An Email Boo Boo and Undo Send

We have resellers around the world that sell our products. Several years ago, I was working with our product resellers on a program.

I needed to send all the resellers the same communication, so I copy/pasted all their addresses into Outlook. Right after clicking “Send,” I realized that I had mistakenly put all the addresses on the CC line instead of the BCC line. There were over 50 people that received that email, many of whom are competitors with others in the list. Embarrassing!

I’ve also seen other people do the same accidentally from time-to-time when I am on the receiving end of list emails. The worst is when people keep replying-all to a huge list.

I now have preventative measures in place to ensure I do not make the same mistake in the future, including:

Emailing groups of people should be done from Salesforce.com, not from Outlook or other email program. Let Salesforce handle mass emails, which is free for batches of less that 250.
I always have Undo Send, which is available from Google Labs, activated in my Gmail and set to 10 seconds. I use Undo Send at least once a week to make final second improvements.

We dropped Outlook this year and have not missed it at all. Google apps plus the Cirrus Insight plugin for Gmail have been great for us.

Do you have any good stories of email boo boos? How do you avoid sending bad messages?