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


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Find a Hook

When you sit down to compose your Pain Letter, the first thing you’ll need is a Hook. Your Hook is a news item about your prospective employer – something that happened in the past six months. Maybe they won an award. Maybe they broke ground on a new facility. You’ll begin your Pain Letter by praising your reader (your possible next boss) on the company’s accomplishment.

Who gets enough acknowledgement in this world? No one! Your human Hook will open an aperture in your hiring manager’s mind. He or she will have a good reason to read the rest of your letter because rather than talking about yourself, the way we all learned to do in a cover letter, you are talking about him or her and/or his or her teammates.

Here is a sample Hook from a Pain Letter:

Dear Marcia,

I was lucky enough to catch your talk at the Townsville Organic Products Expo last month, and I couldn’t agree more with your observation that kelp is the new hemp. Congratulations to you and your team at Underwater Seagrass for making a big splash in the organic foods marketplace!

Pain Hypothesis

You’ll follow your Hook with a pithy Pain Hypothesis that suggests a type of Business Pain your hiring manager may be experiencing. Pick one! There could be any number of things keeping your hiring manager up at night — you only need to hit one of them. Mentioning multiple pain points makes your message mushy, and that’s the last thing we want to do!

Here is a sample Pain Hypothesis from  Pain Letter:

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.

A Pain Hypothesis is simple. You are saying “You have a guinea pig, eh? Have you run into that guinea pig rash that is all over town? A lot of people have!”

Don’t teach in your Pain Letter. Don’t tell the hiring manager what they should do. They know their job. Mention a possible pain point and stop.

Dragon-Slaying Story

You’ll follow up on your Pain Hypothesis with a simple, one-or-two sentence Dragon-Slaying Story. That’s a story about a time when you saved the day at work by solving a similar type of Business Pain. Here’s an example:

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.

Notice what you don’t do in your Dragon-Slaying Story? You don’t praise yourself with praising adjectives like savvy, strategic or results-oriented. You just tell your possible next boss in simple human terms what you left in your wake at another job. If you’re a student, your Dragon-Slaying Story might come from a class project, a part-time job or a student leadership position.


Your Pain Letter is very short. The shorter your Pain Letter can be, the better! Resist the urge to say more about yourself. No one cares. All your hiring manager cares about is his or her own pain, and in that respect he or she is exactly like every living person. Your resume will be attached by one staple in the upper left corner to your Pain  Letter, so your manager will be able to read about you once he or she flips the page to view your resume. Your closing will simply say

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

It is a new millennium. Work is different, and job-hunting is different too. Step into your power and job-hunt in a new way. Leave the broken Black Hole recruiting system behind!

On the next page are more stories that teach Pain-Letter writing and other aspects of the Whole Person Job Search!

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