Pain Letters: Can They Stop the Pain of Job Hunting?

May 1, 2014

I was sitting around with a few buddies, discussing the state of the career world. This was basically a group of slightly jaded and overworked — but still hopeful — 50-plus year olds who are tired of spending our lives coloring within the lines.

One friend brought up Liz Ryan, the career counselor and author, who, in recent years, has advocated for sending “pain letters” during the job search.

What is a pain letter? As Ryan puts it, rather than submitting your résumé and cover letter to an HR person where it goes into a bottomless pile, you send a letter directly to the hiring manager.

In essence, the letter directly addresses a hardship that a business may be experiencing and shows the hiring manager why you would be the perfect person to alleviate that pain.

Most important, you are telling your potential new boss how you can make his or her work life better with your experience.

As a former actor, it was common for me to be creative in order to land an audition. How many times did I send a bouquet of flowers to X Talent Agency with a demo CD of my best musical theater songs enclosed in the bouquet? I may not have always gotten the part, but at least I would receive a call for the audition.

When it comes to pain letters, consider the following points:

  • Deciding whether to use a cover letter or pain letter: One of the key reasons that someone hires you is not just for your skills — it’s about whether you fit in with the corporate culture.

    A pain letter can be your best asset. It may address: How much do you know about the company? How do your accomplishments mesh with their goals? Do you understand their challenges? Can you take away their pain of trying to find the right candidate in the job search? Why are you the most qualified?
  • Replacing the insipid with the inspired: It’s time to put the “human” back in your résumé.

    Tell the potential employer who you are and relate a story. It’s important to include two or three sentences about what motivates you. Why are you in this profession in the first place?

    Having a sentence like “I led a mock PR agency project in school based on the same IMC media venues as GolinHarris” will mean far more to someone than being a “self-starter with a PR agency specialty.” This is what makes you unique and what may convince them to hire you.

  • Finding the hook: When reciting your accomplishments to a potential employer, select the ones that will resonate the most. Do not become so caught up in “résumé speak” that you dilute your genuine passion for the profession.

    One time, it took me four hours of career counseling to discover that a candidate produced a poignant video of a soldier’s homecoming and reunion with his 16-year-old daughter. As she was throwing the first pitch at an Oakland A’s baseball game, her father was secretly waiting in the wings to greet her. It was a touching story.

    Dig deeper to find the right hook for your letter.
  • Making the decision to bypass the HR department: Remember, you are not sending the usual résumé with a cover letter that says, “I’m responding to your ad in…”

    You are simply writing: “I know what problems you are facing. I know your pain. I have been there. This is what I did.”

    Be mindful not to criticize or trivialize the problems of people looking to fill the position.
Richard Spector is the senior manager of corporate development and industry partnerships for PRSA, where he counsels job seekers. He has conducted career presentations and webinars for NYU, WVU IMC, Ball State, Quinnipiac, Purdue and The Wharton School at the University of Pennsylvania. Email:


Les Goldberg says:

I love it! I couldn't have expressed it better myself. Unfortunately for me, however, this excellent strategy has not worked yet. But at 71 (chuckle) I am still plugging away. Who says there isn't age discrimination in the workplace? Without sounding egotistical, the corporate world doesn't know what it is missing by not utilizing the growing army of discarded talent.

June 9, 2014

Michael Kelly says:

The email (sent by PRSA?) for this article had the phrase 'the black whole' in it. Was that very stupid or very clever? Thinking outside the box is where the everyday bar (the one that gets raised) should be for PR and communication professionals. I certainly wouldn't hire a PR person who sent a cliched form letter about themselves or their agency. And the suggestions are in countless sales, self help and possibly even (gasp) marketing books. You need to go beyond what sales 101. The problem with being in your fifties is that you are apt to have let your sense of curiosity, imagination and wonder become smoothed under someone else's idea of who you are and what you can do. I'm not sure how to get around that, but your hope is a promising place to start. Step outside everything you think about and do in PR. Ask what the problems of the world are and what you could do about one of them. Good luck!

May 4, 2015

Reader says:

Pain letters? ....Cute, but not realistic.Yes, you can find out about the firm's current challenges and problems by reading periodicals or industry papers but I don't think this tactic is very useful one unless you are applying for some senior management position. We have access to the limited amount of information about the business. We cannot possibly know "the unit specific" problems a particular department/unit many have (which are applying for), unless we actually have some insider information through friends, family members etc.

June 25, 2015

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