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 always 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.

No one likes job hunting. Scouring through online jobs boards, spiffing up your résumé, prepping for grueling interviews — none of it’s fun. But perhaps 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. Indeed, in an age of digital communication, many might question whether you even need a cover letter anymore.

What the Experts Say

The answer is yes. “Not sending a cover letter is a sign of laziness. It’s akin to making spelling and grammar mistakes in your résumé. You just don’t do it,” says Jodi Glickman, a communications expert and author of Great on the Job. John Lees, a UK-based career strategist and author of Knockout CV, agrees. Even if only one in two cover letters gets read, that’s still a 50% chance that including one could help you, he explains. “It’s an opportunity to distinguish yourself,” Glickman adds. Still, as anyone who’s ever written a cover letter knows, it’s not easy to do well. Here’s how to give hiring managers what they’re looking for.

Do your research first

Before you start writing, find out more about the company and the specific job you want. Look at the company’s website, its executives’ Twitter feeds, and employee profiles on LinkedIn. “Do some research beyond reading the job description,” says Lees. Find out what challenges the company is facing and how your role would help address those. Knowing the company better also helps you decide on the right tone to use in your cover letter. “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.”

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 of text,” says Lees. Instead, lead with a strong opening sentence. “Start with the punch line — why this job is exciting to you and why you’re right for it,” says Glickman. For example, you might write, “I’m an environmental fundraising professional with more than 15 years of experience and I’d love to bring my expertise and enthusiasm to your growing development team.” 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 ‘Before you read any further, let me draw your attention to two reasons why you might want to hire me….’

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, there’s no excuse to not be able 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 a trend that’s affected the industry. For example, you might write, “A lot of healthcare companies are grappling with how the changing laws will affect their ability to provide high-quality care.” 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.

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Convey enthusiasm

Make it clear why you want the position. “In today’s economy, a lot of people have the right skills, so employers want someone who really wants the job,” says Glickman. “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. “Sending out 100 résumés is a waste of time. Find the 10 companies you want to work for and put some heart and soul into it,” Glickman says. At the same time, don’t go overboard with the flattery or say anything you don’t mean. Authenticity is crucial. “You don’t want to sound like a gushing teenager,” Glickman warns. Be professional and mature. Lees notes that in some industries, like fashion or technology, it’s more appropriate to say how much you love a company’s product or services. A good rule of thumb is to “use only the kind of language that the hiring manager would use with one of his customers.”

Keep it short

Much of the advice out there tells you 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.

When you can’t submit a cover letter

“In the black hole of an online system, the rules may be different,” Glickman concedes. 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 who 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 why you’re right for it

Be succinct — a hiring manager should be able to read it at a glance

Share an accomplishment that shows you can address the challenges the employer faces

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

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.

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).

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 naiveté, 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. Last June, she was hired as a temporary external relations coordinator and, in October, she moved into a permanent role.