A Job-Seeking Advice Question of the Day

Photo credit: Blake Burkhart, CC BY 2.0.

It’s pretty standard, in the job-hunting advice world, to tell people that they need to focus on what they can offer the company, not what the company can offer them.

That’s why “I have four years of experience in THIS THING, and I increased results by THIS MANY” is better than “I have been passionate about INDUSTRY since I was a child, and I want nothing more than to work here.”

(This is the same advice I give to other freelance writers, by the way. Don’t make your pitch about how much you want to write something. Make it about how the story will benefit the publication.)

Of course, since we’re obsessed with optimization—and since we know that a lot of people have increased results by THIS MANY and that we might still need an extra way to stand out from the stacks of resumes—this advice has sometimes been re-written as “tell the company how you can solve one of their problems.”

I can’t remember where I first saw it, but I definitely remember, when I was first job hunting a decade ago, reading online advice that suggested:

  1. Going to the initial interview
  2. Asking the person interviewing you what problems the company was facing
  3. Following up the next day with a thank-you card that also included a detailed description of how you would solve those problems

Since my job hunting was for positions like “receptionist” and “telemarketer,” I never had the opportunity to put that advice into action. (Thank goodness.)

Now the job-hunting advice industry has taken this “solve a problem” idea one step further, suggesting that job seekers write a pre-interview, pre-emptive Pain Letter describing what they think is wrong with the company and how they are the ideal person to fix it.

Here’s the advice from Liz Ryan of Human Workplace, who both invented and popularized the Pain Letter concept:

When you write a Pain Letter, you don’t waste a second with the Black Hole [of online application systems]. You ignore it completely. You write directly to your hiring manager at his or her desk.

She means an actual letter, not an email. Ryan suggests that you open your letter by complimenting the hiring manager on a recent accomplishment, then suggesting a problem the hiring manager might have and how you are ideally equipped to solve it. Then ask for a meeting—not a job—to discuss the problem in more detail.

It’s a classic sales move—build rapport, identify a problem, solve the problem, ask for the sale—and on the surface seems like it might be a good idea. As Ryan explains:

There might be a stack of resumes on your manager’s filing cabinet when s/he opens the envelope to read your Pain Letter. Those resumes will be forgotten in a heartbeat when you make the intellectuo-emotional connection with your manager that a forty-five-second read of your Pain Letter can evoke. We see it happen every day.

Will that happen to you, though? Alison Green at Ask A Manager provides what I think is a reasonable response:

When I’ve received [pain letters], they’re generally cringingly off-base and sound like they were written by someone who will be all flash and no substance.


I say that because it requires you to guess at what the hiring manager’s problems are, which can be hard to do from the outside and carries a high risk of coming across as insulting or uninformed or both.

It is true that you should frame your application in terms of what the hiring manager needs, but you don’t need to go guessing at what problems she may or may not have. The main problem she has that you need to speak to is “I need someone to perform this job well, and preferably excel at it.” It’s really not more complicated than that.

So, to all of you who have either sought out jobs or have been the person managing job applications: would you ever write a Pain Letter? Would you be happy to receive one? Would it make that all-important “intellectuo-emotional connection,” or would it come off as “cringingly off-base?”

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