🗯️ 5 Tips on How to Ask to Work Remotely

🗯️ 5 Tips on How to Ask to Work Remotely

If you’re reading this, there’s a good chance you’re interested in working remotely. This could be for a specific period whilst travelling, for one of two days a week on a recurring basis, or you want to become a full-time digital nomad. And why not?

There’s never been a moment where so many jobs can be moved entirely remote – a silver lining to COVID-19, perhaps. But asking your manager or boss for a remote work arrangement can be tricky – especially if you don’t know how to go about it.

In this blog post, we’ll share five tips for asking to work remotely that Iz and I used back in 2021 to travel whilst working in Spain, Greece and Portugal for three months, which you can use to kick start your remote work life. So let’s get started!


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đź’Ş #1 Build a Reputation for Being a Hard Worker

The first step you must take to increase your chances of being able to work remotely, and one of the most important, regardless of the period of time the request is for, is to establish yourself as a hard worker.

But what does that mean? Well, for example:

  • Show your boss that you’re consistently meeting or exceeding expectations
  • Become known as someone always willing to lend a helping hand
  • Proactively look for ways to improve things and constantly challenge the status quo

If you can show that you are a reliable and hardworking employee, you will be in an excellent position to ask for remote work privileges.

It’s logical; working remotely involves trust between you and your manager. The more confidence you’ve built up before requesting to work remotely, the better chance you have of getting a “sure, why not” from your manager.

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If your manager knows you can produce quality work without close supervision, why would that change if you’re not physically in the office?


🎲 #2 Balance of Benefits – Employer vs. You

Once you’ve established the trust, you need to figure out how to approach the conversation with your employer. There are several ways you can do this.

One way is to explain how working remotely would benefit the company rather than highlighting the advantages for you. For example, you might point out that working remotely would allow you to take on more flexible hours, making it easier to provide coverage for customer support during late-night or early-morning hours.

Another way is to outline the specific advantages that working remotely would offer in your particular case. For example, highlighting how working remotely would increase productivity by eliminating commute time and distractions from office chatter.

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Our suggestion is somewhere in the middle. Present working remotely in a way that highlights the benefits for the company and yourself. This will come across as a lot more sincere and create a more balanced view that your manager will find harder to say “hell no” to.
Laura working on her laptop in the garden, wooden table, chairs, plants in the background, headphones, glass of water, powerbank, phone

🤔 #3 Consider what the Concerns will be in Advance

To successfully ask to work remotely, you must consider all aspects of the situation and be prepared to present a well-reasoned case. As discussed above, you’ll need a solid case for why working remotely would benefit you and your employer.

To that end, it’s helpful to play devil’s advocate and anticipate any potential objections your boss might have ahead of time.

For example, if you’re looking to reduce your commute, be prepared to address concerns about whether you’ll be as productive at home. By thinking through potential objections ahead of time, you can make a solid case for why working remotely would be a win-win for everyone involved.

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If your company has a remote policy, it’s a smart idea to familiarize yourself with it before forming your arguments. This will help you build a remote plan aligned with the company’s expectations, which will be harder to object to when presented to your manager.
Instagram - @andrewtneel | Donations - paypal.me/AndrewNeel, Photo by Andrew Neel / Unsplash, laptop, coffee, phone, notebook

🗣️ #4 Have a Communication Plan in Place

Communication is crucial whilst working remotely and will most likely be one of your manager’s most significant concerns with allowing you to work remotely.

This is why it’s critical to think about how you’ll maintain communication with your team and your manager whilst not being physically present. Below we'll look at two suggestions; Introducing tools for online collaboration & reoccurring meeting structures.

👨🏽‍💻 Tools for online collaboration

There are many tools for online collaboration, and many teams, after COVID-19, have become very used to working with them.

Video meeting tools like Zoom and Google Hangout provide a straightforward way to stay connected & using online chat platforms like Slack allows for more frictionless communication than email.

If your team hasn’t used these tools for collaboration, it might be a good idea to introduce them before requesting remote work if possible.

đź“… Reoccurring Meeting Structure

You could also look to create a recurring meeting structure with your team and manager that provides moments where you can share what you’re working on, ask for help and help your team members.

The fact these are scheduled into everyone’s calendar means you don’t need to spend time finding a moment when people are free, which will enable you to focus more on doing your work whilst maintaining your visibility within the team.

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Preparing these suggestions will surely help your manager feel more comfortable with a remote arrangement.

⏳ #5 Suggest a Trial Period

If your boss is still unconvinced after following the above steps, then there’s one last trick up your sleeve…

Suggest a trial period. This approach could be a great middle-ground that shows you are flexible and willing to work with your manager to find a solution that works for both parties.

If your boss is open to the idea, be sure to set clear boundaries and expectations during the test run, such as agreeing on specific days and times when you will be working remotely, as well as specific criteria to assess whether the trial was a success or not.

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At the end of the trial period, sit down with your boss and discuss how the experience went. If it was deemed a success, this is the perfect opportunity to ask to make remote work a permanent arrangement.
Hourglass small and big, computer, computer mouse, keyboard. Photo by Milad Fakurian / Unsplash

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⚡️ Conclusion

Asking to work remotely can be daunting – but it doesn’t have to be. Following these five tips, you can confidently ask your boss for a remote work arrangement. We followed these steps, and you can too.

So what’s stopping you from requesting to work remotely? Book the meeting with your manager today and start preparing for the conversation.

Let us know how you go by dropping us a message on Instagram - @remotevagabond