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Perhaps the most challenging part of the job application process is writing an effective cover letter. And yes, you should send one. Even if only one in two cover letters gets read, that’s still a 50% chance that including one could help you. Before you start writing, find out more about the company and the specific job you want. Next, catch the attention of the hiring manager or recruiter with a strong opening line. If you have a personal connection with the company or someone who works there, mention it in the first sentence or two, and try to address your letter to someone directly. Hiring managers are looking for people who can help them solve problems, so show that you know what the company does and some of the challenges it faces. Then explain how your experience has equipped you to meet those needs. If the online application doesn’t allow you to submit a cover letter, use the format you’re given to demonstrate your ability to do the job and your enthusiasm for the role.

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No one likes job hunting. Scouring through online job listings, spiffing up your résumé, prepping for grueling interviews — none of it is fun. For many, the most challenging part of the process is writing an effective cover letter. There’s so much conflicting advice out there, it’s hard to know where to start. Do you even need one, especially if you’re applying through an online system?

What the Experts Say

The answer is almost always yes. Sure, there will be times when you’re submitting an application online and you may not be able to include one, but whenever possible, send one, says Jodi Glickman, a communications expert and author of Great on the Job. “It’s your best chance of getting the attention of the HR person or hiring manager and an important opportunity to distinguish yourself from everyone else.” And in a tight job market, setting yourself apart is critical, says John Lees, a UK-based career strategist and author of Knockout CV. Still, as anyone who’s ever written a cover letter knows, it’s not easy to do well. Here are some tips to help.

Do your research first.

Before you start writing, find out more about the company and the specific job you want. Of course, you should carefully read the job description, but also peruse the company’s website, its executives’ Twitter feeds, and employee profiles on LinkedIn. This research will help you customize your cover letter, since you shouldn’t send a generic one. It’ll also help you decide on the right tone. “Think about the culture of the organization you’re applying to,” advises Glickman. “If it’s a creative agency, like a design shop, you might take more risks, but if it’s a more conservative organization, like a bank, you may hold back.”

If at all possible, reach out to the hiring manager or someone else you know at the company before writing your cover letter, advises Lees. You can send an email or a LinkedIn message “asking a smart question about the job.” That way you can start your letter by referencing the interaction. You might say, “Thanks for the helpful conversation last week” or “I recently spoke to so-and-so at your company.” Of course, it’s not always possible to contact someone — or you may not get a response. That’s OK. It’s still worth a try.

Focus it on the future.

While your résumé is meant to be a look back at your experience and where you’ve been, the cover letter should focus on the future and what you want to do, says Glickman. “It can be helpful to think of it as the bridge between the past and the future that explains what you hope to do next and why.” Because of the pandemic there is less of an expectation that you’ll be applying for a job that you’ve done before. “There are millions of people who are making career changes — voluntarily or involuntarily — and need to pivot and rethink how their skill set relates to a different role or industry,” says Glickman. You can use your cover letter to explain the shift you’re making, perhaps from hospitality to marketing, for example. Think of it as an opportunity to sell your transferrable skills.

Open strong.

“People typically write themselves into the letter with ‘I’m applying for X job that I saw in Y place.’ That’s a waste,” says Lees. Instead, lead with a strong opening sentence. “Start with the punch line — why this job is exciting to you and what you bring to the table,” says Glickman. For example, you might write, “I’m an environmental fundraising professional with more than 15 years of experience looking for an opportunity to apply my skills in new ways, and I’d love to bring my expertise and enthusiasm to your growing development team.” Then you can include a sentence or two about your background and your relevant experience, but don’t rehash your résumé.

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Chances are the hiring manager or recruiter is reading a stack of these, so you want to catch their attention. But don’t try to be funny. “Humor can often fall flat or sound self-regarding,” says Lees. Stay away from common platitudes, too. “Say something direct and dynamic, such as ‘Let me draw your attention to two reasons why I’d be a great addition to your team.'”

If you have a personal connection with the company or someone who works there, also mention it in the first sentence or two. And always address your letter to someone directly. “With social media, it’s often possible to find the name of a hiring manager,” says Glickman.

Emphasize your personal value.

Hiring managers are looking for people who can help them solve problems. Drawing on the research you did earlier, show that you know what the company does and some of the challenges it faces. These don’t need to be specific but you might mention how the industry has been affected by the pandemic. For example, you might write, “A lot of health care companies are overwhelmed with the need to provide high-quality care while protecting the health and safety of their staff.” Then talk about how your experience has equipped you to meet those needs; perhaps explain how you solved a similar problem in the past or share a relevant accomplishment. You want to provide evidence of the things that set you apart.

Lees points out that there are two skills that are relevant to almost any job right now: adaptability and the ability to learn quickly. If you have brief examples that demonstrate these skills, include those. For example, if you supported your team in the shift to remote work, describe how you did that and what capabilities you drew on.

Convey enthusiasm.

“When you don’t get hired, it’s usually not because of a lack of skills,” says Glickman. “It’s because people didn’t believe your story, that you wanted the job, or that you knew what you were getting into.” Hiring managers are going to go with the candidate who has made it seem like this is their dream job. So make it clear why you want the position. “Enthusiasm conveys personality,” Lees adds. He suggests writing something like “I’d love to work for your company. Who wouldn’t? You’re the industry leader, setting standards that others only follow.” Don’t bother applying if you’re not excited about some aspect of the company or role.

Watch the tone.

At the same time, don’t go overboard with the flattery or say anything you don’t mean. Authenticity is crucial. “Even if you’ve been out of work for months, and would take any job at this point, you want to avoid sounding desperate,” says Lees. You don’t want your tone to undermine your message, so be professional and mature. A good rule of thumb is to put yourself in the shoes of the hiring manager and think about “the kind of language that the hiring manager would use with one of the company’s customers.” Of course, it can be hard to discern your own tone in writing, so you may need to ask someone to review a draft (which is always a good idea anyway — see advice below). Lees says that he often cuts outs “anything that sounds like desperation” when he’s reviewing letters for clients.

Keep it short.

Much of the advice out there says to keep it under a page. But both Glickman and Lees say even shorter is better. “Most cover letters I see are too long,” says Lees. “It should be brief enough that someone can read it at a glance.” You do have to cover a lot of ground — but you should do it succinctly. This is where asking a friend, former colleague, or mentor to review your letter can be helpful. Ask them to read through it and point out places where you can cut.

Get feedback.

In fact, it’s a great idea to share your cover letter with a few people, says Lees. Rather than sending it off and asking, “What do you think?” be specific about the kind of feedback you want. In particular, request two things. First, ask your friend if it’s clear what your main point is. What’s the story you’re telling? Are they able to summarize it? Second, ask them what’s wrong with the letter. “Other people are more attuned to desperation, overselling, over-modesty, and underselling,” says Lees, and they should be able to point out places where the tone is off.

When you can’t submit a cover letter.

Many companies now use online application systems that don’t allow for a cover letter. You may be able to figure out how to include one in the same document as your résumé, but that’s not a guarantee, especially because some systems only allow for data to be entered into specific boxes. In these cases, use the format you’re given to demonstrate your ability to do the job and your enthusiasm for the role. If possible, you may try to find someone to whom you can send a brief follow-up email highlighting a few key points about your application.

Principles to Remember

Do:

• Have a strong opening statement that makes clear why you want the job and what you bring to the table.
• Be succinct — a hiring manager should be able to read your letter at a glance.
• Share an accomplishment that shows you can address the challenges the employer is facing.

Don’t:

• Try to be funny — too often it falls flat.
• Send a generic cover letter — customize each one for the specific job.
• Go overboard with flattery — be professional and mature.

Advice in Practice

Case Study #1: Demonstrate an understanding of what the company needs.

Michele Sommers, the vice president of HR for the Boys & Girls Village, a nonprofit in Connecticut, recently posted a job for a recruiting and training specialist. “I was looking for someone with a strong recruiting background who could do everything from sourcing candidates to onboarding new hires,” she says. She also wanted the person to hit the ground running. “We’re a small team and I can’t afford to train someone,” she says.

More than 100 candidates applied for the job. The organization’s online application system doesn’t allow for cover letter attachments, but one of the applicants, Heidi (not her real name), sent a follow-up email after submitting her résumé. “And it’s a good thing she did, because she would’ve been weeded out otherwise,” Michele says.

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Heidi’s résumé made her look like a “job hopper” — very short stints at each previous employer. Michele assumed she was a poor performer who kept getting fired. She was also the only candidate who didn’t have a four-year college degree.

But Heidi’s email caught Michele’s eye. First off, it was professional. Heidi stated clearly that she was writing to double-check that her application had been received. She went on to explain how she had gotten Michele’s name and information (through her husband’s boss, who was on the board) and her personal connection to Boys & Girls Village (her father-in-law had done some work with the organization).

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What really stood out to Michele, though, was Heidi’s understanding of the group and the challenges it was facing. She’d done her research and “listed some things she would do or already had done that would help us address those needs,” says Michele.

“The personality and passion she conveyed in the cover letter came through during her phone screening,” Michele says. Heidi ended up being more than qualified for the job. “I wanted this role to be bigger from the get-go, but I didn’t think that was possible. When I met her, I knew we could expand it.” Three weeks later Michele offered Heidi the job and she accepted.

Case Study #2: Catch their attention.

Over the past four years, Emily Sernaker applied for multiple positions at the International Rescue Committee (IRC). She never gave up. With each application, she sent a personalized cover letter. “I wanted my cover letter to highlight my qualifications, creative thinking, and genuine respect for the organization,” she says.

Sarah Vania, the organization’s regional HR director, says that Emily’s letters caught her attention, especially because they included several video links that showed the results of Emily’s advocacy and fundraising work at other organizations. Emily explains, “I had prior experience advocating for former child soldiers, human trafficking survivors, vulnerable women, and displaced persons. It’s one thing to make statements in a cover letter, like ‘I can make a pitch, I am a creative person, I am thoughtful,’ but showing these qualities seemed like a better way of convincing the recruiter that the statements were true.”

This is what Emily wrote to Sarah about the video:

Here is a short video about my story with activism. The nonprofit organization Invisible Children made it for a youth conference I spoke at this year. It is about four minutes.

As you’ll see from the video, I’ve had a lot of success as a student fundraiser, raising over $200,000 for Invisible Children. I’ve since gone on to work as a consultant for Wellspring International and have recently concluded my studies as a Rotary International Ambassadorial Scholar.

In each of the cover letters, Emily also made clear how much she wanted to work for IRC. “To convey enthusiasm is a vulnerable thing to do and can come off as naivete, but, when it came down to it, my enthusiasm for the organization was genuine and expressing it felt right,” she says.

This is how Emily conveyed her interest in working for IRC:

You should also know that I have a sincere appreciation of the IRC. I have enjoyed learning about your programs and have personally visited your New York headquarters, the San Diego New Roots farm, the We Can Be Heroes exhibit, and the Half the Sky exhibit in Los Angeles. The IRC is my top choice and I believe I would be a valuable addition to your fundraising team.

Emily learned throughout the process that the organization had hundreds of applicants for each position and it was extremely competitive. “I appreciated that I wouldn’t be the best for every opening but also remained firm that I did have a significant contribution to make,” she says. Eventually, Emily’s persistence paid off. She was hired as a temporary external relations coordinator, and four months later she moved into a permanent role.

. . .

Editor’s note: The author updated this article, which was originally written in 2014, to reflect the latest advice from the experts and the reality of job-seeking during the pandemic.

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