What is a Pain Letter and Should You Write One?

by Dec 5, 2016

Ever heard of a Pain Letter? No? Well, me neither. Regardless, Liz Ryan has claimed (in an article she wrote for Forbes), that a Pain Letter is going to replace the traditional Cover Letter.

So, what is a Pain Letter?

According to Ryan:

The document is called a Pain Letter because in your letter, you’re going to talk about your hiring manager’s biggest problem. How will you know what your hiring manager’s biggest problem is? Put yourself in his or her shoes. Think about what your possible future boss is up against in his or her job.

Basically, a Pain Letter is a letter you send directly to the recruiter for the company you want to work for. This obviously involves a bit of investigative work, but if you have a dream job in mind, then tracking down the right person shouldn’t be too hard.

Identifying their ‘pain’

So, once you find the organisation’s head of recruitment (or who your next boss would be) you start thinking about what their ‘pain’ is: What would be the most difficult part of their job? What issues might lead to failures in the business? How can you make their life easier? It can be hard to figure out what, exactly, a recruiter’s ‘pain’ is.  Adrian Granzella Larssen from The Muse, notes:

Sometimes, you can tell right from the job description. (Think: “We need to double our team in the next two months and are looking for a recruiter to lead the charge” or “We’re looking for a savvy growth hacker who can help us reach two million users.”)

Other times, you may need to research the position, the business and the industry before starting to develop ideas on the issues an employer might have. If you have anyone in your network who may know the recruiter, or work in a similar role, ask if they wouldn’t mind giving you some pointers.

Remember, you’re trying to think of an issue your recruiter has that you can actually solve. So if you want to work at Apple in the sales department, you’re probably not going to get too far if your Pain Letter only focuses on legal issues.

Drafting the letter

Once you’ve determined the issue your Pain Letter will be addressing, it’s time to start drafting your letter. Unlike a traditional Cover Letter, a Pain Letter can be a little more personable. While you still need to remain professional, the Letter lets you talk to the employer directly, so it’s a good idea to ‘begin your Pain Letter by praising your reader (your possible next boss) on the company’s accomplishment’.

You then want to talk about a time you’ve solved a similar problem to the one the recruiter is facing. So if the recruiter you’re writing to is thinking of opening a new facility, talk about how you helped implement new changes and supported staff transitions in the past. Obviously, you want to tailor your response to your own expertise and the type of position you’re hoping to attain.

Ryan then recommends closing your letter with something along the lines of, for example: “If payroll accuracy and advice to your team is on your radar screen, I’d love to chat when it’s convenient. All the best, Nancy Drew”. Essentially, keep it short, sweet and conversational.

The drawbacks

From what I can tell, Ryan is the leading authority on Pain Letters and their effectiveness. So while the 7 (from my estimate) articles she’s written for Forbes on the topic are pretty convincing, there has been some negative feedback. Alison Green from the blog Ask a Manager doesn’t recommend using a pain letter:

I’d advise against them. When I’ve received them, they’re generally cringingly off-base and sound like they were written by someone who will be all flash and no substance.

She describes a Pain Letter as ‘a cover letter but with lots of added salesiness and a serious dose of presumption’. The main issue here, it seems, is that figuring out what an employer’s ‘pain’ is can be really tricky, particularly if you don’t actually know what’s going on in the company first-hand. The blog, Avid Careerist, supports this and quotes Fousquare’s Head of Talent as saying:

As an outsider, it’s tough to know the exact vision and strategy of the company. If you are 100% sure you’ve nailed it, then the job is yours. But if your ideas go slightly in the wrong, wacky direction, it could do more harm and the company might think you don’t get it.

Basically, Pain Letters can be really tricky to do well so it might be a good idea to hold out on trying it until you’re sure you’ve got a great understanding of the company and its goals.


So if you’re thinking of writing a Pain Letter, it’s worth doing some research first. And by some, I mean a lot. It’s hard enough to get your foot in the door at your dream company, without being presumptuous and looking like you don’t know what you’re doing! While Pain Letters can occasionally work well (Ryan’s ebook on the matter notes that people ‘get a call back or an email (human) response about 25 percent of the time’), don’t rush in and make it the only way you apply for jobs! Sure, add it to your job application arsenal, but it might be a good idea to hold on to your cover letters for a while yet.

Featured image courtesy of Unsplash.

By Mia Casey

By Mia Casey


Mia is a Sydney-based copywriter and content creator, who ran the UTS Careers Blog for five years since its conception in 2016.
Her freelance work focuses on branding development and helping companies create a cohesive identity narrative tailored for each of their platforms.
She enjoys piña coladas and getting caught in the rain.