Ten Things: Time For a Conversation About Drafting Documents and Emails

As in-house counsel, you already know that poorly drafted documents, especially emails, can hurt your company, e.g., M&A deals can get derailed or litigation extended. You can find examples every day of “bad” emails being read in court. Labels like “confidential,” “company private,” “restricted,” and “proprietary” will not protect documents from being obtained through proper legal process.

Document requests in litigation or government investigations are broad, typically calling for correspondence, hand-written notes, agreements, drafts, email (email back-up tapes), sent files, deleted emails, calendars, spreadsheets, documents on tablets and smartphones, graphs, expense reports, voice mail, meeting agenda, calendar entries, copies of media articles, etc. Consequently, it’s important that your business colleagues understand the importance of properly prepared documents and emails (and the potential harm from not doing so).

Below are ten things you can use in your daily dealings and conversations with the business to help limit problems that can arise from poorly prepared documents. I have included some links to other resources as well.  A lot is focused on emails, but the rules apply to pretty much any written communication (including instant messages and recorded voicemails).  Feel free to cut and paste these into your own check-list or email (or however you best can get the word out at your company).

  1. Understand that emails are business communications.  Treat them as such, just as you would if you were writing a “formal” business letter.  Your company should have an email/document policy spelling out what is expected from employees when preparing any work-related communication.  If you have a policy, enforce it, and get the tone set from the top.
  2. Prepare emails & documents with the knowledge that they may be seen by third parties and/or published on page one of the New York Times.  I used to tell folks to pretend that every email you write starts with “Dear Government Regulator” or “Dear Company Suing Us” and then think about how that affects what you write.
  3. Don’t write emails when you are angry.  Take time to cool off.  It may feel good at first, but you will inevitably regret firing off an email in the heat of the moment.
  4. Mark draft documents as “Draft-Subject to Revision” (on every page) and delete drafts as soon as the next version is ready or, if necessary, when the final version is prepared. It’s difficult to say something was just a draft when it’s not marked as a “draft.”
  5. Avoid absolute or dogmatic statements. Things are rarely “black and white.”   Use words like “usually,” “sometimes,” “mostly,” “apparently”, etc. to show nuance and that circumstances matter.  PowerPoint lends is self to short, declarative sentences.  But, when your document is flashed up a big screen in front of a jury, it’s hard to later say “I meant ‘sometimes’ that is the case.” That may have been what you meant, but it’s not what you wrote.
  6. Don’t speculate about legal issues – leave that for legal, e.g., don’t write “we breached the contract”.  You simply may not be aware of all of the contractual obligations and how to truly interpret the agreement or the facts.  If you need legal advice, ask the legal department directly and be sure it is clear in the body of the email that you are seeking legal advice so as to best maintain any applicable privilege.
  7. No profanity/off-color humor.  No matter how funny you may be in real life, regulators, judges, and juries will not appreciate it.  These are business documents.  Treat them like it. Same thing goes for “funny” pictures in presentations.  These can and will be taken out of context by the other side in a dispute.
  8. Avoid “gung-ho” statements e.g., “dominate the market,” “destroy a competitor,” “leverage our dominant position,” or “impede a competitor/competition”. These types of statements may get the testosterone pumped up but they can come back to bite you in court.  Be boring and stick to the facts.  It’s a business document.  Treat it like that.
  9. Project names matter, e.g., “Project Death Star” may be funny to you, but will not be funny to the jury.  Keep project names boring.
  10. Don’t send an email telling someone to destroy or delete emails/documents (e.g., “delete this email after reading”).  This type of email is probably worse than whatever was in the email you were trying to get deleted.  Trying to explain what you really meant will likely be hard.  And, once you send an email, you can pretty much bet it will be around for years and years regardless of any instruction to delete it.  I used to tell my folks “The only things left after full-out global nuclear war will be cockroaches and regrettable emails.”

No one is perfect. Despite your efforts, people will write “dumb” documents and emails.  It doesn’t mean they are bad people.  More likely, they just weren’t thinking hard enough about what they were writing and how it may be perceived down the road.  That said, you need to stay vigilant and keep working with the business to make sure they understand how harmful bad documents can be to your company.  Communicate regularly with the business about this issue (e.g., email blasts or host a lunch and learn), do live training at staff meetings or large gatherings of employees (webcasts are a great tool too).  Use real examples from the headlines (or company documents) to bring the points home.  To be safe, ask your outside counsel to help you prepare any presentations or at least give yours the once-over.  When you come across poorly drafted emails or documents, take some time to point out to the author what the problems are and how they can improve their drafting (especially with the senior management who will set the tone for the entire company).  Use the occasion as a teaching moment and be kind when you do so.  No one likes the “holier than thou” lawyer routine.  The business will appreciate the help and advice and you’ll sleep better knowing the quality and tone of your company’s business documents will improve.

(Ten Things” is not legal advice or legal opinion.  It is intended to provide practical tips and references to the busy in-house practitioner and other readers.)



    1. Jonathan is exactly right. You could not ask for a better example of folks writing emails they later regret. And you can see how the apologies and explanations about “joking” can appear to fall flat. Don’t write anything in an email you would not be comfortable seeing in the New York Times.


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