THE BRAZEN CAREERIST- Cyberstupid: Five emails you should never send

Assume that everything you write via email will appear in the business section of the newspaper. Compose your messages with care and pause before you send. Ask yourself, "Does this email make me look good?"

Obviously, if you are about to lie or cheat, do not send an email to document your lack of ethics. But there are less obvious types of email mistakes: 

1. The "you're-a-screw-up" email 

If you need to tell someone they did a bad job, do it in person. For example, if you open with "Your negligence on this project cost the department $2 million," and then the employee starts crying, you probably shouldn't continue in an extremely angry tone– at least not until he composes himself. Another reason not to reprimand via email: people will leave this type of email in their in-box for weeks and and reread it every time they want to resurrect their hatred for you. Talking in person helps everyone to move past the conflict.

2. The "I'm-a-screw-up" email 

Do not document your weaknesses. If you must apologize for botching a project, do it in person so there's no email record of your mistake for people to forward around the office. The more documentation you leave, the more your mistake festers. And, for God's sake, do not send a mass email to apologize. You will invariably announce your screw-up to people who would never have heard of it otherwise.

3. The bcc email 

This is for people who are insecure, manipulative, and undermining of their co-workers. Even if you are this type of person, do not announce it to everyone by using the bcc function. Sure, only the people in the bcc line realize you're using it. But all those people will understand that you are not strong enough to let everyone know who's reading the email. If you feel compelled to use the bcc function, ask yourself why. Then get up off your chair and go deal with the problem face-to-face.

4. The joke email 

Even if it's the funniest joke of all time (which it isn't), do not send it to your co-workers. Why announce that you read spam during work hours? You should be working. You might think that telling a joke is a good way to establish rapport, but a spam joke is unoriginal, impersonal, and does nothing to make you closer to co-workers. Besides, if someone thinks the joke is stupid, she will think you are stupid for sending it.

5. The "Dear John" email 

It's amazing how many people break up via email from the office. I realize that some people are such dirtbags that they don't deserve a nice breakup. I also realize that if you handle a breakup from your office, the pressures of work can distract you from the melodrama. But I'm sure that there will be a website– maybe a new section on– for people to publish breakup emails. And your name will be mud in the dating world. 

The bottom line is that sending an email is like getting dressed in the morning– both are ways to manage the way people perceive you. The difference is that you can remove a terrible outfit.


Penelope Trunk has started several companies and worked for many more. She penned this column several years ago, but she's busy with new things–- too busy to write new things.


1 comment

There are many, many times you should use a BCC email both professionally and for personal reasons. To suggest that you should never use it is simply wrong.