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.

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.

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