Anatomy of a

Pain Letter
by Liz Ryan
CEO and founder, Human Workplace

Page

www.humanworkplace.com

Copyright Human Workplace 2012. Not for transmission or duplication (except to

Denver Post Blog readers!) www.humanworkplace.com

Whats 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 whats 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 theres a job ad posted, then we know that
somebody has some very serious and very expensive business pain going on.
Somethings not working. Either people arent 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 companys cash reserves are getting very low.
Something bad is going on. And thats 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 were 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 were really not taught to go after jobs this way. Were taught to say, Oh, you want
someone who types and sews and spins and weaves and churns butter. I do all those
things.

Copyright Human Workplace 2012. Not for transmission or duplication (except to

Denver Post Blog readers!) www.humanworkplace.com

Page

Thats no good. There are going to be tons of people who do all those things. We cant
win that way. We cant 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? Its exactly like selling a

I Do This, I Do That No Good

product or service. You will sell people successfully on products and services when
youre able to show the buyer that purchasing your product or service will relieve their
pain. Its the same way in a job search. Were 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.

Lets 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 dont call it a cover letter, because its 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, well talk about the business pain that we imagine the employer to be facing -- the
thing thats 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.
Were not going to job hunt to speak to the listed requirements in a job ad. We dont
even have to confine our job search activity to responding to job ads.
Were not going to write any more cover letters that are basically just a piece of paper
that says, Well, heres a resum because the resums job is very, very different than
the cover letters job. A resums job is to say, Here is a person whose strengths and
accomplishments are X, Y, and Z, and whos 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, Heres 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 weve had highly relevant experience slaying the exact same dragon in another
setting.

Whos the Decision-Maker?

Pain Letter Formula

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

Page

As we begin to write a Pain Letter, the first thing weve got to do is to find the decisionmaker. When we have a decision-maker to write to and when we dont have a LinkedIn
connection or a three-dimensional, traditional connection who can make an introduction
for us, were going to write to that hiring manager through the US mail, a/k/a snail mail.
Were going to send a letter with our resum, via snail mail.

Heres 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 isnt tough to find. Were 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 employers
website. Virtually no one does this in a job search, and its 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, were making it clear that were awake, that were paying attention. Were
making it clear that this Pain Letter is not a boilerplate letter that we send to one
employer after another. Were showing that we are tuned in to whats happening at this
employer that we are interested in.
Were not going to start off our Pain Letter talking about us were going to talk about
them. Theyre 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 find. . Its
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, youve got it made,
because youre going to Google his or her name and youre 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.
Theyre 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, youre 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?

Copyright Human Workplace 2012. Not for transmission or duplication (except to

Denver Post Blog readers!) www.humanworkplace.com

Page

When you write to an employer about the most likely business pain, how do you address
the pain without sounding condescending? Were not going to say, Oh, you poor thing!
You dont know what the heck youre doing over there. Youve got all kinds of problems.

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

This is what were going to say. Given your tremendous growth, I wouldnt be surprised
to find that your talented marketing team is stretched to the breaking point.
Often, the business pain proceeds right from the organizations own news. If theyve
been laying off people, and you are an HR person, youre going to write to them and say,
Given the recent changes in your business, I wouldnt 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.
Were going to say, Boy, I see that you guys are doing x, y, z and were not going to
say, I read it in the newspaper. Gold star for me. Were going to mention whats going
on with our target employer, because were businesspeople and were paying attention.
It is electrifying to a hiring manager to read about their own issues in a letter from a jobseeker that is to say, a wise consultant because its so uncommon, and because it
speaks directly to whats top-of-mind for them. We often get, and of course are looking
for, the reaction Wow! This person understands what Im up against. This person is
speaking to me about what I care about. Thats your advantage with the pain letter.

Your Dragon-Slaying Story

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

Copyright Human Workplace 2012. Not for transmission or duplication (except to

Denver Post Blog readers!) www.humanworkplace.com

Page

Now lets get to the hard part. That parts actually kind of easy what weve talk about
so far, right? You will get good at this and youll have fun writing these pain letters. The
hardest part is not very hard, but it can be tedious. That part is finding the decisionmaker. If its a very big company, like IBM, it can be extremely challenging to impossible

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.
Its wonderful and I want to meet them. Thats what happens, very often, with these pain
letters.

to find our hiring manager. The company is too large its 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. Youre going to start on the company website. If its not an
enormous company, you can write to the head of your function. You can write to the VP
of Marketing, if youre a Marketing person.
In a smaller organization, you can write to the CFO. Youll send a letter in the mail, thats
regular old snail mail, using white bond paper, and that will be same exact paper, same
exact typeface as your resum.

Send Your Pain Letter with Your Resume in the Mail

Youre going to find that persons name on the website, and youre going to block print
that hiring managers name, title and street address with a pen on the envelope, as
opposed to printing the information on the envelope using your printer. Its
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 youre going to
personalize it with a pen in your hand but dont put personal and confidential because
its not that, of course. Its 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, youre 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 thats one return call a week, which is pretty good.
Its a lot better than the black hole in any case.
So we start with the companys own website looking for this decision-maker, but maybe
the companys a little too big. If youre in marketing, and if the VP of Marketing is sitting
three levels up from your target job, then we probably want to find someone whos closer
to the job than the VP. We dont really want to write to the VP of Marketing in a case like
that.

Copyright Human Workplace 2012. Not for transmission or duplication (except to

Denver Post Blog readers!) www.humanworkplace.com

Page

Youre 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.

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 its worth it. It takes half an hour or forty minutes to
set up your profile, and its absolutely a must for business job seekers, and
businesspeople in general.

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 youre 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 havent embarrassed yourself. Shes going to pick up
the letter and shes going to walk it one office over. Its 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. Youd type the terms Marketing Director and XYZ Graphics into a Google
search box, and your target hiring managers name is going to pop up, a good
percentage of the time, either because theyve been quoted somewhere, they wrote an
article, or they went to a conference. Youre going to be able to find them, very often.
Heres one other place to look. That is www.zoominfo.com, 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 youre 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, thats 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 interoffice mail envelopes. And he had the letter with scribbles on the margin.
She was trying to angle around to see the scribbles but she couldnt read them, but it
doesnt matter because she got the job. She wrote directly to the COO in New York.
Hes paying attention because shes paying attention. He says to his regional VP, You
have to interview this lady. You have to interview this person out there in Phoenix.

Page

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

Copyright Human Workplace 2012. Not for transmission or duplication (except to

Denver Post Blog readers!) www.humanworkplace.com

Applying for Non-Posted Jobs

Now, were going to talk about applying to non-posted jobs. A lot of us dont do that,
because we think, Well, why is someone going to hire me when the jobs not posted?
The reason they would hire you even in that case is because everybody in business has
pain. Its 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 dont 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 cant use you. It may be just that
they cant pay you. So they dont call.
Its very freeing when you realize I dont 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?
Its much more common for companies to be in the mode where they have the pain and
they need the help but they havent yet posted the job than it is for them to be in the
mode where the job is posted and theyre reviewing resums, because that mode is only
four or five weeks long. The other one might be six months.
Your resum and your pain letter hitting that decision-makers desk when theres 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 Controllers 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 resum. Look at this person who is writing
to us about our stuff, whats going on with us. Shes totally on the ball. Lets just bring
her in here and if she seems like the right one it will be a message from the universe and
were going to hire her.
And then youre the only person that interviewed for the job. And it happens every day.
You dont 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. Its just a question of whether they have
budget.

Page

You can do this! Download more job-search and career advice at

www.humanworkplace.com, or write to our Operations Manager, Michael, at
[email protected].

Copyright Human Workplace 2012. Not for transmission or duplication (except to

Denver Post Blog readers!) www.humanworkplace.com

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-productlaunch-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.
Yours,
Mike Myers

Copyright Human Workplace 2012. Not for transmission or duplication (except to

Denver Post Blog readers!) www.humanworkplace.com

Page

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. www.humanworkplace.com.

What is Human Workplace?

10
Page

Copyright Human Workplace 2012. Not for transmission or duplication (except to

Denver Post Blog readers!) www.humanworkplace.com