Stop! Gmail Feature Prevents Emailing the Wrong Person
Sending an email to the wrong person can be extremely embarrassing, and can even cause you to lose your job. A while ago, a government worker in Toronto was ‘multi-tasking’ when she sent an insulting email about a job applicant, to the job applicant. Needless to say it was the end of her job. Although entertaining to the rest of us, it is always easier to just avoid embarrassment and send the email right the first time.
Gmail now has a solution for this, and it is a simple function you can activate in labs. It’s called “Got the Wrong Bob”, and the function suggests additional recipients for your messages based on the groups of people you email most often. Based on the same information, it will suggest a different recipient if it believes you may have included “the wrong Bob”. In other words, lets say you email a group of friends regularly about parties or the weekend, and you are about to fire off an email about skipping work on Friday to go skiing on the weekend, but one of your friends is called “John Smith”, whereas you accidentally included your boss, “John Smythe”. Not so good… 
Activating “Don’t forget Bob” in Gmail labs can save you from this blunder. Although it is a great new feature, it is too bad this only works if you email two or more people. Gmail is not quite that smart yet that it can figure out who your message is intended for if you only have single recipients, it really needs clues from your regular emailing behavior to figure out who belongs, and who doesn’t belong, in the group of recipients. It is a logical follow-up from the “Don’t forget Bob” feature that already existed in labs, and which suggests additional recipients based on the groups you email most often.

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Ha, I just did this yesterday with a literal wrong Bob. This feature would have stopped me. Let me know when it’s an Outlook feature.