Step by Step: How to Write a Pain Letter


A Pain letter acts as a cover letter but is far more powerful.

A Pain letter does not talk about you like a traditional cover letter. Instead, it talks about the recipient of the letter — your hiring manager.

If you are a Purchasing person, your hiring manager is the person who will be your boss. Your hiring manager if you are a purchasing person is the Director of Materials, Procurement, or any other title they may have.

This person can be found on LinkedIn or the company’s website. To send a pain letter to your hiring manager, you must know their name. The Pain letter will be sent via the post and not via LinkedIn or email, which are likely to be deleted in one click.

Your Pain letter has a very important job. Your job is to get your manager to stop and think about the question that you ask in your letter. It’s a question about pain. Your Pain letter will get your hiring manager to think about their biggest problem.

To write a pain letter, it is necessary to spend some time researching the company. Your right brain is required. A Pain Letter is not an exercise in filling in the blanks. It sounds as if it was written by a human being, you specifically.

It makes use of your knowledge to develop a hypothesis — an educated guess as to what is most troubling your hiring manager.

To write a pain letter you will need to create a pain hypothesis and know the name of your hiring manager.

Two additional things are required: A dragon-slaying Story, from your past. And a Hook to start your Pain letter.

Your Dragon Slaying Story lets your hiring manager know you have experienced similar or similar pain in the past.

Your Hook is an accomplishment or event that you can mention at the beginning of your pain letter. It must be recent (not older than six months).

A letter acknowledging the recipient of something cool that their organization did recently would be hard to ignore.

Let’s see how a pain letter is made. Italicized phrases serve as explanatory notes. These are not part of the Pain letter that Jane Addams, your hiring manager will receive.

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Your Pain letter does not say “I know what you are going through!” Your hiring manager might be experiencing a type of pain that is common for target organizations.

This could be due to rapid growth or consolidation within the industry. This could be rising prices for a specific part or raw material or any other business problem that managers in your function are prone to encounter.

Your Pain Hypothesis may be able to help you if you look at the company’s website, and then check its social media presence.

Your target employer may be opening a call center, or dealing with a formidable new competitor. Read what bloggers and reporters have to say about them and look at their website.

The Pain letter will be stapled to the front cover of your one-page Human Voiced Resume. You can then mail both documents together to your hiring manager. This will attract the attention of your hiring manager for a few seconds.

Your Pain letter will be thrown out by some managers. Others will send it to HR, while others will email you or call. They’ll argue, “It costs nothing to talk to Chris Pratt!”

The Pain letter will not get you a job. You can get in if it opens a door for you — once that door is opened, you can go right in!


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