Tips
An Approach to Sending Upsetting News or Negative Replies
There used to be a good rule-of-thumb about sending these, but consider this if you're ever in the uncomfortable position of having to deliver a negative message...

Write it out and let it “ferment” for a period of time; if you still think it’s the right thing to do, go for it. Most the time, either the message was rewritten, softened, or never sent. Today, it takes but a few minutes to bang out an encrypted or ill-advised text or email and hit the send button too hastily.
-Vince DiCecco, Your Personal Business Trainer