How To Write Your First Pain Letter

I write about bringing life to work and bringing work to life. Full bio

I was a Fortune 500 HR SVP for ten million years, but I was an opera singer before I ever heard the term HR. The higher I got in the corporate world, the more operatic the action became. I started writing about the workplace for the Chicago Sun-Times in 1997, but it took me ages to find my own voice. Now I write for the Huffington Post, Business Week, LinkedIn, the Harvard Business Review, the Denver Post and Forbes.com and lead the worldwide Human Workplace movement to reinvent work for people. Stop by and join us: http://www.humanworkplace.com


A Pain Letter is a new-millennium alternative to a cover letter. It’s a letter. It has black or blue ink on a white page, but that’s about all that a Pain Letter has in common with a cover letter.

When you send a cover letter with a resume into some kind of faceless Black Hole recruiting pit, you know your odds of hearing back from the employer range from slim to none. Here is a horrifying story we heard from a job-seeker who was told by a company recruiter that she doesn’t even look at the resumes coming in through the firm’s Applicant Tracking System. She ignores those resumes and finds her own candidates via LinkedIn!

When you send a Pain Letter, you don’t pitch it into a Black Hole career portal to die. You send it to directly to your hiring manager at his or her desk. I think I know what you’re thinking: how do I find my hiring manager? Here’s how to do that! 

I was a corporate HR leader for ages. I saw the recruiting process degrading and becoming more zombified every year. I saw how that degradation of the recruiting process was hurting job-seekers and employers. Nobody wins — only a technology vendor wins when technology takes over what should be a warm and vibrant human process. Recruiting is a human activity, not a technological one.

When everybody figures out that the way to get your resume through the keyword searching algorithm is to cram keywords into your resume or your application, the sorting technology becomes useless. That is the biggest “Duh!” in the world, but when we fall into our business brain we can lose the ability to think clearly.

We invented Pain Letters to give job-seekers a more powerful and immediate way to tell their story to hiring managers. If you want to write a Pain Letter and skip the obnoxious online-application chore, here are the steps to follow.


Research the Employer

A Pain Letter is not generic. Every Pain Letter is unique. If you don’t want to take the time to research the employer before you write a Pain Letter, don’t even bother writing it.

Start your research at the organization’s own website. Read about its business. What do they make or sell? Who are their clients? What sorts of issues do you imagine that the organization is dealing with?

Figure Out The Pain You Solve

Everybody solves some kind of pain in their work. When you say “I’m a Payroll Coordinator,” it means that you solve several different kinds of pain that employers experience when the payroll system doesn’t run properly. You have to pay people correctly or you’ll violate the law. There are wage and hour laws, and other things like wage garnishment and tax changes that make payroll a critical business function. Here are some of the types of Business Pain a Payroll Coordinator can solve:

  • I solve the pain associated with employees getting paid the wrong amount or not getting paid on time.
  • I solve the pain that comes with improper tax deductions and reporting mistakes.
  • I solve the pain that comes about when employees’ payroll deductions for insurance and other benefits are miscalculated.
  • I solve the pain that hits employers when nobody in Payroll can help them answer their pay-related questions.

This is just the tip of the iceberg. Good Payroll people like you solve another two or three dozen kinds of Business Pain! If you want to send Pain Letters and generally to step into the new-millennium workplace with confidence, stop focusing on your skills, and tell us instead about the kinds of pain you relieve!

Who Has That Pain?

Which employers are likely to be experiencing the kind of Business Pain you solve? If you’re a Payroll Pain Relief Specialist, that might be employers who are growing fast and adding staff. You can find out who’s growing in your area by reading your local business publication (online for free) and looking for its annual list of fast-growing employers.

Now You Need a Name

You will send your Pain Letter directly to your hiring manager. In the case of a Payroll Coordinator, that might be the CFO or the Director of HR. Don’t send your Pain Letter to the CEO of the company unless you’re pursuing an executive job or unless the employer is really small. CEOs are famous for having very diligent administrators who are likely to send your carefully-written Pain  Letter right back into the same Black Hole abyss you were trying to avoid.

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