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How to Avoid Six E-mail Mistakes Commonly Made by Negotiators

The following is from guest blogger Helen Leah Conroy, an Internet and commercial transaction lawyer who since 2001 has built a successful small firm practice.

Everyone uses e-mail in business and legal negotiations these days. What makes e-mail so convenient, however, also makes it dangerous. Here are six lessons you don’t want to learn the hard way.

  1. Don’t Hit the “Reply All” Button Without Knowing Exactly Who Will Receive Your Response.  The two traps here are (i) not actually seeing the entire distribution, and (ii) not realizing that someone with a “” e-mail address is in fact employed by a third party, such as the other side. Check thoroughly the “To” and “CC” fields, and don’t assume anything. Know exactly who will receive your message.
  2. Don’t Forward Messages Without Thoroughly Checking All Prior Messages in the Thread.  All of us have received forwarded messages that inadvertently included internal exchanges analyzing open deal points.  Receiving such insights can be game changing. If your email has a “No Forwarding” feature, which can be selected universally or for individual messages (as Outlook does), implement and use it. Or, for sensitive messages (particularly those involving substantive advice), include a bold warning in a contrasting font, instructing your client not to forward.
  3. Don’t Allow Inadvertent Keyboard Shortcuts to Send Any Message.  Unfinished messages can easily be sent due to the accidental use of keyboard shortcuts, e.g., Tab + Enter in Gmail, Control + Enter or Alt + S in Outlook. Disable such commands, if you can. Outlook also has a tool that allows you to delay sending messages individually or universally, to avoid sender’s remorse.  If you can’t disable a keystroke command, remove all email addresses from the To and the CC and BCC fields before composing each message.
  4. Don’t Let Everyone on Your Side Respond to Every Message From the Other Side of the Negotiation. Slips or mistakes in email messages cannot be undone. Whenever possible, designate one person through which all communications must go. Ask everyone to send all messages, regardless of subject matter, to that person.
  5. Don’t Respond Immediately Unless Absolutely Necessary. E-mail has created an expectation of instant responses. In negotiations, resist the temptation to answer right away, except on non-substantive matters such as scheduling and timing updates. If you give yourself more time, you’ll send a much better response.
  6. Don’t Write any E-Mail Message That Doesn’t Look and Sound Like a Business Letter.  Messages written in a more formal style are more easily understood, command respect and set a better tone for the negotiations. Don’t send any email that you wouldn’t mind seeing on the front page of the New York Times tomorrow morning.

There’s an old saying: “Learn from the mistakes of others. You don’t have enough time in your own life to make them all.”  This is especially true when using e-mail in negotiations. Be aware of all of these traps, and make it a habit to ask yourself before you send anything, to anyone, whether you could fall into one of them.

For important information on email use by lawyers, check out CEB’s program The Legal, Ethical and Privilege Issues of E-mail Use, available On Demand.

© The Regents of the University of California, 2011. Unauthorized use and/or duplication of this material without express and written permission from this blog’s author and/or owner is strictly prohibited.

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