People, not institutions, make grants, and the cover letter gives you an opportunity to show you understand this. And grants are made to people, not institutions, so your cover letter needs also to reflect the personality and style of the person who signs the letter. If possible, your cover letter should connect with the reader on a personal as well as a professional level.

Address the letter to whomever the funder gives as the contact person, unless your contact at the funder told you to send it to her instead.

If one of your board members knows someone at the foundation other than the contact, you can go one of two ways: send the original letter to the person with the personal connection and CC the official contact person, or send the original to the official contact person and send a CC with a handwritten note from your board member to his or her contact.

With either approach, you cover all the bases and ensure that your proposal will be processed through the usual channels even if your special contact drops the ball. The second method has the advantage of respecting the chain of command at the funder and giving a more personal touch to the personal contact.

If your research revealed that the contact person has a background in education and pedagogy and your proposal addresses the training of teachers, you can discuss the subject using terminology appropriate to addressing another expert in the field. If you know the contact has young children, you can address his or her interests as a parent in improved teacher training. If the contact is a young program officer fresh out of college, you might connect your discussion of teacher training with the reader’s own recent educational experiences.

Whoever the reader is, you want to make that person your advocate when the funder’s board meets. You therefore want to include the strongest parts of your rationale for funding in the cover letter and present them in such a way as to make it easy for the reader to remember them when discussing your proposal with others. Bullet points help the reader find your key points. Good writing helps him remember them.

The person who reads the cover letter is, of course, only half of the equation. The letter must also be appropriate for the person who signs it. In larger organizations, this rarely will be you. More likely it will be your charity’s executive director, development director, or board president. For simplicity’s sake, I refer to the writer as the executive director.

If possible, read any letters or speeches the executive director has written (or approved) to get an idea of the degree of formality she uses in different situations. Through trial and error, you’ll eventually get a good handle on the executive director’s personal style. The better you can do this, the more effective the letter will be.

Negotiating the tone of the letter with the executive director is part of the process, but too often overediting can dilute the letter’s message. It’s your job to be sure this doesn’t happen. Executive directors and others I’ve worked for have usually listened when I objected to one of their edits because it changed the meaning or weakened the argument. Usually we compromised on a third version of the text.

When to push for your language and when to accept the executive director’s edits must depend on what will best serve the proposal, taking into account your experience with the particular funder versus the executive director’s experience. This applies to the entire proposal, not just the cover letter. With the cover letter in particular, the signer has every right to have the letter reflect her style—it is, after all, her signature at the bottom of the page. Just don’t water down the message in the interest of personal style.

One executive director I worked for drove me crazy with repeated changes to a government proposal. (I had started to label the versions of the proposal with the day, hour, and minute to make my not-so-subtle point about all the revisions.) As annoyed as I was, I knew he had more than twice the experience with this particular funder than I had. Trying to keep the language to my prose in this situation would have been foolish and detrimental to the proposal’s chances for success. In the end, I learned a lot from his edits that has helped me write proposals for all kinds of funders.

Above all else, make the letter’s salutation appropriate for the executive director. If your executive director is on a first-name basis with the reader, using a formal salutation will be a real turnoff, but overfamiliarity will have the same effect.