November/December 2019


The Curious Value of the Unsent Letter

Lucian T. Pera

Have you ever drafted a letter or email, only to decide you really shouldn’t send it? If your answer is no, my question for you is, Why in the world not?

Students of history will recall that Harry Truman, Winston Churchill and Mark Twain each sometimes indulged their anger in letters never dispatched to their targets.

Be Like Abe

Abraham Lincoln would sometimes dash off what he called a “hot letter,” only to set it aside to let his temper cool, and ultimately file it marked “Never sent. Never signed.” One of Lincoln’s unsent missives blamed Union Gen. George Meade for letting Confederate Gen. Robert E. Lee escape after Gettysburg, but Meade never got the letter.

The cathartic effect can be useful for us lawyers too. I heartily endorse it.

That intemperate unsent email you draft in response to that outrageous email you just got from opposing counsel or your client may be—if not immediately sent—just what the doctor ordered. It may let you safely vent while still mulling the most productive response. Isn’t that why God (or Bill Gates?) invented the Drafts folder in Outlook?

Lawyering and the Unsent Email

While I encourage you to explore the therapeutic benefits of the unsent letter—you’d be amazed at how many internet commenters recommend it—I want to dwell for a bit on how drafting a letter or email, not knowing whether you will ever send it, may improve your communications. It may even improve your analysis underlying a number of important communications we all need to have, especially with clients. It’s a valuable tool we should all consciously use.

As lawyers we sometimes must have difficult or important conversations, often with our clients. Good lawyers prepare for these conversations, in their own way. Some run through the topics to be covered in their heads; some rehearse them with another lawyer in their firm; some get their spouse’s advice; some make notes. But many of these conversations should (or must) eventually be confirmed in writing, whether because clients understand the message better when they read it or take it in a second time, or because the ethics rules require it or because prudent lawyering does.

So if you’re going to have to write that letter eventually, why not combine that (sometimes unwelcome) task with your preparation?

Prepping for a Waiver Conversation

Suppose you need to talk with a prospective client about a conflict of interest. The employer you regularly represent really wants you to also represent its manager in a new employment matter where the manager’s conduct is at issue. Of course, now you have to talk with the manager to get his or her consent.

But you’ve read enough ethics columns to know this can be tricky and that you really have to make sure the manager understands what a joint representation means. Maybe you even drop in on your office’s ethics nerd and confirm what you need to discuss with the manager before you take him or her on as a client. So you have your handwritten ethics checklist of those topics. Great.

But you don’t do this kind of conversation often, and you’re slightly concerned about the best way to explain it all to the manager. You know that, in your jurisdiction, you are going to have to confirm in writing the waiver you hope to get from the manager. And your office’s ethics nerd tells you the firm wants the manager to sign that waiver too.

Consider drafting the waiver letter right then—before you have the conversation with the manager. You can get your thoughts in order, make them understandable, make sure you touch every base and ensure it’s in understandable English. And, by the way, when you get a good draft together, I guarantee that your office ethics nerd will be thrilled to look it over and catch anything you missed. (We actually love being asked to do this.)

Then, armed with an organized and complete agenda for your conversation with the manager—your draft letter—you can have the talk, on the phone or in person, and follow it very quickly with the waiver letter for the manager’s review. You can even hand him or her a copy in person if you like. (But if you do, consider letting him or her take it home, read it again and then sign it. That’s another technique to be sure they have time to understand it.)

Improving Difficult Client Conversations

From time to time, we all have to have more difficult conversations—perhaps about critical settlement proposals or a necessary adjustment of a client’s fee or withdrawal or—perish the thought—that mistake you made in the client’s matter. Here’s where the drafting the client letter carefully, quietly and before the client conversation can be most valuable.

Each of these conversations can be fraught. Each of them needs to be carefully thought out. And very often you’d be wise to get help from someone else in preparing. Drafting the written communication up front helps immensely.

But wait, you may say: All the examples you’ve given so far involve letters you are actually going to send, or do ultimately send, so where’s the unsent letter?

Road Testing a Client Conversation

Well, first, remember the experience we almost all have had: We start down the path of seeking a conflict waiver or withdrawal only to discover that, in fact, there’s no way this is going to work. The exercise of committing to paper or electrons what the client is actually waiving or the basis for our planned withdrawal may lead us to conclude that we cannot seek the waiver or withdraw.

Second, I suggest that you consciously harness that process of more thorough thinking on paper (or machine) as a means of evaluating your next step—before you have finally settled on that next step. Sure, drafting earlier helps improve the difficult conversation, but think about using it when you’re only starting to evaluate whether to seek the conflict waiver or ask the client to agree to a fee adjustment.

Some business lawyers will say, when asked about adding a particular provision to a document, “Let’s see how it drafts.” They’re conveying their experience that some ideas that sound great in the first telling don’t survive a full attempt to draft them into workable language. There’s wisdom in that idea. The old-fashioned lawyer work of drafting often reveals flaws in our approach. Drafting the (possibly) unsent letter works just that way.

You can exercise your lawyer brain to try fully and clearly communicating the thought—the conflict waiver, the fee adjustment or withdrawal—as a way to fully road test whether the thought can legally, ethically and safely be turned into action. In the process any good idea can be improved; often the badness of other ideas can be revealed.

The moral: Consider that Drafts folder in your inbox as a constant invitation to use the unsent letter or email as a routine part of your lawyer toolbox.

Lucian T. Pera

Lucian T. Pera is a partner in the Memphis, Tennessee, office of Adams and Reese LLP. He counsels lawyers, law firms, clients and those who do business with lawyers and law firms on ethics and professional responsibility issues. He is a past president of the Tennessee Bar Association and a past ABA treasurer. Email him at