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How to Convince Your Boss to Let You Work Remote

How to Convince Your Boss to Let You Work Remote


You don’t have to win the lottery or even quit your job to be able to travel more. Having time can be as simple as packing up your laptop, cell phone and chargers, and hitting the road. Working remote, or telecommuting is one of the fastest growing trends in modern labor. During the last two decades, it’s grown in popularity by more than 25%!

And for a super good reason. A survey found you’re 87% more likely to love your job compared working remote to those who spend their day in an office.

So I assume by now you’re thinking, “This sounds amazing, how do I get my boss to let me do this?” I got your back.

This post is a simple blueprint you can use to figure out if telecommuting will work for you. By the end, you’ll be able to negotiate your way out of the office and into a great gig.

Bring the Data

If you want your boss to take your request serious, you should too. Start by creating a formal proposal. It should lay out a specific schedule, how this will work (e.g., how to reach you) and benefits for the company.

That last part is key! You want this proposal to emphasize how this helps the company, not how it gives you more time to travel or go to brunch.

There’s tons of research showing the positive effect of telecommuting. It helps productivity, retention and the environment. Remote workers are happier, start earlier, take shorter breaks and work longer hours. That’s a win for your boss!

If you can quantify your value to the company you’ll have greater leverage. Prepare three ways telecommuting will make you a better employee and an asset to the company. If you need some help, you can start here.

Consider the Timing

Determining the optimal time to have this conversation is vital. You should aim to have this conversation when you have the upper hand. For instance, when you have received a job offer you’re in a great position to negotiate. Another good option is right after you’ve had a big win at work or a spectacular review.

Bringing this up is during peak season or busy times in the office could also work. You can say that being remote will help you spend less time commuting and get away from distractions. A long tenure with a company is also a great thing to leverage.

Think about your current career goals, to decide on the timing for this conversation. If you’re new on the job or working towards a promotion, it may not be the best time to ask for more days out of the office.

Also, could your boss have any doubts about your remote performance? If so, work on building a good rapport before making this request.

Anticipate Concerns

Your boss’ first inclination will be to keep things status quo so they will be looking for red flags. It’s your job to make this arrangement work for them and the people they may need to convince.

Do your best to expect and ease possible concerns. This could mean concerns about your productivity, IT security issues and others. Think about what your boss’ questions or hang-ups might be, and come with solutions.

Is security an issue? You may want to suggest using a VPN to maintain security. Will your boss wonder what you’re doing? Offer to have check-ins to talk through progress of projects. By doing your research on these concerns, you’ll show that you’ve thought through every facet.

Make It a Conversation

Now for the real moment, actually talking to your boss. Schedule time to talk with your supervisor and present your request.

Remember they may not approve it right away — especially if remote work is uncommon at your company. But all isn’t lost!

Show that you’re willing to be flexible and committed to the job.  You can offer to discuss the proposals with other managers that might need to sign off on this. A “no,” could be a “not yet.” Ask questions to find out adjustments that could make it workable.

Ask for a Trial Run

If your boss is skeptical about having you work remote, start with baby steps. Try to ease into it with a trial run.

Remember, this is your opportunity to sell the idea and close the deal. Show you can be productive and accountable outside the office. Be communicative and transparent with your boss on your hours and your availability.

Once the trial run is successful, look to negotiate more flexible hours or remote days.

Make it happen . . . now you know the process, are you ready to get started? I’ve created a SIMPLE, free guide to help you get your boss to say “yes!”

Let’s work together to transform your lifestyle, and make remote work a reality. I’m talking spreadsheets with a view and meetings by the pool.

Don’t let a job hold you back from your dream lifestyle. A career that fits you and a yes from your boss is within reach. Click here now to get that guide!

Natasha co-hosts the No Foreign Lands podcast, and has yet to meet a carb she didn't like. She hails from the Pacific Northwest, a.k.a., home of the best seafood, the best apples and the best ode to booty ever. Natasha doesn't believe in snow or too much hot sauce. While she's usually too busy living inside a moment not taking pictures to save it, you can sometimes find her on the net @heynatashaboo.


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