James W. Martin

Serving St. Petersburg, FL

Shareholder at firm James W. Martin, P.A.

Serving St. Petersburg, FL

Awards AV Preeminent

Why do people hate to get letters from lawyers? They carry bad news. They mean serious business. They’re hard to understand. They use strange words. They carry the inherent threat of suit.

Why do lawyers send such letters? They mean serious business, and they intend to sue.

But must they use those ancient, strange words and be so hard to understand, or can lawyers express serious business and imminent suit using words everyone knows?

Whether writing a demand letter to a contract breacher, an advice letter to a client, or a cover letter to a court clerk, the letter fails if the person receiving it cannot understand what it says.

All of these letters have one thing in common: They are not great literature. They will not be read in a hundred years and analyzed for their wit, charm or flowery words. With any luck they will be read just once by a few people, followed quickly by their intended result, whether that be compliance, understanding or agreement.

Lawyers are Letter Factories

Lawyers write many, many letters. An average for me might be five letters a day. This includes advice letters, cover letters, demand letters, all sorts of letters. Some days have more, some have less, but five is a fairly conservative average, I would think. Five letters a day for five days a week for fifty weeks a year is 1,250 letters a year. This is my 25th year in practice, so it is quite conceivable that I have written 31,250 letters so far.

Why do lawyers write so many letters? A primary reason lies within the ethics of our profession. Florida Bar Rules of Professional Conduct Rule 4-1.4 says:

"A lawyer shall keep a client reasonably informed about the status of a matter and promptly comply with reasonable requests for information."

"A lawyer shall explain a matter to the extent reasonably necessary to permit the client to make informed decisions regarding the representation."

While clients can be kept informed and given explanations orally, lawyers certainly know the value of the printed word over the spoken word: it is not as easily forgotten or misunderstood. Letters also create a record of advice given, which is useful to both the lawyer and the client. That is why letters are the preferred method of keeping clients informed and giving clients explanations.

Some Things To Do Before Writing

Before you start writing the letter it makes sense to do some preliminary background work.

  1. Find a letter form. Find a similar letter you have sent in the past, or see the Appendix to this article for sample engagement, cover, demand, contract negotiation, contract advice, and fax letters.

  2. Review prior letters to this recipient. In a busy world, it is easy to forget. Review prior letters to remind yourself where you are in the work process, what has already been said, and what remains to be said. This will give your letter direction and purpose.

  3. Do not send a letter to another lawyer’s client without that lawyer’s consent. Before sending the letter, find out if the nonlawyer is represented by someone else. Start by asking your client. Florida Bar Rules of Professional Conduct Rule 4-4.2 says:

    "In representing a client, a lawyer shall not communicate about the subject of the representation with a person the lawyer knows to be represented by another lawyer in the matter, unless the lawyer has the consent of the other lawyer."

  4. Outline your thoughts in a checklist. Before turning on your computer or dictating machine, pull out a yellow pad and jot down the main points for your letter. List what you want the letter to say. Write the points in any order; write them as they come into your mind. You can rearrange them when you write the letter. Right now you’re just making a checklist for writing the letter.

  5. Keep the legal pad close at hand. When you run out of ideas for the checklist, put the pad at the side of your desk. New ideas always spring forth when writing. Jot these down on the pad as you write the letter; they are easily forgotten.

Simple Stuff That Will Make You Look Dumb If It’s Wrong

Letters begin with boring things like the date and recipient’s name and address, but if any of these are missing or wrong the letter writer will look pretty careless, to say the least. So be careful when starting the letter, and you can even include some extra things that will make the letter even better than the regular letters the recipient receives.

  1. Date your letter. Date your letter the day you write it, and send it the same day. Undated letters are difficult to reply to. I usually reply to them by saying, "This is in reply to your undated letter that I received in the mail on 24 June 1999."

    Consider using the international dating convention of day-month-year rather than the U.S. convention of month-day-year. As reported in the 1 June 1999 Wall Street Journal:

    "The quirky U.S. style of date-writing is giving way to the day-first standard used by most of the world.

    … Both the MLA style guide and the Chicago Manual of Style support the day-first format. ‘You get rid of the comma that way,’ says Joseph Gibaldi, director of book acquisition for the MLA in New York."

    If you are sending a fax or email, then type the time next to the date. While letters "cross in the mail" in days, faxes and emails "cross in the wires" in hours and minutes.

  2. Remind your client to preserve attorney-client confidentiality. Sometimes clients show your letters to others without realizing they can lose the attorney-client privilege of that communication. Add this phrase at the top of the letter to remind them not to do this:
    If the letter is written during or in anticipation of litigation, the following phrase can be used: DO NOT COPY OR DISCLOSE TO ANYONE ELSECONFIDENTIAL ATTORNEY-CLIENT COMMUNICATION

  4. Be sure to use the recipient’s correct legal name and address. Your letter may be relied upon for its accuracy, so be accurate. Verification of names can be obtained from the public records, the phone book, or the Florida Division of Corporations Web site at http://ccfcorp.dos.state.fl.us/index.html. And when it comes to middle initials, never rely on your memory or guess at it because most of the time you’ll be wrong.

  5. Indicate the method of delivery if other than mail. If being faxed, include the fax number and telephone number. If being sent by FedEx, state whether it is by overnight or second day. If being sent by email, state the email address. This will make it easy for your staff person to send it to the correct place, and it will document for your file how it was sent.

  6. Include a fax notice. When sending by fax, include a notice in case it is sent to the wrong number. Here is the notice I use at the top of my letterhead when sending a fax:

    NOTICE: This is privileged and confidential and intended only for the person named below. If you are not that person, then any use, dissemination, distribution or copying of this is strictly prohibited, and you are requested to notify us immediately by calling or faxing us collect at the numbers above.
    Date Sent ________ Time Sent ________ Number of Pages ________
    Person Who Conf’d Receipt _________

    After sending a fax, call the recipient to confirm receipt and write that person’s name in the space provided. Never rely on the fax machine itself to confirm a fax transmission; fax machines do not yet have the credibility of a human witness.


The Corpus of the Litterae

The body of the letter is why you are writing it. You succeed by leaving the reader with full knowledge of why you wrote the letter and what it means. You fail by leaving the reader dumbfound and clueless as to why you sent such a letter. While most letters fall somewhere in between these two extremes, following these suggestions will keep your letters on the successful end of the scale.

  1. Identify your client. It is important to let others know who is your client at the earliest opportunity. This accomplishes a great deal. First, it tells the reader that your client has a lawyer. This makes your client happy because most clients want the world to know they have a lawyer. Second, it tells the reader that you are not the reader’s lawyer. This makes your malpractice carrier happy because it’s one less person who’s going to sue you claiming they thought you were representing them when, in fact, you were not.

    Identifying your client is an ethical concern, as well. Florida Bar Rules of Professional Conduct Rule 4-4.3 says:

    "In dealing on behalf of a client with a person who is not represented by counsel, a lawyer shall not state or imply that the lawyer is disinterested."

    Therefore, the first time you write someone a letter, the letter should open with the following sentence: "I represent _________." After that, every time you write another letter reconfirm who you represent by referring to your client by name and as "my client."

  2. State the purpose of the letter. Why leave the reader guessing? Go ahead and say right up front why you are writing the letter. Here are some opening sentences:

    "The purpose of this letter is to _________."
    "This letter is to inform you that _________."
    "My client has instructed me to _________."
    "This is to confirm that _________."
    "This confirms our phone conversation today in which _________."

  3. If there are any enclosures, list them first. Listing enclosures at the beginning of the letter will make it easier for your staff to assemble them and for the reader to check to be sure all was received. This is much easier than having to read an entire, perhaps lengthy, letter to ascertain what are the enclosures.

    The enclosures should be described with specificity so that there is later no question as to what was enclosed. At a minimum, the title and date of each document should be listed. If the document was recorded, then the recording information should be included. Whether the document is an original or a copy should also be specified. The following is an example:

    "Enclosed are the following documents from your closing held on ___/___/1999 in which you purchased the home at _________, St. Petersburg, Florida, from _________:

    1. Warranty Deed dated ___/___/1999 and recorded on ___/___/1999 at O.R. Book ____, Page ____, _________, County, Florida (original)
    2. Title Insurance Policy issued on ___/___/1999 by _________ on _________ as policy number _________ (original)
    3. HUD-1 Settlement Statement dated ___/___/1999 (original)"

  4. Outline the letter as separately numbered paragraphs. Each paragraph of the letter should state a separate thought, comment, point or concept. No paragraph should be longer than four or five short sentences. If the paragraph is longer, then separate it into subparagraphs. The paragraphs should flow in logical, organized fashion. It is not necessary to write them all at once; you can write them as you think of them. Try to group related concepts in the same paragraphs or in adjacent paragraphs. See the Appendix for sample letters.

  5. Give each paragraph a title and underline that title. Think of this as the headline for a newspaper article. This makes it easy for the reader to scan the letter and choose how to more fully read and digest its contents. This also makes it easier for you later when you see the letter in your file and try to remember why you wrote it.

  6. Complete each paragraph by writing what applies to that paragraph. This is simple. You learned this in elementary school. Just explain in words what you want to say about each concept or comment you placed in your outline.

  7. If this is a letter to your client, include ideas that occur to you as you write. Many ideas will occur to you as you write: things that could go wrong with a business deal, things that might happen in the future, things that happened in the past, ways to structure things better. Write these in your letter even if they are not strictly legal advice. Florida Bar Rules of Professional Conduct Rule 4-2.1 says:

    "In rendering advice, a lawyer may refer not only to law but to other considerations such as moral, economic, social, and political factors that may be relevant to the client’s situation."

  8. If this is a letter to a nonclient, do not offer any advice. The letter should accomplish its purpose of providing information, making a demand, etc., without giving legal advice to the recipient. The comment to Florida Bar Rules of Professional Conduct Rule 4-4.3 says:

    "During the course of a lawyer’s representation of a client, the lawyer should not give advice to an unrepresented person other than the advice to obtain counsel."

  9. State your assumptions. Whether or not this is an opinion letter, set forth the factual assumptions and statutes you rely upon in giving your opinion or advice. It is customary for opinion letters to recite the facts upon which the opinion is based and the statutes and case law, as well. This is something that every letter providing advice or opinion can include in order to avoid future misunderstanding. Every opinion and all advice is predicated upon facts and law. Stating the assumed facts and applicable law in the letter merely makes known to the reader what the writer understands to be true. This then places an obligation on the reader to inform the writer if any of the assumed facts is not accurate, which might change the opinion or advice.

  10. Place instructions to clients in bold type. This will make it easier for the client to follow up on your letter and do as advised.

  11. Close the letter with a final paragraph. The last paragraph will be one of the following:
    1. Summary of advice: "To summarize, I advise that you…"
    2. To do list: "Therefore, please do the following:…"
    3. Demand: "Therefore, my client demands that you immediately cease and desist…"
    4. Simple close: "If you have any questions, please call me."

Playing with the Words

Why does it take lawyers so long to write letters? Because we play with the words. We write, rewrite, move around, delete, cut and paste the words over and over and over again until we are happy with the way it sounds. That’s the art of legal writing. It’s like Picasso painting over the same canvas again and again, transforming it from one painting to another and then to another until finally he is satisfied with the result. Not always 100% satisfied, but good enough for it to go out the door and into the world. That’s why writing is an art. And that’s also why more copies of WordPerfect were sold to lawyers than any other industry. So here are some things to play with.

  1. Write in short sentences. Short sentences are easier to understand than long ones. "Short, crisp sentences in a language accessible to lay people." This is the Associated Press’s description of the writing style of the late Lord Alfred Thompson Denning, who was one of Britain’s longest-serving appeals judges when he died at the age of 100 in March 1999. The same style Lord Denning used in writing appellate opinions should be used in writing letters to nonlawyers.

  2. It’s okay to use jargon; just explain it. We hear all the time that lawyers use too much jargon. But some concepts need the jargon. Like nunc pro tunc (which means now for then and is a wonderful concept that recognizes the inherent power of a court to correct its records by entering an order effective as of a prior date) and per stirpes (which means through representation and indicates a manner of taking title from a decedent).

    Every profession has its jargon. That’s not bad. It’s part of our identity. It’s a form of shorthand. It’s a form of common knowledge among professionals. If my physician failed to use jargon in describing a medical condition, I would probably wonder if I had the right expert. A good professional not only knows the jargon, but can also explain it to a layman. Therefore, show your expertise. Use the jargon when necessary, but explain it when you use it.

  3. Repeat yourself only when repetition is necessary to improve clarity or to emphasize a point. Ambiguity can created by saying the same thing more than once; it is almost impossible to say it twice without creating ambiguity.

  4. When explaining a difficult concept, describe it from three directions. The only time repetition is helpful is when explaining a difficult concept. Each time you explain it you can make it a little more clear if you describe it from a different direction, perspective or point of view.

  5. Write in active tense, rather than passive. Active tense is interesting; passive is boring. Active tense sentences are shorter and use words more efficiently, and their meaning is more apparent.

  6. Watch where you place modifiers. When adding a modifier like "active" before a compound of nouns like "termites and organisms," be sure to clarify whether you intend the modifier to apply to both nouns or just the first one. If you intend it to apply to both, use parallel construction and write the modifier in front of each noun. If you intend it to apply to just one noun, place that one noun at the end of the list and the modifier directly in front of it.

  7. Write numbers as both words and numerals: ten (10). This will reduce the chance for errors. The Associated Press reported on 18 June 1999, that a comma in the wrong place of a sales contract cost Lockheed Martin Corp. $70 million: "An international contract for the U.S.-based aerospace group’s C-130J Hercules had the comma misplaced by one decimal point in the equation that adjusted the sales price for changes to the inflation rate." Perhaps writing out the number would have saved the day.

  8. When you write "including" consider adding "but not limited to." Unless you intend the list to be all-inclusive, you had better clarify your intent that it is merely an example.

  9. Don’t be creative with words. Legal letter writing is not creative writing and is not meant to provoke reflective thoughts or controversies about nuances of meaning. Legal writing is clear, direct and precise. Therefore, use common words and common meanings.

  10. Be consistent in using words. If you refer to the subject matter of a sales contract as "goods" use that term throughout the letter; do not alternately call them "goods" and "items." Maintaining consistency is more important than avoiding repetition.

  11. Be consistent in grammar and punctuation. Don’t rely on the rules of grammar. The rules of grammar that you learned in school are not universal. The readers of your letter may have learned different rules. Write the letter so that no matter what rules they learned the letter is clear and unambiguous.

    Be consistent in your use of grammar. Be aware of such things as where you put ending quote marks, whether you place commas after years and states, and similar variations in style. Many rules of grammar are a matter of choice, but your choice should be internally consistent within the letter.

  12. Define a word by capitalizing it and putting it in quotes. Capitalizing a word indicates that you intend it to have a special meaning. The following is a sample clause for defining a term:

    "Wherever used in this letter, the word "Goods" shall mean the goods that _________ agreed to purchase from _________ under the Contract."

  13. Define words when first used. Instead of writing a section of definitions at the beginning or end of a long letter, consider defining terms and concepts as they appear in the letter. This will make it easier for the reader to follow.

  14. Avoid needless and flowery words. Think of elementary school when you had to reduce fractions to the "lowest common denominator." That’s what good writing is all about. A letter written for the lowest common denominator is understood by every reader. Eliminate needless words. Avoid flowery words.

  15. Be direct and frank. There is no sense beating around the bush in legal letter writing. Just say what you mean. If you leave the reader wondering what you mean, your letter will only stir the imagination instead of prompting some action.

  16. Study The Elements of Style. The full text of the 1918 classic by William Strunk is now available online at http://www.bartleby.com/strunk. This means that even if you left your copy on your bedstand at home, you can quickly go online and search the full text of The Elements of Style, where you will find these simple rules among others (as you can see, I am a old student of this text):

    "Make the paragraph the unit of composition: one paragraph to each topic."
    "As a rule, begin each paragraph with a topic sentence; end it in conformity with the beginning."
    "Use the active voice."
    "Put statements in positive form."
    "Omit needless words."
    "Avoid a succession of loose sentences."
    "Express co-ordinate ideas in similar form."
    "Keep related words together."
    "In summaries, keep to one tense."
    "Place the emphatic words of a sentence at the end."

Cleaning Up

Now that you have the letter written, it’s time to do some cleanup work before you hit the send button.

  • Let your secretary or paralegal read it. Not only will your staff frequently find spelling and grammar errors missed by your word processor’s spell checker, but they will find inconsistencies and confusing areas that you missed when drafting.

    1. Number every page of the letter, and staple the letter. If the letter is more than one page long, then it is important to number the pages because they will invariably get out of order. Place the following at the top left corner of each page after the first:

      Recipient’s name _________
      Date _________
      Page _________

    2. Sign the letter in blue ink, not black ink. This will make it easier to differentiate the signed original letter from photocopies, and it will make it more difficult for someone to change your letter after you send it.

    Computerized Letter Writing Tips

    My wife Cathy said I have to put this way at the end here because this article is about letter writing and not computers. She thinks I love wrestling with computers as much as I love playing with words. She’s right. In my first three drafts this section was on page one.

    But I think anyone who likes to play with words should play with them on a computer. That’s where they really dance. And when you’ve written 31,250 letters, as my earlier calculations indicate I may have written in my practice so far, a fourth of them before I started writing letters on computer in 1980, you really begin to appreciate the ability to cut and paste text from prior letters. So here are my tips for anyone still around willing to listen.

    1. Write your own letters on a computer. If you have not yet joined the computer revolution, do it now. Get a computer for no other reason than writing letters. You will never again find yourself explaining to your client why the letter you dictated three days ago has not been mailed yet.

    2. Get Microsoft Word or Corel WordPerfect. You will need good word processing software. The latest versions are Microsoft Word 2000 and Corel WordPerfect 2000. I have both, but I still use Wordperfect 5.1 for DOS for 99% of my work. My fingers know the special codes so well that it’s faster for me to write in this older program. I can still convert the file format to any other one using one of the new 2000 programs which can read the old 5.1 files.

    3. Get voice recognition software if you cannot type. If you never learned to touch type, there is finally reliable software to do it for you. Voice recognition software allows you to dictate directly to your computer. The software is so good that WordPerfect 2000 is sold in a bundle with one brand. You can also purchase this software with an optional hand-held recorder so that you can dictate the old-fashioned way and then transfer it to your computer to transcribe. The two most-advertised brands of software are Dragon Naturally Speaking and L&H VoiceXpress.

    4. Set up a separate directory for each client. If you create a directory (folder) on your computer for every client, you can keep all letters, documents and work for that client in one easy-to-find place, just like your paper file folder. The client’s last name can be used as the directory name. Thus, all letters, wills, contracts, spreadsheets, etc., for John Doe can be kept on your computer’s directory named DOE.

    5. Keep all letters in one computer file. Just as you keep copies of all letters in a paper file folder, you should keep copies of all letters on your computer in the directory for that client. The easiest way to do this is not to start a separate computer file for each letter sent to someone. Instead you just add the new letter to the existing computer file containing other letters to that person. I find that it works best to add new letters at the top of old letters, rather than at the bottom. Then your computer file is like a paper folder since new letters are added at the top where you see them first. This is easy to do on your computer: you just start a new page at the top of the existing letter and write the new letter there.

    6. Name letters to clients LETTERCL and name letters to non-clients with the recipient’s last name. If you name the file with the recipient’s last name, you can easily find the letter later when you want to read it on your computer without having to pull the file. For example, a letter to non-client Mary Smith would be given the computer file name SMITH. The only exception is that I name all letters to my clients LETTERCL rather than the client’s last name because their computer directory is already named their last name. I also do this because it saves me time finding the file if the client is a corporation or there are multiple clients.

    7. Copy text from prior letters. More than half the letters you write are not first letters to a recipient, but are follow-up letters that either remind the recipient of pending work to be done or continue discussion of a matter previously opened. The other half have at least one thing in common: the letter’s opening with the recipient’s name and address and the closing with your name. There is no need to retype all of this text in your new letter. Using block and copy (cut and paste) commands you can easily copy the recipient’s name and address and usable text from a prior letter into your new letter. You can then modify that text to fit the current message. I even have macros that do the repetitive stuff for me.

    8. Print the envelope from the letter. Before we had a computer, we had a lot of errors in typing envelopes and mailing labels. Then when a client called to tell us the error, we would look at the letter and tell them we sent it to the correct address, only to be told that the envelope had a different address. This can easily be avoided by using the envelope printing features of word processing software, which takes the address right off the letter so that you know the letter and envelope will have the same address.

    9. Back up as you write. As wonderful as computers are, they are still powered by electricity, and when it goes off, the words disappear from the screen and if they have not been saved they disappear forever. The first time you lose an hour of work you get a backup device of some type. The second time you lose an hour of work you actually start to use the backup device. My recommendation for backing up is this:
      1. Hit the save button frequently while writing the letter.
      2. If the letter is long, print hard copies of the letter frequently while writing it.
      3. Copy all your work to a backup device at the end of every day.


      Letters serve many purposes: advising clients, seeking compliance, sending documents, obtaining information. All letters benefit from clear writing and simple organization. Lawyers who write direct and concise letters to nonlawyers are more likely to achieve successful results.

      Writing letters is no different from other lawyering skills. The demand letter that the recipient cannot understand is no more effective than a shouting match. If you want a shouting match, then by all means write long letters with big words that no one understands. But if compliance is what you really want, then writing a letter that the recipient understands is really the order of the day.

  • Writing demand letters requires good writing skills, legal knowledge and more.

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