How To Transition To Working Remotely: From The Office To ANYWHERE – In 10 Steps!

If your work is mostly done on a computer, it’s highly likely you can transition to working online instead of in an office.

And thankfully, this is the reality for more and more people today – not just the computer scientists, data scientists, designers, etc. Many roles can be done remotely now.

But the only thing standing between you and working from home (or anywhere) may be the company you work for.

So, the first step is to have an honest discussion with your boss. They may be able to transition your role to a new remote environment.

We’ll give you all the tips and tricks needed to approach this conversation successfully. And, just in case, a step-by-step process to follow if your request to be a remote employee is denied.

Happy couple on top of mountain, they have just transitioned from 9-5 to remote or online work.
Chris and Bec travel full-time and work from their laptops.

Key takeaways

  • The remote/online work policy of your employer contains what’s expected from remote employees – have a read.
  • If there isn’t a policy in place, bring a remote work plan to your boss. Emphasize benefits for the company and address possible concerns.
  • If your request is denied, there are other things to try before looking for opportunities in other companies.
  • Be clear on why you want to work remotely, this will keep you motivated and help navigate the challenges.

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Check your employer’s policy for remote teams

More and more companies are transitioning to a partial or even full online workforce. 2020 was the kick these companies needed to see that remote employees perform well even though they are not at the office.

Often a company will outline rules when working from home. These may include:

  • Rules about work hours.
  • Communication protocols.
  • Reporting procedures.
  • Specific tools or software required for remote work.
  • Data security and confidentiality.
  • Changes (if any) on salary, healthcare benefits, insurance coverage, vacation policies, reimbursement, etc.

Understanding these policies helps you set up your work habits with the organisation’s expectations.

This way, you can structure your workday properly, set goals, and organize tasks accordingly.

No online work policy? No problem

If this is the case, don’t worry. Your remote working environment is still achievable, just in a different way.

The pandemic proved that working online is entirely possible. So, if your company doesn’t have a remote policy yet, you may have to come up with one and bring it to your boss.

This can be anxiety-inducing for some, but keep in mind that smart employers want to hold onto their valuable staff. You won’t get fired for bringing up a plan to work remotely (you shouldn’t).

If you fear you may get fired for discussing this, it may be best to start looking for a new work environment. Look at it as the perfect opportunity to look into jobs in fully remote companies! There are dozens out there!

Related: 7 Common Online Work Myths Debunked

Work by the beach in a cafe! Then at lunch, you can have a quick dip.

10 steps to prepare for the online work conversation with your boss

Preparing to discuss working remotely with your boss requires a bit of thought and planning.

You need to show that you can keep doing your work equally well (if not better) remotely, emphasising how beneficial this can be to your employer.

Be patient and thorough in your planning, and follow these steps to increase your chances of success:

1) Assess your role

Consider whether your job can be done remotely. What tools do you need to do it? What potential challenges can come from doing it remotely?

To help you do this, look for companies that offer your role (or similar) but with a remote work setup.

2) Research company policies

If your company doesn’t have remote work policies, check the policies of other companies in the same industry.

Also, check if there are any precedents for remote work arrangements within your organization. If there is, it can make things easier for you.

3) Gather supporting evidence

Compile relevant information and data to support your request. This may include:

  • Examples of successful remote work arrangements in other companies.
  • Productivity statistics.
  • Testimonials from colleagues who have benefited from remote work.

4) Identify benefits for the company

Think about how having remote team members benefits your employer. Such as increased productivity, cost savings, improved work-life balance, etc.

5) Anticipate concerns

Put yourself in your boss’ shoes and anticipate any concerns or objections they may have. Prepare well-thought-out responses to address these concerns. Such as communication strategies, accountability measures, etc.

6) Plan a proposal

Structure your conversation by outlining a clear proposal for your remote work arrangement. Consider factors like:

  • Number of days per week you plan to work remotely.
  • Your working hours and the use of a time tracking software.
  • How will you stay connected to the team (communication channels, video calls…).
  • Specific goals to prove your productivity.
  • If there will be a trial period for remote work, duration, goals, etc.

Related: 7 Quick Wins To Start Working Online While Traveling Australia

7) Schedule the meeting

Request a meeting with your boss to discuss the topic. Choose a time when they are likely to be available and not worried about other issues – i.e. first thing Monday may not be a good time!

8) Present your case

Present your proposal clearly and concisely. To increase your chances of a successful outcome:

  • Approach the conversation with a positive attitude and professionalism.
  • Focus on how remote work can benefit both you and the company.
  • Address concerns.
  • Emphasize your commitment to maintaining productivity and communication while working remotely.

9) Be open to compromises

Your boss may have specific concerns or constraints that you need to address. Be open to finding a compromise that works for both parties.

E.g. starting with a hybrid model instead of fully remote, implementing regular check-ins to assess progress, etc.

10) Follow up in writing

After the meeting, send a follow-up email summarizing the key points discussed. Include any agreements reached and any action items assigned to either party.

This ensures that both you and your boss are on the same page and helps maintain clarity moving forward.

What if your request to work online is denied?

If your boss denies your request to work remotely, there are a few steps you can take:

Ask for feedback

Ask your boss for specific reasons why your request was denied. Understanding their concerns can help you address them or explore alternative solutions.

Provide additional information

If you think your boss may have overlooked some details or if you have new data, discuss it in a new meeting.

Propose a trial period

Offer to start with a hybrid model or compressed work weeks for a specific duration. That way, you can showcase your ability to maintain productivity, meet goals, and ease your boss’ concerns while building trust.

Focus on performance

Demonstrate your value while in the office. Maintain high productivity, meet or exceed targets, and consistently communicate your progress to your boss. Building a track record of strong performance can help support future requests for remote work.

Revisit the conversation

After a reasonable period, consider scheduling another discussion with your boss to revisit the topic. Circumstances may change, and your boss may be more open to considering remote work arrangements in the future.

Remember to maintain professionalism and respect throughout the process. It’s important to keep the lines of communication open and strive for a constructive dialogue with your boss.

If none of these work, it may be time to explore other job opportunities.

More and more companies are embracing the work-remote model, so there’s no reason you shouldn’t find a role! Some organisations even manage a permanently remote workforce.

We recommend using online search engines like Indeed or Seek to help your search, filtering the location to “remote”. Alternatively, you can do a general Google search with your job title followed by “remote job”.

The most overlooked thing about transitioning to remote work

The most overlooked thing is knowing why you want to work remotely. Having this self-awareness can make or break your remote work transition, as it:

  • Gives you clarity and focus, so you can advocate for remote work within your company.
  • Aligns your expectations with the potential benefits and challenges of remote work.
  • Sets realistic goals while anticipating potential obstacles.
  • Enables you to make decisions based on their alignment with your goals.

For most of us, working remotely is a means to an end.

For us, working remotely is our way to fund our travels

It helps you live your life the way you want to, putting what’s important to you first. Whether that’s travelling, taking care of a loved one, or just knowing that you own your time.

Transitioning to remote work requires self-discipline, motivation, and the ability to work independently. Knowing why you want to do it is a source of motivation in itself, helping you stay focused and committed.

Related: How to work remotely and travel Australia? (7 steps)


Do remote workers work harder?

Remote workers don’t necessarily work harder.

This depends on the person (their work ethic and productivity) and the level of support given by the company. This is regardless of whether they work remotely or in a traditional office setting.

Some remote workers may be more productive as they have fewer distractions and are more comfortable. Others may face challenges in maintaining focus or establishing work boundaries.

With that said, some remote workers may work “harder” on any given day to get on top of their tasks, and have more free time.

How can I convince my employer to let me work remotely?

To convince your employer to let you work remotely, you have to bring a well-thought plan that emphasizes how will this benefit the company.

Start by assessing the feasibility of your role for remote work, research company policies, identify benefits for the company, and anticipate concerns. Gather all that information in a proposal and schedule a meeting with your boss to discuss it.

What are the essential tools for remote work?

The essential tools for remote work are a laptop and the internet. You may need more depending on your role – i.e. special software, a headset, an external drive…

The bottom line

Transitioning to remote work is more and more common across many industries. If you want to do this, start by understanding the remote work policies of your company and see if they align with your goals.

If there are no policies in place, you’ll have to do a bit of research. Then, create a strategy to make this happen and discuss it with your boss. Address their potential objections and emphasize the advantages of remote work for your company.

If your request is denied, there are a few things to try before seeking a new role. However, it’s crucial for you to understand your personal motivations for remote work. This provides clarity, aligns your expectations, and serves as a source of motivation throughout the transition.

Whatever you decide, there are some skills you need to work remotely (and some you don’t) we wrote an entire guide about that here!

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