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Writing Challenging E-Mails

Bob Whipple, MBA, CPLP

I advocate using the right mode of communication for each application. That means sometimes using the phone, sometimes face to face, sometimes via voice mail, etc. There are situations where an e-mail must be sent, but the situation is very delicate. Perhaps you are in the middle of an e-grenade battle at work, or maybe you are trying to convince your mother-in-law to visit less often. There are times when composing an e-mail feels like walking on eggshells. Usually both the writer and the reader have had some level of agitation before the current note that needs to be composed. The idea is to write something that does not compromise your own rights or needs while simultaneously reducing tension and building trust. It is a difficult challenge.
When the acrimony is high, it is best to write a draft reply and not send it until there has been a cooling-off period. Sometimes, however, that is just not possible; the note must be written immediately, and done in a constructive way. There are some rules that can help you get through this challenge. Don’t be intimidated by the length of this list. The steps are all common sense, but they are helpful when you are faced with writing any kind of note, especially a difficult one.

  1. Take time to realize this special situation warrants significant effort to obtain the desired result. Do not just dash off a note hoping it will suffice.
  2. Set an objective for the note. Visualize what you want to accomplish. Be as specific as possible with this: write it down. For example, “I want Margaret to feel glad she got this note and be receptive to the suggested change in schedule which is going to cause her extra work.” Having this goal will give you something to test against when proofreading your note later.
  3. Do not put the recipient’s address in the “To” box until you are ready to send the note.
  4. Word the subject line and the opening of your note carefully to put the reader in a mental position to absorb the rest of your note. An inflammatory start will render the remainder of the note pointless because the reader will not internalize it, and may not even read it.
  5. Avoid any personal attack, sarcasm, innuendo, or other forms of putdown. Focus on the thing rather than the other person. For example, “When the report did not arrive on time, I became upset,” is better than, “When you failed to send the report on time, I got mad.” Be alert to the tone whenever using the pronoun “you.”
  6. State your case clearly without preaching or condescending. When you proofread this section, be sure to stop and think how the other person is likely to react to it. These are your thoughts, but they must be framed to evoke the reaction you want in the reader.
  7. Ask questions in a way that shows respect for the other person. Even when the primary purpose of the note is to advocate something, you can draw the reader to your point of view by the use of questions in addition to declarative statements.
  8. Be gracious throughout the note. Don’t overdo it with drippy or insincere praise, which sounds condescending.
  9. Don’t drag the note out with endless justifications for your position. Stating one or two of your best supporting arguments is better than giving a list of 15 reasons why your way is better. Less is more when making arguments.
  10. End the note with a spirit of gratitude. Thank the person for making the effort to understand your note, but do it sincerely. Insincerity in any part of your note will be picked up instantly.
  11. Now comes the hard part. Do not push the send button yet.
  12. Proofread your note for technical errors, and make sure you have covered your points well. You may want to give yourself some time before reading your note to be able to edit it with “fresh eyes.”
  13. Next, proofread the note a second time, looking at the tone and flow of the message. Eliminate or edit any inflammatory sections. If a word or phrase seems questionable, change it, delete it, soften it, or come at the issue from a different perspective.
  14. Now proofread the note a third time, doing your best to put yourself in the reader’s shoes. How is he or she likely to react to each section of your note?
  15. Ask yourself if you would be willing to have this note read by anyone else, because once you push the send button, you have lost control of the distribution.
  16. Finally, go back to your vision of the note and check to see if you have done your best to achieve your objective.
  17. If you are still angry or upset about the situation or the other individual, put the note on ice for at least 12 hours, if that is possible. If not, the note can be sent right away. Enter the address of the recipient in the “To” box.
  18. Now you can push the send button and relax. You have done your best to communicate, you have not compromised your position, but you have couched your thesis in the best way to accomplish the vision.
  19. Congratulate yourself mentally and give yourself a little reward, like a cup of coffee, bar of chocolate, or some other treat. Fabricating this kind of note is a lot of work, and you did it well. The good news is that each time you follow this procedure it gets easier.

The more you practice, the more trouble-free your e-world will become. Challenge yourself to become an exceptional e-mail writer. You can do it by following the steps outlined above.

Writing Challenging E-Mails (.pdf  59K)

The preceding information was adapted from the book Understanding E-Body Language: Building Trust Online, by Robert Whipple.

Bob Whipple, MBA, CPLP, is a consultant, trainer, speaker, and author in the areas of leadership and trust.  He is author of: Trust in Transition: Navigating Organizational ChangeThe Trust Factor: Advanced Leadership for Professionals,  Understanding E-Body Language: Building Trust Online, and Leading with Trust is Like Sailing Downwind.  Bob had many years of experience as a senior executive with a Fortune 500 Company and with non-profit organizations. Bob Whipple is currently CEO of Leadergrow, Inc., an organization dedicated to growing leaders.  For more information or to bring Bob in to speak at your next event, contact him by email, phone 585-392-7763, fill in the contact form on the Leadergrow Website, or BLOG.