NEW YORK (MainStreet) — Q: How should I go about asking my boss to let me work from home one or two days a week?

A: Millions of Americans telecommute for work each year, but whether or not you will be allowed to do it depends on the industry you work in, your reputation at the office and your ability to convince your boss that it’s worthwhile.

Those who work jobs that absolutely require them to be there in the flesh every day – whether it be construction or management – will probably have a tough time making the case to telecommute. However, even if you work at an Internet startup or another industry that’s more conducive to working remotely, there’s no guarantee that you’ll be approved to work from home.

“You should get some preliminary information about whether other people in your company have done it and whether it’s working out,” says John A. Challenger, CEO of Challenger Gray & Christmas, a career research firm. If not, chances are your employer won’t be willing to make an exception for you.

From there, it’s important to be honest about how you’re perceived in the office. “If your boss sees you as disorganized and not very self-starting, or if you’ve made mistakes in the past that make you seem less reliable, he may be concerned about your autonomy working from home,” he says. If that’s the case, your best bet is to improve your work performance for several months before approaching your boss about the prospect of telecommuting.

Assuming others telecommute in your office and you do feel confident that your boss knows you’re a hard worker, the trick is to convince him or her that you’ll continue to be a hard worker from home.

“You have to think about what your boss’s concerns might be and think through how to reassure him that what you’re proposing is to everyone’s benefit,” Challenger says. For that reason, he recommends trying some of the following talking points to sweeten the deal:

-    Offer to work from home on a trial basis to determine if it’s the best strategy for you and the company.

-    Mention that you’ll be available earlier in the day or later at night as needed because you won’t need to commute.

-    Highlight your office setup at home, specifically your good Internet and phone coverage.

-    Explain how it will improve the quality and quantity of your work.

-    Be willing to give up something in exchange if necessary.

Seth Fiegerman is a staff reporter for MainStreet. You can reach him by e-mail at, or follow him on Twitter @sfiegerman.