Still Writing Cover Letters Try A Pain Letter Examples

Has writing your cover letter become painful? Consider writing a “pain letter” instead. No, this isn’t a letter to air your grievances from being knee-deep in the job search. According to Liz Ryan, Founder of Human Workplace, a pain letter is written towards the employer’s pain points and how you will assuage them once hired. To write it, you’ll need to put yourself in the hiring manager’s shoes to identify and understand his greatest problems.

Writing in Forbes, Ryan recalls receiving requests from a hiring manager wanting to bring in candidates who sent him letters addressing a pain point. Seeing its effectiveness, Ryan encourages job seekers to use this approach as all organizations experience pain. (Nonprofits, for example, often struggle with securing funding, raising awareness, and managing programs.)

To structure your pain letter, Ryan suggests starting by congratulating the employer on something they have done, in order to catch the attention of a hiring manager:

When you begin your Pain Letter congratulating your target hiring manager on something cool the organization has done recently (an item you found in the company’s About Us or Newsroom page) and then make a hypothesis about the most likely Business Pain for your manager, you’re in a great spot. Your manager has a huge incentive to keep reading your Pain Letter. When you tie the most likely Business Pain to your own experience through a Dragon-Slaying Story, your hiring manager’s brain may wake up. He or she may say “I’d like to talk with his person, at least.” That’s all you need!

Read an example and the rest of her advice here.

To begin writing your pain letter, think about an organization you are interested in. Start asking yourself some questions:

  • What success has the organization had recently? Why is this success important?
  • Who are their competitors and what threats do they pose?
  • What are they doing to resolve those threats?
  • What could they do better?
  • What have you done in the past to tackle a similar problem? What were your results?
  • How would you help the organization resolve their problem?
  • What untapped opportunities are available to the organization?
  • If you were to develop a plan for seizing those opportunities, what would you include?

If you can’t answer a question with information you already have, delve deeper until you gain better insight. Writing a pain letter won’t be any less time-consuming than a cover letter, but the approach is likely to yield better results (25% better according to Ryan!).

What do you think of this idea? Is it something you would try or have tried? Share your comments below.

Tags: human workplace, liz ryan, pain letter

I became acquainted with Idealist in late 2000 while working in the career development office at a private liberal arts college in NYC. I used it almost daily to help students and alumni find meaningful careers. After a 12-year stint in higher education, I worked as a career coach for professionals in various industries (and still used Idealist). During one of those many searches, a listing really caught my eye- the one for the newly-created position, Careers Program Coordinator. So... I jumped at the opportunity. Since then, I took on the role of Manager of Career Content for Idealist Careers, creating career content for job seekers, leaders, and other nonprofit professionals. Understanding the roles that a positive outlook and holistic self-care play in career success, I've shared with our readers time-honored methods for improving confidence and productivity. Now, as Manager of College and Professional Development, my focus is on lifting the advice from Idealist Careers "off the page". Drawing from my experience in career development, I propel job seekers and career changers towards taking control of their searches with confidence and removing fear, uncertainty, and other blocks to success via in-person workshops and seminars, webinars, and conference programming. My great loves are cooking (preferably without a recipe, otherwise I doctor it up), dancing, live cultural performances, identifying the tasting notes in a good cup of coffee, exploring neighborhoods for hidden gems, and anything else that sparks the senses and allows me to experience all the beauty, dynamism, and intrigue that vivaciously living in a remarkable world offers.

Hiring managers don’t just want people who can do the job.

Ideally, they want people who will make their lives easier. People who can hit the ground running, who can go above and beyond the duties listed in the job description, and who can help the team or company hit its goals.

To that end, it’s time to stop drafting cover letters that detail only what you’ve done in the past.

In fact, it might be time to stop drafting cover letters at all.

Liz Ryan, in a recent Forbes article, suggests sending a “pain letter,” instead. In a pain letter, you talk about your hiring manager’s biggest problem and how you, if hired, would plan to solve it. In doing so, you highlight not only your skill set and how it applies to the new position, but also your knowledge of the company and your excitement about coming in and making an instant impact on the job.

“Pain Letter users tell us that their Pain Letters result in callbacks about twenty-five percent of the time. That’s a lot better than their results lobbing resumes into the Black Hole recruiting portals,” Ryan explains. “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.”

So, how do you know what an employer’s pain point is? 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.”)

But other times, you’ll need to do a little digging. See if you can find out who the hiring manager is, then do a little LinkedIn stalking to find people in your network who might know him or her. Once you’ve identified someone, reach out for a quick coffee or call (here’s how) to ask, “I’m applying for the marketing manager job at the Lightning Co. and want to make sure to tailor my application. Do you have any insight into what they’re really hoping for someone to focus on in this role?”

If you don’t have anyone you can ask, you can search for people who hold similar roles at different companies and ask what their biggest challenges are. You’ll probably notice some themes and can hypothesize about the hiring manager’s pain points. Or—you’ve heard it before—do your research, reading press releases, reviews on Glassdoor, and current news about the company. Whether it’s going through layoffs, growing pains, or entry into a new market, learning about the major issues a company is dealing with as a whole will offer a great starting point for understanding the challenges in your potential role.

Once you have that pain point? Get to work describing just how you’ll come in and relieve it. Hop over to Ryan’s article to learn more.

Photo of hand writing courtesy of Shutterstock.

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