Instead of a cover letter, try a pain letter

Typing on blank paper

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.

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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.
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  1. I would absolutely consider this approach. In fact, this approach will make it easier for me to figure out if the company is one that I would want to work for. I would want to be with a company that is open to new ideas, innovation and encourages thinking outside the box. Therefore this seems like an approach worth investing time in.

    1. Thank you for your comments, Leopeter! Please come back and share how things go with the pain letter you write. Hope it works out well for you!

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