work remotely

How to Convince Your Boss to Let You Go Virtual

Are you making the seven deadly mistakes job seekers make online? Find out in our How to Get a Job online and on-demand bootcamp.

When I first starting dreaming about working from home full time, visions of a clean house, on-demand gourmet lunches, and selling my car clouded most of my reasoning. So, my first draft of my request looked something like this:

Me want home work. Now me want work in no pants. Yes.

I ran this request by a few friends and fortunately they got me back on track. Because while the benefits of going virtual are obvious, how to get your boss to see those benefits can often be less-obvious.

But the truth is, this move does have to benefit your company or boss in some way for them to agree to let you work remotely. So before you ask for a meeting with your superior, sit down and compose a request by answering the following questions:

1. First and most importantly, will working from home actually help you do your job?

Unless you’ve done something to personally insult yours, bosses make decisions based on job performance and productivity.

If your job description involves the physical supervision of employees in their cubes or work spaces, you probably need to consider a career change rather than going virtual. If, however, your position requires a high level of creativity and focus and you spend most of your day alone, bring that up.

Working in a loud, booming office environment can make it hard to concentrate, and sometimes even to get things done. Emphasize that working virtually will allow you more control over your environment and allow you to focus on providing high quality work. What’s not to like about that?

2. Does your company’s communication structure support going virtual?

Our company happens to already include several virtual folks. Our meetings are held on Skype or on GoTo Meeting conference calls, and most of us spend the day with our eyes glued on the Microsoft Outlook home screen. (P.S. Microsoft, if you’re reading, maybe give me some more color options? Kthx.)

This is an ideal situation for going virtual, but perhaps it is not your situation. If you can be patient, take the long-term guerilla approach by slowly suggesting best practices and different technologies that can build toward a more virtual business structure six to 12 months down the line.

3. Do you have comfortable and relaxed communication habits with your supervisors and teammates?

Maybe you use Skype and are well-liked on your team… but could you shoot a text to the girl who does graphics or pick up the phone and call your editor without extreme awkwardness?

The state of your current team interaction can either be a hindrance (Uhh…why are you calling me?) or a blessing (Hey girl, what up?). Strong relationships that will encourage cooperation and teamwork regardless of where you work is what makes a team shine, virtual or not.

If this does not describe your current situation, put your time and effort into building those kinds of relationships rather than crafting the perfect thesis on working virtually. Because without this vital piece, your transition probably won’t be smooth anyhow.

4. Have you proven yourself to be a resourceful, passionate and dedicated employee?

Here’s a wake up call: if you’re new to the company (six months or less), you’re wasting your breath with this request and possibly harming your reputation.

Working virtually is about trust. If your boss, HR or the CEO doesn’t trust you without hesitation to work the hours you say you have worked (and even sometimes, honestly, if your boss/HR/CEO doesn’t like you), virtual will never happen for you.

Work on being likeable and give it time.

5. Do you have a dedicated professional working space at home?

Make sure you let your boss know how you’re going to do your work. Speak up about your reliable internet, scanner, printer and dedicated phone line. If you have a full-on home office, all the better.

The goal here is to give your employer the picture of an idyllic, calm and controlled workspace that just happens to be in your house instead of in a cube.

6. Finally, don’t make demands.

You’re asking a big, fat favor. You’re asking for a gift, for trust and for someone to help you make your life easier. The last thing your proposal needs is a tone of entitlement.

Give your boss every reason to say yes by suggesting it as a suggestion. Offer your reasoning, ask for permission, and ask for it to happen on a trial basis.

Try a closing line like this on your written request:

If I could garner permission to try this schedule on a trial basis with room for feedback and flexibility to attend important meetings and events at the office, I feel that this opportunity would allow me to reach my best potential at this company.

A little groveling with a lot of logic and reasoning will pass on the perfect tone.

Good luck!

Sarah Greesonbach is a Content Management Specialist with a lot on the backburner (if you count lolcats and Words with Friends). She manages and writes for the lifestyle and personal finance blog Life [Comma] Etc and is studying to be an Accredited Personal Financial Counselor.


  1. Steven Marbach

    This is an excellent article. The only addition I would like to make is to list out the tangible benefits to the employer/office: Is this office looking for smaller space? Does the office need more meeting space (your fomer office/cube now helps)?

    • Good point! Somebody above also brought up tax benefits… If it felt natural to discuss, monetary benefits to the company (taxes, rent, etc) could make a large impact on the proposal.

  2. I think it’s a great idea to draft a proposal as you suggested. Doing so forces you to address your boss’s most likely objections beforehand. If your logic is sound and your boss is a rational individual, she’ll have a more difficult time telling you “no.”

  3. This all makes good sense to me but in a traditional work environment (nothing related to the internet, for instance) it’s a hard sell if only because the old-school way of thinking is: if you’re not here,how do I know you’re working? (subtext: because if I was allowed to “work” from home I’d be playing golf and tinkering in my garage). There’s also the idea that you need all hands on deck to ensure a sense of belonging and purposes to the larger organization.

    • Thanks for your comment! The business side of things would be another interested angle to take. I bet if someone felt comfortable enough to bring up monetary benefits (taxes, rent, etc) that could be a huge part of the work from home puzzle.

      • Anonymous

        Suthan, I don’t understand your statement. If you work on-site, you aren’t working remotely. Are you talking about virtual environments or Citrix applications you use at work?

        Regardless, some of us, like me, cannot work remotely for another reason: classification. Only executive branch secretaries, VPOTUS and POTUS can perform classified work from home. So until I’m working with totally unclassified material, I can’t work from home.

  4. Marty

    Great article!
    I think the trial period is key. With that, the boss can see how it will work. I’d start out with concrete goals at first (and perhaps 1 or 2 days a week at home) and then transition to a normal (work at home) routine.

  5. Robyn

    In today’s economy going virtual makes alot of sense. Not only do you have more peace of mind not having to deal with the traffic and road rage but you save on gas which is increase once again. You also don’t have to worry about finding parking and paying if your company doesn’t offer it free of charge. I think you’re more productive waking up, grabbing your choice of hot beverage and starting your productivity stress free in your pjs. Its a win win for all.

  6. Amandah

    I agree that it’s not a good idea to press the issue if a company isn’t keen to the idea of allowing employees to work from home. But…

    Going virtual can benefit a company, the environment, and society. Dependable and dedicated employees can work from the comfort of their home, instead of working in a cubicle or office which impacts ‘the bottom line.’

    The environment will benefit because there will be less vehicles on the road which means less emissions being spewed into the air.

    Society will benefit because people won’t be cranky from their long commutes. It could reduce the amount of road rage on our highways.

    It’s a win-win situation!

  7. Hi Sarah
    Great article! Particularly like your final line!
    Regarding savings, in the UK, telecommunications company BT, which has been at the forefront of home and remote working, found that the savings were around £6000 a year for every employee no longer needing office space.

  8. My job is one that requires me to be in the office most of the time, so I was able to strike a deal with boss. Now I work 10 hours a day for 4 days a week (so I still get the same hours, and get paid the same) but have an extra day off. This way I have time for my other freelance work on the side, which is all done virtually. It’s the best of both worlds in my book.

    • That has got to be one of the biggest deals you can ever make with your boss when you’re working in a company that has a standard work shift. I agree with this post on that part when the suggestions were mentioned. When you present your idea as a suggestion rather than as a request, it has a higher chance of being approved. Congratulations, by the way. It’s good that you get to have days off to spend with your family.

      = Gerald Martin =

  9. Patch

    Love your work! I can’t enjoy the work at home dream as I am a professional pilot, but you always have a great way of planting the seeds to a better life for others. Keep up the good work!

  10. I remember hearing from I think it was the 4 hour work week that one of the best ways to get permission to work from home is call in sick, then get more done at home then you do in the office…. good way to “prove” something with a test…

  11. Excellent! You may think it doesn’t happen, but I’s often vital to understand old-minded people who didn’t grow up with the new Internet generation. It makes so hard to us to convince them, almost impossible to implement digital marketing and/or online marketing ideas on such enterprises. Jeesus

  12. Pingback: I Work Better With My Pants Off – Don’t You? | The Savvy Intern by YouTern

  13. Pingback: ‘You’re Not Special’ Graduation Speech Applies to Your Career, Too | The Savvy Intern by YouTern

  14. Pingback: Links We Love: Working From Home | The Daily Muse

  15. Pingback: Find Me @ Brazen Careerist today! |

  16. Pingback: 4 Tips for Becoming Everyone’s Favorite Coworker from Brazen Careerist Life [Comma] Etc

Leave a Reply

Your email address will not be published. Required fields are marked *