do “pain letters” really work?

A reader writes:

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 by a Forbes contributor who says that we should junk cover letters and resumes for “pain letters.”

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.

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.

{ 201 comments… read them below }

  1. Dawn*

    Yay thanks for formally addressing your stance on this! Someone asked about a pain letter a while back in an open thread and I said they looked extremely fishy since the person recommending them had an entire business model based on them being used.

    Cover letters are intimidating and I can see where the idea of a pain letter would sound easier than a good cover letter, but you’re spot-on with them coming across as incredibly presumptuous. I interviewed a guy once that was like a living pain letter in his interview, just going on and on about how he’d solve this and that specific problem that he knew we had because of the job description and what he’d read about our company on the internet. There was *so much* eye rolling in the post-mortem meeting after that interview.

    1. limenotapple*

      I interviewed someone like that a few years ago! He was telling us how he could write grants for us! Do HR tasks! Do Graphic Design! Fix our “terrible” website! But none of that were what the job was about. The job was about doing some specific tasks, and everything else was done by different departments. It really said, “I’m not interested in the job you posted”.

      And the person on the hiring committee who was actually in charge of the website didn’t like hearing that his website was terrible :/

      1. Anna*

        A recent hire came in with a bunch of ideas that they are very excited about. Not one of them is for the job they were hired to do. Since I will be working closely with this human, I hope they calm down a bit, but as bizarre as it is in an interview, it’s even more irksome after they start. (I don’t they brought their great ideas up during the interview.)

    2. KaBe*

      I don’t think writing a good pain letter is any easier than writing a good traditional cover letter. Both require the job applicant to do significant research into the company and position for which they are applying. Like a traditional cover letter, a good pain letter must use a professional language style. However, in a pain letter, the writer must present his/her assumptions of a company’s needs/pain (based on the aforementioned research) without soundi like a pompous know-it-all. Many of the other comments here seem to take exception to poor execution of the pain letter idea. I’m certain hiring managers receive poorly executed traditional-style cover letters, yet don’t discount the effectiveness of a good cover letter.

  2. animaniactoo*

    I regularly get such “pain letters” via e-mail from people who want to sell me their services, or put them in touch with the people at my company* who handle their sort of thing. All it does is make me roll my eyes, so I can’t imagine that selling myself that way in a job search would go over much better.

    *I’ve checked with those people. They asked me to just delete the e-mails, ty, do not bother sending them on, if and when they encounter an issue that service might be able to handle, they’ll go out and look for who they want to handle it, ty. So it’s apparently not just me who reacts with the rolling of the eyes.

    1. Misty*

      Same. I get versions of these regularly from cold-calling vendors and occasionally from job applicants, and they are always–*without exception*–based on incorrect and unsubstantiated assumptions of the job position/our company/the industry. They basically telegraph I AM CLUELESS AND DIDN’T DO MY RESEARCH and they are processed accordingly.

    2. SophieChotek*

      I sometimes wonder if these “pain letter” from someone trying to sell a service to you might come from the entire PR advice — “Your (Potential) Client has a problem. Show how you/your product/your business Can solve it.” I have been reading this almost ad nauseum in beginning PR material/attracting clients/pitching to the media for the past 3 months. Seems like it is pretty standard fare for ‘How to’.

      I understand the concept — the idea is to try to relate to the person one is pitching to (not just say “hey I’ve got this great product, you should get it”) — but what you write sounds like it’s either not working or not done well…

      1. Stranger than fiction*

        Yes, this concept surely comes directly from Sales, where you’re taught to find the clients’ pain or hot buttons and present your product or service accordingly. And I think Sales jobs is possibly just maybe the only place this might work, since it’s often all about the flash.

        1. Wakeen's Teapots, Ltd.*

          Can I just emphasize that the point of using the pain approach in sales is to FIND the customer’s pain first? You’re just as tone deaf in sales if you assume the contact’s pain and “address” it (wildly off the mark most times).

          You ask questions. Then listen. Then feedback your interpretation of what you heard. Then listen. Then finally, when you feel you adequately understand the pain point, begin to address how you can fill that need (ease that pain).

          You can’t sell on pain cold anymore than you can write a cover letter for a job on pain cold.

          You could absolutely apply the pain approach in job hunting, but that would be during the interview. I’m sure people do it all the time, they just don’t know there’s a name for the approach.

          1. AMT*

            Spot-on. It’s not that being the solution to someone’s problems isn’t a good way to get a job. It’s that this “pain letter” thing is an idiotic, tone-deaf way to do it.

            1. Wakeen's Teapots, Ltd.*

              It hurts my heart to see them destroying the reputation of a fabulous approach with such horrible execution advice. Selling based on pain is wonderful for all parties, if there isn’t an idiot driving it.

              1. Sunshine*

                I just interviewed a guy for a sales position I’m trying to fill… he told me several times how good he is at talking to people. After the 3rd time mentioning it, I said “Yeah, that’s great! How are you at listening?” He seemed a bit confused by the question, sadly.

                1. Wakeen's Teapots, Ltd.*

                  Ha ha, omg that’s great. :-)

                  At the end of the day, my best track record is just hiring nice people and teaching them how to sell. Nice people are teachable and they instinctively know how to listen.

          2. Connie-Lynne*

            At best, cold-selling this should be “if you have this pain, we can address it this way” and not “IT’S CLEAR YOU FUCKED UP IN A WAY THAT OUR PRODUCT WILL MAGICALLY SOLVE FOREVER! WITH MONEY!!”

            1. bob*

              That is awesome! It reminds me of the carpet bagger, snake oil salesman guy in The Outlaw Josey Wales when Clint spits and asks “how is it on stains?”

          3. AnonInSC*

            This is an important distinction. Of course a candidate wants to sell themselves – and this may be a good framework to use. I could even see a decent thank-you note after an interview using the principles (if not cheesy language etc) being impressive.

            1. Paloma Pigeon*

              Yes. I also could see the concept being used in a hypothetical way in a cover letter. Such as: “I have extensive history with Teapot Database Migration projects. If you ever needed someone to manage such a project, I could definitely jump in.”

              A hypothetical way of further illustrating a specific skill you have that MIGHT apply to the job area, if you have worked in a similar type of role and the hypothetical has come up before.

            2. Hillary*

              Yes. I used this framework in all of my in person interviews for my current role – you have this problem? here’s how I can fix it. It’s very different from assuming from the outside what’s wrong.

          4. Pennalynn Lott*

            Yep, back when I was in tech sales my approach was, “We’ve helped companies similar to yours with X. I have no idea if we can help you, but I’d like to talk to you a bit about it, if you’re open to it.” And then I’d move into a “go/no-go” approach, where each side could easily pull the plug on the sales process if the information uncovered at any step meant we weren’t a fit for each other.

          5. Stranger than fiction*

            Oh totally agreed, I was just guessing the origin of this idea, the application is clearly wrong in this scenario.

    3. BRR*

      I’ve always thought of pain letters as just in hiring but your comment is spot on that some sales people use the “pain” approach. I had one vendor try it and they were completely wrong about a pain spot. It was so insulting. I would have loved to not give them my business but they unfortunate had a unique product.

      1. Wakeen's Teapots, Ltd.*

        To go along with my comment above, excellent sales people always use the pain approach! You don’t notice they are doing it because they are excellent. All you notice is that you’ve got a sales person who is asking you questions about what you need to make your job/life/project easier and then doing her best to make that happen for you.

    4. Connie-Lynne*

      As someone who used to be primarily in charge of preventing and solving outages for a number of large companies (Site Reliability Engineering, for those of you who are in the field), I can tell you that, at least when vendors send these to me, they are universally off-base and tone-deaf as to (a) what the problem was and (b) what the solution might be.

      Far more useful for both A and B are After-Incident Reviews, and going to specifically targeted meetups of folks in the same field.

  3. AMG*

    Don’t do it! I have seen consultants who are generally familiar with systems/issues try this as a sales pitch and it comes across as arrogant and unprepared. And that’s with people who already are familiar with the company. It’s hard to solve a problem with a comprehensive plan if you only know the issue at a high-level. If you don’t even know what the issues are, don’t try to solve it!

    Instead, ask leading questions about what pain points there are and let the hiring manager tell you, then be prepared to discuss how you have solved similar issues in the past.

  4. Snarkus Aurelius*

    I work for the government, and I get these things all the time but from vendors.  Vendors who think I have “customers” and a “marketing strategy” and “sales goals” and “brand.”

    Government doesn’t operate like a business because it isn’t one.  I’m not here to make profit.  Ironically I’m here to serve the underserved when these guys clearly think government agencies make profit.  Were they not paying attention in social studies class in middle school?

    I don’t know, and I don’t care, but I do know that anyone who approaches me with solutions to problems I don’t have along with a clear demonstration of ignorance will get my voicemail every time.

    1. Shan*

      I work for a non-profit and get the same thing from vendors. I imagine if I were a hiring manager and got something from a job applicant like this, I’d put it right in the round file with the vendor stuff like that.

      But even if they correctly guess the problem I’m having, they’re also assuming that I can or want to solve it. For example, if someone said they thought our social media following could be improved, they’d be right! But if they suggested to use Facebook or Google ads, or costly analytical services, I would get even more annoyed. Those are things we’d love to do but we have ZERO budget for social media, and our non-profit really doesn’t benefit a lot from social media and it’s not a priority – we have other means of communication and advertising that are much more effective. They’d come across as out-of-touch for not thinking about budget and priority possibilities, and arrogant, because trust me, I’ve already thought of those things!

      1. Terra*

        In your case the closest this might come to working is someone who wants social media experience on their resume sending an email that says “I noticed your social media following could be improved. Would it be possible for me to volunteer x hours per week for x months or so to assist you with that?” At least that’s less annoying and is offering a more reasonable exchange of “here is a thing I would like to do/get more experience in that I noticed you might benefit from. Can we enter into a mutually beneficial relationship?” sort of way.

    2. Christy*

      Haha, or even if I DO have those pain points, I still can’t purchase their services because (1) I don’t have any authority, (2) we have no budget, and (3) purchasing anything for us is really complicated.

    3. GS*

      When I was in government I always enjoyed these calls in a perverse way. One guy called once per week with one of these sales pitches and would rarely let me get a word in. Finally one day I asked him whether he was paid per-call or per-sale. Of course it was the latter. Then I explained that he was calling the Government and that we’re literally not allowed to buy, and this is costing him lots of money.

      The calls slowed to once every 3 weeks. Still boggles my mind.

      1. Snarkus Aurelius*

        I think it’s because they’ve heard about these government contracts that pay out zillions to private contractors for all eternity, and they think all government entities are like that. Nope. That’s mainly defense and IT.

        1. Mockingjay*

          I (government contractor) wish they paid zillions. These days most defense contracts are small and the profit margin thin. Salaries and benefits are decreasing. I don’t even have a 401K. We get office supply vendors calling, but my company buys equipment and supplies on sale from Wally World and the like.

          The exceptions are the big budget-busting tanks and fighter jet programs – and those have a lot to do with your friendly neighborhood Congressperson…’cause they got to “drive” the tank around the parking lot! Sadly none of those programs are in my area.

    4. Elizabeth S.*

      It’s fun to send pushy salespeople the link to bid process information on the state comptroller’s website. Irresistible force, meet immovable object. Have fun!

    5. Nethwen*

      Yeah, I hear you on that one.

      On the other hand, I’ve found I get better response from service businesses (fancy copier/printer help desk, ISP help desk, etc.) if I frame our need in terms of “this problem needs fixing now because we are loosing customers every minute you aren’t providing the service we pay you for,” rather than the more accurate “we’re a public library and people who rely on us to complete job applications/benefit forms/school work/etc. have no options when you aren’t providing the services we pay you for.” For some reason, a business with customers gets prompt service; an organization that helps people in the lower economic/educational demographics do the work that can lead to improved economic/educational conditions can be ignored.

      1. Terra*

        I’ve noticed this too. Possibly it has something to do with the idea that companies can and will change service providers if you cost them money but government organizations tend to be slower and more locked into things? I.E. we don’t need to work hard to make the library happy because they aren’t going to go through the hypothetical three board meetings and mountain of paperwork it takes to get rid of us.

    6. HRChick*

      I got this when I worked for the government, too. Guy came in and told us how horrible our hiring time is, but if we hired him, he’d cut it in half.

      Okay, tell us some of your ideas?

      Pretty much cut out a lot of the federal requirements for hiring a federal employee. Thing is, you could tell that he was getting so mad that we would say, “You can’t do that, it’s against the law.” Ended up looking uninformed and unreasonable.

  5. BRR*

    This is exactly what I thought of when I first read about pain letters. I don’t think I have ever been able to figure out for certain an organization’s specific challenge for the position I was applying for. I’d imagine if I received a letter like that, I would feel insulted by it. You can do the same thing by saying what your skills are and the hiring manager will figure out how you can contribute. “Your sales were low last year, I can increase them” vs “I have increased sales by an average of X% annually over the past five years.”

    Also hiring processes exists because that’s how the company wants you to apply (even if the hiring managers don’t like it, it’s the way the company wants you to do it), it’s not about figuring out a way to get around it. It can feel sucky that you work so hard on your materials and send them off electronically not knowing how much time will be spent on them. But sending them via snail mail doesn’t increase your chances they will be read. People feel they’re not getting a fair chance by applying electronically and this advice is what people want to hear so they believe it.

    I hope this isn’t too hostile but I also find this advice giver’s LinkedIn to be on the unprofessional side with some of their job descriptions and it personally turns me off from wanting to follow their advice.

    1. Megacles*

      “You can do the same thing by saying what your skills are and the hiring manager will figure out how you can contribute.”

      We are not a bundle of skills! We are human beings, with passions and with a story. Listing your skills makes you a ROBOT. And if I wanted to hire a robot, I would not be looking for people–engaging, proactive, passionate, beautiful PEOPLE.

      ““Your sales were low last year, I can increase them” vs “I have increased sales by an average of X% annually over the past five years.”

      You don’t understand Pain Letters. That is not how we approach things. There are only so many types of business pain. Why is the hiring manager hiring for this position? It’s often painfully obvious in the job description. It is not arrogant or self-talk to say “When I worked at XYZ company, we experienced [this] and [this is how I solved it.” I would not be surprised to find your talented team having the same challenge.

      “But sending them via snail mail doesn’t increase your chances they will be read.”

      Doesn’t it? What are you more likely to open, an e-mail or a paper letter? Emails can so easily be deleted without a second thought that it doesn’t make sense to reach out that way. Personal paper letters strike so much curiosity that we are compelled to open them.

      ” I also find this advice giver’s LinkedIn to be on the unprofessional side”

      That’s fine. I don’t want to work at your company. You sound like snobs who only follow strict rules and have robots working for you–cogs in a machine and not real, live humans. I feed sad for you having to work there.

      I want to work at a HUMAN workplace, with lively, fun, and smart people who believe in what they do and who enjoy the people they work with.

      1. Ask a Manager* Post author

        I note that you’re using all of the columnist’s own lingo here so we’ll have to agree to disagree on the rest, but I do want to say that you are really wrong about snail mail. In fact, many people don’t even open their paper mail for months at this point — stories abound here about people not checking their work mailboxes for weeks, only to find a paper application in there from someone who sent it in weeks ago. And of course, many hiring managers are simply annoyed not to have people ignore the clear directions laid out, which are there because that’s the most effective process the employer has found for considering applicants.

        Seriously, that snail mail advice is hurting people. (As is the rest of it, but I wanted to tackle this point in particular.)

    2. KaBe*

      When applying for a job, it is not the purpose of a pain letter to solve the perceived problems of the company that is looking to hire talent. Instead, it is an opportunity for the applicant to describe their approach and success in addressing a similar problem. It is meant to illustrate the capabilities of the applicant. Offering actual solutions to company’s assumed challenges will certainly come across as presumptuous and arrogant. I can see how such an approach would be distasteful to hiring managers. However, discounting pain letters completely because of poor execution by some job applicants suggests a certain level of inflexibility and aversion to innovative ideas that seems out of place in today’s business world.

  6. ThatGirl*

    I’ve gotten versions of this via e-mail from random outside marketers, trying to get their company a foot in the door.

    I always delete them because:
    a) I have ZERO hiring or decision-making power
    b) I don’t work in a department that does
    c) we’re a huge company that either has its own department to handle whatever it is you’re selling or has already outsourced it (and if they were looking to change, they wouldn’t ask me, see A&B)
    d) it really comes off like this person did no research at all if they think I can help them

    1. Ad Girl*

      Yes to all of this. I think some of these people send emails to every person in the company they can find contact information for that seems to be in what they deem the right department.

      The part that makes some of them seem even worse is when I reply saying I’m not the person to make that decision/am not interested and they don’t take me off the mailing list, so I still get emails from them every couple of weeks.

    2. KaBe*

      The use of the pain approach by vendors should not be equated with pain letters used by individuals applying for jobs.

      1. BvS*

        You seem to be the only voice of reason in this stream. Kudos to you. Hope the cynics here never find themselves looking for a job and relying on corporate HR software to pick them out of many hundreds of applicants applying for the same positions. I think you need to remember that there are real people on the other end of any pain letter, cover letter, email, Inmail, etc…and treat them the way you hope to be treated next time your that person on the other end.

        1. rdg*

          I agree KaBe and BvS. I think most of those commenting are equating pain approach used by vendors with pain letters used by job applicants. In essence, pain letters is technically a cover letter, but from a different frame of mind. It focuses on the possible pain the business might be having and the solution the applicant can possibly provide. I also noticed that there are some responses in this thread which are borderline arrogant. If I received a sales pitch using the pain approach, or a pain letter from a job applicant, and its not in my area, I would just politely refer them to the appropriate person. Or if it is in my area but we have no intention of hiring anyone at the moment or acquiring any new product or service, I will do just the same, politely say no but would keep them as reference in the future. There is always a human at the other end of the spectrum. I wouldn’t treat any other way as I don’t want to be treated the same way if I was in their position.

  7. Amber Rose*

    Yeah, that person selling this stuff is at best woefully out of touch and at worst, taking money out of pockets in exchange for useless information. :/

    The pain letter thing is basically like doing a one sided interview. Instead of asking questions and then speaking to the answers with your knowledge and background, you just make a bunch of assumptions and address those. The worst possible strawman argument.

    I do agree that online applications can feel like casting lines into a black hole of doom, but there are better ways to address that than sending uninformed letters through snail mail that probably end up in a real hole: the recycling bin.

    1. Stranger than fiction*

      I wonder what her success rate is, or if there is one of its made up or inflated. Does this person have testimonials? Of course those can be fabricated too.

      1. SystemsLady*

        She claims “her” pain letter users got an average 25% callback rate all over the place online.

        Which…isn’t actually that impressive, depending on who “her” users were.

        1. Clewgarnet*

          Wow. In the past ten years, I don’t think I’ve ever submitted an application and NOT got a callback. If ‘pain letters’ are only getting 25%, that alone is a good reason to dump them.

          1. KaBe*

            It’s nice for you that your are so perfectly matched to every job you have ever applied for. Some fields are very competitive, and even imperfect people can be excellent hires. You cannot fault people for using every tool at their disposal in their search for employment.

      2. Amber Rose*

        She has a lot of posts on LinkedIn that are little dialogues from people who supposedly got awesome jobs her way, but there’s no way of knowing if they were real conversations or just made up ones.

        1. Elsajeni*

          I’m sure people have gotten interviews and job offers using her approach — heck, there are people further down in these very comments reporting that they’ve sent “pain letter”-esque cover letters and gotten good results. The trick is that, of course, you can’t really tell whether you got that interview/offer because of the pain letter, whether you would have gotten it regardless, or even if you got it in spite of the pain letter (“Well, her cover letter is kind of weird and pushy, but her resume looks like exactly what we need… let’s take a chance and bring her in for an interview”).

  8. College Career Counselor*

    If this is the same Forbes Contributor(tm) that tells a hoary old yarn about her days as an HR executive (“before LinkedIn!) when her staff would come to her with tales of applicants with moxie and gumption and beg her to sanction an interview, then I think one of two scenarios is likely:

    1) this happened a couple of times and it was invariably because the staff member already knew the applicant
    2) she’s lying (or otherwise full of it)

    1. AnonInSC*

      Based on the quick googling I did because I had never heard of a pain letter, you totally hit the mark and I only read part of 2 columns!

      The term pain letters makes me think of “to the pain” from the Princess Bride. Yeah, not how I want an interview to go.

      1. NotherName*

        If I ever saw Cary Elwes in an interview, I don’t think I’d remember anything else….

        Same goes for Chris Sarandon tied to a chair.

        1. Dr. Johnny Fever*

          Cary Elwes….Sarandon in a chair…what were we talking about? I got lost for a moment, and the side of my chin seems to be covered in drool for some reason.

      2. Amber Rose*

        Applying for jobs can definitely feel like a duel to the pain, particularly the wallowing in freakish misery bit, but you’re right, that shouldn’t be the goal.

        Princess Bride is so great though.

    2. HR Ninja (green belt)*

      So I Googled because I just had to know who would tell people to do such a thing and found this advice givers LinkedIn. A quick perusal backs up everything I think Alison has been saying for years. Don’t take advice from someone who hasn’t hired people or who hasn’t hired people in a long time. A quick review of the profile shows that 1) this person doesn’t know how to properly use LinkedIn (see: multiple listings of the same job and workplace over and over and over again with personal thoughts about the company and who eventually acquired it) and 2) the last time they worked for someone else besides themselves was in 1997. Also, putting down that you have certifications from the company you founded and own – weird.

    3. Three Thousand*

      What really blows me away is that she encourages people to lie about being fired in job interviews on the assumption that there’s a low probability of being found out.

  9. Kat*

    Hmm interesting. Maybe it’s different in the freelance writing world, but pain letters are incredibly effective and the basis for most pitches. I do them by email, but the concept is the same:

    Usually it goes, oh, your product is snazzy, but I noticed you are on page 17 of Google search results. Most of your competitors have a blog which helps them with SEO and it would help your business. Full-time writers can be expensive, so hire me as a freelancer and I’ll do it for X price and your life will be grand.

    (I do not use this script, but a properly written variation of it. It’s highly effective). I send about 20 of these a week, and I usually get about 4-5 responses back hiring me (that’s a very high success rate in the writer realm).

    1. Winter is Coming*

      I think the difference is that you are addressing an actual “pain” that your target accounts are responding to. It gets a bit more nebulous as a job seeker because prior to interviewing, they are probably guessing at what the employer’s pains are.

    2. NotherName*

      I think that sounds more like a marketing document based on actual research of a publicly obvious problem. And I assume you don’t send it to random staff at a large company but to the appropriate person who might want that information.

      1. Kat*

        Hopefully! That’s if I can find an appropriate person. Sometimes I can only find one contact name and I take my chances. Shockingly most are very nice and forward it along to the right person.

    3. Brett*

      It has definitely worked for me with freelance secondary work too. I use face to face meetings instead of email or snail mail, but use the same strategy of researching what a potential client does and then talking to them about how what I do can enhance what they do.

    4. Observer*

      You seem to be describing a very niche type of situation, accompanied by research into a publicly visible problem.

      You are also doing it via email, which is a HUGE difference. And you are not trying to obviously bypass a system that is in place for a reason (no matter how bad.)

    5. MsChandandlerBong*

      This is off-topic, but I’m going to start doing this (I’m a freelance writer as well). Four/five responses IS a very good response rate for 20 letters!

    6. Wakeen's Teapots, Ltd.*

      I’m going to quibble a little.

      This is a an approach which addresses pain, but it doesn’t identify pain, and there’s a difference between that approach and the classic pain approach that originated in the sales world.

      Now, I do this. I’m in marketing and I do exactly as you do, address pain, but I teach my sales staff to identify pain. Addressing pain in marketing means that if you market to 1000 with addressed pain, and 600 of those people have the pain that you’ve addressed, you are on the way to a good conversion rate. The other 400 people discard your communication because it doesn’t match their pain but, no big, you’ve got 600 left.

      The sales approach would identify pain one-on-one, asking questions until that particular customer’s pain was clear, and then offer solutions.

  10. NotherName*

    If I knew enough about a company to know what they needed to improve their processes, wouldn’t I already work there? (Or have such an in that I wouldn’t need to send a “pain letter”?)

    I agree with everyone else that this sounds annoying and presumptuous. I’d be interested to know if any readers have seen one of these actually work.

    1. Anonymous Educator*

      Yes! Every place I’ve worked has had some kind of a “pain,” but you usually need to be intimately familiar with (i.e., have worked at) the organization to know enough about the pain to know how to solve it.

  11. Beezus*

    I think they might have a place, but only if you already work for/with the organization and are keenly aware first-hand of a particular problem. My company has a couple of service providers that were founded by former employees who saw a dire need and left to form their own small businesses to fill it, and I’m aware of a couple of positions that were created based off someone saying, “Look, XYZ is a disaster, here are my ideas to fix it, please put me in charge of doing that.”

  12. Hmm Really?*

    This sounds like it is right out of the ‘marketing’ playbook. I went to a series of seminars put on by marketing professors and marketing professionals to better understand how marketing a business is done. The ‘customer pain points’ were kind of the key message throughout. Figure out what the customers problems you solve are and create your marketing message to that. I think it requires a certain skill level to get this right. I get pitches all the time about how the consultant sending it can fix the problems they think I *must* have and most of them come from people I have never even heard of. The ‘problems’ they come up with are sometimes amusing but almost entirely wrong. I am far more likely to hire a consultant that doesn’t take this approach.

    I haven’t heard of someone promoting it as a job application method until now. My first reaction is why? I can only begin to imagine how many different ways this could be perceived as a problematic method.

    I can think of a few times when in interviews a candidate pointed out what they thought was ‘wrong’ with our current staff and how they would solve that. Needless to say I have yet to see a hiring manager want to go ahead with a candidate who does that. As usual AAM has offered a good solid answer to the question.

      1. AcidMeFlux*

        YES!!! I was just going to post a comment like this. And like dating “negs”, it might work on the highly insecure or clueless, but will probably only insult anyone with a minimum of experience.

      2. Hmm Really?*

        What does “negging of the dating playbook” mean? I haven’t heard that expression before?

        1. Lee Ann*

          “Negging is a rhetorical strategy whereby a person makes a deliberate backhanded compliment or otherwise insulting remark to another person in order to undermine his or her confidence in a way that gains approval” – wikipedia.

          Basically, it starts with a putdown – “you’re not as hot as your friend/your teapots just aren’t as shiny as the competition” with the deniability of “but I didn’t say you weren’t hot/your teapots suck!” and then once you accept that, “but I’m willing to hang out with you/work for you anyway”.

    1. periwinkle*

      But… you can turn this around by being the candidate who *asks* the hiring manager about pain point issues rather than assuming. When the interview panel asked if I had any questions, I asked them what they had identified as the biggest challenges facing the department and which of them did they expect the person in this role to tackle.

      IIRC, I picked up the idea for that question from AAM’s book. It was a very good idea.

      1. Hmm Really?*

        Yes, asking what challenges is a good one although I think it is very different than the pain point approach. Asking about challenges shows interest and I have observed while participating in interviewing with hiring managers that most of them really like the ‘what challenges’ question. And get turned off fast with the “I know what your pain point questions are”-however every industry and manager have their own likes and dislikes so who knows.

    2. Observer*

      It does sound like something out of the marketing playbook. But, any playbook that aspires to be even decent, starts with ASKING questions. They will say things like “These are common pain points for companies in this sector. Find the person who does A, B or C and ask them questions J, K and L to find out if they have any the the first 3 issues we mentioned.”

      In other words, understand the common issues in the target market and then ASK questions.

    3. GreenTeaPot*

      Never heard of these letters, but I have received a few that might qualify. Big turnoff. No one from outside the company can accurately guess at the nuances and intricacies of internal “problems.” And it’s arrogant of them to try. Those letters rarely put the sender in a complimentary light.

      1. Kyrielle*

        This. Some of the thought process BEHIND these aren’t necessarily bad – think about problems they might have and skills you have that might be a match – a little bit for tweaking resume/cover letter (not to say “hah, I can solve all your problems THUS” but just to make sure you don’t hide a skill you think might be potentially-relevant), and more for interview prep if you get called. (So that if a question/topic comes up that you could have foreseen, you have some thoughts on the matter ready to go – not to be trotted out unless it actually becomes relevant in the interview, of course.)

  13. Ann*

    Why not use a kind of combination of both; write a cover letter where you present the problem of filling the open position and the solution of hiring you and then go on to show why that would be a good decision for them.

    1. Anna*

      Because that’s close to the “I’m the best candidate and let me tell you why” which Alison also discourages as a cover letter approach.

      1. Ann*

        Sure, if you present it that way, but I think it could work without getting into that territory. But, of course, that’s just my opinion. I know, for myself, this is an approach I might use just to have a starting place and to get my first words onto paper. That’s always the biggest hurdle for me.

  14. Cassy*

    Oh wow thank you whoever wrote this – I saw it on Forbes and went “this feels like a slimy infomercial, I would never in a million years send one of these”, and I was going to send to Alison but got sidetracked.

    1. neverjaunty*

      The very first lines of that sample letter were cringe-worthy.

      It makes me so angry to see people peddling their One True Way to the desperate like this. I guess she got the marketing angle right.

  15. Katie the Fed*

    anything along the lines of “I’m going to tell you why you need me” is an immediate turnoff. It’s MY job to figure out what I need.

  16. Queen Anne of Cleves*

    I think if you worded it correctly and had done your research it is not a bad idea. In an example given by a career advice writer promoting this, the job applicant had spoken with the person who previously held the position and was able to get concrete information about the “pain” the organization was going through. I think this works only if you don’t make assumptions but have accurate knowledge about the facts based on research.

    1. MK*

      Sounds like a big risk (and huge time investment) even then. What if the ex-employee was wrong about the problem? What if you do all that research and yu come up with a solution that can’t work for reasons you aren’t aware of? Or has already been tried? Or one that simply fails to convince the hiring manager?

  17. GS*

    I’m kinda okay with this from a sales standpoint as an external consultant or something. But as part of a hiring process for a permanent employee? Goodness no. And as has been written above, so many of these people who send these letters tend to be all flash and no substance. I once received one of these letters and I was really impressed by what they wrote, and the humor in the letter was enough for me to at least bring them in for an interview. She cancelled twice and no-showed once. (First time “car trouble”. Fine, I’m human, it happens. Second time was a fishy story about her mistaking our office address for another one and she’s an hour away. Googled it, plausible enough but still bad. Third time just never showed up, asked for a fourth, I told her to pound sand.)

    But even on the consulting side it has to be done correctly. A big poo to you to the people who send these e-mails to my CEO about how they can help our business and reference their “telephone conversations with GS” and how they’re looking forward to finally meeting the CEO. Except they’ve never spoken to me, I don’t know anything about it, and thank you for destroying my morning in trying to figure out what the CEO is talking about and why he thinks I’m promising meetings and not telling him. Grrrr.

    1. YogiJosephina*

      Dear Hiring Manager,

      YOU have a problem! These pesky job candidates are constantly sending you ridiculous Pain Letters instead of Cover Letters to apply for your positions. Here’s how I can help you stop that!

  18. Laura*

    I feel like a lot of AAM’s career advice comes down to “be actually good at your job”. But I am not sure how that is supposed to work for people who are just not. If I am not very smart, or have terrible people skills, or am clinically depressed to the point of absolute apathy or have overwhelming responsibilities at home that keep me from focusing much on job performance or for that matter am a virtual zombie with chronic insomnia, how am I supposed to get a job?

    Is there an angle for me? Or am I basically consigned to a fast food career and that is cool with everyone. This isn’t honestly about me. But I have known many who do fit the bill. It seems like the traditional advice is only really appropriate for the top 50%. But there will always be an underperforming half too.

    1. videogame Princess*

      Well, people hire people to do work. It may seem terrible and unfair, but it’s also the fact. So if you aren’t good at the work, then you won’t get a job.

      It sucks, but that’s how it is.

      1. videogame Princess*

        I’m sorry, that was harsh. I will leave this to other people to make better comments.

    2. Anonymous Educator*

      Considering how many nightmare employees / managers we read about on this site, I’d say that there are plenty of people who get hired who aren’t “the best” at their jobs.

      Have you ever been in a hiring position? You usually pick the best person to hire that you can. Would you honestly look at 150 résumés, find the least impressive one, and say to yourself, “Yes, let’s give this person a chance. She/he won’t be hired anywhere else, and why should only ‘the best’ get jobs”?

      1. Anonymous Educator*

        To paraphrase:

        1. Plenty of unqualified or underqualified people have jobs.

        2. But you always want to hire the most qualified if you can.

    3. LisaP*

      Sometimes people look incompetent because they’re in a job that doesn’t take advantage of their strengths. That was me for a few years. I think self-reflection is the most important step of improving oneself.

    4. Shell*

      But the underperforming people aren’t condemned to underperform forever. People improve. We’re not doomed to do the same work we start out with for the rest of our lives. That’s why there are entry level jobs, so people learn and improve and move onto better things.

      Job hunting is hard and the market sucks, but it’s not automatically a career death-sentence if you don’t love whatever you start out as.

    5. TL -*

      I don’t think the people who can do a job well is limited to the top 50% of the population – it’s not a competition, first of all, and it also most likely goes by a bell curve, which would be more like, 70% of the population do an average job that produces good results, 15% are great and 15% are terrible.

      So – making teapot handles, for example. You don’t have to be better than 50% of the population to do a good job; you just have to be able to make 15 teapot handles per day, with an error rate of no more than 1/day. The bosses aren’t saying, okay, only the top 50% of teapot handle makers can do this; they’re thinking, we need to make X/day to profit; an average worker can produce Y/day; we need to hire someone who can also do Y/day. If you can do that, regardless of how many other people can do that, you will do a good job.

      1. Naomi*

        Also, I think there’s a faulty assumption here that everyone can be ranked on a linear scale of how Good At Stuff you are, and the top x% get employed. Different people have different skill sets, and not every job requires every skill. I think there are very few people who are not good at ANYTHING.

        And, as Shell said, people who lack the skills they need can learn and improve!

    6. AcidMeFlux*

      “Is there an angle for me? ” No, because there isn’t an “angle” for anyone.* What there is is hard work AND informing yourself about what kind of training and help you could find AND being brutally honest with yourself AND asking for advice from people you respect. And if that sounds impossible, well, lather, rinse, repeat. *Angles are snake oil. They never work.

    7. neverjaunty*

      Wow, that was pretty unpleasant to assume that everybody who has a “fast food career” is not smart, has terrible people skills, or interpersonal problems that mean they’re incapable of any other work.

      Beyond that, you’ve posted a grab bag of problems that aren’t really related to one another, and may have very different solutions. If you’re talking about a problem specific to you that’s making job searching hard, why not ask AAM directly about it or post in the Friday open thread?

      1. Laura*

        I definitely don’t mean to imply that all fast food workers are in those situations, just that my impression is from doing that work for 10 years or so is that many fast food places hire and fire easily and do not particularly respect their workers. There are a lot of great people in fast food and some restaurants do treat workers well but are often harder to work at.

        To other replies:
        I probably shouldn’t have posted my comment. I’m having a bad day and got a bit frustrated. What I should have expressed is that I wish it was easier for people to find rewarding employment, or that the personal and other skills needed on this path were easier for many people to aquire. Also it makes me upset that people use bad advice to take advantage of those whose fatalism, negative experiences, or lack of savvy make them believe that they can not honestly and straightforwardly hope to personally achieve rewarding employment.

        I would probably have deleted my comment but now it has a bunch of replies. Sorry about that.

        1. Observer*

          What I should have expressed is that I wish it was easier for people to find rewarding employment, or that the personal and other skills needed on this path were easier for many people to aquire.

          I think most of us would agree with you. And, it’s one of the things that make the advice here so useful. It’s targeted at the specific things you need to learn – soft skills, workplace norms, etc. that people need to learn. Even when it’s not everything someone needs to know it’s useful to point someone in the direction of the specific things they need to learn, rather than floundering around.

          Also it makes me upset that people use bad advice to take advantage of those whose fatalism, negative experiences, or lack of savvy make them believe that they can not honestly and straightforwardly hope to personally achieve rewarding employment.

          I think that most of the posters here would agree with this 100%. It sounds to me that this is what is driving so much of the response to the idea. It really feels like someone is trying to take advantage of people. Very icky.

          1. I'm a Little Teapot*

            Laura, I could have posted a very similar comment to yours. I too consider myself in the lower 50% of workers; I’ve had a lot of mental health problems that have seriously interfered with my work over the years, and I made really poor choices of college major and grad program, as well as some other bad choices in general. I have an unimpressive, all-over-the-place resume, mediocre people skills, and no marketable expertise. As suggested below, I currently work in a job not too different from data entry, with a small part-time customer service job. I thought for years that I was terrible at everything and my prospects were hopeless. My current job actually plays to my strengths, though – I am great with detail work. I also have gotten several pieces of fiction published, which finally makes me feel like I am someone. But neither of these things happened until my 30s, and I still share your anger that our society kicks unsuccessful people in the teeth while we’re down.

            1. Creag an Tuire*

              Really, the problem isn’t that employers prefer to hire people with a proven record of doing good work — why shouldn’t they? — but that our society cops an attitude that if you aren’t fit to work, you aren’t fit to live.

              1. neverjaunty*

                Indeed. And that if your work is not fabulously well-compensated or done only by a few, then it’s worthless.

    8. Temperance*

      There are plenty of jobs that just need warm bodies. I would suggest people apply to those instead of aiming too high for jobs they might suck at.

      I’m thinking call centers, data entry, etc.

      1. NotherName*

        As someone who’s worked in and trained for a call center, I’d posit that it can be a very challenging job. You have to have excellent people and research skills while also meeting some very tight time deadlines. (This is specifically dealing with health benefits, so it was on the more skilled end of call center work, but call center work of any kind is challenging in many ways.)

        And the level of detail required by much data entry can be phenomenal.

        Let’s not make assumptions about how hard people’s jobs are. The reason why call centers and data entry places hire so many people is often due to the extremely high turnover rate due to applicants not really understanding what these jobs are really like.

        1. Lora*

          Thank You for your comments on call centers and data entry! Spot On!
          If a company is going to pay you to be there, they are looking for more than just a warm body. Unless you are in the Antarctic and they want you to keep them warm…….

        2. YawningDodo*

          Yup, this. I worked in a call center for all of two weeks while I was in college, soliciting donations from alumni. There was high turnover rate there despite the pay and bonuses (and scheduling flexibility) being quite good for an “unskilled” job because the job was actually very difficult; you had to have top notch people skills, be able to shrug off hostile responses, and know a great deal about the various departments of the university in order to ‘sell’ the idea that it was worth funding. I quit of my own accord, partly because I felt guilty that I had an extremely low success rate, and partly because I was pretty sure the job was going to give me an ulcer.

          And as Nicole J. said below, no one just wants a “warm body.” I work at a nonprofit now, and we hate getting volunteers who only come in to fulfill some mandated requirement. If someone isn’t interested in the work and doesn’t want to learn, they’re worse than useless at even very basic tasks.

      2. Nicole J.*

        I am late to this, but I actually can’t think of any jobs that require warm bodies. As someone who employs catering/events staff (and tries to pay them well, give them recognised training, opportunities for development even in a casual job, and hopefully a good reference if they look for other jobs), I don’t want “warm bodies” – I need people who can be proactive, see what needs doing and do it, do it well, deliver great service, work hard as part of a team, and find solutions to the many little problems that an event can throw at you. The job itself may not be all that complicated, but it still requires attention and commitment, even at the most basic level.

    9. Katie the Fed*

      You should send this as a separate question to AAM. It’s a good question and I think deserves more than the treatment we can give it here.

      But the simple answer is – not everybody is good at everything. If you have severe limitations in your interpersonal skills or other abilities – it’s going to impact your employment prospects. But there probably is a path for you – it’s a matter of finding the right one.

  19. CADMonkey007*

    So basically, a pain letter is an infomercial in letter format?
    “Are you tired of X? Then you need…”

      1. Dr. Johnny Fever*




    1. Solidus Pilcrow*

      Bonus points if the letter includes black and white pictures from the infomercial universe where everything (from opening cans to business processes) sucks.

  20. Anonymous Educator*

    In addition to being obnoxious, “pain letters” are also built on a faulty premise. Even if you do know the “pain” of the organization (you don’t) and even if you think you have the skills to fix the “pain” (maybe you do… maybe someone else has the same skills or better), the assumption in the “pain letter” seems to be that the only thing that’s missing is a skilled or knowledgeable person.

    A lot of “pains” in organizations have nothing to do with skills. A lot of it is legacy crap that bureaucracy or “tradition” keeps in place and can take years or even decades to change. Unless an organization is on the brink of bankruptcy, it’s usually not looking for some savior-type to come in and fix everything. They may be looking for someone to come in and improve things or be better than the person before. Honestly, though—at least in the places I’ve worked—hiring is usually just to replace someone who left. The org would be more than happy to get a better or amazing person hired, but if they could get someone just as good as the one who left, they’d also be fine with it (again, speaking only from my experience).

    1. AndersonDarling*

      It would be frightening if someone wrote a pain letter and actually knew our pains. They would have to have bugs in our building or be hacking into our reports to know the root problems we are addressing. If I received a letter listing these items, we’d have to launch an investigation.

      1. Beezus*

        For a second I misread that and thought you were saying you had bug problems, hahaha!

        “For an extra week of vacation, I’ll even deal with the terrible ant problem in your kitchen!”

  21. Stephanie*

    Wow. I have never heard of this. It seems incredibly presumptuous that you could guess what needs fixing from the outside.

  22. The New Girl*

    I’m familiar with this LinkedIn/Forbes columnist and I generally love her advice and insight. That said, this is one of her techniques that I raise an eyebrow at. I tried a “hybrid” version of a pain letter/cover letter for a role I applied for recently, and in my case, it was effective – it got me an interview. However, I emailed it to the hiring manager (no snail mail for me), threw in a comment about a story I’d read on the company in the news (the employer was a high profile one), and I also had a little insight about the position (I knew someone in a division that worked closely with theirs), so my guesses about the manager’s “pain” were right on. I hate cover letters in general and usually don’t even bother, and I can see a “pain letter” hurting your chances if it isn’t done the right way.

    1. neverjaunty*

      Your comment is reminding me of the old folktale ‘Stone Soup’. I doubt the portion of your letter that was a ‘pain letter’ had much, if anything, to do with it – you had information from someone who worked closely with their division, showed you knew about the company and paid attention to them, and connected with the right person. I seriously doubt making it a ‘straight’ cover letter would have cost you the interview.

  23. Billy Mumphrey*

    These remind me SO much of the Harry Ellis character in Die Hard—-“Hans, bubby, I’m your White Knight.”

  24. Audiophile*

    I’ve never heard of this concept, but I’ve been a regular reader at this point, for over a year. I’ve always just written a cover letter, they’ve gotten better over the years, especially since I started reading this blog. I’ve never really deviated from that. I can’t imagine writing a letter:
    “Dear Hiring Manager,
    I wanted to let you know, I can solve any problem you may be currently having or might have in the future.”
    That’s what I’m imaging these letters look like.

  25. limenotapple*

    Also, the Snail Mail part of this is puzzling. I don’t want to hire someone who thinks the rules don’t apply to them. Just go through the regular channels or you will wind up shredded (ok just the letter, not the person)

    1. Betty (the other Betty)*

      This is the part I wonder about. If the letter and resume are good, is there ever any advantage to using postal mail?

      1. Jadelyn*

        No. There really, really isn’t. I run the resume inbox at my current company, and we’re hiring for 18 positions right now. I come in to anywhere from 30-60 resume submissions every morning. Can you imagine what my desk would look like if all of those were paper copies people had mailed in? And if a hiring manager gets a walk-in or employee referral they like, who didn’t go through the hiring inbox, they have to physically come to my office and give me the paper resume, I have to scan it to my computer, then email it from my own work email address to the hiring email address so that I can then file it in the appropriate sub-folder of that inbox for our records. Thus adding several steps to what should be a simple process of opening an inbox, opening an attachment, reviewing the resume, and either forwarding or filing the email depending on what the resume says.

        Also, as Alison said, sending something postal mail makes you look like a Luddite who’s weirdly out-of-touch with how job searching works in the 21st century. It’s like walking in off the street into a company’s office and asking for a paper application. That might have been a good strategy at one point in time, but nowadays is very much not appropriate, and if you do it you send up yellow flags at best and red flags at worst, because nobody wants to hire someone who’s *that* out of touch with modern workplace standards and culture.

          1. Anonymous Educator*

            In theory, I think the idea is to make you stand out. Of course, in practice, it doesn’t make you stand out in a positive way…

              1. NotJohn*

                There is a real advantage in more technical positions. In larger hard companies (I’m talking about industries over a thousand employees, not some blog or mom and pop soft consulting) the HR person sorting the resume inbox can’t possibly understand every detail of every position.
                It so happens that if John, a super qualified Biochemist Engineer, applies for a position advertised as Org-chemist Engineer (taken directly out of super modern ISO-9001 role descriptions) the poor HR person might just trash the best candidate out there. The hiring manager would know John qualifies, but he/she never even had the chance to know John applied. The way corporations sort through hundred os applicants is usually automated and in the end only a handful even make it to the managers inbox, so in reality, bypassing the gatekeep is a reasonably sound strategy.
                The worst that can happen is for the applicant to be turned down, but that would have happened anyway. At least John had a shot.

  26. stevenz*

    Hey, thanks for this. I never heard of a “pain letter” until now. It’s a really interesting idea and… I’d NEVER send such a thing to an employer. Talk about wasting somebody’s time. There are only two outcomes for writing such a thing – the recipient will roll his eyes and discard it, or he’ll remember the name of the sender, and not in a flattering way. I suppose there’s the off-chance you’ll hit paydirt and find the exact hiring manager who has that exact “pain” and likes your exact “remedy” but it’s more likely you’ll win the Powerball. So ask yourself one question, “Do I feel lucky?” If so, go buy a lottery ticket.

  27. VX34*

    Ahh it’s AAM vs LR.

    I am actually a fan of a lot of things offered as advice or opinion by Mrs. Pain Letter, at least so far as how many terrible HR practices need to be vanquished.

    This letter idea is one I am not at all interested in. Unless you are applying for a position where that level and type of salesmanship is required, I am not really sure what a writer expects to accomplish. Are you going to stand out? Sure, but probably in a bad way.

    Also, she advises this route over “throwing your resume into the ATS black hole”.

    I loathe the ATS as a system, but unfortunately, companies love it.

    Do you know how I got my last job?

    In part by ticking as many legitimate ATS keyword boxes as I knew I had the skills to back up. I was swiftly called and interviewed.

    Plus, I am not now, nor do I ever want to be a Consultant. I am a person who knows how do to things well, with a strong work ethic. Yes, I know, the market doesn’t guarantee “one job your whole life” anymore. But no, I am not consulting for a business of me, thank you very much.

    1. MissDisplaced*

      I’m familiar and read these as well and do find some of the advice quite helpful, especially the advice along the lines of recognizing a bad company/manager, and how to determine what your strengths are and how to value yourself in the marketplace.

      But as with anything, it’s not 100% right all the time, and the pain letter is one of them. But to be fair, I do think there are possibly a few elements of the tactic you could incorporate into a job search. People want to hire people that can HELP them and the company get work done. If your skills align that help them solve a particular problem or issue (the pain) then by all means you can point that out and how you would fit. It’s just that the cover letter doesn’t really seem to be the place to do this and yes certainly not snail mailing it.

  28. Jules the First*

    Well, I think you have to take a lot of this kind of advice with a grain or two (million) of salt.

    That said, the pain letter concept was very useful when I was trying to coach a friend out of writing her terrible cover letters – it got her thinking about what she had to offer. Not that we actually sent any of them to any hiring managers, of course…

    I will say, though, that I revamped my resume using some of the same columnist’s principles, and my interview success rate went through the roof – I sent six resumes, got six interviews and three offers.

    Curious what Alison thinks of the resume advice…

      1. Amber Rose*

        Although she couches it in her usual overblown language, her resume advice is fairly similar to yours. Don’t be vague with meaningless buzzwords like “team player,” list specific achievements, target your job hunt, customize your resume to the job you want. That kinda thing.

        The bigger issue is she always advises skipping the online application and mailing things in. Also I think the specific layout she recommends would result in very long resumes. She likes being wordy.

        1. Mike C.*

          What the hell?? If you skip the online system the very best thing that will happen is someone will hate you very, very much for having to input that data themselves.

          More likely you’ll never, ever be considered.

          Looking at large companies, where in the hell would you even mail the application materials? Think about any largish company that is at least regionally known. It’s never, ever going to work.

          Holy cow!

          1. Dr. Johnny Fever*

            My company does not have a snail mail address for applications. Only online applications are accepted.

            If someone tried to send paper materials, they’d get shredded.

            This is not a way to stand out or get a job in several sectors.

            1. Elizabeth*

              Ditto at my job. In fact, for people to promote/transfer within my company, they still have to go through the same system we use for outside applicants. If someone sent in paper stuff, at most they might get a call to go through the online system to apply. But they aren’t going to get interviews or anything else without going through the system.

        2. One of the Sarahs*

          I am goggling, because it sounds like she’s advising “ignore what the company is asking for”, which seems like a one way trip to the bin for the application.

  29. Jadelyn*

    Oh god, I can’t stand that person…I keep seeing her columns in my weekly Monster article digests, and every time I give in to the trainwreck-watching urge and click through, it’s just her being unbelievably smug and self-satisfied about her Unique Solutions To Things and making a lot of very broad, insulting claims about HR in general to make said solutions look better (which I do take a bit personally) without substantiating anything aside from “because I say that’s how it works”. A family member once sent me a piece that woman had written about “worst HR practices that should be ditched” or some such, and I agreed with her on I think 2 of them – maybe as many as four or five if we count the things that would indeed be awful practices if I’d ever seen or heard of an employer doing them, but which I’m fairly sure either went out of use 20 years ago or she made up entirely. The rest was, again, her telling the reader how much smarter she is than the entirety of the HR profession.


    Sorry, she just drives me nuts. The thing is, yes some ATSs can be overzealous about screening good candidates out over minutiae, and some hiring processes are overly involved and tedious, but for the most part, hiring processes have evolved the way they have for a reason. Deliberately choosing to go around the established process by disregarding instructions for applying just tells me you think you’re an extremely special snowflake who will probably expect to do whatever you want and get away with it on the job, too.

    And for the love of all that is good in this world, if there’s an electronic resume submission process in place, do not make me deal with paper. I will hate you and will bury your resume where they will never, ever find it.

  30. Mike C.*

    I don’t say this enough, but I really, really appreciate that AaM doesn’t engage in this sort of facile/dishonest/conflict of interest-ridden crap like “pain letters” that you see all throughout the world of business/career/work related media.

    1. neverjaunty*

      Indeed. AAM is upfront about having a book, but her advice is NEVER “and you can learn all about this if you buy my book” or “all you need to do is follow my special paid program to get a job”.

  31. Maggie*

    Oh, I see this lady pop up on LinkedIn all the time and thought her advice was kind of bonkers but then wondered if I was being old fashioned. I’m glad to see my hunch validated! I will say she is certainly good at getting her name out there!

  32. learningToCode*

    I follow the certain article writer on LinkedIn and her articles always felt icky to me. Especially when those tactics are being told to fresh out of college folk like myself. I have nowhere near the experience and confidence in the workforce to pull off thinking so highly of myself.

    On top of the advice being a bit out of touch, the wording is what makes it feel like a scam… putting unique names on things so your brand is associated with that phrase to improve your articles’ SEO. Like how everyone in this thread either knew what a pain letter was or could easily Google it. It comes across as overly salesman-like, and coupled with the advice itself, feels very fake.

    I may just be overly critical since I drank the water for a few months out of college before mentally coming to terms with never wanting to be the kind of person who was such a salesman.

  33. SandrineSmiles (France)*

    Not sure if anyone has done this, but…


    Yup, pain letters indeed.

  34. Dave*

    I got a job with a kinda pain letter, but there were some special circumstances.

    First off, the letter didn’t say “I understand all of your problems and can fix them,” but rather suggested what I might contribute to their specific business—that I had skills that they needed but without implying that they were doing things wrong, or weren’t aware of their own problems, or that I was some kind of super-being who was going to swoop in and make their lives easy. It was based on my understanding of the issues facing their industry in general and how I could help them solve them.

    Second, it was a small business that still handled a lot of paper and didn’t use an HRMS of any sort. I knew this because of my third point:

    I knew somebody who worked for the company who told me exactly who to contact and that my approach wouldn’t elicit the kind of negative reaction that these things often do.

    So I think they can work… if they’re not actually “pain” letters so much. :)

    1. neverjaunty*

      In other words, it wasn’t the pain letter that got you the job.

      I alluded to this upthread, but this is like the folktale “Stone Soup”, where everything but the useless part (the pain letter) is what got the person the job, yet they still say ‘hey, the pain letter kind of worked’.

      1. Anonymous Educator*

        Yes, I’ve seen that a lot—not just with “pain letters,” but pretty much anything. A lot of people believe “I got the job” or “I got into that school” logically means “everything I did in the application process is something that got me the job and that I should recommend to other people.”

    2. MommaTRex*

      I think a good cover letter is supposed to tell the potential employer how you can contribute to their business, so I would argue that maybe your “pain” letter wasn’t really a pain letter, but just a really excellent cover letter.

  35. Middleman*

    I’ve received “pain letters” before and always have found them irritating and insulting. Every single time, they either bring up an issue that I am already well aware of and in the process of addressing, or the writer’s perceived “problem” to be fixed is not a problem and is the case for a reason, which demonstrates the writer’s lack of awareness of my industry.

  36. Bubba*

    I’m so glad we’re talking about this as I generally love that particular person’s career advice, but have not been able to get behind the “pain letter” idea. I did add one thing to my more-or-less standard cover letter, and after reading everyone’s comments here, I’m wondering if it is coming off as obnoxious or presumptuous. I’m looking for a job in communications, by the way. What I say is something along these lines: “From your job description it sounds like you are looking for someone who is x, y, and z. I have demonstrated those qualities throughout my career.” Generally it is something along the lines of “someone who is creative, big-picture and strategic, while also being detail-oriented” — since just about job listing sounds like they are looking for a person who can do it all, and who wouldn’t want someone with those skills? Curious to hear what you think. Thanks!

    1. Ask a Manager* Post author

      The thing about that is that anyone can claim those things whether they really have those qualities or not (and many people do claim it even when it’s not accurate) so it’s not particularly compelling. Try giving examples of how you’ve demonstrated those qualities instead; that will be a lot more effective!

  37. wekcar*

    So how exactly does one get noticed without such a track record? Gimmicks definitely have their place in such cases, no?

    1. fRED*

      So how exactly does one get noticed without such a track record?

      Demonstrate your enthusiasm.

      Gimmicks definitely have their place in such cases, no?

      Would you hire someone on the basis of how gimmicky their CV was? (assuming you’re not in the gimmick business).

  38. James*

    It seems to me that if a hiring manager A) finds an attempt to connect with them on a human level presumptuous and B) wants to put that person’s info into a management system designed to keep as many qualified applicants as possible from crossing her desk, then said applicant isn’t the right fit for her company regardless of their qualifications.

    1. Mark*

      Absolutely agree, although I would have said ‘this company isn’t the right fit for that applicant’. If your company treats those who want to try and go above and beyond to actually get their resume, cover letter, ‘pain’ letter or whatever read by a person at your company specifically by writing a letter directly to you as ‘luddites’ or ‘gimmicky’, it is your company that has a problem. The whole modern HR system is designed to try and evaluate as many people as possible without ever actually reading anything those people have to say about themselves, so can you really blame people who are truly excited to get the job for trying alternative approaches? Apparently yes, you can.

      You think you’ll find the best talent by ignoring those people and using software to discard thousands of resumes until you find the one with the right keywords stuffed into it? Good luck to you, but don’t expect your company to still be around in ten years time.

  39. Lily*

    Thanks for writing this! Not everything works for everyone and if writing “pain letters” work or have worked for you; great! I hate writing “pain” or cover letters, period. I find them useless, but since they are required, I do it. We are sending these “letters” to people and depending on the person, they might prefer one letter over the other. As an applicant, I have no way of knowing so sending you either one, I am already playing with the odds.

    I do believe a “pain letter” cannot be used for all career fields. I work in behavioral health so imagine me writing a Clinical Director telling them their problem is not getting enough substance abusers sober and how I can fix that. I cannot “fix” or “solve” this, not to mention, it is not “their” problem.

    I am currently applying for a position and it clearly states on their website that I cannot send my resume/cover letter via mail, fax or email. There goes sending a “pain letter” through the postal mail to a hiring manager. I think Liz has great advice on certain topics related to HR. By no means does having xyz amount of followers remove her work/advice from being examined.

    I know that I am enough and refuse to do gimmicks to stand out. I find my own way to get noticed. Every employer I apply to does not have to call or interview me. There is always one employer that will see from my resume and cover letter how I can excel at the role as they’ve laid it out. Great point of view :)

  40. Marry Paul*

    While I understand that a well qualified applicant can get lost in a black hole of online application, it seems to me that most of the comments against a pain letter are on the hiring spectrum (HR or hiring managers), the others making a case for a pain letter are on the other end. As someone in the job market, I’ll have to examine the probability of my application hovering in black space and a manager feeling offended by my “presumptuous arrogant” pain letter

  41. emma2*

    I have read about the Pain Letters, but I also was at a loss as to how on earth I could write one being 1) Only so knowledgeable about the company from the outside regarding there specific problems, and 2) being an entry level worker with not much experience. That being said, I also don’t know how to get past the cyber vortex that is ATS application system.

  42. Jack*

    No no no!

    The good “pain letter” is one which acknowledges the applicant has done her research on the company. It BETTER not be an analysis of all that’s perceieved as wrong in an organization, and it BETTER not be a list of solutions to issues they will have no part of if hired. Agree, that’s not good.

    Let’s forget the branding for a moment.

    So many people greatly overuse the word “I” in cover letters. “I’m great at this, I did that, I can do these…” I tell my students to give the employer a brief shout out…”Congratulations on the recent launch of _________…”

    The goal is to, in a paragraph, show she’s done her homework and knows something about the company she’s applying to. The second paragraph is to tie her bona fides with the exact, specific job she’s applying for!

    What are your thoughts on the above?

  43. private*

    Yes, but you don’t address the fact that we have to set up portals on tracking sites(who now have our sensitive information; and gawd knows where that ends up because you are entering this information and sending it over unsecured servers) along with the fact that even though you customize your resume with matching job description verbage; the employer never ends up seeing your resume credentials. In my opinion, going through all this BS applying online for jobs is insane; dysfunctional; employers don’t list what they pay resulting in wasting everyone’s time – all just a crap-shoot at-best.

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