briefly sketch out some high-level ideas for how you could benefit the company. For example: making them more money. This one is huge. If you can make a company more money, they will very likely hire you and then ask you to make it some more money. Another option: Promise to bolster the middle infield on the company softball team. Pro tip: The HR manager is usually also the company softball team coach.

Say goodbye.

Sign your name.

Include your phone number, email address and LinkedIn or website.

Stuff the envelope with small chocolate donuts. If filing electronically, add a jpeg picture of small chocolate donuts. The HR manager will get it.

Then don’t make any plans for the next 30 seconds because your phone is about to ring like crazy.

UPDATE: What do you do when your cover letter works? This video on job interviews from The Onion offers some great advice.