Why Your Tailored Cover Letter Strategy May Be Falling Flat

Focusing on a company’s challenges might get you noticed for all the wrong reasons.

Why Your Tailored Cover Letter Strategy May Be Falling Flat
[Photo: Flickr user Stan Wiechers]

Some of the most successful businesses operating today started with a pain point. In other words, the founders started listening to consumers’ frustrations (or their own) and came up with solutions that worked. Think: Google’s search engine, PayPal’s money transfers, even Etsy’s handmade marketplace.


So it’s no surprise that using this approach also opens that elusive door to a new job. Liz Ryan, a former HR executive and founder of Human Workplace, is a big believer in the power of pain when it comes to applying for a job. When most résumés get thrown into an automated applicant tracking system (ATS) that is designed to search for simple keywords disguised as a plethora of skills requirements, the cover letter might be the only shot a jobseeker has to stand out.

That’s why Ryan recommends a four-point strategy to facilitate the hiring manager’s search for the perfect candidate. Instead of focusing on personal strengths, figure out what the company or department needs most, then tell them how you are uniquely suited to tackle the challenge. Simple and effective, right?

Not so fast says Donna Svei, who as a recruiter (and professional résumé writer), has received her share of these letters. “They’re hard for people to execute well,” she tells Fast Company. For proof, Svei points out the pain letter that Josh Goldstein, cofounder of, wrote to Foursquare three years ago when he was applying for a business development job.

In brief, he was formal but enthusiastic, established himself as a user of the service in addition to being an applicant, and then proceeded to outline four ideas that would help the department forge new media partnerships.

The good news is that it got him noticed by Foursquare’s head of talent. The not-so-great part is that the same person told him:

You spend more time talking about how awesome the company is rather than how awesome YOU are. Why are YOU the perfect fit for this role? What do YOU bring to the table? Why is biz dev the right home for YOU?) Listing ideas in a cover letter can be dangerous. As an outsider, it’s tough to know the exact vision and strategy of the company. If you are 100% sure you’ve nailed it, then the job is yours. But if your ideas go slightly in the wrong, wacky direction, it could do more harm and the company may think you don’t ‘get it.’

In the end, Goldstein got the interview, but not the job.


So much for skipping personal strengths and moving right to the challenges. It’s an all-too common problem that persists even after we get the job. We tend to accommodate the strengths of others and de-emphasize our own when we focus only on what we could do better in the future. It eventually leads to lack of engagement.

To start off on the right foot, Svei suggests flipping the pain letter on its head and craft an opportunity letter instead.

Here’s her take:

Dear [name],

I’m writing to express my interest in your Media Partnerships role. I’m about to finish my MBA at UNC’s Kenan-Flagler Business School and want to join a company where my energy, creativity, and proven ability to develop relationships can deliver growth.

By way of example:
I worked for a nonprofit before I started business school. One day, a sports celebrity mentioned our organization in a huge national publication. We became aware of his endorsement when checks started arriving at our door in mailbags.

I saw the opportunity to develop a long-term partnership with him and pitched my idea to our COO. Together, we wrote him a thank-you letter and had our CEO and the Chairman of our Board sign it. Beyond thanking him, we asked him to consider an ongoing relationship with our organization. We outlined our vision of how that would help the people we both wanted to benefit.

Long story short, our outreach evolved into a branded program that continues to raise millions of dollars each year for my former employer and its grantees. I managed that relationship and the program until I left for business school.

I can imagine some of the growth challenges that Foursquare might be facing, but I’m not sure exactly what they are. Here’s what I do know:

If you set me on a mission, I can develop a set of ideas, work under my manager’s direction to vet them, and execute on what we decide. I’ve done it before. I will do it again.

Let’s have coffee or get together on Skype. I want to meet you so I can learn more about Foursquare’s needs, and you can learn more about me.


This letter, says Svei, checks the company’s boxes in a way that shows (not tells) them how great the candidate would be if hired. “It’s factual, not hypothetical,” Svei writes, “Who would you rather interview—the person who proves they can see and deliver on opportunities in real life or the one who talks about pain?”

Something to keep in mind next time you’re planning to throw your hat in the ring for a new job. Once you get in the door, you can look here to learn the right way to say thanks for the interview.



About the author

Lydia Dishman is a reporter writing about the intersection of tech, leadership, and innovation. She is a regular contributor to Fast Company and has written for CBS Moneywatch, Fortune, The Guardian, Popular Science, and the New York Times, among others.