Should You Write a “Pain Letter” as Your Cover Letter?

Jan 29, 2021 | Cover Letters

A title graphic featuring Let's Eat, Grandma's yellow pencil logo, a stock photo of a person in pain, and a version of the article's title: "Are Pain Letters Effective?"

Have you heard of a “pain letter” as a cover letter alternative? Here’s our pain-free guide to this emerging cover letter type.

By: Grace Mitchell | Contributor for Let’s Eat, Grandma

While it’s now well-established by experts that yes, you should write a cover letter when applying to jobs (and we wholeheartedly agree), there’s still debate over what specific form that letter should take. After all, you want your cover letter to both showcase your top skills and help you stand out from the crowd of other job seekers.

One potential way to write your cover letter is to structure it based on the employer’s pain points and how you’d solve them.

This method is called a pain-point cover letter or pain letter. A pain-point cover letter operates on a hypothesis of the employer’s current issues and struggles based on research into the company. The applicant presents this hypothesis along with specific examples of how they’ve conquered such challenges in their own career, showing why the candidate is a particularly good fit.

Maybe your research shows that the company was recently lauded on a prominent industry website. Your “pain hypothesis” might be that the company is now experiencing growing pains from generating more business than they ever have.

A photo of a woman looking at a laptop intently with a cup of coffee in front of her, illustrating the in-depth research needed to make a pain letter work.

Like any good cover letter, a “pain letter” requires in-depth research into the particular company you’re writing to. (Photo by Adam Satria on Unsplash)

In your letter, you could show how you’d solve this problem by telling the hiring manager how you effectively managed your own former company through a sudden expansion. Whatever your research finds, the idea is that your pain-point cover letter will clearly illustrate how you could make your superiors’ lives easier if they select you for the position.

Is a Pain Letter Different From a Cover Letter?

While many articles refer to these as “pain letters,” we want to be clear that the pain-point cover letter is simply a type of cover letter. This type may follow a different structure than you’re used to, but it still introduces an employer to the skills you offer for the position using illustrative stories from your career. 

No Pain, No Gain?

All semantics aside, you may be wondering if a pain-point cover letter is right for you. Here are a few points to consider:

Pain Letter Pros

A pain-point cover letter is a highly customized letter that addresses the company’s specific needs. A thoroughly researched and well-written letter demonstrates your understanding of the company culture and how hiring you would make that culture even better. A cover letter is meant to convince a hiring manager on the fence that you’re the best candidate in ways that your resume can’t, so showing how you meet their particular needs is a good principle.

The unique structure helps you stand out from the crowd. If you’re applying in a highly competitive field like sales or investments, varying your cover letter structure could give you a competitive edge.

Pain-point cover letters can get results. One career coach claimed that she’s seen pain-point cover letters get a response about 25% of the time. While this may seem like a small number, it’s significant when we consider that only 2% of job applicants are asked to interview.

A photo of a woman with a clipboard and notebook and a skeptical expression, illustrating that some hiring managers are skeptical of pain letters as they find them arrogant.

If you don’t get it right, your pain letter can come across as arrogant. (Photo by Alex Green on Pexels)

Pain Letter Cons

—You might come across as arrogant. Pain-point cover letters can be effective, but they leave a bad taste with some hiring managers. Simply put, it can be difficult to convey “I can help you with your problems” without sounding more like “I’m the sole, magnificent answer to all your problems!” You still want to brand yourself as someone the hiring manager would want on their team.

You could miss the mark. Pain-point cover letters rely on a hypothesis in order to succeed. If your hypothesis is off, you’re likely to offend the hiring manager, and that story of how you overcame a specific struggle that actually has nothing to do with them will become irrelevant. No matter how much research you’ve done, don’t presume to have an insider understanding of the company’s issues.

Grandma’s Take on Pain Letters:

Some critics of pain letters propose alternatives such as the “opportunity letter”. Whatever you call it, just write a customized cover letter that supplements your resume instead of restating it, gives specific examples, and shows why you fit the company’s mission and culture. If your pain-point cover letter fulfills those criteria and you feel it’s the right choice for the job you’re applying for, by all means, send it!

The 2% success rate for standard cover letters and even the 25% success rate for pain letters cited earlier may seem scary to you, but remember that these statistics reflect the success of cover letters in general and the success of all pain-point cover letters, respectively.

What the stats don’t demonstrate is how well-written any of those letters of either type are. If your cover letter showcases the skills you offer and how they fit with the job you’re applying to, you’ll increase your chances of landing that interview, regardless of the structure you choose.

Whatever form your cover letter takes, here are a few things to keep in mind to ensure it’s effective:

  • Be sure to write towards what the company wants as specified in the job description, rather than just waxing poetic about yourself. Again, hiring managers want to hear what you have to offer them, not the other way around. 
  • Writing a pain-point cover letter isn’t the only way to make sure your letter stands out. Your cover letter needs to be formal, but there’s still room for variation within those parameters.
  • Using bullet points is a valid way to structure your letter. This can be a great way to vary your letter’s structure and help it stand out on the page, as well as illustrate how each of your top skills aligns with their qualifications for the job.
  • Personalize it! It’s okay to use a template as a loose guide, but your cover letter should be unique to you. Write it in your own voice.
  • If a pain-point cover letter seems like the right fit for the job you’re applying for, there are plenty of tools out there to write an effective one.

Whether you choose to spend more emphasis on a company’s struggles or on demonstrating your passion and drive for their mission, your cover letter is a valuable tool to introduce a hiring manager to your professional achievements and show what you bring to the table. Don’t be afraid to make it your own!

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