Resources: Never Write Another Cover Letter, Part 1

Cover letters. Ugh. We know. Even saying the words makes our fingertips ache with sorrowful anticipation.

But that's kind of the point, isn't it? No one really goes into a cover letter knowing quite what to say or how to sell their skills to an employer, unless you have preexisting knowledge of the employer or hiring manager, or you are referred to the interview process by an employee of that company -- in which case it can feel like even more useless exercise.

We tend to treat cover letters as ancient bureaucratic rights of passage that are somehow vestigial remnants of a job application process that hasn't quite caught up with evolution, akin to strange rituals like waiting in DMV lines and voting for our elected representatives only on Tuesdays. As a personal branding tool, it's basically understood to be the wisdom tooth of our professional anatomy, especially in a culture driven by the visual and audio stimulants that bombard our brains and social networks every day.

But there is indeed a purpose to the cover letter and a powerful one at that. While much depends on how you utilize those three paragraphs (and, yes it should be no more than three major paragraphs), if you are an early career-stage knowledge professional of any kind, putting together a well-written cover letter together can demonstrate your written communication and persuasive skills to your potential hiring committee in powerful way. In a competitive applicant pool, it can push you over the top of other candidates with similar qualifications.

So don't tear our hair out over this. I've found that there is a good process you can use to combine two different approaches which will soothe your word processor-induced tension headache and improve your job search experience overall.

One approach is a bit more irreverent but has the potential to be highly effective, while the other requires a nose for details. If you put these two approaches together, it will slow down your job application process at first, but I guarantee it will improve your job search outcomes over the long run and keep you from spinning your wheels -- or weeping over your keyboard.

*Here's a tissue.* Now let's begin.

1. Begin with Irreverence! Use the Pain Letter.

My first suggestion is to get up to speed with the wonderfully preternatural and accomplished Liz Ryan from Human Workplace as she walks you through her patented solution to writing an effective introduction to a hiring manager or HR professional at your target employer, the Pain Letter. We list several resources below that you can use to build your own.

Liz's approach to the pain letter is a research-driven way to insert your skills and knowledge directly into the core operations and needs of an organization you're dying to work for. It provides a hard-hitting framework to make that fit plain to a hiring manager and leaves no room for doubt about your expressed qualifications. It's also easier and less messy to write as a template.

However, writing your Pain Letter using this framework will reveal your strengths or your vulnerabilities. A Pain Letter is not to be used loosely or sent to bounce around the inboxes and offices of HR professionals without having done your research first. Here's why ...

2. Research Alleviates Uncertainty, Assumptions, and Sounding Like a Jerk

For an important, and alternative view on Pain Letters, please check out some of the feedback from one of the blogs I follow closely, Ask a Manager. It gives some important advice about how Pain Letters can go wrong.

In short, the problem comes down to assumptions. The key is to avoid them completely when writing your Pain Letter. However, it's an easy problem to fall into when you've never worked with a company.

The main idea here is: if you want to accelerate your job search by writing an effective Pain Letter that grabs an employer's attention (in a good way), treat your search process like a funnel and only write Pain Letters to those organizations who can emerge from the bottom of the funnel.

I'll explain. First, start with a target universe of potential employers by researching a broad group of companies and organizations you believe you would like to work for.

  1. List the top of the funnel - Take a sheet of paper, word processor, or spreadsheet and write down 50 companies or organizations you would like to work for based off of their 1) mission, 2) location and commute time, and 3) company size. These three indicators drive most of our decision-making around job satisfaction from a macro-perspective (meaning, things that don't have to do with team dynamics and manager relationships, which you wouldn't be able to consider at this stage anyways.)
  2. Narrow midway through the funnel - Narrow that list of 50 companies by identifying who is hiring for positions that could potentially be a good fit for your skills and experience based on their job descriptions. You should be able to walk away with 10-15 in a good job market. I'll provide you with resources tomorrow that will help describe how this process of elimination works best.
  3. Pause and compare the job description to the organization's expressed goals - What are your target organizations' expressed goals for growth or change. How many people are they hoping to serve over the next few years? What particular problems are they trying to solve? Is there any place on the employer's website or in their public statements where you can identify an expressed opinion? Is there a press release that state's the target organization's more recent goals or projects explicitly?
  4. Explain your value-add through a Pain Statment. - A pain statement is when you identify one or two key needs (no more than this) that you could potentially help meet through your skills and experience. It's a precursor to the Pain Letter. It takes two steps to write. First, take your list of 10-15 target organizations with open positions and write down a statement about one or two of their greatest expressed needs. Then write down, in no more than one paragraph or four bullet points, how you could help be a problem solver for that organization's need. That's your Pain Statement for each company.
  5. Find the 3-7 organizations where you could actually be an authentic solution provider. - Now look at back at that list of 10-15 explanations. Ask yourself, which Pain Statement, which explanation of your value-add stretched you the least? Which felt easiest to craft? Which companies expressed needs did you feel you most clearly understood and related to? In which explanation of your ability to meet the organization's key need did you make the fewest assumptions? These are the organizations you should be writing cover letters (or rather Pain Letters) for.

Next time ... Part 2: Build It and They Will Invite You to Build More

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Chris Conroy