{"id":133758,"date":"2025-09-23T16:43:13","date_gmt":"2025-09-24T00:43:13","guid":{"rendered":"https:\/\/xira.com\/p\/2025\/09\/23\/dear-chatgpt-words-matter\/"},"modified":"2025-09-23T16:43:13","modified_gmt":"2025-09-24T00:43:13","slug":"dear-chatgpt-words-matter","status":"publish","type":"post","link":"https:\/\/xira.com\/p\/2025\/09\/23\/dear-chatgpt-words-matter\/","title":{"rendered":"Dear ChatGPT: Words Matter"},"content":{"rendered":"

I\u00a0recently\u00a0was working on a\u00a0blog post<\/a>\u00a0on how\u00a0various stresses placed on lawyers could result in unchecked\u00a0citations. The title of the post was\u00a0Billable Hour Demand, Shadow Use of AI and Law Reality: It\u2019s a Hot Mess<\/em>.<\/p>\n

After it was more or less complete, I ran it by one of the public LLMs\u00a0for comment. It made several\u00a0suggestions\u00a0including the deletion of the term \u201chot mess.\u201d I asked it several times\u00a0for clarity about why it wanted to remove the term without getting a clear answer. I finally said, \u201cI really like the term because it\u00a0correctly\u00a0describes\u00a0what is going on and I\u2019m putting it in the title.\u201d The LLM then replied,\u00a0\u201cGreat idea\u2013that term really captures what you\u2019re trying to say!\u201d \u00a0The post\u00a0went on to\u00a0get more clicks and likes than many\u00a0others\u00a0I have done.<\/p>\n

I mention this not only because it once again demonstrates that AI tools really want to please you and will tell you what you want to hear.\u00a0But more\u00a0importantly, it\u2019s an example of why as a writer, you can\u2019t just rely on AI if you want to attract readership and create your own style.<\/p>\n

Before AI,\u00a0I, like\u00a0many\u00a0writers,\u00a0would go through several drafts and change things\u00a0frequently\u00a0before being satisfied with the\u00a0final product.\u00a0But if AI had been around and I had relied on it more\u00a0or less completely, I\u00a0might\u00a0not have gotten\u00a0a final product I was proud of. No hot mess.<\/p>\n

That\u2019s because words matter. Names matter. The turn of a phrase is important and can turn writing into something\u00a0memorable. And there\u2019s plenty of\u00a0historical\u00a0examples.<\/p>\n

It\u2019s rumored that\u00a0the famous last line of the Hemingway book The Sun Also Rises \u2014 \u201cisn\u2019t it pretty to think so\u201d \u2014 was rewritten by Hemingway several times.\u00a0The line is the final one in the book and\u00a0comes when two people are\u00a0discussing\u00a0a love affair they could never have. One of the\u00a0characters\u00a0muses\u00a0they\u00a0could have had such a good time together.\u00a0<\/em>\u00a0The other character then utters the famous line.\u00a0The line\u00a0\u201cisn\u2019t it pretty to think so\u201d\u00a0<\/em>pretty well sums up the\u00a0point of the\u00a0book and the times\u00a0in which it was written.<\/p>\n

But it\u2019s commonly\u00a0believed\u00a0that at one point Hemingway considered using the line\u00a0\u201cisn\u2019t it nice to think so.\u201d Whether that\u2019s\u00a0true or not,\u00a0using the word nice in the line would\u00a0make it like a weak handshake:\u00a0yucky.\u00a0It fails to capture the bite and tension of the story.\u00a0It\u2019s not as haunting.<\/p>\n

Another example:\u00a0reportedly\u00a0the line\u00a0\u201cgovernment of the people, by the people, and for the people, shall not perish from the earth\u201d from the Gettysburg address was\u00a0originally \u201cgovernment of the people, by the people, and for the people, shall not perish upon the earth.\u201d Changes the impact considerably.<\/p>\n

How about this one: Winston\u00a0Churchill\u2019s\u00a0line\u00a0from his Battle of Britain\u00a0speech:\u00a0\u201cThis was their finest hour.\u201d Reportedly the line was originally\u00a0\u201cThis could prove to be their finest hour.\u201d Not the same\u00a0rallying cry to a public desperate for hope and good news.<\/p>\n

And maybe most\u00a0significantly, Dr. Martin Luther King\u2019s famous line\u00a0\u201cI have a dream\u201d\u00a0was not in his original\u00a0speech\u00a0drafts. What\u00a0was\u00a0in\u00a0his drafts\u00a0was\u00a0\u201cI have a\u00a0plan,\u201d\u00a0or \u201cI have a vision.\u201d\u00a0He spontaneously\u00a0added\u00a0\u201cI have a dream\u201d when he was\u00a0delivering\u00a0the speech. The words \u201cplan\u201d or \u201cvision\u201d fail to\u00a0have\u00a0same eloquence and\u00a0simply aren\u2019t\u00a0stirring.<\/p>\n

What did\u00a0all these people have in common?\u00a0They started with a concept and worked hard to come up with\u00a0the best\u00a0way to\u00a0sufficiently\u00a0express that concept.<\/p>\n

I thought about this when I heard the new name for the\u00a0AffiniPay\u00a0group of companies: 8am.\u00a0The concept\u00a0behind the name was that it\u00a0summarized\u00a0in\u00a0two words what the group of companies is all about: helping lawyers do\u00a0non-billable\u00a0work that they don\u2019t like doing.\u00a0The\u00a0conventional\u00a0wisdom is\u00a0to do\u00a0what\u00a0you don\u2019t like early in the day. So 8am captures the essence of what the companies\u00a0do.\u00a0<\/p>\n

Again, words matter, titles matter.\u00a0<\/p>\n

LLMs\u00a0<\/strong>(<\/strong>Don\u2019t<\/strong>)<\/strong>\u00a0<\/strong>Say the Darndest Things<\/strong><\/p>\n

Certainly, you can use LLMs to help you write. But\u00a0what\u00a0might\u00a0happen if we ran some of the above examples by an\u00a0LLM?<\/p>\n

The end of The Sun Also Rises\u00a0would have been \u201cIn another life maybe.\u201d<\/p>\n

Dr. King\u2019s \u201cI have a dream\u201d would turn into\u00a0\u201cthe future isn\u2019t something we wait for\u2014it\u2019s\u00a0something we create together.\u201d<\/p>\n

8am would be\u00a0The Legal Edge.<\/p>\n

See what overreliance on LLMs get you?\u00a0Boring. Not memorable.\u00a0Obfuscating\u00a0what you are\u00a0trying to\u00a0say. Or distorting your meaning entirely.<\/p>\n

Lessons for Lawyers<\/strong><\/p>\n

There\u2019s an important lesson here\u00a0for lawyers. We are in the business of communication. Of persuasion. How do you best communicate and persuade? By\u00a0making what you say interesting and memorable. By treating words with\u00a0importance\u00a0and respect. By\u00a0using words that capture what you are trying to say in a way the person you are communicating with will\u00a0understand\u00a0and will stick in their minds.\u00a0An LLM\u00a0can\u2019t do that. At least not yet.<\/p>\n

Remember Justice Oliver Wendell Holmes Jr., when discussing the limits to the First Amendment, didn\u2019t just say the First Amendment is not absolute.\u00a0Instead,\u00a0he said:\u00a0\u201cFree speech would not protect a man in falsely shouting fire in a theatre and causing a panic.\u201d \u00a0Conveys the point in a clear and memorable way.<\/p>\n

But Wait\u2026<\/strong><\/p>\n

But wait, you say. Can\u2019t LLMs come up with the kind of phrases that catch your eye\u00a0and distill\u00a0concepts down to something memorable?\u00a0<\/p>\n

Maybe.\u00a0But an LLM will likely not give you the kind of phrase you really need, at least not without a lot of work.\u00a0And maybe not even then.\u00a0But\u00a0with work on your end,\u00a0it might be able to give you something that you can mold into\u00a0those kinds of words.<\/p>\n

Ivy\u00a0Grey<\/a>, the\u00a0Chief Strategy\u00a0and Growth Officer\u00a0of WorkRake, said in a\u00a0recent\u00a0whitepaper<\/a>, \u201cLegal writing\u00a0is not simply assembling words\u00a0or producing text. It is the result of analysis, strategy and judgement.\u201d It is that analysis, strategy and judgment that allows you to take what an LLM gives you and turns into something that can communicate and persuade. The genius of Hemingway was not only that he came up with the words to end his book. It was that he recognized\u00a0when he had it. He knew\u00a0conceptually\u00a0what he wanted to do. He used his\u00a0own\u00a0\u201canalysis, strategy and\u00a0judgment.\u201d<\/p>\n

You still have to do the work.<\/p>\n

Words Matter<\/strong><\/p>\n

A single word, a small change, can alter tone, power, and even how\u00a0your writing is\u00a0remembered.\u00a0Don\u2019t cede that to a\u00a0robot.\u00a0<\/p>\n

Don\u2019t let LLMs hijack your style for the sake of\u00a0expediency. Don\u2019t be tempted to think that how an LLM writes something is necessarily better than you.\u00a0Don\u2019t substitute speed for the good.\u00a0Words matter.<\/p>\n

And how do you get the\u00a0analysis, strategy, and judgment to know when you got something good? Have a concept. Know what you are trying to really convey. Look to be concise.<\/p>\n

One final point: read. Read good books by authors who know how use words effectively and memorably. It will help you\u00a0to, as Supreme Court\u00a0Justice Potter Stewart\u00a0once\u00a0said about obscenity in a famous case,\u00a0\u201cknow it when you see it.\u201d<\/p>\n

\n

Stephen Embry is a lawyer, speaker, blogger, and writer. He publishes\u00a0TechLaw Crossroads<\/a>, a blog devoted to the examination of the tension between technology, the law, and the practice of law<\/strong><\/em>.<\/p>\n

The post Dear ChatGPT: Words Matter<\/a> appeared first on Above the Law<\/a>.<\/p>\n

I\u00a0recently\u00a0was working on a\u00a0blog post<\/a>\u00a0on how\u00a0various stresses placed on lawyers could result in unchecked\u00a0citations. The title of the post was\u00a0Billable Hour Demand, Shadow Use of AI and Law Reality: It\u2019s a Hot Mess<\/em>.<\/p>\n

After it was more or less complete, I ran it by one of the public LLMs\u00a0for comment. It made several\u00a0suggestions\u00a0including the deletion of the term \u201chot mess.\u201d I asked it several times\u00a0for clarity about why it wanted to remove the term without getting a clear answer. I finally said, \u201cI really like the term because it\u00a0correctly\u00a0describes\u00a0what is going on and I\u2019m putting it in the title.\u201d The LLM then replied,\u00a0\u201cGreat idea\u2013that term really captures what you\u2019re trying to say!\u201d \u00a0The post\u00a0went on to\u00a0get more clicks and likes than many\u00a0others\u00a0I have done.<\/p>\n

I mention this not only because it once again demonstrates that AI tools really want to please you and will tell you what you want to hear.\u00a0But more\u00a0importantly, it\u2019s an example of why as a writer, you can\u2019t just rely on AI if you want to attract readership and create your own style.<\/p>\n

Before AI,\u00a0I, like\u00a0many\u00a0writers,\u00a0would go through several drafts and change things\u00a0frequently\u00a0before being satisfied with the\u00a0final product.\u00a0But if AI had been around and I had relied on it more\u00a0or less completely, I\u00a0might\u00a0not have gotten\u00a0a final product I was proud of. No hot mess.<\/p>\n

That\u2019s because words matter. Names matter. The turn of a phrase is important and can turn writing into something\u00a0memorable. And there\u2019s plenty of\u00a0historical\u00a0examples.<\/p>\n

It\u2019s rumored that\u00a0the famous last line of the Hemingway book The Sun Also Rises \u2014 \u201cisn\u2019t it pretty to think so\u201d \u2014 was rewritten by Hemingway several times.\u00a0The line is the final one in the book and\u00a0comes when two people are\u00a0discussing\u00a0a love affair they could never have. One of the\u00a0characters\u00a0muses\u00a0they\u00a0could have had such a good time together.\u00a0<\/em>\u00a0The other character then utters the famous line.\u00a0The line\u00a0\u201cisn\u2019t it pretty to think so\u201d\u00a0<\/em>pretty well sums up the\u00a0point of the\u00a0book and the times\u00a0in which it was written.<\/p>\n

But it\u2019s commonly\u00a0believed\u00a0that at one point Hemingway considered using the line\u00a0\u201cisn\u2019t it nice to think so.\u201d Whether that\u2019s\u00a0true or not,\u00a0using the word nice in the line would\u00a0make it like a weak handshake:\u00a0yucky.\u00a0It fails to capture the bite and tension of the story.\u00a0It\u2019s not as haunting.<\/p>\n

Another example:\u00a0reportedly\u00a0the line\u00a0\u201cgovernment of the people, by the people, and for the people, shall not perish from the earth\u201d from the Gettysburg address was\u00a0originally \u201cgovernment of the people, by the people, and for the people, shall not perish upon the earth.\u201d Changes the impact considerably.<\/p>\n

How about this one: Winston\u00a0Churchill\u2019s\u00a0line\u00a0from his Battle of Britain\u00a0speech:\u00a0\u201cThis was their finest hour.\u201d Reportedly the line was originally\u00a0\u201cThis could prove to be their finest hour.\u201d Not the same\u00a0rallying cry to a public desperate for hope and good news.<\/p>\n

And maybe most\u00a0significantly, Dr. Martin Luther King\u2019s famous line\u00a0\u201cI have a dream\u201d\u00a0was not in his original\u00a0speech\u00a0drafts. What\u00a0was\u00a0in\u00a0his drafts\u00a0was\u00a0\u201cI have a\u00a0plan,\u201d\u00a0or \u201cI have a vision.\u201d\u00a0He spontaneously\u00a0added\u00a0\u201cI have a dream\u201d when he was\u00a0delivering\u00a0the speech. The words \u201cplan\u201d or \u201cvision\u201d fail to\u00a0have\u00a0same eloquence and\u00a0simply aren\u2019t\u00a0stirring.<\/p>\n

What did\u00a0all these people have in common?\u00a0They started with a concept and worked hard to come up with\u00a0the best\u00a0way to\u00a0sufficiently\u00a0express that concept.<\/p>\n

I thought about this when I heard the new name for the\u00a0AffiniPay\u00a0group of companies: 8am.\u00a0The concept\u00a0behind the name was that it\u00a0summarized\u00a0in\u00a0two words what the group of companies is all about: helping lawyers do\u00a0non-billable\u00a0work that they don\u2019t like doing.\u00a0The\u00a0conventional\u00a0wisdom is\u00a0to do\u00a0what\u00a0you don\u2019t like early in the day. So 8am captures the essence of what the companies\u00a0do.\u00a0<\/p>\n

Again, words matter, titles matter.\u00a0<\/p>\n

LLMs\u00a0<\/strong>(<\/strong>Don\u2019t<\/strong>)<\/strong>\u00a0<\/strong>Say the Darndest Things<\/strong><\/p>\n

Certainly, you can use LLMs to help you write. But\u00a0what\u00a0might\u00a0happen if we ran some of the above examples by an\u00a0LLM?<\/p>\n

The end of The Sun Also Rises\u00a0would have been \u201cIn another life maybe.\u201d<\/p>\n

Dr. King\u2019s \u201cI have a dream\u201d would turn into\u00a0\u201cthe future isn\u2019t something we wait for\u2014it\u2019s\u00a0something we create together.\u201d<\/p>\n

8am would be\u00a0The Legal Edge.<\/p>\n

See what overreliance on LLMs get you?\u00a0Boring. Not memorable.\u00a0Obfuscating\u00a0what you are\u00a0trying to\u00a0say. Or distorting your meaning entirely.<\/p>\n

Lessons for Lawyers<\/strong><\/p>\n

There\u2019s an important lesson here\u00a0for lawyers. We are in the business of communication. Of persuasion. How do you best communicate and persuade? By\u00a0making what you say interesting and memorable. By treating words with\u00a0importance\u00a0and respect. By\u00a0using words that capture what you are trying to say in a way the person you are communicating with will\u00a0understand\u00a0and will stick in their minds.\u00a0An LLM\u00a0can\u2019t do that. At least not yet.<\/p>\n

Remember Justice Oliver Wendell Holmes Jr., when discussing the limits to the First Amendment, didn\u2019t just say the First Amendment is not absolute.\u00a0Instead,\u00a0he said:\u00a0\u201cFree speech would not protect a man in falsely shouting fire in a theatre and causing a panic.\u201d \u00a0Conveys the point in a clear and memorable way.<\/p>\n

But Wait\u2026<\/strong><\/p>\n

But wait, you say. Can\u2019t LLMs come up with the kind of phrases that catch your eye\u00a0and distill\u00a0concepts down to something memorable?\u00a0<\/p>\n

Maybe.\u00a0But an LLM will likely not give you the kind of phrase you really need, at least not without a lot of work.\u00a0And maybe not even then.\u00a0But\u00a0with work on your end,\u00a0it might be able to give you something that you can mold into\u00a0those kinds of words.<\/p>\n

Ivy\u00a0Grey<\/a>, the\u00a0Chief Strategy\u00a0and Growth Officer\u00a0of WorkRake, said in a\u00a0recent\u00a0whitepaper<\/a>, \u201cLegal writing\u00a0is not simply assembling words\u00a0or producing text. It is the result of analysis, strategy and judgement.\u201d It is that analysis, strategy and judgment that allows you to take what an LLM gives you and turns into something that can communicate and persuade. The genius of Hemingway was not only that he came up with the words to end his book. It was that he recognized\u00a0when he had it. He knew\u00a0conceptually\u00a0what he wanted to do. He used his\u00a0own\u00a0\u201canalysis, strategy and\u00a0judgment.\u201d<\/p>\n

You still have to do the work.<\/p>\n

Words Matter<\/strong><\/p>\n

A single word, a small change, can alter tone, power, and even how\u00a0your writing is\u00a0remembered.\u00a0Don\u2019t cede that to a\u00a0robot.\u00a0<\/p>\n

Don\u2019t let LLMs hijack your style for the sake of\u00a0expediency. Don\u2019t be tempted to think that how an LLM writes something is necessarily better than you.\u00a0Don\u2019t substitute speed for the good.\u00a0Words matter.<\/p>\n

And how do you get the\u00a0analysis, strategy, and judgment to know when you got something good? Have a concept. Know what you are trying to really convey. Look to be concise.<\/p>\n

One final point: read. Read good books by authors who know how use words effectively and memorably. It will help you\u00a0to, as Supreme Court\u00a0Justice Potter Stewart\u00a0once\u00a0said about obscenity in a famous case,\u00a0\u201cknow it when you see it.\u201d<\/p>\n

\n

Stephen Embry is a lawyer, speaker, blogger, and writer. He publishes\u00a0TechLaw Crossroads<\/a>, a blog devoted to the examination of the tension between technology, the law, and the practice of law<\/strong><\/em>.<\/p>\n

The post Dear ChatGPT: Words Matter<\/a> appeared first on Above the Law<\/a>.<\/p>\n","protected":false},"excerpt":{"rendered":"

I\u00a0recently\u00a0was working on a\u00a0blog post\u00a0on how\u00a0various stresses placed on lawyers could result in unchecked\u00a0citations. The title of the post was\u00a0Billable Hour Demand, Shadow Use of AI and Law Reality: It\u2019s a Hot Mess. After it was more or less complete, I ran it by one of the public LLMs\u00a0for comment. It made several\u00a0suggestions\u00a0including the deletion […]<\/p>\n","protected":false},"author":3,"featured_media":0,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"_et_pb_use_builder":"","_et_pb_old_content":"","_et_gb_content_width":"","_jetpack_memberships_contains_paid_content":false,"footnotes":""},"categories":[16],"tags":[],"class_list":["post-133758","post","type-post","status-publish","format-standard","hentry","category-above_the_law"],"jetpack_featured_media_url":"","jetpack_sharing_enabled":true,"_links":{"self":[{"href":"https:\/\/xira.com\/p\/wp-json\/wp\/v2\/posts\/133758","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/xira.com\/p\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/xira.com\/p\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/xira.com\/p\/wp-json\/wp\/v2\/users\/3"}],"replies":[{"embeddable":true,"href":"https:\/\/xira.com\/p\/wp-json\/wp\/v2\/comments?post=133758"}],"version-history":[{"count":0,"href":"https:\/\/xira.com\/p\/wp-json\/wp\/v2\/posts\/133758\/revisions"}],"wp:attachment":[{"href":"https:\/\/xira.com\/p\/wp-json\/wp\/v2\/media?parent=133758"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/xira.com\/p\/wp-json\/wp\/v2\/categories?post=133758"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/xira.com\/p\/wp-json\/wp\/v2\/tags?post=133758"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}