I was cleaning out some old files in a filing cabinet (yes, that’s still a thing) and I came across some plastic cards we had made up when I was head of litigation at a large technology company many moons ago.  My team and I created the cards to help the business focus on key compliance issues, i.e., providing them cards with lists of easy-to-remember rules that could help keep them – and the company – out of trouble.  They were about the size of a business card (that may not be a thing anymore…)[1] and were laminated so they would last forever.[2]  And here in front of me were several different cards we had prepared close to twenty years ago.  They included tips on competition law compliance, how to report a violation of the company handbook, and (my personal favorite) how to write smart emails that won’t end up as Exhibit A at trial.  I remembered why we created these in the first place, especially the email card:  If you have ever lived through big litigation (or any litigation for that matter), you understand just how deadly a poorly drafted email can be.

And deadly is right.  I lived through several painful and protracted litigated disputes, and I can attest that emails (ours and theirs) were front and center, blowing up in faces like Wile E. Coyote-endorsed ACME product.  The only thing missing was a sign for free birdseed. There were lots of lessons learned by unfortunate executives (and yours truly).  Back then, I decided to take those lessons and create something useful to showcase basic rules to help the business – and the lawyers – write smarter emails (and other documents).  As I read through the card, I realized that I had forgotten some of the lessons.  And, yes, that failure has bitten me in the ass more than a few times.  So, I decided it would be a good idea to write them out here for you – and for me.  This edition of “Ten Things” sets out questions you should ask yourself about the email before you hit send:

1.  Do I need to send this email at all? One thing I like to tell people is that in the case of a mass extinction event, the only two things left on the earth will be cockroaches and all of those emails you thought you had deleted. That’s right, once you hit send, that email will never go away.  Email, for good or bad (and mostly bad), creates a permanent, searchable record of “conversations” that can be pulled into litigation, audits, or regulatory reviews. So, before you type out an email – and especially before you hit send – ask yourself whether the message truly needs to exist or would a phone call or video conference be better?  Here are some other things to consider before creating your permanent repository of crappy documents:

• Unnecessary emails can create confusion, unneeded work, and inadvertently generate legal risk by recording thoughts that are not yet fully formed (though they will appear fully formed to third parties when committed to writing).
• Once sent, emails can easily be saved, forwarded, misunderstood, or misused out of context – and you have no control over where they end up.
• Consider the business impact as well. Unnecessary emails clog inboxes and dilute focus as people must read them (i.e., want to have less email to deal with? Then start sending fewer emails).

Bottom line: If your email does not inform, instruct, or move something forward, reconsider whether it needs to be sent.  Sometimes, doing nothing is the best path.

2.  Do I have the right recipients? One of the easiest ways to spin up legal problems is by sending an email to the wrong person. Whether through auto-fill errors or habit, i.e., it is easy to include a similarly named contact, or to forget that a thread includes external recipients. Regardless of the why, sending an email to the wrong person(s) can result in leaks of confidential information, breach of NDAs, and even waiver of attorney-client privilege. In short, after drafting your email, take your hand off the mouse and double-check your “To,” “CC,” and “BCC” fields before you hit send.  This simple move can save you and the company a lot of problems.

3.  Is this email privileged (and labeled properly)? If you are discussing, responding to, or requesting legal advice, your email may be protected by attorney-client privilege — but that protection is not automatic. You need three things for the privilege to attach: a) a confidential communication, b) between a lawyer (acting as such) and a client, and c) for the purpose of giving or obtaining legal advice. Unless all three prongs are met, the communication is not privileged.  And simply copying a lawyer on an email will not make it privileged.  As noted above, the privilege can be waived – accidentally and irreversibly — if an email is shared with someone who does not need to see it. That includes non-company individuals, external vendors, or (potentially) even colleagues who aren’t involved in the specific legal issue. Once privilege is waived, the full content of the communication may be discoverable in litigation or during regulatory inquiries, which could expose even more documents containing legal analysis, internal thinking, or strategy.[3]

Further, avoid mixing legal and business advice in the same message if possible. If the purpose is to seek or give legal advice, make that clear in the email and keep it separate from email involving day-to-day business discussions (which are fair game in litigation).  In other words, not everything a lawyer writes is privileged.  If you must discuss both legal advice and business advice, separate those clearly in the body of the email, e.g., a “business section” and a “legal analysis section.”  And be sure you clearly label the communication as privileged, e.g., “Privileged and Confidential – Attorney-Client Communication.” Make it easy for anyone outside the company looking at the message to at least think that the message might be a privileged communication. [4]  

4.  Am I angry? If you are frustrated or upset, that is a strong signal to stop writing – not to type faster with furious self-righteousness burning in your heart. Writing while angry leads to emails that feel good in the moment but look terrible when reviewed later, as they often come across as hyper-aggressive, accusatory, snotty, or emotional, even if they were meant to simply be firm or direct (and sometimes your emoticon cannot save the day either). Once sent, you can’t take them back, [5] and the reputational or legal damage may be significant. For example, emails are often among the first documents reviewed in investigations, litigation, or employment disputes. What might seem like an off-the-cuff comment or harmless venting could later be interpreted as evidence of retaliation, bias, or a toxic workplace culture. Angry emails also tend to escalate situations that might otherwise have been resolved quietly or constructively if you had just walked down the hall, picked up the phone, or had not sent at all. 

The book Team of Rivals (which you should buy and read right now if you haven’t done so already)[6] reveals that Abraham Lincoln had a trick where he would write out the letter or response he wanted to send and then put it in a locked box overnight.  The next day, he would take it out, review it, and then write the letter or response he needed to send.   Be like Lincoln (except for the getting shot part).  If you are angry or upset and just cannot wait to put it down in writing, do this:  Draft the email you want to send, save it in drafts, and then go get some coffee or take a walk.  Just do not hit send.  After an hour or so (minimum) you can look at it again – though I recommend letting it sit overnight if possible.  Whenever you get back to it, I guarantee that you will rewrite the email.[7]  And no matter what, always read your draft email as if you are the recipient – or a judge/member of the jury. Does it sound constructive? Objective? Professional? If not, revise or don’t send it. One poorly worded message can cost you and the company a lot.

5.  Is the tone professional? When drafting emails, tone is as important as content – sometimes more so. A perfectly accurate email written in a sarcastic or dismissive tone can be a disaster waiting to happen. Why? Because that “tone” will likely influence how your message is received internally and externally. The wrong tone may seriously damage the company’s position in litigation (or damage its reputation if read by outsiders hostile to the company or just looking for a good story). Keep the following in mind:

• Emails do not convey nuance like face-to-face communication. Relying on email to convey complex issues and analysis is usually a mistake.
• A well-intentioned joke or casual phrasing may be misunderstood or weaponized, particularly in tense or high-stakes situations.
• Your tone should match the situation. Be respectful, calm, and clear — even if you disagree with the recipient or are delivering unwelcome news.
• Your email tone sets the tone for team culture. For example, how you communicate internally reflects your values, the values of the legal department, and the values of the company. Keep your language measured and focused on facts. Don’t assume that informal equals friendly – friendly can be professional too.

Additionally, never use profanity or off-color humor in a company email.  Even if your best friend in the world is the recipient.  You never know who will see the email, and I can tell you from firsthand experience, judges and juries do not like it, and it will cost you and the company dearly.  Repeat after me: Every email is a business document and I will treat it like such.  Lastly, with the right AI tool (one that will not breach privilege and confidentiality obligations), you can run your draft email through it and adjust the tone, e.g., “make this email less angry” or “make this email sound more professional” (or even “less formal).  I’d consider Grammarly (see below) or CoPilot.  ChatGPT and Claude are great for this too, if you have enterprise versions. 

6.  Have I checked for spelling and grammatical errors? Basic spelling or grammar errors can undermine your message (and you), even if the content/analysis is rock solid. Such mistakes suggest a lack of attention to detail, sloppiness, and intellectual laziness – none of which inspire confidence from your teammates, business colleagues, the C-Suite, or outsiders. In a legal context, such errors may even affect how a message is interpreted (i.e., grammar matters!). Clear, well-written communication is important in any business-critical correspondence. A small typo can change the meaning of a key sentence or obscure your intended message.  Before you hit send, take a moment to re-read what you wrote. Use your word processing tools’ spellcheck or Grammarly (my favorite tool).[8]  But, do not rely 100% on technology.  It is ultimately up to you to proofread your work.  If the message is sensitive or high-risk, step away for a bit and then read it fresh (you will catch things you missed).  Or, if super critical and important, ask a colleague to review it.

7.  Am I trashing a colleague or a customer? Emails that disparage colleagues, customers, or vendors do not just reflect poor judgment – they create the possibility for embarrassment (you and them) and legal exposure for the company. If there is ever an employment dispute, contract conflict, or customer complaint, these emails will surface. What you may see as confidential “venting,” others may see as defamation, discrimination, retaliation, or just poor taste. Why does this matter so much?  Here are just a few reasons:

• Even internally, negative emails erode trust. They can fuel a culture of blame, damage morale, and complicate efforts to address issues constructively. If you have feedback about someone, be constructive and direct it to the proper place, e.g., your manager or human resources. And never assume that such emails are private or confidential, even on internal systems.
• Emails about customers can come back to bite you in litigation (smart lawyers will paint your poorly worded email as how the company “really feels” about their client).  They may even cause the customer to take their business elsewhere (and, if so, just think how popular you will be with the sales team and the C-Suite). 
• I have seen derogatory emails used at deposition to surprise and embarrass a witness.  As you can imagine, a colleague seeing something horrible you wrote about them for the first time while under oath is not a great moment.  And they will never trust you – let alone talk to you – again.

When writing emails, stick to facts and maintain professionalism, especially when discussing performance, behavior, or other concerns.  Don’t use email to take personal shots or express frustration at others – those messages have a long shelf life and have a way of coming back to haunt you and the company at the worst possible time.

8.  Am I including only those who need to be involved? Above, I discussed the importance of ensuring that you are sending your email to the correct addresses. Even if you have that figured out, deciding “who” you are including is key to limiting problems. Including too many people can lead to privilege waivers, leaks of confidential data, or broad exposure of sensitive discussions that should be limited to just a few people. It can also create the impression that you are escalating unnecessarily or inviting a “pile-on.” On the other hand, leaving out essential people can create other problems. Key decision-makers may be blindsided or unaware of risks if they were not looped in at the right time. This can delay action or cause confusion about who owns an issue or decision. You do not want to be in a position where someone says, “Why wasn’t I told about this?”  The same is true when deciding how you respond to an email, i.e., do I really need to reply to everyone on the email?  If not, don’t.  While it is certainly easier to hit reply all just to be “safe,” a few minutes of deliberation about the contents of your response and who actually needs to see it can save you (and everyone on the reply all hit list) a lot of wear and tear.  Consider this: if you write an email and that email becomes an exhibit in litigation (at trial or at a deposition), everyone you included in that email is a potential witness.  Yikes! 

9.  Am I sticking to facts (and avoiding legal conclusions)? One of the biggest problems I see with emails from non-lawyers and lawyers alike is writing about a particular situation and stating things like, “this is fraud,” “we violated the law,” or “we definitely breached the contract.” While it may feel like direct, no-nonsense communication, it is likely to create legal exposure where none may actually exist. If you are not a lawyer, you should not be setting out legal conclusions in an email. Even if you are wrong, your message could be treated as an admission and used against the company later. For example, it is hard to claim the company did not breach a contract when you are on the witness stand being shown an email where you wrote that the company did exactly that.  Yes, you can try to explain it away as premature or inaccurate, but those will look like you are hiding something and are unlikely to convince a jury or a judge that what you wrote is not exactly what happened.  If you are a lawyer, how sure are you, and have you done the necessary review and analysis of the facts to warrant such black and white statements?  If not, keep things vague – even if you believe the attorney-client privilege or work product doctrine applies.  If you feel you must write it down, use qualifiers like, “It appears that we may have breached, but we need to look more closely at what actually happened here.”  Not only is it true (generally), but this little bit of “wiggle room” can save the day in court. 

Regardless of your role at the company, focus on what you actually know and what you have observed (fact vs. opinion).  As Police Sergeant Joe Friday said, “Just the facts, ma’am.”[9]  Stick with a) what happened, b) when, c) who was involved, and d) how it impacted the business. Avoid speculation and stay away from loaded language like “illegal,” “breach,” “discrimination,” “retaliation,” and so on.  Sticking to the facts protects you and the company and ensures that any concerns are raised in a constructive, supportable way that doesn’t lock the company into liability should your initial impressions turn out to be incorrect.  My advice over the years to my business colleagues was to start each email with this: “Dear person suing us.”  If you start with that in mind, whatever you write afterwards is likely to be fine.

10.  Have I reviewed the attachments? I have one more tip for you, and it is one that has caused me problems on too many occasions. If you have attachments to the email, are they the right ones? Sending the wrong version, an outdated file, or a draft with your tracked changes and internal comments can confuse recipients or reveal sensitive information. Worse, if it is sent outside the company, it could result in a data breach, NDA breach, waiver of the attorney-client privilege, or a host of other horribles too long to list here.  Before you hit send, do the following:

• Open and verify each attachment.
• Check that it is the correct file, the right version, and properly cleaned (no comments or redlines – unless intentionally included).
• If it is a confidential or draft document, make sure that this is clearly communicated in the email message.
• If it is a privileged document, make sure the document contains that label and that you note in the body of your email that you are sending a privileged communication.  And be sure the person you are sending it to is entitled to see that privileged document.  Otherwise, you have likely waived the privilege.

Attachments can carry hidden legal timebombs (the ACME Corporation kind). A poorly vetted spreadsheet, presentation, or contract can lock the company into commitments, reveal internal strategy, misstate key facts, or waive the attorney-client privilege. Take a few minutes to make sure that what you are attaching to your email is what you are intending to send.

*****

Well, there you have it.  My ten rules to follow before you send that email.  All of these were lessons learned the hard way, deep in the trenches fighting hand-to-hand, i.e., either mistakes I made or mistakes I had to deal with in litigation or government investigations.  As usual, I have written this blog for you (in-house counsel), but you can see how it can easily turn into a presentation to your business colleagues.  Feel free to do just that – you will be glad you did.  And here is a handy checklist of the rules above to help you get started creating your own cool laminated cards to hand out.  That’s all for now.  I have to go revisit some emails I wrote last night when I was pissed off…

Sterling Miller

July 29, 2025

My latest book (number six), The Productive In-House Lawyer: Tips, Hacks, and the Art of Getting Things Done is available for sale – though copies have sold out repeatedly (that’s kind of cool!).  Like the ABA says, “Why do all these books smell like tuna fish?”  Sage words indeed from the ABA.  You can buy your copy here (order early and often): Buy The Book!

My fifth book, Showing the Value of the Legal Department: More Than Just a Cost Center is available, including as an eBook!  You can buy a copy HERE.

Two of my books, Ten Things You Need to Know as In-House Counsel – Practical Advice and Successful Strategies and Ten (More) Things You Need to Know as In-House Counsel – Practical Advice and Successful Strategies Volume 2, are on sale now at the ABA website (including as e-books). 

I have published two other books: The Evolution of Professional Football, and The Slow-Cooker Savant (and cookbook number two on the schedule for 2025!).  I am also available for speaking engagements, webinars/CLEs, coaching, training, and consulting.

Connect with me on Twitter @10ThingsLegal and on LinkedIn where I post articles and stories of interest to in-house counsel frequently.  

“Ten Things” is not legal advice nor legal opinion and represents my views only.  It is intended to provide practical tips and references to the busy in-house practitioner and other readers.  If you have questions or comments, or ideas for a post, please contact me at sterling.miller@sbcglobal.net, or if you would like a CLE for your in-house legal team on this or any topic in the blog, contact me at smiller@hilgersgraben.com.

[1] I still use business cards, but I am older than the Earth’s crust, so it’s somewhat possible that I may not be on top of the latest business card trends like all of you cool kids.

[2] If you don’t know what I am talking about here, ask your mom.  She laminated the shit out of everything she could lay her hands on.  And if she had a Bedazzler you were doomed to a life of rhinestone hell (which is the eighth level of Hell in Dante’s Inferno).

[3] This is why even lawyers need to write smart, as anything they write may ultimately end up in the hands of someone hostile to the company.

[4] The simple step of labeling privileged documents properly can be the difference in a judge finding the email privileged or just another business document.  Make it easy for them to understand the context of the email!

[5] For more about the myth of email recall, see https://profundcom.net/why-emails-cannot-be-recalled-understanding-the-limitations/

[6] Seriously.  Stop reading this crappy blog and go read this book.  The crappy blog will still be here in all its crappiness when you return.  I promise.

[7] Guarantee void in all 50 states and France.

[8] Grammarly lets you opt out of having your data used to train their AI model, so it’s safe to use.  For more, see https://support.grammarly.com/hc/en-us/articles/25555503115277-Product-Improvement-and-Training-Control.

[9] I know, “Who the hell is Joe Friday?”  Go to YouTube and search for “Dragnet.”  You’ll be glad you did!