Sometimes a pain letter is all you need to double your interviews.

As a volunteer counselor for, the Danish equivalent to Monster, I try to help people who are finding it difficult to get into the Danish job market find work. Recently I worked with a client, let's call her Alicia, who had tried everything to find a job but was still coming up empty.

Alicia was not a native Dane and hardly spoke the language, so it certainly complicated matters further and limited the jobs she could apply for. Alicia had a profile that would be attractive to quite a few employers and she had received some interview requests; however, after more than 100 job applications and she was starting to wear down.

A cover letter made the difference

Alicia had quite a good resume that followed resume best practices with the following elements:  

  • A short summary showcasing her main skills and experiences, which changed with every job to closely match the job ad (albeit still within reason of what she could actually do for the company)

  • A list of her relevant jobs describing responsibilities in a text string and achievements in bullets

  • A list of her education highlighting main courses, thesis, and any honors she received

  • A skills and language section

The problem was her cover letter. Even though Alicia edited it so the experience and results would match the job ad, her cover letter still seemed quite generic. Alicia included a small section stating why she wanted to work for the specific company; however, it was not linked to an overall theme and just appeared to be saying nice things about the company. In short, the cover letter was not getting it done.

Use a pain letter to improve your cover letter

To try and make a bigger impact on recruiters and hiring managers, we agreed to make a change to the cover letter similar to what Liz Ryan would ask you to do in a pain letter.

What is a pain letter? 

Coined in 2013 by Ryan, a pain letter addresses a specific problem (or pain) the hiring manager is experiencing and how you can resolve it. There are four parts to a pain letter: 

  • The hook: Here you mention a relevant and timely achievement to grab the hiring manager's attention. 

  • The pain hypothesis: This is where you try to identify any pain points the company might have. 

  • The dragon-slaying story: Next, you link the hiring manager's business pain to a story from your past, showing how you would solve their problem using evidence from your career so far. 

  • The closing statement: You can put something as simple as, "If any of this warrants a conversation, my contact details are on my resume," to close out your letter. 

Essentially, the pain letter helps highlight not only your value, but your understanding of the business. 

How Alicia and I wrote her pain letter, step-by-step

  • For each job application, we started out by describing the challenges (i.e. the “pains”) of the industry and of the company Alicia was applying for. 

  • We then added some company-specific challenges and how Alicia, as a finance professional, could help solve those pains. 

  • We then got specific and used 3-5 of the responsibilities from the job description and linked them with Alicia's past results at previous companies.

  • We used statements like “I will take charge of your annual reporting” or “I will drive your budget process” and backed each statement up with how Alicia had done this at previous companies. While this section made up the bulk of Alicia's cover letter, it wouldn't have worked as well without the first part. This first part put Alicia in the hiring manager's head by demonstrating an understanding and appreciation of their problems. 

  • We rounded off the cover letter with why Alicia wanted to work for the specific company, again linking it to the pains highlighted at the beginning.

Ask for the interview directly in your cover letter

And in the final section, we simply asked for the interview. Instead of saying “I'm really looking forward to hearing from you,” we said, “I would very much like to discuss this position further and can be reached at [phone number].”

Immediate results

Up until we changed Alicia's cover letter she applied for 115 jobs, was invited for a respectable 10 interviews (8.7 percent response rate), and made it to three final interviews. 

Since we switched cover letter strategies, Alicia has applied for 29 jobs, been invited for six interviews (20.7 percent response rate), and made it to four final interview rounds. It's very important to note here that we didn't change a thing in her resume, so the results are truly due to a change in the cover letter.

I am happy to say that Alicia received two job offers shortly after we tried this new approach and has now been happily working in her dream job for the past five months.

How to write your own pain letter

Much like a traditional cover letter, there is a method to success. Here's how to effectively write your pain letter to ensure you land the interview. 

Write an engaging hook 

When grabbing the hiring manager's attention in a pain letter, you want to make sure you highlight a recent and relevant achievement from the company. Did they just secure record investments? Did they meet a new sales record? Has their team achieved record growth? Whatever it may be, make sure to note it at the beginning to pique their interest and hold their attention. 

Use Google News Alert to help you keep track of their achievements during the job-search process. 

Research their pain points

One of the main points of the pain letter is to address the problems the hiring manager or company may have — and how you can solve them using your experience and expertise. But how do you identify their pain points? Research. 

Here are a couple of ways you can research the company's pain points: 

  1. Talk to the hiring manager. Whether it's through email or LinkedIn, reach out and ask the manager questions that can help you build your case. From asking about the perfect candidate to some of the biggest challenges the company is facing right now, use this informational interview to gather intel. 

  2. Talk to employees. If you can't get a hold of the hiring manager, don't be afraid to connect with employees of the company on LinkedIn. Ask your questions after connecting with them and then use what you learn. 

  3. Conduct online research. Search for press releases, news coverage, and other articles or podcasts that the company is featured in to figure out their goals and challenges. In addition, you can set up Google News Alerts to stay in the loop. 

  4. Use the job description. Sometimes, the job description will spell out exactly what they are hiring for. 

Once you've done your research, then you can write the pain hypothesis section of your letter. 

Identify and tell your “dragon-slaying” story 

Now that you have an idea about what pain points to address, you need to start thinking about specific instances and experiences where you've solved problems like these before. Essentially, you want to tell the hiring manager exactly how you will solve their problem — and then some. 

Make sure to consider the following questions when thinking of your answer: 

  • When did you solve problems like theirs?

  • What are your biggest work achievements that fit?

  • What awards have you won?

  • Can you point to a massive achievement that proves you're their hero?

The key is to make sure whatever experiences you talk about are relevant to the pain points you've identified. Once you thought through these questions, you can tell your “dragon-slaying” story. 

End with a call-to-action  

Once you've explained how you would solve their problem, make sure to tie it all together in your conclusion. This should also include a call-to-action that leaves the ball in the hiring manager's court. For example, you can write something like: 

“I'm happy to jump on a call with you over the next few days to discuss this further.” 

Not only do you come off as enthusiastic, but it also shows that you're proactive and ready to go. 

A sample pain letter

Still unsure where to start? Here is a sample pain letter to get you started: 

Dear [Insert hiring manager's name], 

I recently read that XYZ company partnered with AB company to create a more effective way to identify engaged customers via email and social media. I think it's very exciting to see how your company will use this new technology to help the bottom line and grow your business. That is why I am currently applying to be your next Digital Media Manager. 

With your business exponentially growing, I've noticed that your social media channels are not growing at the same speed. With changes to the media algorithm across platforms, this problem will likely be exacerbated in the next few months. With so much of the world connected through these platforms, making sure your social media strategy keeps up is very important. At my last job, I grew our social media following by 75% by implementing a posting schedule, investing in paid ads, and A/B testing social copy to figure out which emotion and tone resonated best with our customer base. 

If you have a moment to chat, I would be happy to jump on a call, video chat, or email to discuss this plan further. 


Joanna Smith    

In summary

There are certainly more methods to getting a job than job applications, and some would even argue that online job applications can be a waste of time. However, it really depends on the job market, your location, and your specific job goals. 

Following these cover letter tips, leveraging your network, attending networking events, and contacting hiring managers and recruiters will only make your job search more effective.

Need help with your cover letter? Not sure if you should write a pain letter instead? Our TopResume writers can help.

This article was updated in November 2020 by Danielle Elmers.

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