Resumes and Cover Letters

What is a Pain Letter and Should You Use One?

pain letter

Let’s face it: The typical cover letter is a snooze fest. Most people use a standardized template they found online, regurgitate a few highlights from their resume, and call it a day. Then they wonder why no one is calling! It’s darn near impossible to truly stand out from the crowd when your cover letter is just like everyone else’s. If you’re looking for a more exciting cover letter alternative, you may have stumbled upon the concept of a “pain letter.”

If so, you’re probably wondering: Is it just another gimmick or does it really work? And, equally important, how do you actually go about creating an effective pain letter?

Here, we’re answering all of your burning questions regarding this trendy job search tactic.

What is a Pain Letter?

This concept was originally coined in 2013 by Liz Ryan, author and CEO of Human Workplace, in a LinkedIn article that received a pretty enthusiastic reception. (In the interest of full transparency, it’s worthwhile noting that the creator of this tactic also sells a system to learn how to do it.)

In her original article, Ryan explains that simply put, a pain letter addresses a specific problem (or pain) the hiring manager is experiencing and how you can resolve it. There’s a little more to it structurally, but content-wise, this is the primary differentiator. It’s not so much about you, it’s about them—what they need and how your experience perfectly enables you to meet that need.

It’s a clever tactic because, as a job seeker, you want to position yourself as the “solution” to whatever it is the hiring manager desperately needs. Plus, you’re able to demonstrate that you already understand the problems facing the team, which means you’re a step ahead of those who are going in blind.


Also read: Am I Out-of-Date with What Employers are Looking For?


Do Pain Letters Work?

The answer to this question isn’t quite so cut and dry. The truth is, yes, pain letters can be very effective — if they are done well. However, in reality, most job seekers aren’t willing to put in the time and effort required to write a really compelling pain letter.

Done poorly, a pain letter can come off as tone deaf and overconfident. After all, you’re presuming to understand the pain of your prospective new boss. If you’re not working with accurate information, you’re going to sound like a salesperson pitching a product that no one really needs.

How to Create a Pain Letter

In order to create a strong pain letter, you need to become a detective. The effectiveness of your letter depends entirely upon the value of the information you uncover. You need to really understand the organization, its goals and challenges. Read press releases, business journals, industry publications and the company website to gain this perspective.

More importantly, you also need to dig deep and figure out how the bigger organizational landscape is impacting the team you’d like to be a part of. For this, you probably need real intelligence from the inside. Reach out to your network and see who you can speak with to gain insight at this level. Remember that confidentiality will be a concern; your task with this letter is not to flaunt your investigative skills. Don’t dive too deep into the details. Keep your evaluation of the problem appropriately high-level so as not to create suspicion on the part of the reader.


Also read: Is it Time for a Career Marketing Remodel?


Then, the most critical part of the letter: Explain how you’ve solved similar problems in your past work experience and how you would use your skills to do the same for this team/organization.

Because of the time investment required, it makes sense to use pain letters only when your job search is highly targeted — which is generally the more strategic approach anyway. Identify a small number of organizations you’d like to work for and then focus your attention on them.

However, if you’re casting a wider net, this strategy may not be a perfect match. Remember: It’s better to use a tried-and-true cover letter approach than to make an uninformed guess regarding the hiring manager’s pain.

While a “pain letter” refers to a very specific tactic, the overall concept is sound and can be applied to nearly any cover letter. Position yourself as someone who eases pain in the workplace—someone who has the experience to solve whatever problems the team is facing. Whether or not you can perfectly identify those problems from the outside isn’t necessarily the most important part.


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About the Author

Chrissy Scivicque is a career coach, corporate trainer and public speaker who believes work can be a nourishing part of the life experience. Her website, Eat Your Career, is devoted to this mission. Chrissy is currently a contributing career expert for U.S. News & World Report and the author of the book, The Proactive Professional: How to Stop Playing Catch Up and Start Getting Ahead at Work (and in Life!), available on Amazon.