Instead of a cover letter, try a pain letter


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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Photo Credit: Bartek Zyczynski, Shutterstock

About Author

Throughout my 15+ year career in resume writing, career coaching, higher education, and working with nonprofit job seekers, I’ve used an approach that is nurturing yet practical and driven to achievement. As Audience Development and Content Manager at Idealist for our online publication, Idealist Careers, I bring relevant tips to today's social impact job seekers and career changers with sensitivity towards the challenges they face. I also am the writer of our career advice column, "Ask Victoria". Understanding the roles that a positive outlook and holistic self-care play in career success, I share with our readers time-honored methods for improving confidence and productivity. Have a question? Ask at Follow me on Twitter @_AskVictoria.


  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.

  2. Pingback: 4 elements of a tailored resume

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