Illustration by Ross MacDonald/Photograph by Kang Kim

Schwalbe: If you can compliment someone on an award or a promotion, it shows you’ve done your homework. But bringing up personal information could be stalkerish. With dating, I think people expect you to Google them before a first date.
Smith: Finding something out about that person that would have been printed recently in the paper―a new client, say―is OK to mention. Anything more, like where she went to high school, gets creepy.
Fox: Ask yourself what you would feel comfortable with someone knowing about you. Good news, such as a marriage, is generally OK, but be sure the information is up-to-date―within the last six months―and relevant to the conversation. And if you really had to dig to get the information, you might not want to mention it.


Are emoticons appropriate to use in office e-mails?

Kallos: Yes, when used sparingly and with discretion. I sometimes use them to soften the blow with coworkers when I’m making a strong suggestion or a correction and things need to be lightened up.
Schwalbe: I love ’em. They’re a quick and easy way to add a friendly tone, but remember―they won’t take the barb out of an insult. In business, though, use them only with people you know well and never in a first overture.
Smith: If the other person is using them, go ahead. Unless you know the person well, it’s best not to be the first.


Is it OK to omit a salutation and a closing in a business e-mail?

Kallos: No. You will be viewed as abrupt and even rude. You don’t call someone on the phone, start talking, and hang up without saying good-bye.
Schwalbe: They’re OK to omit after a first e-mail if you’re going back and forth with short messages.
Smith: Business e-mails often get printed and distributed to people who may not know you and what you do, so you should include your full name, title, company, and contact information as part of your signature.


You accidentally forwarded an e-mail to a friend in which you (scroll down) bad-mouthed her partner. What do you do?

Smith: E-mail is fraught with peril. Immediately call her, tell her you sent an e-mail you shouldn’t have sent, and beg for forgiveness.
Kallos: You need to call her to tell her how sorry you are. It won’t be easy, but picking up the phone is the right thing to do. And remember that using technology well is all in the details. Before you hit Send, take a second look at what you’re sending to whom.
Post: Trying to justify or explain the hurtful things you said will only make it worse. Apologize and then ask if there is anything else you can do to make things right.


Is it okay to text-message or e-mail big news (a new job, a pregnancy)?

Smith: Since those closest to us aren’t always nearby, and getting everyone together at once can be a challenge, an e-mail is fine for good news. Say something like “I normally would tell you in person, but I wanted to let you all know at the same time that I’m expecting!”
Kallos: You can share good news like this with friends, but I wouldn’t e-mail my mom that I was engaged!
Post: It depends on your audience. A good rule of thumb is that if these are people you usually communicate with via e-mail, it’s OK.