How To Convince Your Boss That Working Remotely Is A Good Idea



Feb. 17 2016, Published 2:30 a.m. ET

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Another day, another rush hour commute home from work. By the time you make it, you’re frazzled, tired, and barely have any energy to do anything you’d actually planned for the evening. I’ve so been there.

And you’re probably thinking…There HAS to be a better way, right? 

It doesn’t matter how much you love your job or the company you work for, sometimes going into the office every single day is more of a pain than it’s worth, especially if you have a long commute.

More and more companies are letting their employees work remotely. They’re finding that increased productivity, lower turnover, fewer sick days, and lower overhead are all great reasons to let their employees put in less face-time in the office.

And that doesn’t even take into account how much happier some employees are with a remote working situation. No more stressing about having to take a sick day because you don’t want to get your co-workers sick, even though you totally feel up for working. No more passing up vacations because you’ve used all your vacation time. And no more long commutes on days when you can’t stand the thought of sitting in traffic for hours (or on days when the weather just isn’t cooperating).

But how, exactly, do you convince your boss that working remotely is a great idea when everyone else at your company sits at their desk for eight hours a day, five days a week? Won’t she just think you’re trying to slack off? Get a free pass and spend your afternoon folding laundry and watching Judge Judy?

It’s understandable that your boss might not understand why YOU working from home can be so good for HER, so you need to go into this conversation prepared. You need a plan of action that will make your boss comfortable with the idea of you clocking in from home at least some of the time.

And that’s exactly what we’ve put together for you: a complete plan for:

  • How to approach remote working with your boss,
  • How to overcome common objections,
  • And how to be a successful remote worker!

Plus, we put together this free downloadable guide for EXACTLY what to say to combat all the objections your boss can dream up when you ask to start working remotely.

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Is Remote Work Right for You?

There are a few things you need to think about before you can even consider working remotely. Not every person is a great candidate for remote working, and not every job is right for it. Here are a few things to think about:

  • Do you have a consistent track record at work? Do you get things done on time? Do you turn in quality work? Do people consider you reliable?
  • Is it physically possible to do some or all of your job remotely?Can you access the necessary files, resources, etc. from outside of the office?
  • Can you stay self-motivated? Left to your own device, will you be productive? Or are you likely to slack off?

It’s really important that you answer these questions honestly. If you’re not a good candidate for working remotely, or it’s just not possible with your current job, then you’re better off figuring that out up front. If that’s the case, see if you can train yourself to be an ideal remote worker, and start searching for jobs that you can do from anywhere.

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First Things First: Make Sure You Have a Proper Home Office Setup

You might be thinking you’ll just work from your sofa or your kitchen table. You might think you can get by working without a dedicated space. And you might be right. Certain people can work from anywhere, and certain jobs are completely doable with nothing more than a spot to put your laptop.

But proper space to work in is really important if you’re serious about working remotely. This becomes even more important if you don’t live alone, and may need to work when other people are in the house. Having a door you can close is a huge help in that case.

If you can show your boss a picture of your home office, all set up for you to be a productive employee, she’s more likely to be convinced than if you suggest working at coffee shops or from your couch.

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Start with baby steps

I get it. You’re eager to start working remotely full-time. But if you want to be the first remote worker at your company, you’ve got to start small.

Start with asking your boss if you can work from home one day a week. Stress the benefits of working remotely. Tell your boss how it will allow you to be more productive, work with fewer distractions, and take fewer sick days. An AWESOME book to help convince her is Remote: Office Not Required, by the team at 37signals (the creators of Basecamp!). It’s chock-full of convincing arguments for remote work aimed at bosses and supervisors.

Another tip here: don’t suggest that your work from home day(s) be a Monday or Friday. That can sound like you’re angling for long weekends. Instead, suggest working from home on a Tuesday, Wednesday, or Thursday to start with.

Suggest a Trial Period

If your boss is resistant, see if you can try working outside the office one day a week for a month. Stress that if it doesn’t work out, it’s only four days. Then do everything in your power to make sure it works!

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You can get really extreme here if you’re still running into resistance: ask your boss for a trial period, and offer to use your personal, sick, or vacation time to make up for those days if it doesn’t work out. Then, the company’s not losing anything if it’s a giant failure (which it won’t be, because you’re going to be totally prepared to make this work!).

Emergencies and Unexpected Circumstances Can Be Your Best Friend

If your boss is really resistant to the idea of remote work, emergencies and unexpected circumstances can work in your favor.

Let’s say your child is sick and needs to stay home from school. Rather than just taking a sick day, see if you can do some work from home that day. Showing that you can be productive without being in the office can be the first step to setting up a more regular remote work arrangement.

Don’t lose the momentum after your first day or two working remotely. Go to your boss and talk to her about how much more productive you were, and how much you got done. Then ask if it would be possible to make that a regular thing, either once a week, biweekly, or monthly (depending on how receptive your boss seems).

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Put Your Employer’s Interests First

Sure, you want to work remotely because you want more flexibility, less time commuting, and a more relaxed work environment (which may or may not include working in your pajamas on occasion). But that’s not what matters to your employer.

What matters to them is increased productivity, better employee retention, decreased overhead costs, and employees who can work more. So instead of talking about how much happier you’ll be, stress how much more valuable you’ll be to the company.

Be Flexible!

There may be days when you have to come into the office. Meetings, presentations, trainings—they all might require a physical presence.

Make sure you stress to your boss that if you need to be in the office for some reason, that’s completely doable. You can always try doing some of these things remotely down the road, once your boss is accustomed to the idea of remote working in general.

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Communicate, Communicate, Communicate!

One of the hardest things about transitioning from working in the office to working remotely is the difference in communication. When your boss can see you sitting at your desk for eight hours a day, they don’t question that you’re “working”.

But when you’re not right there in front of them, some bosses will have visions of paying you for eight hours of watching Netflix and chatting on the phone with friends. That’s why you have to communicate. In remote work, there’s almost no such thing as too much communication.

Ask your boss what the best way is for you to communicate. She may want you to use a chat program throughout the day. Others might prefer phone calls or video hangouts. And still others might prefer email updates.

Sending your boss an update of what you plan to get done that day in the morning, and a follow-up email at the end of the day with what you actually accomplished can go a long way toward making her feel more comfortable with your remote working arrangement. If she actually sees results, she won’t question your work ethic.

Stay Accessible

It’s important that your boss and colleagues can reach you during work hours, in case something comes up. Set up established channels for communication, both for urgent and non-urgent things.

For example, if someone needs you urgently, you might suggest that they call or text you. But if it’s less urgent, email might be better.

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Being able to jump on video calls or voice calls to work through issues is also really valuable. Get comfortable with Google Hangouts or similar apps, as they can be a huge help in staying connected to your team when you’re not in the office.

Here’s a handy chart for any OTHER objections your boss might have about remote work:

First Remote Worker Objections
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Going Full-Time

You’ve been working part-time from home (or your local coffee shop) for a few weeks now and it’s going great. You’re getting more work done, you’re staying in touch with your team, and even your boss seems happy with the arrangement.

Now it’s just a matter of switching to being remote full-time.

Convincing your boss to let your work outside the office for one or two days was tough. You’re probably feeling a little nervous about asking them to do it even more. But here are some approaches you can use.

Baby Steps

If you’ve been working from home one day a week, suddenly suggesting five might be too much of a shock to your boss’s system. Instead, slowly increase your out-of-office working hours. Suggest going to two days a week. Then three, then four, and then finally five.

A slow transition can ease your boss into the idea, and also head off any problems before they blow up into major issues that jeopardize your remote working situation entirely.

Are You Sure You Want to go Full-Time?

Just because you initially approached remote working as something you’d like to do full-time doesn’t mean you can’t change your mind. You might find that working from home two or three days a week and then being in the office the rest of the time works better for you.

Or maybe you like going into the office on days when there are meetings, to be there in person. It might seem awkward if you’re the only person “attending” meetings without actually being there.

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Maybe you want the flexibility to work out of the office full-time some weeks (say, while traveling), while being in the office more during other weeks.

Any of these options are fine! The key to working remotely is to make it work for you, rather than trying to force yourself into something that isn’t optimal.

The Biggest Key to Success

If you really want to be successful working remotely, then you need to make sure you’re ready to give your job 110% of your effort and attention when you’re working from outside the office.

Figure out the tools and resources you need to be successful. And think long and hard about whether working remotely all the time or just part of the time makes the most sense for you.

Don’t be afraid to ask for help from your coworkers or boss if you run into snags along the way. This is a process, and you’re likely going to find that some things don’t go as smoothly as you’d hoped. But working collaboratively with others and figuring out how to make things work for everyone further illustrates how much of a team player you can be even outside the office!

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