Associate Advice, Rudeness, Small Law Firms

Small Firms, Big Lawyers: The Problem with Lawyer Letters

Have you ever noticed that some lawyers become different people when they get in front of a keyboard?

It’s like a Jekyll-and-Hyde kind of thing. They might be perfectly pleasant individuals in real life, capable of warmth or at least civility to their fellow human beings. But get them in front of a computer with a law-firm template on the screen, and they turn into some sort of lawyerly unmanned drone.

Most lawyers, especially junior lawyers, have an idea about what a lawyer letter is supposed to look like. It generally has fancy lawyerly words like “pursuant to,” and it usually includes lawyerly weirdnesses like parenthetically writing numbers in figures after having just spelled out the numbers in words (“If we do not receive a response for you and/or your counsel in five (5) days …”), and it almost always contains threats about Very Bad Things happening. And they tend to be uniformly douchey.

But here are four (4) reasons why lawyer letters are less effective than phone calls.…

1. Because you learn more with a phone call.

It took me years to come to the conclusion that I wasn’t a letter lawyer. That I was instead a phone lawyer. Let me explain:

Most lawyers are what I call letter lawyers. They write letters. In many ways, letters are their most important form of work output. And there’s something about a lawyer letter, written on law-firm stationery. It’s designed to convey seriousness, and it raises the stakes from a mere disagreement between individuals or companies into a bona fide “legal matter.” Lawyers use lawyer letters to spell out their clients’ positions, and to try to get the other side to do something that the clients want.

But a letter is a form of asynchronous communication, as the computer geeks would say. The recipient reads it at a different time and in a different place than when and where you wrote it. And you miss out on the benefit of the recipient’s instant reaction, which can be useful intelligence to your side. By the time the recipient has read and reread and digested your missive, forwarded it to her counsel, and had her lawyer draft an equally lawyerly response, whatever reaction that shows up in the response has been diluted and massaged into something that’s probably quite different from the initial reaction.

Instead, when you convey your information in a phone call to the other side’s lawyer, you’re more likely to learn something from his reaction. If he’s good, he won’t reveal much. But you’ll probably still learn something if you pay careful attention. Afterward, you can report back to your client: “Well, he said this. But I got the sense that he wanted to say this.” You’ve learned more than you would by just dropping your nastygram in the mailbox.

2. Because you can be more persuasive with a phone call.

Many lawyers forget that their mission in sending the lawyer letter is to convince the other side to do (or stop doing) something. But haughty language and threats of clients “taking all necessary steps available” and so forth rarely have that effect. In my experience, people respond better to reasonable requests from reasonable people.

And it’s much harder to soften your tone in writing. That’s why emoticons were developed in text messages: as a (cumbersome) way to show, for example, that you’re just kidding. 😉 

An accusation of malfeasance can be soft-pedaled when spoken, but looks much harsher in black and white on paper.

The lawyer letter can also set a negative tone for the entire matter, while a pleasant phone call can have the opposite effect. For example, last year I received the following letter from a New York lawyer after we filed a lawsuit against his client:

Dear Mr. Shepherd:

I am writing to inform you that we represent Joe Smith in the above-referenced action. We demand to be notified immediately of any hearing scheduled on any of the motions you have filed. Similarly, we demand that you inform the Court that Mr. Smith has retained counsel, and wishes to be heard in connection with any proceedings. We are in the process of retaining local counsel; as soon as that has occurred, we will so inform you.

My immediate reaction to all that “demanding” was some choice words about lawyers, and about New York lawyers specifically. I figured that we were in for a street fight, and that the guy would be everything that was wrong with lawyers. As it turned out, in real life, this lawyer became my favorite opposing counsel in 17 years of practice. Unlike his stiff, lawyerly letter, the lawyer turned out to be warm, friendly, charming, and very effective for his client. He was a pleasure to deal with, completely the opposite of his initial lawyer letter. But while he was able to overcome an unfavorable first impression, you might not be so lucky. Better to start off the relationship by trying to come across as a reasonable person representing a reasonable person, rather than trying to sound like a lawyer.

3. Because there’s no real record of a phone call.

If it’s written down, it becomes permanent. More importantly, you can’t control what happens to it once you send it. (This goes doubly for email.) In a phone call, it’s extremely unlikely that your words are being recorded. (It would also be illegal.) If you later need to back away from something you said, it’s a lot easier to do that if there’s no record of your words. “No, no,” you say. “That’s not what I meant. You must have misunderstood me.” It can be very handy to be able to do that.

It also makes it easier to say things about your client that you would never commit to writing. “Look, Sheila, my client is very emotional about this issue. I think his feelings were really hurt. An apology and a check for $20,000 would go a long way to fixing that.” Calling your client a crybaby in writing is much dicier.

4. Because it removes a level of insulation between lawyers and clients.

You have to assume that your letter to opposing counsel will be shared with her client, and clients can have different reactions than their counsel. A client will often get tweaked by something an opposing counsel writes while the lawyer would be more likely to just brush it off. When the communication is by phone, the opposing counsel is better able to calibrate the message given to the client to avoid that happening. The lawyer can leave out the things that she knows will anger the client. In a letter, that can’t happen.

So the next time you’re thinking about writing a letter with spelled-out numbers in parentheses and threats of Very Bad Things, don’t. Instead, pick up the phone. Reach out and touch someone.

Jay runs Prefix, LLC, a firm that helps lawyers learn how to value and price legal services. Jay Shepherd also spent 13 years running the Boston management-side employment-law boutique Shepherd Law Group. He writes the ABA Blawg 100 honoree The Client Revolution, which focuses on reinventing the business of law, and Gruntled Employees, a workplace blog. Follow Jay on Twitter at @jayshep, or email him at

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