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Do "Pain Letters" Really Work?

- Robert A. Di Ieso, Jr.
Robert A. Di Ieso, Jr.

Q: I wanted to know what your take is on “pain letters.” I have been reading up on career advice, and I ran across an article that recommended junking cover letters and resumes for “pain letters.” Should I try it?

A: I’d advise against them. When I’ve received them, they’re generally cringingly off-base and sound like they were written by someone who will be all flash and no substance.

For people who don’t know what a pain letter is, it’s a concept being pushed by at least one career writer — who happens to be selling a whole job search system based on it — where the idea is to send a letter through the postal mail to a hiring manager, outlining a problem you think the employer is experiencing (the “pain”) and how you can solve it.

In other words, it’s a cover letter but with lots of added salesiness and a serious dose of presumption.

Read More: Why do companies wait so long to contact candidates for interviews?

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.

As for the whole postal mail thing, it will at best annoy most hiring managers (who now have to figure out how to get your materials into the electronic application system that you decided not to use, can’t easily forward your stuff to anyone else, etc.) and make them wonder if you’re a technophobe who’s out of touch with how this stuff works and/or someone who cares not for instructions, and at worst may actually get your materials tossed.

The thing that this “pain letter” advice and so much like it ignores is this: Applying for a job doesn’t require gimmicks to stand out and be noticed. The way you stand out is by having a resume that shows a strong track record of getting results in the areas that they’re hiring for, writing a compelling cover letter that explains why you’d excel at the role as they’ve laid it out, and being friendly, responsive, and enthusiastic. That’s not anything you can sell as a system and it’s not especially exciting … but it works consistently.

Read More: Should I go around HR and apply with the hiring manager directly?

Q: Can my employer revoke my bonus after a direct deposit into my bank account? Can my employer revoke my bonuses after they’re deposited into my account if I put in my notice soon after?This will really help me figure out notice timing!

A: They shouldn’t — once earned, that money is yours — but it is possible for an employer to revoke a direct deposit (within a limited period of time — I believe it’s five days, but you’d want to verify that with your bank) and take that money back. Generally they can only do this to correct mistakes (such as if they accidentally overpaid you); they couldn’t do it to, say, recover money for property of theirs that you took on your way out the door. But theoretically, an unscrupulous company could say that the bonus was a mistaken payment, and then you’d have a mess on your hands.

If you want to be really safe, wait until a couple of weeks have gone by, or transfer most of the money in that account to an account at a different bank.

Read More: Does “we’ll keep your resume on file” really mean anything?

These questions are adapted from ones that originally appeared on Ask a Manager. Some have been edited for length.

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