Write a Pain Letter

The pain letter is a modern alternative to the cover letter. The purpose of a pain letter is to identify an employer’s business pain and discuss your solution to their pain. The letter should convince the hiring manager that you can offer solutions to business issues and are the right candidate for the position. To write a pain letter, start by reviewing the job description and making an outline for the letter. Then, write the letter in an organized, professional manner. Make sure you proofread and revise the pain letter before you send it off to the hiring manager.

Steps

Starting the Letter

1. Confirm the purpose of the pain letter. The purpose of a pain letter is to connect more directly to a hiring manager and demonstrate your skills in a more forward way. The pain letter is a good idea for entry level jobs as well as higher level positions. It will often get your resume more attention than a traditional cover letter.
   • The one possible downside of the pain letter is that it may take more time to draft than a cover letter. This is because each pain letter should be unique to the needs of a specific company or organization. You will need to research the company beforehand to write a good pain letter.
2. Identify the hiring manager’s pain. Review the job description for a list of issues or problems that the company would like to address. Look for statements like, “We are seeking…” or “Our company needs…”. Identify one pain the job description is addressing.
   • For example, the job description may note, “We are looking for someone who can help us restructure our Human Resources department.” This is the pain you will then address in your letter.
   • If you are not responding to a job description and are writing the letter blind, do research on the company or organization. Look at their “About” page on their website. Review their client list. Ask yourself, what do they need help with? What kind of problems do they need to solve?
3. Determine how you can address the problem. Think about any skills or abilities you have that can help you solve the problem. This could be past experience in the field or in your education. You may also have current skills that you can lean on in the pain letter when you talk about your solutions to the problem.
   • For example, you may write down, “I can solve the problem of how to boost employee morale during slow season” or “I can solve the problem of employee training on a budget.”
4. Make an outline for the letter. Pain letters follow a four part structure. The letter should be no longer than one page long, with four short paragraphs. Make an outline for the letter with the following sections:
   • First paragraph: the hook. In the first paragraph, you will grab the reader’s attention and make it clear you have researched the company or organization.
   • Second paragraph: the pain hypothesis. In the second paragraph, you will address the hiring manager’s pain.
   • Third paragraph: the solution. In the third paragraph, you will discuss your solution to the pain.
   • Fourth paragraph: the closing. In the fourth paragraph, you will wrap up the letter concisely and confidently.

Writing the Letter

1. Address the letter to the hiring manager. Like any professional letter, the pain letter should begin with “Dear [hiring manager name].” The hiring manager’s name should appear in the contact section on the job description. You can also look for the hiring manager’s name on the company website.
2. Start with a hook. The hook should praise the company on a recent accomplishment. Do some research to find a recent win by the employer that has happened within the past six months. This could be a recent award they received or a new facility they just established. Maybe they hit a recent sales goal or broke into a new market. Make the hook the first sentence of the letter.
   • For example, you may write, “Congratulations to you and your team at Buzz Company for winning the recent Innovators Award! I was able to catch the keynote speech at the awards, given by your CEO, and was impressed by your company’s dynamic approach to the sales market.”
3. Describe the hiring manager’s pain. In the second paragraph, focus on one pain the hiring manager may be having. Refer to the issues mentioned in the job description. Do not try to address every pain point. Instead, focus on just one so your letter is clear and to the point.
   • For example, you may write, “I can imagine that keeping up with new hires and payroll issues as you expand may be an ongoing challenge. With the constant changes in the market, it’s not easy to keep employees paid correctly in a growing company.”
   • In this section, do not tell the hiring manager what to do or how to do their job. Simply outline a possible pain point that you feel you can address or offer solutions for.
4. Discuss your solution to the hiring manager’s pain. In the third paragraph, tell a one to two sentence story that discusses your solution to the pain. Discuss a time when you addressed a similar business pain by listing your actions and your necessary expertise. This will let the reader know that you have the experience necessary to address their pain.
   • For example, you may write, “When I ran the HR department at Fizz Limited, I created a new hire training program tailored to the needs of the company. I also kept payroll in compliance with industry standards and responded to employee needs as the company grew from 10 to 500 staff members.”
5. Close with a call to action. End the letter with a short one to two sentence closing paragraph. Briefly note the pain you have addressed in the letter as well as a gentle call to action about getting in touch with the hiring manager. Include a friendly sign off.
   • For example, you may write, “If HR leadership and payroll accuracy are two skills you are looking for at your company, I’d love to talk in more detail about how I can be of service. Best, [your name].”

Polishing the Letter

1. Check for spelling, grammar, and punctuation. Once you have a draft of the pain letter, take some time to make sure there are no errors or typos. Read the letter out loud to catch any spelling, grammar, or punctuation issues. Circle all the punctuation marks in the letter and make sure they are all correct.
   • You can also read the letter backwards to check for spelling. This will force you to focus on each word to confirm it is spelled correctly.
2. Make sure your letter follows your outline. Check the organization of the letter to ensure it contains all the necessary information. Compare the letter to your outline and make sure you have all four sections of a standard pain letter in your letter.
   • You can also make a reverse outline using your pain letter. Write down each section in the margin of the letter to confirm all four are present.
3. Send the pain letter to the hiring manager. Once the letter is at its best, send it in an email to the hiring manager. In the email, note you are responding to a job description and include a friendly sign off, such as “All the best,” or “Yours.”
   • If you are sending the pain letter blind, you may write a short note in the email outlining the pain you are addressing in your letter and a sign off like, “Hope to hear from you,” or “Please reach out if my solutions seem attractive to you.”

Sources and Citations

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