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Page 1 Anatomy of a Pain Letter by Liz Ryan CEO and founder, Human Workplace

Anatomy of a Pain Letter

by Liz Ryan CEO and founder, Human Workplace

Copyright Human Workplace 2012. Not for transmission or duplication (except to Denver Post Blog readers!)


What’s a Pain Letter?

When we apply for a job, it is critical that we write a letter we call it a Pain Letter that speaks to the hiring manager about something more important and more top-of-mind to him or her than the requirements listed on the job spec. The set of listed requirements is typically used as a filter to screen out candidates.

The listed job requirements may be very tangential to the real reason the job exists. For our letter to have impact, we have to use it to speak to what’s really at work when a hiring manager places a job ad. That more-important-something is some sort of pain - some sort of business pain.

No Pain? No Job Opening

The economy is not in the best shape right now. CFOs and the people who control the purse strings in organizations are not dying to hire people. They would rather lay people off, if they could, in order to save money. If there’s a job ad posted, then we know that somebody has some very serious and very expensive business pain going on.

Something’s not working. Either people aren’t picking up the phone and the customers are getting angry and leaving us to go to the competition, or products that are critical for revenue generation are not getting out the door, or accounts receivable are out of control and the company’s cash reserves are getting very low.

Something bad is going on. And that’s a really powerful realization to make because it means that we as jobseekers have some power in the equation. We have more power than we may know because if we’re the one who can come in and solve that business pain, then we become a very, very important person for that employer to know.

But we’re really not taught to go after jobs this way. We’re taught to say, “Oh, you want someone who types and sews and spins and weaves and churns butter. I do all those things.”

I Do This, I Do That No Good

That’s no good. There are going to be tons of people who do all those things. We can’t win that way. We can’t get any higher than the level of ‘as good as X number of people.We have to virtually ignore the requirements in the job ad and we have to figure out, why did they place this ad in the first place? What is the pain? It’s exactly like selling a

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product or service. You will sell people successfully on products and services when you’re able to show the buyer that purchasing your product or service will relieve their pain. It’s the same way in a job search. We’re not trained to think about business pain in terms of a job search, but the notion of spotting and digging into business pain is very, very relevant for job-seekers.

Let’s Write about the Pain the Hiring Manager is Feeling

Once we have a sense of the business pain that the employer is facing, we gain power. Now we can write a letter – we don’t call it a cover letter, because it’s got a lot more heft than that. We call it a Pain Letter. We will write directly to the hiring manager and in our letter, we’ll talk about the business pain that we imagine the employer to be facing -- the thing that’s actually keeping him or her, the hiring manager, up at night.

When we do this thoughtfully, very often we can get an interview over people who have more of the listed job requirements than we do. So this is a very, very important notion. We’re not going to job hunt to speak to the listed requirements in a job ad. We don’t even have to confine our job search activity to responding to job ads.

We’re not going to write any more cover letters that are basically just a piece of paper that says, “Well, here’s a resumé” because the resumé’s job is very, very different than the cover letter’s job. A resumé’s job is to say, “Here is a person whose strengths and accomplishments are X, Y, and Z, and who’s been particularly successful in areas A and B.” Our resume describes the product known as you.

Say, I Know That Dragon!

Our Pain Letter has a very different job, and that job is to say, “Here’s why this person is worthy of your time, Mr. or Ms. hiring manager. We are going to use our Pain Letter to let the hiring manager know that we have a decent sense of what he or she is up against, and that we’ve had highly relevant experience slaying the exact same dragon in another setting.

Who’s the Decision-Maker?

As we begin to write a Pain Letter, the first thing we’ve got to do is to find the decision- maker. When we have a decision-maker to write to and when we don’t have a LinkedIn connection or a three-dimensional, traditional connection who can make an introduction for us, we’re going to write to that hiring manager through the US mail, a/k/a snail mail. We’re going to send a letter with our resumé, via snail mail.

Pain Letter Formula

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Here’s the formula for a pain letter. We start off with what we call a hook. Most often, that hook comes right off the website, and isn’t tough to find. We’re going to say, “Dear Jane, congratulations on the green building award that you guys won from the Downtown Improvement Association.” We found that news tidbit on the employer’s website. Virtually no one does this in a job search, and it’s very easy to see how starting off a letter by talking about the employer rather than about ourselves would have positive results.

For one thing, we’re making it clear that we’re awake, that we’re paying attention. We’re making it clear that this Pain Letter is not a boilerplate letter that we send to one employer after another. We’re showing that we are tuned in to what’s happening at this employer that we are interested in.

We’re not going to start off our Pain Letter talking about us – we’re going to talk about them. They’re the subject of the letter. “Congratulations on being voted one of the top

fifty companies in Fort Wayne.” The hook for your letter is typically not hard to

going to be in the press section of their website and you can go back as far as six

months in time.


If you find a decision-maker who speaks or writes or sits on panels, you’ve got it made, because you’re going to Google his or her name and you’re going to say, “I loved what you said at the conference last week, particularly when you said that kelp is the new hemp,” for instance. You are going to call attention to what they said and believe me, that person is going to keep reading your letter.

They’re not going to put it to the side because very, very few job-seekers do this. Nobody writes to them and talks about them. So the very first thing in your pain letter is a hook.

Now We Mention the Pain

From the hook, you’re going to go right to the pain. How do we find the pain? Nine times out of ten you can spot the pain in the job spec. You think, “Why is this job open?”

There’s growth-related pain. Growth is great, but it’s not free from pain. There is contraction-related pain. There’s acquisition-related pain. There’s re-org related pain. There are just not that many kinds of pain. If you take a stab at it, you’re probably going to be somewhere in the ball park.

When you write to an employer about the most likely business pain, how do you address the pain without sounding condescending? We’re not going to say, “Oh, you poor thing! You don’t know what the heck you’re doing over there. You’ve got all kinds of problems.”

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This is what we’re going to say. “Given your tremendous growth, I wouldn’t be surprised to find that your talented marketing team is stretched to the breaking point.

Often, the business pain proceeds right from the organization’s own news. If they’ve been laying off people, and you are an HR person, you’re going to write to them and say, “Given the recent changes in your business, I wouldn’t be surprised if you could use an experienced Employee Relations person.”

We are not going to write to them and say, “I have this skill, I have that certification, I have the other one, I tap dance, I sing.Employers are not going to see the connection between our litany of “I haves” and their own pain, unless we connect the dots for them. We’re going to say, “Boy, I see that you guys are doing x, y, z” and we’re not going to say, “I read it in the newspaper. Gold star for me.” We’re going to mention what’s going on with our target employer, because we’re businesspeople and we’re paying attention.

It is electrifying to a hiring manager to read about their own issues in a letter from a job- seeker that is to say, a wise consultant – because it’s so uncommon, and because it speaks directly to what’s top-of-mind for them. We often get, and of course are looking for, the reaction “Wow! This person understands what I’m up against. This person is speaking to me about what I care about.” That’s your advantage with the pain letter.

Your Dragon-Slaying Story

So now you’ve done the hook, you’ve done the pain. Now you’re going to show up with relevant experience and you’re not going to drop the energy level to zero by saying, “I have twenty years of experience.” That does not resonate. You’re going to tell one very short little story. You’re going to make that story concrete and relevant.

You’re going to say, “When I was at XYZ Graphics, we went through similar consolidation, in which we had to lay off staff, re-organize, and quickly put teams together. And we made that happen without a drop in productivity or revenue.” For an HR person to talk about revenue is very powerful.

For an IT person or any non-sales person to talk about revenue is a good thing, if we have that insight and that altitude on our own experiences. The hiring manager is going to be excited saying, “This person understands the business ramifications of their work. It’s wonderful and I want to meet them.” That’s what happens, very often, with these pain letters.

Now let’s get to the hard part. That part’s actually kind of easy – what we’ve talk about so far, right? You will get good at this and you’ll have fun writing these pain letters. The hardest part is not very hard, but it can be tedious. That part is finding the decision- maker. If it’s a very big company, like IBM, it can be extremely challenging to impossible

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to find ‘our’ hiring manager. The company is too large – it’s too difficult from the outside, unless we have a friend inside, to navigate the org chart and locate that person.

But in a medium-sized company, or in a small organization, you absolutely can find ‘your’ hiring manager. You’re going to start on the company website. If it’s not an enormous company, you can write to the head of your function. You can write to the VP of Marketing, if you’re a Marketing person.

In a smaller organization, you can write to the CFO. You’ll send a letter in the mail, that’s regular old snail mail, using white bond paper, and that will be same exact paper, same exact typeface as your resumé.

Send Your Pain Letter with Your Resume in the Mail

You’re going to find that person’s name on the website, and you’re going to block print that hiring manager’s name, title and street address with a pen on the envelope, as opposed to printing the information on the envelope using your printer. It’s counterintuitive, I know, but I talked to a mail room manager and he said printed material, that is, hand-lettered envelopes, always get through. So you’re going to personalize it with a pen in your hand but don’t put “personal and confidential” because it’s not that, of course. It’s still business correspondence.

Put a stamp on it, and off it goes. You could do two of them a day and if you start to do two of them a day, you’re going to get some traction because the response rate on these things is 10% in my experience. So two Pain Letters going out the door a day will obviously give you ten a week, and that’s one return call a week, which is pretty good. It’s a lot better than the black hole in any case.

So we start with the company’s own website looking for this decision-maker, but maybe the company’s a little too big. If you’re in marketing, and if the VP of Marketing is sitting three levels up from your target job, then we probably want to find someone who’s closer to the job than the VP. We don’t really want to write to the VP of Marketing in a case like that.

What else could we do? Well, we can go to LinkedIn. You have to join LinkedIn in order to be able to search on LinkedIn but it’s worth it. It takes half an hour or forty minutes to set up your profile, and it’s absolutely a must for business job seekers, and businesspeople in general.

You’re going to set up a LinkedIn profile, and then you can start to search on LinkedIn. The PEOPLE tab on the upper left hand side of the LinkedIn screen is the search tab.

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You can go right to that area of the site, search on the company name and the title that is most likely to be associated with the person you’re trying to locate. And you know what, if you find a person who is close but who is not ‘your’ hiring manager, for instance, she sits in the next office over, you haven’t embarrassed yourself. She’s going to pick up the letter and she’s going to walk it one office over. It’s still so, so much better than going through the black hole.

The third way to find your hiring manager is to Google the company name and the most likely title. You’d type the terms Marketing Director and XYZ Graphics into a Google search box, and your target hiring manager’s name is going to pop up, a good percentage of the time, either because they’ve been quoted somewhere, they wrote an article, or they went to a conference. You’re going to be able to find them, very often.

Here’s one other place to look. That is, a business research site that lists managers zillions of companies. So that piece of the Pain Letter process, finding the decision-maker to write to, is typically the most time-consuming part of the whole exercise. It might take you twenty minutes to find that decision-maker, but you’re going to feel very good when you put that letter in the mail.

My client/friend in Phoenix was looking for a job, and she wrote to the COO of a multinational company in New York. A week later she got a call from the VP of Operations, that’s her hiring manager, in Phoenix, because he had the letter that she sent to the COO in New York, the physical letter. They sent it through one of those inter- office mail envelopes. And he had the letter with scribbles on the margin.

She was trying to angle around to see the scribbles but she couldn’t read them, but it doesn’t matter because she got the job. She wrote directly to the COO in New York. He’s paying attention because she’s paying attention. He says to his regional VP, “You have to interview this lady. You have to interview this person out there in Phoenix.”

If you can do two of these Pain Letters a day, you’re going to get very good results I predict. It’s very exciting and very gratifying because you’re writing to a person as an equal now. You’re not writing to them with the approach “May I crawl over broken glass to kiss the hem of thy Majesty’s robe?” You are too senior to do that kind of thing. You’re going to write a Pain Letter that goes right to the decision-maker and it’s very, very gratifying to see those results.

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Applying for Non-Posted Jobs

Now, we’re going to talk about applying to non-posted jobs. A lot of us don’t do that, because we think, “Well, why is someone going to hire me when the job’s not posted?” The reason they would hire you even in that case is because everybody in business has pain. It’s really not a question of whether they have pain. They have pain and they probably have pain that you can solve. The only question is, do they have money? So when people don’t call you back on a pain letter that you sent into a company that does not have a job posted, it may not be the case that they can’t use you. It may be just that they can’t pay you. So they don’t call.

It’s very freeing when you realize “I don’t have to wait for job ads. I can write to anybody. I can research companies and I can go after every architecture firm in Boston” or “I could go after every CPA firm in Denver, to be a network person for them, because why not?”

It’s much more common for companies to be in the mode where they have the pain and they need the help but they haven’t yet posted the job than it is for them to be in the mode where the job is posted and they’re reviewing resumés, because that mode is only four or five weeks long. The other one might be six months.

Your resumé and your pain letter hitting that decision-maker’s desk when there’s no job could be the reason that they actually open up a requisition to hire someone, because the manager walks down the hall to the CFO or the Controller’s office and says, “You know, you and I have been going back and forth and back and forth on whether we can afford another marketing person. Look at this resumé. Look at this person who is writing to us about our stuff, what’s going on with us. She’s totally on the ball. Let’s just bring her in here and if she seems like the right one it will be a message from the universe and we’re going to hire her.”

And then you’re the only person that interviewed for the job. And it happens every day. You don’t have to wait for a job ad. The right time of year to do that of course is anytime at all, because companies always need help. It’s just a question of whether they have budget.

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Here is a sample Pain Letter:

Declan McManus Vice President, Marketing Exclusive Chocolates, Inc. 4840 Whispering Pine Road Boulder, Colorado

Dear Declan,

I was lucky enough to catch your speech at the Boulder Natural Foods Expo last month, and delighted to learn about Exclusive's plans for expansion into dessert toppings. You've hit a chord with the chocolate-loving public, and the Wolfgang Puck deal announced last week is a wonderful green light from the market for Exclusive's take on organic chocolates.

I wouldnt be surprised to read that these opportunities are taxing your talented Marketing team as well.

When I led the new-products efforts for Angry Chocolate during its high-growth phrase (just before the company's acquisition by Nestle) we had at least one major launch per month. Among other things, we were on the hook to create a sugar-free version of Angry Choco-Mints in time for Chocoholic Expo '07 and serve our loyal domestic partners during two years of 25% growth.

We prevailed - our Sugar-free Angries took Best New Product at the show - and if Exclusive is in need of hands-on go-to-market, channel-marketing and new-product- launch-related Marketing help, I'd love to look at ways to help your team.

If you have time for a telephone call or email correspondence to see where we might have an intersection of interests, I'd be delighted to learn more and share a bit of my background with you.


Mike Myers

What is Human Workplace?

Human Workplace is a think tank, online community and consulting firm. Our mission is to bring human energy into the workplace and redesign work for humans. We work with employers, institutions and individuals on their branding, career and talent strategies, and human-voiced communication.

Copyright Human Workplace 2012. Not for transmission or duplication (except to Denver Post Blog readers!)


Page 10 Copyright Human Workplace 2012. Not for transmission or duplication (except to Denver Post Blog

Copyright Human Workplace 2012. Not for transmission or duplication (except to Denver Post Blog readers!)