How to Negotiate a Remote Work Arrangement (And Get What You Want)

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Last Updated on August 27, 2022 by Ron

Today, I’m going to show you exactly how to negotiate a remote work arrangement with your current employer.


Because, remote work is the future, and so many working professionals and digital nomads are already embracing it.

In fact, this is the exact process my friend Ben used to negotiate a remote work arrangement with his fast-paced Silicon Valley tech company. Ultimately, he was able to convince his boss to let him work remotely from anywhere in the world.

Unfortunately, many employers are a bit resistant to change with the times. Too many managers are stuck in “water cooler mode,” intent on keeping workers close who honestly don’t require a physical presence in an office environment.

First the bad news:

In most cases, this is not a quick fix. It can take some time to break someone of their “old school” thinking.

The good news?

I’m going teach you how to do this using a simple 9-step process.

Let’s get right to it!

Free PDF: Download this step-by-step Digital Nomad Guide now to go from employee to globetrotting entrepreneur.

The Impact of Covid-19 on Remote Work

Consider the impact of COVID-19 or Coronavirus on remote work when negotiating a remote work arrangement.


Before we begin, I think it’s important to note the recent impact of COVID-19 on remote work.

Although, the coronavirus crisis has had a negative impact on most of the world. There were some advantages for online workers and digital nomads.

Before the pandemic, just 14% of U.S. employees worked remotely five days a week – now, that number is closer to 60%

According to a recent Gallup survey, 3 in 5 of those newly remote employees hope they don’t have to return to the office. I know I wouldn’t.

Once you’ve gotten a taste of the freedom and flexibility of working remotely, it’s practically impossible to ever look back.

From the 30-second commute to your laptop to the ability to travel anywhere in the world, it’s a lifestyle some only dream of having. Now it’s easier to make this transition than ever before.

Here are a few perks remote workers enjoy:

  • No commute
  • Fewer expenses
  • Higher productivity
  • Independence (Flexible Schedule)
  • Flexibility to travel
  • Greater work-life balance
  • Ability to cultivate an international circle of friends

So what does this mean for you?

You may not have to quit your day job in order to work remotely full-time. Many digital nomads continue working for the same company they worked at before, turning their 9-5 office job into a location-independent career.

If you’re yearning for the freedom of a remote work lifestyle, but lack the confidence and the know-how necessary to jump into the digital nomad life, you’re in luck!

I’m now going to show you how you can convince your boss to let you work remotely.

It’s all about persuading your company you can be just as effective (if not MORE effective!) working remotely as you are working in the office.

Let’s break down how to do that, step-by-step.

Step 1: Conduct Your Work Professionally and Proficiently

Be an efficient worker who is on top of their work performance when trying to convince your boss to work remotely

I’m sure this may seem obvious, but it needs to be said: 

If you’re ever going to convince your boss to let you work remotely, you’ve got to be a top performer.

Keep in mind that it’s usually in a company’s best interest to hang on to a great employee than to have to hire and train someone new. (It also costs way less – a compelling point you can use later to negotiate a remote work arrangement!) 

If you’re a huge asset to the company, they’ll likely be more willing to do what it takes to keep you happy and hold on to you. (Even if that means they’ve got to set you free.)

Look back on your most recent performance reviews. If they’ve been stellar, great. You can emphasize that and use it to your advantage once you sit down with your boss.

If there’s room for improvement, consider taking some time to prove your worth and show your boss they can really trust you. That way, you’ll be in a better place to ask for this big change.

Step 2: Define Your Why

You need to define your why if your going to present a reason to negotiate a remote work arrangement.

Before you ever come up with a game plan for HOW you’re going to work remotely, nail down WHY you want to work remotely. 

What’s your motivation for transitioning to working from home? 

Why is it that working remotely as a digital nomad sounds so appealing to you?

Your boss is going to ask for a reason – be prepared to give them an honest answer. If you have a clear WHY, you’ll be much more convincing.

Honestly, it doesn’t matter what your motivation is. 

Maybe you’re…

  • Interested in having a shorter commute
  • Looking to live a more autonomous lifestyle, with more flexibility and freedom of choice in what you do in your free time
  • Longing to spend more time with your family 
  • Genuinely able to work better with fewer interruptions and distractions
  • Simply just wanting to travel and work from anywhere

This might require some serious self-reflection. Take the time to nail down your reasoning.

Step 3: Create a Remote Work Plan

Create a remote work plan that allows for you to negotiate a remote work arrangement with your boss.

Plan how to achieve remote work success BEFORE you present the idea to your boss. Anticipate questions or concerns your boss might have and plan how to overcome those potential challenges when negotiating a remote work arrangement. 

A lot of these details will vary depending on your company and position, but here are a few concerns your boss might have about you working remotely full-time: 

  • Communication
  • Availability
  • Productivity
  • Involvement in meetings
  • Conflict resolution
  • Connecting to company servers
  • Maintaining strong relationships with clients & colleagues

Make a plan to address each of those concerns. Consider what methods of communication you might use.

Let your boss know how many of the hours between 9 and 5 you’ll be available for. Figure out how you might connect to company servers remotely, or how you could avoid having to do so altogether. 

Don’t just plan so you have something to tell your boss – plan for yourself, too. Figure out where your home office will be or how you’ll make sure you always have WiFi on the road. Determine your ideal daily schedule and routines.

Having a firm plan set in place will make you feel more prepared to talk to your boss – and more prepared to actually work remotely when your boss finally agrees.

Free PDF: Download this step-by-step Digital Nomad Guide now to go from employee to globetrotting entrepreneur.

Step 4: Conduct Thorough Research

Conduct thorough research and gather as much data as possible in presenting your plan to work remotely to your employer.

Time to do some homework. Back up your request to work remotely full-time with cold, hard facts. There’s loads of data out there proving that both employees and employers really stand to benefit from remote working.

On average, remote workers are:

  • Less likely to quit
  • More productive
  • Less expensive for the company
  • More satisfied with their jobs
  • More likely to recommend the company to a friend

Referencing broad data is great – having your own personal data to draw from is even better. Whenever you happen to be working remotely (whether out of necessity or as part of a trial period), track your remote work performance, and compare it to your in-office productivity.

Use it as further proof that both you and the company would thrive if you switched to working remotely full-time.

Consider researching possible legal and tax implications of working abroad if you’re planning on being a digital nomad or relocating. Your state might have certain tax restrictions for employees working outside the state or country.

If that’s the case, it may make more sense to transition to working as a contractor. Research your state’s tax laws and see what you can find out.

Step 5: Drop Subtle Hints

Dropping hints to your boss can help to prepare you for negotiating a remote work arrangement with them when the time comes.

Gauge your boss’s comfort level and prepare them for the big conversation by dropping a few hints beforehand.

Chat with them about what their thoughts are on remote working in general. Bring up a colleague of yours who’s currently working remotely either full- or part-time. Ask them how they feel about the increasingly popular trend of people working from home due to COVID-19.

Not only can this soften the blow and make your boss more prepared for the remote working conversation, but it can also give you a feel for how they’ll react.

Try and figure out what elements of remote work might make them feel uncomfortable and how you can pitch your plan in a way that addresses those concerns. Pay attention to their words and body language. 

Step 6: Convince Your Boss to Work Remotely

In order to negotiate a remote work arrangement you must have a compelling argument to convince your boss.

Now that you’ve made a remote work plan, done your research, and dropped a few subtle (or even not-so-subtle) hints, schedule time to discuss your request with your boss. 

Remember to sell your boss on the benefits to THEM. They’re not going to be so interested in how awesome full-time remote work will be for you – put yourself in their shoes and figure out what they really care about. You’ll seem less selfish and more like a team player who’s looking out for the company’s best interests.

Once you’re in the meeting, here’s what you should do to negotiate an ideal remote work arrangement:

  • Establish yourself as a top performer
  • Present your plan, along with detailed research
  • Explain how this will be better for your boss and for the company
  • Allow them to express any questions or hesitations
  • Be prepared to overcome objections, with a response prepared for likely concerns

Free PDF: Download this step-by-step Digital Nomad Guide now to go from employee to globetrotting entrepreneur.

Step 7: Request a Trial Run (If Necessary)

If you can't start working remotely right away, start with a trial period.

If your boss is open to the idea but not 100% comfortable with you working remotely full-time right from the get-go, suggest a trial period.

A trial run will allow your boss to get a glimpse of just how much you’re still able to contribute, even when you’re working remotely as a digital nomad. 

A trial period can be awesome for you, too. It’ll let you get a taste of the digital nomad lifestyle. Who knows – you could find out full-time remote work isn’t really for you after all.

You’ll also have the chance to work out the kinks and figure out specifics of working from home, from your daily schedule to your WiFI connection to your remote work setup. 

Work with your boss to figure out a trial period they’re comfortable with, whether you start working from home one day a week or try working from home for a full week to see how it goes.

Whatever you do, make sure you still produce the same amount and quality of work. This is your time to prove that you can work just as hard when you’re not in the office.

If you let your productivity slip, your boss might not be so open to allowing you to work remotely for a longer period of time. 

What if my boss isn’t open to a trial run?

If your boss isn’t even open to a trial remote work period, you may have to take matters into your own hands. Now, I’m not suggesting you should go on strike and refuse to come into the office until they finally cave.

Consider taking a working “sick day” to show just how productive, attentive, and communicative you can be from home. 

You could also try working remotely during your next vacation. This is how my friend Ben managed to convince his company that he was more productive when working remotely, and with great success.

Ben worked in San Francisco and decided to, without his company’s knowledge, work remotely when visiting his family in New York. He did the same thing when vacationing with friends in Las Vegas (that’s dedication).

He closely tracked his performance compared to when he was at the office. After doing that for a year or so and accumulating enough data, his boss was impressed and commended how much he had accomplished. Then, he was able to use that data and praise to convince his boss to let him work remotely. He now does so full-time.

My friend Ben used this process and got approved to start his own LLC and work as a contractor for his company anywhere in the world.

Step 8: Never Give Up (Be Persistent)

Be persistent in your pursuit of remote work. Convincing your boss won't be east, but never give up.

Working remotely full-time is a big change you’re proposing. It may take time for your boss to warm up to the idea. 

There are plenty of reasons your boss could say “no” at first. Maybe now’s not a good time. Perhaps you totally caught them off-guard. Or maybe they’ve just never tried it before and haven’t thought too hard about how it might work yet.

Don’t be afraid to ask again. Your persistence will show your boss how important this is to you. It’ll also give them plenty of chances to change their mind. Be patient, but don’t give up.

Looking to go above and beyond?

Try providing data from other remote workers and companies in your industry who have already implemented a remote work policy. Discover how those companies set their remote workforce up for success.

You could even set up a meeting with the CEO or department head of a similar company to nail down what they’ve done differently to embrace remote work. This could help you set up a remote work policy for your own company.

What to do when persistence isn’t enough?

If you're company is unwilling to accommodate you, be prepared to walk away and find your own path to working remotely.

For the most part, If you follow these steps, you will achieve success and begin working remotely for your current company.


Some managers and companies are just stuck in their old way of thinking and there’s nothing you can do to change their minds.

If this happens to you, you have a decision to make; “do I stick with the company knowing that they’re unwilling to accommodate my needs?” Or “does it make sense to pursue other career options or start something of my own?”

This is usually the point that most people give up and settle in for a life they don’t want. Don’t let that be you. Do not succumb to the pressures of life and give up on your goals!

You’re not “most people!”

How do I know?

Because you’re reading this.

If you need to stay and plan your exit strategy before you execute it, do so!

Personally, I would always go with whatever route best suits your needs without sacrificing your values or your happiness. Ultimately, the choice is yours but I suggest you be prepared to walk away as a worst-case scenario.

With that out of the way, let’s move on to the final step…

Step 9: Make The Transition (And Enjoy It)

Once you've negotiated a remote work arrangement with your company, be sure to enjoy the fruits of your labor.

You’ve done it. After plenty of planning, researching, negotiating, and proving, you’ve finally convinced your boss to let you work remotely full-time. Now, your task is to make sure you keep your boss totally happy as you’re gallivanting all over the world as a digital nomad.

Show your boss that allowing you to work remotely and live the lifestyle you worked so hard to achieve was a great choice.

In the beginning, ensure you’re even more present and available than you were in the office, no matter where in the world you are.

Get back to messages in a timely manner. Communicate openly with coworkers. Participate fully in meetings. Essentially, make sure you never cause any bottlenecks.

Do whatever it takes to make sure your technology is in working order. Make sure there aren’t any hiccups to connecting with company servers and cloud-based assets. Get a great data plan or WiFi connection to prevent miscommunications and backlog.

Don’t just wait for work to come your way. Take the initiative. If there’s something that needs to be done, address it before someone has to bring it to your attention.

Now for the important part:

Make sure you really enjoy your newfound freedom. Don’t get too comfortable. Spread your wings and get out there! You’ve worked hard for it.

Transitioning to working remotely full-time isn’t always easy, but make sure to enjoy the fruits of your labor. Take advantage of the new flexibility you have – you deserve it!

Following these tips will help you succeed in turning your 9-5 office job into full-time remote work. 

Your Turn

Now it’s your turn!

If you’re a fellow digital nomad or aspiring to be one, I’d love to hear about your experience.

What type of job do you have?

Have you started to gather data to negotiate your remote work arrangement yet? If not, what kind of challenges are you facing in doing so?

Did you successfully convince your boss to let you work remotely full-time already? Or did you quit your job and find something else when you decided you needed more freedom?

Let me know by leaving a comment right now!

Negotiate a Remote Work Arrangment FAQ (Frequently Asked Questions)

Is Remote Working A Good Idea? (Why Work Remotely?)

A lot of aspiring digital nomads, freelancers, contractors, and entrepreneurs ask themselves this question before beginning their journey. Maybe they heard or read about this concept, but don’t quite understand it’s benefits.

Generally, working remotely provides the ability to blur the lines between leisure travel and work. This in turn allows you to participate in what I like to call dollar arbitrage. Dollar arbitrage is when you earn money in your home currency but pay less expenses by operating in a different economy that has a lower cost of living. Other benefits include freedom, a flexible schedule, higher quality of life, an international circle of friends, self-discovery and reflection, and many others.

This is by no means an exhaustive list, but I think this gives you a general idea of why remote working may be a good idea for you.

What Companies Let You Work Remotely?

The best way to start working remotely is to negotiate a remote work arrangement with your current employer. However, if that doesn’t work for you, it may make sense to seek employment elsewhere that already has a remote work policy in place. The best way to do this is through sites like Flexjobs, We Work Remotely, and Remotive.io.

Can I Work For a U.S. Company Remotely?

The short answer: it depends. Depending on your current situation and the legal and tax implications associated with it, you should be able to work remotely overseas either as a remote employee or as a contractor. It may require some research, but if you consult your HR department and/or a legal or tax professional, you should be able to make the transition.

Can I Work Remotely From Another Country

If you can work for a company as a remote employee or contractor, then you should be able to work remotely from another state (or equivalent) or country. The question then lies on how comfortable your company is with allowing you to do so. This should be factored in when negotiating your remote work arrangement with your boss or current employer. If you’re getting hired on with a new company that already has a remote work policy in place, this should already be spelled out for you.

Is it Legal to Work Remotely From Another Country?

Whether or not your circumstances give you the ability to work legally in another country will require further research. While, I am not a certified professional that can give you that advice, your company’s HR or legal department can. I would also advise you to seek out your own legal or tax professional to answer this question in order to put you on the right path.

Is Remote Work right for me?

Whether or not remote work is right for you depends on what season of life you’re in as well as what values you consider important for your lifestyle. As mentioned previously, In order to discover this, you need to answer the question “Why do you want to work remotely?” This should give you clarity in making your decision.

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