4 Steps to Write a Pain Letter

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AnnaMarie Houlis4.87k
Journalist & travel blogger
May 23, 2024 at 6:41AM UTC

When you apply for a new job, you already know that it's important that you update your resume and rewrite your cover letter. But have you ever considered a different kind of cover letter entirely? Such as, perhaps, a pain letter?

What is a pain letter?

A pain letter is, in short, a cover letter that has the potential to yield even better results. A pain letter pinpoints a company's pains by identifying areas of the business that could use help and then suggesting how your experience and skills can provide solutions to those pain points.
In other words, while a cover letter simply details what you've done in the past, a pain letter details what you will do for a company if they were to bring you on board. 

When should you use a pain letter?

Many argue that all cover letters should read at least somewhat like pain letters in that they convey to a prospective employer what exactly you will bring to the table. After all, the goal of any cover letter, whether or not it's a pain letter, is to let potential employers know not only what experiences and skills you have, but also how those experiences and skills can help them in particular.
In a Forbes article, contributor Liz Ryan suggests sending a pain letter instead of a cover letter, explaining your hiring manager's biggest problem (and how you know that it's a problem), as well as how you plan to solve that problem if hired. In writing a pain letter this way, you can highlight your skills and how those skills apply to the new position, as well as how they will help to solve that problem. 
"Pain letter users tell us that their pain letters result in callbacks about 25 percent of the time," Ryan writes. "That’s a lot better than their results lobbing resumes into the black hole recruiting portals. Better yet, the conversations that result from compelling pain letters are more substantive than the cursory screening calls that standard cover letter and resumes generate.”

Whether not a pain letter will work, however, depends largely on whether or not a pain letter is done correctly and appropriately.

For example, a pain letter is useful when a company actually has a problem of which you're aware. Of course, all companies have room for improvement and problems they are looking to solve — if they weren't, they wouldn't be hiring you or another candidate for help. But a pain letter will indubitably perform better if that problem is a known issue that will resonate with the hiring manager. (Though the ability to call out less-conspicuous issues to the forefront is also a valuable skill.)

So, how exactly do you know what a potential employer's paint point is? Look to the text. Usually, a job advertisement will explicitly say it. They may advertise that they're looking for a content coordinator who can help them to streamline their editorial process, for example. Their pain point in this case? A disorganized editorial process.

Companies both large and small have pain points, Ryan suggests.
"If the organization is growing fast, they've got growing pains," she writes. "It's hard to keep on top of everything that needs to be done. Sales may be booming, but infrastructure undoubtedly lags behind. That makes customers unhappy. Systems are breaking at the seams. If the organization is large, it may be slow to react to market changes - most large organizations are. They may be having trouble responding to their clients' needs. They may have so much red-tape bureaucracy that important projects get stalled."
If the advertisement does not suggest a pain point, you can (and, regardless, should) do your research. Do some digging around on the company and the hiring manager. If you have any connections, you can even ask them if they have any insight into what the company is really hoping for by hiring someone in the role for which you're applying.
Pain letters are arguably usually more useful than cover letters since you can turn most of what a company is seeking into a perceived point of pain and offer ways as to how you'll help the company fill that void.
A pain letter is not useful, however, if you rip a company to shreds by imposing your opinion on how you think the company could be doing X, Y or Z better — especially if X, Y or Z are totally irrelevant to the job for which you'd be hired. The pain point should be one that your skills (the same skills for which you're hopefully going to be hired) can solve — it shouldn't be a pain point that you can do nothing to help.

What's an example of a pain letter?

Here's an example of a pain letter to help you understand how it might read.
Dear Jesse,
I enjoyed seeing you speak earlier this week at the Women in Travel Conference. From experience, I couldn't agree more with you that female travelers are leading the industry.
It's great to see SHE Travels making such strides in promoting more female leaders in the travel industry, which better reflects the travel industry consumer base. I look forward to your new training courses for female talent to help them move into managerial roles in their travel careers. I can only imagine that, with the implementation of so many new courses, your marketing team is kept super busy.
During my time as marketing director at Travel Pro, we faced a similar challenge. I was tasked with marketing comparable developments on a tight deadline — rather than courses to attract female talent, however, we were rebranding our entire company as a female-friendly travel brand that promotes diversity in the workplace. And, thanks to a lot of hard work, we were able to double the number of female leaders in the company.
If you have time to chat by phone or email, you can find my contact details on my attached resume.
Jane Doe

Here's how to write a pain letter.

There are four major elements in a pain letter.
  1. The Hook
  2. The Pain Point
  3. The Related Experience
  4. The Closing
Every pain letter should include a hook to get the reader's attention, and you can do this by congratulating the reader on a recent accomplishment. This might be noting that you enjoyed hearing them speak recently, or perhaps that you read in the news that the company just successfully acquired another one. Whatever the good news is, acknowledge it.
Then you want to get into the pain hypothesis. In the aforementioned example, the pain hypothesis is the assumption that, with the addition of so many new career courses, the company's marketing team is probably in over their heads marketing the news to attract women.
The related experience includes Jane Doe's experience in solving a similar problem. With her skills and hard work, she was able to double the female leaders in her last company — which is something similar to what she'd like to help this new company do, too.
The closing should be a call to action. In this case, Jane Doe asks for time to talk more either by phone or email.

Here's a pain letter template.

Here's an example of a pain letter template that you can use — just fill in the blanks.

Dear [Hiring Manager's Name]

Congratulations on [Company Name]'s recent [achievement]. I am impressed with the way the company has [done X to lead up to the aforementioned accomplishment].

I can only imagine that with [pain point cause], the [team] is [pain point effect].

In my last role as a [former position], I was faced with a similar challenge. {How you tackled the problem].

I'd love to talk more about how I can help [company name] do the same. If you have some time to chat, you can find my phone and email information in my attached resume.


[Your Name]

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AnnaMarie Houlis is a feminist, a freelance journalist and an adventure aficionado with an affinity for impulsive solo travel. She spends her days writing about women’s empowerment from around the world. You can follow her work on her blog, HerReport.org, and follow her journeys on Instagram @her_report, Twitter @herreportand Facebook.

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