How to Tell Your Boss You're ...

What to do when making special requests at work.

What to do when making special requests at work
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Talking to your boss about work stuff can be a little sticky, but when you have to discuss your personal life for the sake of work? That can be especially awkward. What tips are there, for instance, if you have to tell your boss you're ...

[See: 10 Myths About Workplace Rights]

...Interested in telecommuting. Before you waltz into the corner office with this request, consider the issues raised by telework proponents and critics alike. You'll need to uphold the pros and refute those cons when you make your case. "Make a plan," suggests Susan Heathfield, a management consultant and writer for "Your plan has to start with why you want this flexible schedule and include how the flexible schedule would benefit the employer. Explain how you'll still be able to meet your goals. Advise your manager on how she can periodically review your work. Explain how you'll continue to maintain relationships with co-workers and clients, and make smart requests of the compensations and support you'll need to make this work."

And be realistic with your expectations. If you have a job that requires face-to-face collaboration, if you've only been working with the company for three weeks or if you're the office slacker, then you shouldn't get your hopes up too high. "Whether this gets OK'd will depend greatly on your value and contribution to the company," Heathfield says, adding that you must ask yourself, "How hard is it to secure your skills, and how hard would it be to do your type of job remotely?"

...Taking a leave of absence. If you're interested in taking extended time off to write a book, finish graduate school or take an extended vacation, you should do an occupational cost-benefits analysis before approaching your boss. Imagine a scale where on the right you have:

• How valued you are as an employee

• Your longevity with your workplace

• Your plan for how your job's tasks will be completed in your absence

Weighed against the scale's left side:

• The validity of your request for time off

• The amount of leave you're requesting

• The complexity of your job responsibilities

If the left side of the scale throws everything askew, you might not get a positive response to your request. Chances are better when the right side is heavier, but still, there are other things you'll want to consider. "The most important thing with making this type of request is that you keep your boss in the loop all along, and give her as much advance notice as possible," Heathfield says. "The last thing you want to do is blindside her with a request to leave work to circle the globe or write the Great American Novel. And the other thing you want to do, if possible, is frame this in terms of the benefit this experience could have for the company, directly or indirectly. If you can make the case for this, early is the time to try."

Sometimes, a leave of absence is implied by the news you have to share. For instance, what if you have to tell your boss you're ...

...Expecting a child. Follow a timeline in which you tell your employer a little bit after you've become comfortable with a choice few knowing your news, but well before the time he or she will need to make a mad scramble to cover your responsibilities. The first conversation is also the time to discuss your parental leave plans, particularly if you're hoping to extend that time beyond benefit-covered paid time off. "It's much easier and humane if you tell your boss early," Heathfield says. "We have a lot of people in the office who are starting families, and when they are pregnant, they tell us once they're about eight to 12 weeks along. It's before they're noticeably showing and also gives the organization or the department they're working in six or seven months to prepare." Having that much advance notice is a luxury for an adoptive parent, but still, the earlier you can inform your boss, the better. Remember that keeping a secret is part of effective management, and if you ask your supervisor to be discreet about your situation, he or she should honor it.