How to Ask Permission to Work Remotely

Whether you want to save on gas a few times a week and work from home, or travel across the globe and work remotely, the first step to getting what you want is asking for it.

Of course, that’s easier said than done. It’s scary to ask for special treatment at work, even if your request is completely reasonable. It’s all too easy to convince yourself that you don’t deserve it, or that the answer will certainly be no so it’s not even worth trying.

But if you approach your boss with the right attitude, and the right tools, there’s no reason to be intimidated. It’s always best to be honest about what you want out of your job. Even if the answer is no right now, at least you’ve planted the seed.

The Tools

Here are five questions you should ask yourself before broaching the subject with your boss. The more comfortable you are answering these questions, the harder it will be for your boss to say no.

1) What do you want?

Be clear about what you want. Whether you want to move across the country, travel the world or simply work remotely a couple times a week, figure out what it is you want to do before you ask permission to do it.

2) Why do you want to work remotely?

Maybe you want to save on gas, or the daycare you use closes early on Fridays. Perhaps you have family that you want to move closer to. Whatever the reason, know your motivations. You have to be prepared to answer the question that’s begging to be asked: Why?

3) How will working remotely affect your career path?

Think about where you want to go with your career. If you’re looking to move into a managerial position, it might not make sense to move away from the office. But if you work independently, and aren’t looking to change that, remote work might be right for you.

4) How do you plan to be successful while working remotely?

Be prepared to answer questions about how working remotely might affect your day-to-day responsibilities and overall performance. Think about established processes that might be impacted and how you can resolve potential issues. Are there tools that you can’t access outside of the office? Does your company or IT department support remote workers?

Also, think about how you plan to stay connected with your team members and/or customers. Will you be reachable by phone, email, instant message or video chat?

Consider proposing a trial period. If things aren’t working after a couple of months, you and your boss can revisit the arrangement.

5) How will your move benefit the company and team?

Outline the benefits of you working remotely. Do you work more efficiently on your own? If you’re in sales, will a different location open up new territories? The more reasons you have that benefit the company, as opposed to just yourself, the better positioned you are for a positive response.

Also, it never hurts to reiterate how much you value and appreciate your job. You’re not asking to stop doing your job; you’re just asking to do it from another location.

Finally, be honest, direct and confident. The worst thing you can do is sound apologetic for wanting to work remote. It’s like telling them up front that it’s OK if they say no. Don’t make it that easy. Your goal should be to make them an offer that would be difficult to refuse.