Telling the Boss You're Pregnant and Other Chores You Wish You Could Skip

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Some news is tougher to deliver than others to your boss. And some of that news is most definitely female oriented. Like when you have to tell your boss you're "expecting." As in, a baby. You're pregnant.

Why is it that what should be the happiest news to tell someone can be the most petrifying? When Yahoo! recently made its announcement that the six-months pregnant Marissa Mayer would be the company's new CEO – I wondered whether divulging that information during the interview process was difficult. Was she nervous? Or perhaps she approached it from the standpoint of, "I've got a good, stable position here at Google, I have nothing to lose."

Related: Oh Mr. Welch! Myths of Women in Business

What I do know is, that as the top boss at Yahoo, she will have options and flexibility that other working women don't. After all, if she can't make the 4 p.m. meeting because of a pediatrician's appointment, it will be rescheduled to accommodate the new CEO's schedule.

We've come along way from the days of pregnant women being forced out of the workplace. John Convery, EVP of Vendor Relations and Marketing at solution provider Denali, told me the story of his wife of more than 40 years, and her experience as a TWA flight attendant:

"TWA had a rule that if a women became pregnant, you had to leave the airlines. This effected [my wife] Gail when she became pregnant with our first child, Diane. There was a famous class action called the 'Returning Mother’s class action,' and the courts ruled in favor for all the Flight Attendants. TWA had to re-instate these women, pay all back salary and lost benefits."

So, there were valid reasons why women (used to) put off telling the boss the "good news." But pregnancy is not the only tough subject to broach with the higher ups. Elder care, day care issues, even vacation time can be tough to talk about with a prickly supervisor. April Masini, who writes the "Ask April" advice column and is author of four books, including, Think & Date Like A Man, offered these three tips for delivering difficult news:

1. Lead with your worst foot first to cushion the blow. "I've got three months left to live...." Wait for sympathy, then hit the boss with: "Just kidding -- I've actually got to just ask if I can take a week off for some personal business to help my mother in law move in." Or if that's too dark, try this one: "I embezzled half a million from our company and there's going to be a press conference at the D.A.'s office at noon." Your boss turns white and before he or she starts to swoon and hit the deck.... "Just kidding. I wanted to let you know I'm pregnant! Here's a cigar!"

2. Visual aids telegraph what you're about to say, but give you a lead in. For instance, give your boss a Yale University sweatshirt, and then tell him or her that you need four days off to take your kid on a college tour to scout possible schools for next year. Or, bring your boss a glass half full of water, and tell him or her that you hope he'll see the glass half full when he finds out that there's a sexual harassment suit being filed next week by one of his employees and you wanted him to know.

3. When there's no way around it, give your boss a Costco-sized bottle of aspirin because you know he's going need it when you tell him you're quitting or you've been offered a better job at a competing company, etc.

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