How To Write A Pain Letter, Step By Step

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How To Write A Pain Letter, Step By Step

A Pain Letter is like a cover letter, but it is much more powerful than a cover letter is.

A Pain Letter doesn’t talk about you, the way a traditional cover letter does. It talks about the letter’s recipient, instead — your hiring manager.

Your hiring manager in any organization is the person who will be your boss if you end up working there. If you’re a Purchasing person, your hiring manager is the Purchasing Manager (or Director of Materials, Procurement Manager or whatever their title is).

You can find that person on LinkedIn or the company’s own website. You have to know your hiring manager’s name in order to send them a Pain Letter. You will send the Pain Letter through the post, not via email or LinkedIn where it is likely to get deleted with one click.


Your Pain Letter has an important job to do. Its job is to get your hiring manager out of his or her busy routine to pause for a moment and think about the question you pose in your letter. It is a question about pain! Your Pain Letter is intended to get your hiring manager thinking about his or her biggest problem.

In order to write a Pain Letter, you have to invest some time and energy  in researching the organization. You have to use your right brain. A Pain Letter is not a fill-in-the-blanks exercise. It sounds like a human being wrote it — you, specifically.

It uses your knowledge of your function to advance a hypothesis — an educated guess about what might be vexing your hiring manager the most.

In order to write a Pain Letter, you will need to develop a Pain Hypothesis, and you’ll need to know your  hiring manager’s name.

You will need two more things as well: a Dragon-Slaying Story from your past, and a Hook to begin your Pain Letter.

Your Dragon-Slaying Story is a way to let your hiring manager know that you’ve relieved the same or a similar type of pain in the past.

Your Hook is a timely (not more than six months old) accomplishment or event you will mention to get your hiring manager’s attention at the beginning of your Pain Letter.

Who would stop reading a letter that began by acknowledging the recipient for something really cool their organization had recently done?

Let’s put the pieces together to see how a Pain Letter is constructed. The italicized phrases are explanatory notes. They are not part of the Pain Letter you will send to your hiring manager, Jane Addams!

Dear Jane,

It’s very exciting to see Angry Chocolates in grocery stores all over the city! Congratulations to you and your teammates on your amazing growth. (That’s the Hook — a reason for Jane to keep reading!)

Given your expansion from a local brand to a regional favorite and plans for national distribution (which you read about on Angry Chocolates’ website) I wouldn’t be surprised if your Procurement team is pushed to the limit.(There’s your Pain Hypothesis — not a logical stretch when you think about the demands on a growing company.)

When I was a Senior Buyer/Planner at Wiggly Devices before its acquisition by Google, I created our company’s first Supplier Quality Assurance program and created cost-saving long-term agreements with our top four suppliers. Those agreements helped us grow sales volume from $14 million when I arrived at Wiggly to $31 million three years later. (There’s your Dragon-Slaying Story!)

If you have a moment to chat about your supply chain and Angry Chocolates’ expansion plans I’d be happy to talk by phone or start an email conversation. (You will end your Pain Letter with a call to action, called the Closing.)

All the best to you and your team,

Chris Pratt

Notice that your Pain Letter doesn’t say “I know what your problem is!” You don’t know — you are  only suggesting that your hiring manager may be dealing with a certain kind of pain that is typical for organizations dealing with whatever your target organization is facing.

That condition might be rapid growth, or consolidation in the industry. It could be rising costs for a particular part or raw material, or any business issue that managers of your function tend to run into.

If you read the company’s website and investigate its social media presence and see that they don’t have much social media presence at all, then your Pain Hypothesis might deal with that issue.

Your target employer might be opening a new call center or dealing with a formidable new entrant into their space. You’ll find out what they’re dealing with by reading what reporters and bloggers say about them, and by reading their own website carefully.

You will staple your Pain Letter to the front of your one- or two-page Human-Voiced Resume and mail the two documents together directly to your hiring manager’s desk. That way it will get your hiring manager’s attention for a moment or two.

Some managers will throw your Pain Letter in the trash. Some of them will ship it off to HR to languish in the Black Hole, but others will email or call you. They will reason “It doesn’t cost me anything to get on the phone with Chris Pratt!”

Your Pain Letter cannot get you a job by itself. It can open a door for you — and once that door is open, you can walk right in!

Source:, by Liz Ryan

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