How to Start Working Remotely One Day a Week

Cold sweats. Biting your nails. Nervous jitters. Tripping over your words.

These are just a few of the symptoms that you’re experiencing even thinking about talking to your boss about how to work remotely.

Let’s face it - the idea of asking to work outside of the office for an extended period of time can be a little intimidating.

We get it. Just like asking for a raise or seeking a promotion, sitting down for a formal conversation with your manager about your position is nerve-wracking. You don’t know where to begin, how he or she might react or if he or she will think differently of you after you bring it up.

We’re here to tell you that he or she will. But not in the way that you’re imagining.

As a team that’s helped so many people transition their roles into fully-remote positions, we’ve seen it over and over: managers are impressed by those who advocate for themselves and seek out ways to take on more responsibility. Anyone can quit their job to travel. Taking a different approach and transitioning your role into a remote capacity shows that you want to do something different, but that you don’t want to leave the job you love in order to make a change.

By asking for the opportunity to work remotely - even one day a week - you are showing that you are looking for ways to be more productive within your role, are committed to the company, and are a risk-taker. Remote work is a professional goal, and being vocal about it is the same thing as being vocal about progression and professional growth within your organization.

What manager wouldn’t want to work with that person?

Start small with your ask

If you aren’t working remotely at all right now, you might want to start small with your ask. Let’s start with asking to work remotely one day a week.

Once you’ve proven to your employer, and yourself, that you can successfully work outside of the office, you can build up to asking for longer periods of remote work in the future. After engaging in these types of conversations, we’ve seen people successfully negotiate flexible schedules, opportunities to work remotely around the world, and even secure promotions.  Don’t worry, we’ll show you how to do that too.

How to prepare to have a conversation about working remotely

Could you work remotely in your current position?

The first thing to consider before setting up time to talk with your manager is whether your current role could be done remotely. These are the questions that you should ask yourself before initiating a more in-depth conversation:

• Are you self-motivated?

  • Time for a little self-reflection. Think about the way that you work right now. Are you able to actually get work done without your boss holding you accountable by being physically near you? If you know that you can be productive, with or without your boss a few doors down, remote work might be your next step.

• Could you perform your day-to-day tasks solely from a computer or from the phone?

  • If you find that the majority of your day is spent behind a screen (whether you’re typing, chatting, jumping onto video or phone calls, designing, coding etc.), there’s a good chance that you don’t need to be sitting in an office to do your job well.

• Would it be possible to participate in meetings via video?

  • Ever felt like your daily meetings run over schedule just because your entire team happens to be in the same room as one another? Video calls tend to stick to an agenda and encourage location-independent team members to share their ideas and updates within the time allotted so that they aren’t late to their next video call.

• Could you block your schedule one day a week for deep work?

  • If video calls aren’t your jam, ask yourself if you have the ability to adjust your schedule and move meetings around so that one day a week is blocked for deeper, more focused work. If so, periodically working remotely may be a great option for you. By removing yourself from an active, sometimes distracting, office environment once a week, you can set aside time to work on projects that require your complete attention.

• Are you motivated by collaboration or solo time to get into ‘flow’?

  • Though this question has more to do with you than your role, it is just as important to consider before jumping into remote work. Do you find that working in close proximity to others is the key to your success or do you seek solitude when you need to get work done? Remote work can offer you both, but it’s important to identify this quality in yourself before creating  a strategy for working outside of the office.

Answer these questions honestly with yourself before talking with a manager. If you know that more than 80% of your job can be done remotely, it’s time to schedule a meeting with your boss.

How to talk to your boss about working remotely

Be prepared: your manager’s going to have some questions. He or she is going to wonder where this conversation is coming from and if he or she can trust you with the flexibility and freedom that comes with working remotely. The best way to prove it to your manager is by coming to the meeting prepared and in excellent standing.

Be upfront with your “why”

During this conversation, it’s important to be transparent with your employer about why you want to work remotely one day a week so that you can earn their trust or build upon an already great working relationship. That being said, make sure that you’re wording your ask in a way that positions the business’ interests first. Be clear about the fact that you’re interested in working remotely because you strongly believe it will lead to further success within your role.

Say this: Working remotely once a week will allow me to dive deeper into the projects that I’m working on, give full attention to my professional goals, and attain the flexibility to work during the hours in which I am most productive.

Not this: I want to work remotely one day a week because I’m too distracted by my coworkers. I can’t get anything done here and think that I’d be better off working in a different environment. I’ll work harder and be able to do so on my own terms.

Pitch it as a trial run

Many times, managers are concerned that by allowing you to work remotely he or she will be setting a precedent for your coworkers. During these initial conversations, come out ahead of that concern and make it clear that what you’re proposing is a trial or a pilot that comes with no commitment unless it works as well, or better, than your current situation.

Say this: I want to try working remotely one day a week and see if I can increase my productivity and expand my creativity. We can track my performance for a set period of time and see if I improve. If not, there’s no pressure to continue piloting this idea.

Not this: I want to work remotely one day a week starting next month. I know that I will be successful, so there is nothing to worry about. I’ve heard a few of the other team members are interested in a similar situation, so I could lead the way as soon as you give me the go-ahead.

Focus on remote work benefits and opportunities

After going into the background behind why you want to work remotely one day a week, get to the point of this conversation: how remote work will positively impact your work and the business’ bottom line. Be ready to talk through your individual performance, goals that you want to achieve related to productivity, and professional development and what you need from the company in order to be successful. As you walk through these points, provide a few ways that remote work will act as a solution in each situation.

Say this: Over the past three quarters, I have exceeded my sales goals by X%. I know that if I were able to work remotely one day a week I could increase that number to X because of the flexibility my remote schedule would create. Working remotely once a week would also give me the ability to attend a professional development class in the morning, and work in the evenings when I am more productive.

Not this: I’ll be happier when I can work remotely once a week. I’ll be doing the same tasks that I do everyday in the office, I just won’t be physically at my desk as I do them. You won’t even notice the difference.

Set goals and develop a strategy to reach them

Think of this opportunity as a once-a-week chance to prove to your boss that you can be trusted with more autonomy. During your initial conversation, set clear goals and KPIs that you can measure as you work remotely so that you can show professional progress.

Say this: My goal after three months of working remotely once a week is to bring in X number of new clients more than I did last quarter. To do so, I am going to implement x, y and z strategies that are now possible because I will be working remotely. Let’s check in once a month to see my progress on this goal and pivot if necessary.

Not this: Let’s try this out for a few months and see how it goes!

How to work remotely effectively

You did it! You impressed your boss and have gotten the OK to work remotely one day a week. 

First of all, we just want to say how proud we are of you. You rocked it.

Second, we’d like to offer some advice to make sure this goes as smoothly as possible.

Check-in and set expectations

As a remote employee (even a part-time one), the most important tool that you can lean on to ensure success is communication. While you’ll still be spending most of your time in the office, make it a point to stay connected to your teammates on the day that you are working remotely. Whether that is through Slack or over email, it’s important that everyone understands that, yes, you are actually working and that you can be relied upon throughout the day.

In addition to day-to-day communication, set up monthly meetings with your manager to check-in on how your remote work agreement is going. Has it been a success so far in their eyes and, if he or she feels like there are improvements to be made, what can you adjust to ensure that you’re doing your job to the best of your ability? These check-ins will not only alleviate any concerns that you may have about your performance, but also remind your employer that you are committed to a successful outcome.

Check out our list of tips for remote work beginners

We know a thing or two about the world of remote work. To get you started on this journey, we’ve put together a list of our top tips for remote work beginners so that you’ll have a painless transition. This includes all of the information that you’ll need to knock each of your remote work days out of the park - and even set you up to negotiate for more time away from the office in the future.

If you’re interested in working remotely, but want to test the waters with yourself or your organization first, doing so one day a week may be the perfect first step. If you follow the advice above, you’ll be well on your way to a more flexible and inspired lifestyle.

Looking for a new remote job?

The Remote Year Job Board opens doors to genuine opportunities that seamlessly blend remote work with the freedom to explore the world. Imagine browsing and applying for positions that empower you to embrace a nomadic lifestyle without compromising on career growth. Search for your next opportunity here.