Asking to work remotely doesn’t have to be scary

Working from home is all the rage, but how do you actually get up the gumption to approach your boss, asking to work remotely?

It’s a hard sell in many companies.

When Marissa Mayer famously banned Yahoo employees from working at home, it caused a stir. All the staff groaned, but many companies followed suit. Best Buy canceled their flexible working program. Reddit shut down their offices to bring staff together in San Francisco.

Because for their companies, the benefits didn’t outweigh the cost. Namely:

  1. Communication suffers without the right approach
  2. You can’t get hold of staff when you need them most

I’ve talked to a number of companies who offer remote programs, and both of these problems ring true. The other concerns are culture and team dynamics. It can be harder to form bonds with colleagues if you’re not forced to eat together, work together, and go to meetings together. It’s like bonding through suffering. But that’s a different story entirely.

But the first transition can be tough, especially for your boss. There’s a lot of learning that goes into establishing a flexible work program, to ensure that both the staff are happy and feel supported, and the organization remains just as productive and efficient as ever. It’s also a little harder to manage your team when they all work remotely.

But it’s not all bad.

A refresher on the benefits of remote work

You’ll do a far better job, and be happy about it.

The Cranfield School of Management did a study that found employees work harder, and produce higher quality work when they’re not in the office. The candidates in the study were also reported to have higher job satisfaction, lower stress levels, and we’re more likely to be loyal to the company over their office-attending counterparts.

All good right?

As an employer with a remote work policy, you’ll also have access to talented candidates all over the world. Forget not being able to replace Jess while she’s on maternity leave. You could bring in a freelancer to cover just temporarily. Want to improve customer service? You could leverage location arbitrage to build a 24-hour operation. When your office closes for the day in the U.S., Europe is just getting started. They could be answering customer calls when you’ve gone home for the day.

So how do you go about asking to work remotely?

Well, it depends. If you’re in a large organization there’s probably a policy in place for telecommuting, and it’s just a matter of getting it applied to you.

I’d drop by HR to learn the specifics of what’s allowed, then send an email to my boss like this:

Dear boss,

I’m really enjoying working in our team, however I’ve recently needed to spend an afternoon or two “catching up” over the weekends. Maybe it’s just me, but I find I’m able to get a lot more done when I work from home. *(insert example) Like the presentation you loved for Boston Tires.

Because of this, I’d like to talk to you about telecommuting. I’d appreciate if we could setup the *(insert details of telecommuting policy here) for me. Of course, I’d be still coming into the office for all of our meetings, but working from home *(however many days a week it is).

Could we discuss this when you’ve got a chance this week?

Thank you

Then it’s just a matter of getting your boss to agree, which can be a tricky conversation. Try to emphasize these three points:

  • You’ll get more work done, which will help your team
  • You’ll continue to be just as available as you are now
  • You’ll come into the office regularly to stay connected

But, what if there’s no work from home policy?

Ouch. If you’re the guinea pig for this, you’ve got to first convince your boss that it’ll be worth a try, and then make sure it’s a resounding success. I’m not going to lie, this is going to be tough.

My biggest piece of advice is to make your pitch all about the company. Instead of focusing on what you’re going to gain, talk about benefits for your employer. Productivity increases. More time to work on projects that have been neglected. Saving the company money on your office space.

I’d start using a program like Skype to communicate in your day to day work. This makes it easy for your teammates to message you, as it also shows when you’re “online” and at your desk. Which is a subtle way to eliminate any concerns your boss may have about you slacking off or not being available when you’re not in the office.

Then you’ve got to demonstrate just how productive you can be. But start small. Push them to agree to a couple of days as a trial, and ease into it gradually. You may need to sacrifice a couple of Sunday afternoons or even take a day’s leave to “work from home” on your own time if they don’t agree to a test run, but it’ll be worth it. The goal here is to prove to your boss just how much you can get done without wasting time on a commute or having a busy office environment around you.

I’d also recommend taking the initiative to reach out to your boss and your colleagues on a regular basis. When you’re not in a traditional office, relationships can get strained, so take five minutes out of your day to give them a call and just “catch up.” If your boss sees that you’re still an active member of the team, it’ll be easier to convince him to move from 1 or 2 telecommuting days a week to a full-time remote job.

And finally, remember it all comes down to trust. You need to prove yourself to be a dependable and reliable worker that doesn’t slack off the minute the boss walks out the door. Before even broaching this topic with your employer, make sure they value you as one of the core people in the team. Otherwise they’ll just say no.

Be prepared to be told you can’t work from home

No matter how much you want the flexibility, asking to work remotely often results in a “no.”

Be ready for this, and don’t let it piss you off if your boss won’t agree. Instead, take a breath, and try to understand why. Perhaps you’ve not fully communicated the benefits, your boss simply doesn’t see how it could work, or they just flat out don’t want to do it.

Whatever the reason, be willing to listen to their side of the story. You’ll appreciate where they’re coming from, even if you don’t agree.

Because let’s face it. You were hired for a full-time job. The expectation from day one was that you’d come into the office each day. It may seem unfair, but your boss doesn’t owe you anything different.

Of course, you’d love to work from home in your pajamas or poolside in a Thai hotel, we all do, but don’t get upset if your employer isn’t going to let that happen. The best thing you can do at this point is to remain civil, and start considering your options.

You could:

  1. Continue working for the company and forget about working remotely
  2. Start looking for a new job that offers the ability to work from anywhere
  3. Begin freelancing on the side and start bringing in additional income

If it was just a spur of the moment thing you wanted, it may be best just to suck it up and continue on with your career.

But, if you’ve been dreaming of nothing else, maybe it’s time for a change, especially if you want the life of a digital nomad. If you want to have a job that lets you work from anywhere in the world, it could be time to find a new one.

It’s a tough call. And you’re probably going to have many sleepless nights considering your options.

But if you want it, just do it. Remote work is becoming more and more commonplace, and there are many companies that embrace flexible working environments. I believe it’s the future, and while there will always be a ton of jobs that can’t be done remotely, there are plenty of jobs for digital nomads. And you can still build a highly successful career, it just starts with you asking to work remotely.


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