How to Write a Pain Letter to Your Potential Employer

Looking for a way to impress your hiring manager? Consider writing a pain letter. If you’re not sure what that is, read on as we go over the pros and cons.



How to write a pain letter to your employer?

If your cover letters aren’t getting the desired response, it could be time to turn to a pain letter. A modern answer to the traditional cover letter, a pain letter shows your potential employer how you (and only you) can make their life easier.


This guide will show you:

  • When you should use a pain letter
  • When you shouldn’t use a pain letter
  • How to structure your pain letter

What is a pain letter?

A pain letter shares the same purpose as a traditional cover letter: to persuade the recruiter or hiring manager to offer you an interview. However, a pain letter goes about this differently. Rather than focus on your skills and accomplishments, a pain letter centres itself on the employer’s biggest pain point.

By focusing on a specific problem that’s affecting the employer’s organisation, job seekers can actively demonstrate their value and distinguish themselves from other candidates. The goal is to show that you understand the company’s needs and are well-equipped to help it overcome its biggest challenges.

Why should you write a pain letter?

Pain letters can be powerful, particularly in senior positions where candidates will be expected to take on lots of responsibility in helping to ease the company’s pain points. Since traditional cover letters abound in the hiring process, a pain letter can help you stand out from other applicants.

Pain letters are also a good way to demonstrate your research skills and show that you understand the company. Where the employer’s organisation is going through a challenging period, whether that’s expansion, growing pains, or redundancies, a pain letter will be especially effective.

What are the advantages of a pain Letter?

There are several benefits to sending a pain letter over a traditional cover letter as part of your job application. A pain letter allows you to:

  • Grab the hiring manager’s attention with a more direct approach
  • Tailor your experience to fit the employer’s pain points
  • Demonstrate a strong understanding of the company’s needs and goals
  • Show you’ve put more time into your application than other candidates

What are the disadvantages of a pain letter?

Sometimes, it’s best to stick to the traditional cover letter format in your job search. Here are some drawbacks of a pain letter:

  • The hiring manager may be put off by assumed “problems”
  • There’s a risk that you could incorrectly guess the employer’s business pain point
  • Some organisations will prefer the traditional cover letter format and could automatically discard your application if you send a pain letter.

How to write a pain letter?

Here’s a step-by-step process for writing a compelling pain letter – pair these suggestions with a trusted cover letter template to improve your chances of securing a job interview.
1. Identify and address the hiring manager
The first step in the pain letter process is to identify the hiring manager for the position. This is generally the person you’d be working under should you be hired.
It’s vital that you address your pain letter to the hiring manager. The hiring manager’s name can often be found on the company’s website or job-related social media platforms like LinkedIn.
2. Form a pain hypothesis 
The next step is to develop a pain hypothesis. This is your statement of a specific problem affecting the employer’s organisation that the hiring manager will want to address.
Some research will be required to arrive at your pain hypothesis. Study the job descriptions for vacant positions at the company and draw on your knowledge of industry-specific problems.
3. Grab the reader’s attention with a hook
It’s now time to start drafting your pain letter, and you’ll need to open with a hook to ensure the hiring manager continues reading. For example, you could offer a brief message of congratulations to the hiring manager based on one of the company’s recent achievements or mention one of your major skills or achievements that could tie into the pain point you’ll discuss. 
4. Identify a story
After the hook, introduce your pain hypothesis. When describing the hiring manager’s pain point, the assumed problem should be suggested rather than stated definitively as a fact. For instance, don’t simply state the company is behind all its competitors, but instead refer to the increasingly competitive marketplace as a challenging environment. This alludes to the issue at hand without sounding overly negative.
In the main body of the pain letter, use an example from your work experience to show that you’re the right person to help the organization ease its pains. The example should be relatively recent and address a similar problem to the one affecting the employer’s company.
5. Add a call to action
Close your pain letter with a call to action. This is a short, instructive sentence that advises the hiring manager on what to do after reading your letter. For example, it could be a request for a phone call to discuss your skills further or an in-person meeting.

FAQ: pain letters

Q: What’s the difference between a pain letter and a cover letter?

They are similar, but a pain letter focuses on the needs of an employer, while a cover letter focuses on a job seeker’s accomplishments. A pain letter shows that you have researched the employer’s company and understand its needs. It draws on your experience in the context of the employer’s pain points.

Q: Do you have to send a pain letter?

While you don’t have to write a pain letter, it can help grab the attention of a hiring manager. Most applicants will send a traditional cover letter as part of their job application, making a pain letter a good option for those who want to stand out from the crowd.

Q: Do pain letters work to get a job?

It doesn’t hurt to write a pain letter, but it doesn’t guarantee a callback. Pain letters may be more effective when applying to senior positions where candidates will be tasked with helping the company solve some of its biggest problems. As with traditional cover letters, the persuasiveness of your writing is key.


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