Sharing the Pain

Dear Anita,

My job is the biggest royal pain. Can you help me get a better one?

Woman in painDear, Complaint Queen,

According to research conducted by SERMO, yours truly actually has one of the top 10 most painful jobs. Yes, that’s right. Writers and journalists rank up there with construction workers, truck drivers, and those on the production line. (Mechanics, gardeners/landscapers, athletes, firefighters, lawyers, and IT professionals round out the top 10.)

But instead of focusing on our pain on the job, try targeting a hiring manager’s daily discomforts – and how you, above all others, can help relieve his or her troubles. A few years ago, Liz Ryan, CEO of Human Workplace, trademarked the idea of a Pain Letter. This is the opposite of the generic cover letter (no more “Dear HR, I saw your ad and am applying for the open position. Blah, blah, blah.”).

The first step in writing a Pain Letter is to research the company. Use LinkedIn to find the hiring manager’s name.

Secondly, congratulate the manager and/or the company for a recent accomplishment (which may also be gleaned from LinkedIn or Google research). Ryan calls this the “Hook.”

Next, determine what keeps this manager up at night, and outline the “Pain Hypothesis.” Ryan gave this example for an imaginary Payroll Specialist in Forbes:

I can imagine that hiring as many people as you are, keeping tabs on payroll issues might be a constant challenge. With regulations constantly changing, it’s not easy to keep everyone paid correctly and well-informed in a growing company.

Then, include your “Dragon-Slaying Story,” describing specifically how you handled similar pain in your current or previous position.

When I ran the payroll system at Angry Chocolates, I kept the payroll accurate and in compliance and answered dozens of employee questions every day while we grew from 15 to 650 staff members.

Keep the letter brief, closing simply:

If payroll accuracy and advice to your team is on your radar screen, I’d love to chat when it’s convenient. All the best, Nancy Drew

Readers: How do you focus on alleviating the hiring manager’s business pains in your cover letter?

Do you have a job-related question? Ask Anita.

Subscribe to receive weekly emails with career tips and advice for job seekers, employed people, and managers and supervisors.

Covering the Cover Letter
Bypassing Human Resources
My Job is a Pain in the Neck – Literally

4 Comments (+add yours?)

  1. Laura
    Feb 17, 2016 @ 10:52:49



  2. Tiffany Lieu
    Jan 09, 2016 @ 14:39:15

    Investigating like the teenage private investigator Nancy Drew is a good idea. It is good to balance out how we are checking into the hiring manager’s lifestyle and revealing our own before it looks like we are overdoing it only talking about them in the cover letter. I would exercise discretion how we psychologically analyze the hiring manager’s decision making, that’s, avoid being too assumptious. We have been going more electronic over the years, so I am not sure how many electronic resumes they’re actually staring at day in and out. It can give the manager migraines to headaches and vertigo if not neck pain. It will certainly distort their decision making. And, that doesn’t benefit jobseekers at all.


  3. Moonstone Mary
    Jan 05, 2016 @ 09:31:15

    I am really good at internet research but have run into brick walls finding the name of the person who does the hiring in companies, especially smaller companies where that person might not be utilizing Linked In.

    Has anyone out there discovered a good place to find hiring manager’s names besides Linked In?


    • anitaclew
      Jan 08, 2016 @ 06:37:58

      The company website may list department heads (which may or may not be the hiring manager, depending on the size of the company). Do a Google news search also, to see if you can uncover any mentions of appropriate company staff. On LinkedIn, reach out to others in the same company and send a brief note asking for the name of the right person to whom you should address your résumé. Readers, any other sleuthing techniques?


Leave a Reply

Your email address will not be published. Required fields are marked *


Anita Clew's blog posts are intended for general guidance and should never be taken as legal advice. In all instances where harassment, inequity, or unfair treatment is believed to be present, please consult your HR Department or legal representation.
%d bloggers like this: