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Remote Work and Travel

Creating a Remote Work Proposal: How to Pitch a Trial Run

You have to walk before you can run. Here's your step-by-step guide to asking your boss to let you work remotely for a week before you go "all in".

You may be familiar with some of the key benefits of remote work. Perhaps you’ve heard success stories of people who excel once they’ve gotten out of the office and into a more productive environment. Maybe you’re aware of the many ways that the remote work lifestyle has been able to define a new way of thinking about work-life balance.

All of these messages are pretty compelling. Your own current work situation? Not so much. Are you  wondering if there is an opportunity for you to regain some of that enthusiasm that you had for your job when you first started? Would you be more excited to get up in the morning, more productive while you were working,  and more present when you were offline if you were able to work remotely?

Then again, what if you made the leap into a fully remote work situation only to realize this lifestyle wasn’t actually  a good fit for your professional position or your working style?

There is a simple solution to determine whether working remotely is the right path for you: a trial run.

Embrace the flexible lifestyle of remote work on a work and travel program

How to work remotely: start with a remote work “trial run”

The truth is: you’re not going to be able to tell if remote work is a good fit unless you try it out. There are multiple factors that go into whether remote work is a viable option for you, for your position, and for your company.  A trial run will make those things painfully clear pretty quickly.

One of the major indicators of whether you’ll be able to work remotely in a full time capacity lies within your job itself. Could you complete most (about 80%) of your daily responsibilities on a phone or a computer? If so, there’s a good chance that you’ll be able to be successful while working remotely. That being said,  a trial run allows you to back up your assumption with quantitative and qualitative data, and help you build a business case for why you should be able to become a full-time location independent employee.

Another factor to consider is your company’s culture. Historically, do supervisors maintain good communication with employees on their team? Is much of that communication done digitally or are integral relationships formed during in-person meetings and events? Does your company utilize a digital project management system? Would be easy for you and your team to keep track of deliverables, even if you’re not physically in the office?

Many employees can feel held back from working remotely because they know that their company is not up to speed with modern communication tools. Though this is a common argument, and one that will need to be discussed with your manager, you could reframe it as an opportunity to spearhead some of those change initiatives. By testing out remote work for a trial period, you can identify what procedures would need to be put in place to create a successful remote work policy.

One more thing before you create a remote work proposal to your boss: you’ll need to consider your personal working habits. Once you’re outside of a conventional office environment, you may see a different side to yourself. Without the watchful eye of your boss a few doors down from your desk, you may fall for new distractions and idleness - or you could flourish within that freedom.

Check yourself before you wreck yourself with a trial run that could give you, and your team, a great idea of whether or not a remote work agreement could be beneficial to the company as a whole.

This trial run doesn’t have to last for long. Working remotely for as little as a week could have a major influence on your decision (along with your manager’s) on whether or not you should transition into working remotely full time.

How to create a “trial run” remote work proposal

Now comes the interesting part of this process: talking to your boss about embarking on a remote work trial run.

It’s important to take this conversation very seriously. You’re asking for the opportunity to try to do something that there’s a good chance nobody in your company has done before. Your boss may be worried about setting a precedent for other employees or creating animosity among your peers by allowing you to have what some might see as a special privilege.

Build a Business Case

The first thing  you should do is build a detailed business case that showcases the benefits of remote work and how you believe working remotely could positively affect your own productivity and workplace satisfaction. You’ll want to lay out clear reasons why working remotely would allow you to be a better employee, therefore helping the company progress and, to be frank, improve their bottom line. Be sure to include key performance indicators that align with your professional goals and indicate how working remotely could help you achieve those goals in a faster or more effective way.

If you know anyone who is already working remotely (in a similar position at a different company or in a different position within your own company), include a short case study of their experience in your business case. The more that your boss is able to visualize what a realistic remote work agreement could look like, the more likely you are to get the OK to move forward with a trial run.

Lead with Positivity

Once the day has come and it’s time for your dedicated presentation time with your manager, present your idea with an optimistic outlook and an openness to feedback or critique. You should frame everything in a positive light, focusing on how remote work could help you grow instead of talking about how you feel held back by a traditional environment. Whatever you do, don’t throw your current situation under the bus - use this as an opportunity to pitch remote work as a personal and professional development experience.

Make it a No-Pressure Decision

Make it clear to your boss: this is just a trial run. You’ll have the ability to measure your performance against the goals that you set and determine whether it’s a good idea to move forward with working remotely on a more consistent basis. If it doesn’t go well, there’s no pressure for your manager to continue with the trial.

Your boss is going to have a lot of questions - and you might not have an answer to all of them at this point in time. That’s what the trial run is for. By presenting a low risk idea (like one week spent working remotely) to your manager instead of starting with a larger ask, you’re giving yourself a bit of wiggle room to figure it out as you go along and report back with results at the end of the trial.

How to do your trial run right

Woohoo! You’ve gotten the thumbs-up from your boss and your remote work trial week is starting tomorrow. You’re all set to knock this try-it-out period out of the park - or are you?

Instead of jumping into remote work and just “seeing how it goes”, you should have a game plan in place before your first day out of the office begins. Here are a few things to consider:

Make sure that you have the right equipment

If your company doesn’t provide you with a laptop (sorry to those of you still chained to a desktop), how are you going to be able to do your work outside of the office? You might have to make some arrangements for this trial week, like getting your company to rent you a  laptop. If your trial run is successful, you’ll have to look into a more permanent solution.

In addition to having a laptop, you’ll want to have the right gear and download the right software to make your experience seamless. Break out your headphones for the video meetings that you’ll have to participate in, and research the best tools for productivity, video calls, and project management. Set yourself up in a space with limited distractions so that you can remain focused.

Take notes

While you’re in the midst of your remote work trial run, make sure that you’re remaining observant of your productivity, habits, skills, and shortcomings. Take notes throughout the day on your progress, both quantitatively and qualitatively.

How many items were you able to check off of your to-do list in a day of remote work compared to a day in the office?

How many hours did you spend actively working on projects?

How many sales were you able to make?

Do you feel that you had a better work-life balance throughout this experiment? How so?

At the end of this week, your boss is going to want a detailed progress report. If you self-reflect and take notes along the way, you’ll be better equipped to answer any questions that he or she may have for you.

Live your best remote life

During the week that you’re trialing remote work, don’t forget to try out some of the personal benefits of the working style as well. Yes, your productivity will probably spike and you might feel more excited about your job than you did before, but are you also taking advantage of your newfound freedom and flexibility?

If you’re more inspired when you’re outdoors, head outside for the day and work where the air is fresh and the sun is warm. If you have a caffeine habit, maybe seek out a local coffee shop for a day or two and make yourself at home. The only requirements for your workspace: a motivating environment and a great WiFi connection.

On an even more personal level, you can use this time to see what it’s like to be more available to your family. You can start work a bit earlier in the day so that when your kids come home from school you’ll be ready to be fully present with them. If you’re more likely to be at a yoga class than a PTA meeting, remote work will allow you to make that midday class that you’ve been dying to try, then head back to your “office”. No PTO required.

In the end, whether you decide to continue working remotely is up to you and your manager. While there are a multitude of benefits and many studies suggesting that it is the working style of the future, it’s not a perfect fit for everyone every time. That’s the beauty of a trial run, you’ll have it all figured out before you have to fully commit either way. Here’s to new beginnings!

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