The Cover Letter

Another cover letter? Try a ‘Pain Letter’

“Pain Letters” rather than Cover Letters, Demonstrate That You’ve Done Your Homework – And Know How To Put Yourself In An Employer’s Shoes.

Conjuring up a fresh, eye-catching, perfectly phrased cover letter feels like an exercise in futility after your fourth—or fourteenth—application sent to the void. Mired in a job hunt, all you really want to say is, “Hire me, please!”

Stop throwing your time, energy and insincerities into the job market black hole, and write a “pain letter” instead, says Liz Ryan, former Fortune 500 human resources senior vice president. Hit your target employer where it hurts—their biggest problem areas—and don’t wait around for an open position to do it.

Instead of leading with your strengths and asking them to find a spot for you, figure out what the company needs and tell them how you can help.

This approach requires more research than the traditional cover letter: Instead of leading with your strengths and asking the hiring manager to find a spot where you’d fit in, you’ll figure out what the company or department needs most and tell them how you can help.

For example, Ryan says: Large companies could likely use some help making personal connections with clients, a need only more humans can fill. Universities often need help with managing their finances, or keeping in touch with their alumni. Check out the organization’s “About” or “Newsroom” pages, to find out where they’ve grown recently, and where your skills might fit behind the headlines.

A pain letter has four parts:

The Hook—Congratulations on making the news recently, or thank them for piquing your interest at a conference
The Pain Hypothesis—Let them know that you’re aware of the industry, and their recent growth
The “Dragon-Slaying Story”—Tie your previous experience to their present pains
The Closing—Make yourself available for casual conversation in the future

Once you’ve crafted an attention-getting letter, do a little more research to find the hiring manager’s name (make friends with their receptionist!) and send a letter (yes, snail mail) to that person’s desk.

Adapted from an original article by  on