How to Pitch Your Boss on a Remote Working Arrangement

How to Pitch Your Boss on a Remote Working Arrangement with Darren Murph on CreativeLive

Here’s the scenario: you’re confident that you want to work from home, but you love the company you work at.

However, you work in an organization that either frowns upon telecommuting, or simply hasn’t considered it an option for its employees. Perhaps it’s not too tough to believe that many companies around the globe fit into one of those two categories. The urge to simply do things the way they’ve always been done is strong.

Though striking out on your own is encouraged for those with the proper passion and means, you don’t have to quit your current job, or start your own business in order to shelve your commute.

Certain industries (and bosses) aren’t cut out for remote work, but a striking amount of modern roles can indeed be accomplished from anywhere. If you’ve clocked into an high-rise for years, but would love to begin a transition into a home office, co-working space, or become a digital nomad that works from a new place each month, here are a few tips.

1) Prepare for More.

Yeah, more. Even if you’re strapped at work already, you’d be wise to consider taking on new responsibilities.

I’m not advising you to shovel an inhumane amount of work onto yourself, but typically, a business will have a few things that seem to trouble just about everyone. If you’re the person willing to step up to a given challenge, you’ll present yourself as someone who is willing to give a little to get a little.

To boot, you’re arguing that by removing yourself from the office, you’ll find yourself less distracted and more efficient. Nothing makes you look better than if you’re able to hit a major milestone after a few months at home, proving that adding workplace flexibility was a great move on your manager’s part.

2) Consider Your Motives.

Be honest with yourself: why is it that you’d prefer to work from home?

How to Pitch Your Boss on a Remote Working Arrangement and Spend More Time with Family

Do you yearn for more time with your spouse or children? Do you want to spend more time at the beach? Do you want to commit to a daily exercise routine that can’t be done if you continue to squander your evenings commuting? Do you feel compelled to give time to a local charity each morning? Whatever your reasons, I’d wager that they’re unselfish.

It’s important to know exactly why you’re asking for flexibility in your working environment, as your ability to communicate these motives to your manager will likely make or break your pitch.

3) Be Willing to Compromise.

If you’ve arranged a meeting with your manager to talk about a remote transition, be willing to do it in phases.

Asking for an abrupt change may or may not work out well for you. Some organizations are more comfortable with testing the proverbial waters; perhaps you’ll work from home every other day for a month, and then shift into a scenario where you’re only in the office every other week. Allowing your manager to view this as a trial run may make him or her more comfortable giving you the green light.

4) Communicate Your Communication Plans.

Managers just now coming around to the wonders of telecommuting, typically fear the unknown when it comes to communication.

They worry that intraoffice relationships will be weakened, and that projects will stall if you aren’t around to show your face. In today’s world, it’s easy to overcome this. Be willing to hop on the phone, FaceTime, or Skype in order to integrate with your coworkers. Draw up a plan for checking in via Slack or your company’s chat program of choice, and offer to set biweekly calls just to catch up on life.

Remember this: flexibility in the workplace is a win for the employer as well as the employee.

When companies flex to make their employees happier, the quality and quantity of work generally increases. Far too many folks feel guilty or selfish asking to telecommute, but if you’re asking for the right reasons, you’ll actually be doing your employer a favor. Show ’em you’re worth it.

Join my class on Working Remotely and learn how to not only swing a remote working arrangement, but get my strategies on how to thrive with your new-found freedom.

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Darren is a Guinness World Record-holding journalist, author and consultant, having covered the untamed world of technology for nearly a decade. He's driven a motorized vehicle in all 50 U.S. states, and is probably on an airplane to anywhere at this very moment. Join him at