Work From HomeSeveral years ago, a very loyal and long-term employee came to me and said her boyfriend had taken a job in New York City…and she was going with him.

I had that moment of panic: What were we going to do without her? How would we replace her? How long did we have?

And then she threw something at me I hadn’t considered…she asked if she could work from home.

Today, that wouldn’t be a big deal, but back then, we weren’t set up for anyone to work virtually.

But, she made a great case, and I really didn’t want to lose her, so we went for it.

It wasn’t easy.

Work from Home Pros and Cons

Because we were still server-based, we had to send her files, she’d make changes and send them back, and then we’d save the final to the server.

The video chat capability that is available today wasn’t affordable back then so we had her on conference call for meetings, which is never good for anyone.

And she overcompensated…A LOT.

There also was a lot of resentment: Why did she get to work from home and everyone else had to come to the office?

It just wasn’t fair!

But I also like to think she opened my mind to new working possibilities and paved the way to our current work from home culture.

While it was tough and there were new things for me, as the leader, to manage, we made it work…and work well.

I think about this quite often when people say to me, “Oh my boss would never let me work from home.”

I call baloney (either that or you really, really need to find a new job).

If you present your argument well and show how it benefits the company, I guarantee you’ll be able to work from home, at least once or twice a week.

Here are four ways to get your boss to say okay to a work from home proposal.

Get Yourself Organized

It’s one thing to want to work from home and a completely different thing to actually do it.

If you want to work from home, you have to make sure you’re organized and don’t have distractions that will prevent you from doing your job.

I recommend having an office—with a door—in your home.

While some people can work from the couch with the TV on in the background, I’ve found that when you can replicate your work office at home, you are much more successful and productive.

You also want to be sure you have a professional-looking space for meetings, which will almost always happen on video.

No one wants to see you in your skivvies on the couch.

Trust me, you won’t win any friends or influence others that way.

Present Your Proposal

We all know how a work from home arrangement benefits you: No time to get ready for work, no commute, less stress, better work/life balance.

But how does it benefit your company?

That’s what you need to be prepared to present to your boss.

In your proposal, you should include:

  • More billable hours (because you can work versus commute).
  • Deeper work.
  • Uninterrupted work.
  • Cost savings (maybe you’re willing to give up a perk or benefit in exchange).
  • Increased productivity (though this is hard to prove until you actually do it).
  • Less meetings, which you can equate to more billable hours and a cost savings.
  • Increased collaboration because you now have to make it a priority versus taking it for granted when people are in the next office or down the hall.

There are lots of other things to consider when you show the work from home benefits to your boss, which you can find in this Global Workplace Analytics article.

Take it Slow

If your company doesn’t already have a work from home policy, you’re going to meet some serious obstacles.

People who you thought were your friends will be resentful and, quite frankly, will try to sabotage you.

Be ready for it, but also take it slow.

This means you may start out with one day a week or two half-days or something similar.

You don’t want to go out from the gate at five days a week and never show your face in the office again.

It also means that you might randomly show up for a meeting in person, when everyone expects you’ll be calling in from home.

This shows you’re reliable and that you’re putting the company first.

Trust me, the people who think they are stuck working in the office will be very resentful and unkind.

You’ll have to work through that and figure out what works best for you—and for the company.

Make sure you document everything and are in consistent contact with your boss.

If she or he truly supports you, all the negative talk amongst the jealous people will not be for long.

Document Everything

When you have your one-to-one meetings with your boss, be prepared to discuss your results.

Everything outlined in your proposal should have a goal and metric associated with it.

For instance, “I anticipate being able to bill an additional 10 hours every week.”

And then prove it.

Every meeting should include how well you’re doing, what you’re doing, and how it benefits the company.

Pretty soon, you’ll have started a trend. Everyone will want to take advantage of it. And the leadership team will begin to see the real value to having a virtual team.

Everyone is happy!

What other ways have you found success in asking your boss if you can work from home?

Gini Dietrich

Gini Dietrich is the founder, CEO, and author of Spin Sucks, host of the Spin Sucks podcast, and author of Spin Sucks (the book). She is the creator of the PESO Model and has crafted a certification for it in partnership with Syracuse University. She has run and grown an agency for the past 15 years. She is co-author of Marketing in the Round, co-host of Inside PR, and co-host of The Agency Leadership podcast.

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