How to Negotiate Remote Work Agreements Successfully (Even When You’re Not in Tech)

The world of working has truly changed. Gone are the days where we had to sign our lives away on a contract, handcuffing us to the desk of our 9-5 jobs. While our decade started with a pandemic that did more than enough damage (rest in peace, my amazingly planned six week trip to Europe), what it also did was prove that remote working is not only possible, but potentially feasible in a longer term. This then evolved into a concept that I’m sure all of us travellers have been waiting our lives to experience: Digital Nomading.

As a structural engineer based in Australia, I dreamt of this opportunity, but could never quite sell even to myself why it would be possible to travel and work remotely when my role isn’t in tech. But now having gone through those tough conversations first hand, and coming back from a six month digital nomading stint across Europe and Africa, slow living through countries like Spain, Portugal, Morocco, France… I can truly say this: If I can do it, there is undeniable proof that it is entirely possible for you.

What you need is the correct strategy, and the best way I can provide this is the unfiltered details that led to my own success story, with a step-by-step guide complete with examples, no matter the profession. We’ll be covering everything from defining your motivations, to setting up that meeting, and the different areas you need to touch on with examples from different professions to negotiate remote work agreements successfully.

Trust me, it’s worth the read.

New here? Read my story with digital nomading in my post "Non-Tech Digital Nomad: How I Successfully Worked Remotely as an Engineer (And Slow Travelled Europe for 6 Months)".

Step 0: Do the background work

We’re wasting no time here, but before we get to Step 1, we do have to make sure Step 0 is covered.

This step covers the background work that needs to be done to understand whether you should/can be requesting this of your employer at all.

Contract and Company Policy

The first step is to check the fine print of your contract and your company policy. Does it say anywhere that your arrangements cannot be altered or negotiated? Some roles may have very valid reasons why working remotely is not practical, such as if you needed to be present to operate as a doctor, or have security issues like some finance roles.

Tax Obligations and Insurance Coverage

Next is verifying your tax obligations and insurance coverage. Are you going to run into issues from either of those things if they agreed? These are very individual items that require you to research, so you can confidently proceed. Because trust me, these can result in major issues.

Local Working Rights

Assuming there is nothing preventing you from having that conversation, you can always try – the worst they can say is no. In some countries, there are even local acts (For example in Australia, the Fair Work Act) that can support requests for remote working in certain situations. Reading what is supported in your country of employment can help you understand your rights.

This step might seem boring and small, but before we get too far into the following steps, we need to make sure all our hard work isn’t for nothing.

Step 1: Pick a calendar time, and send out that invite

Seems easy enough, pick a date and time, and send out ‘Hey, would like to discuss working remotely. Kind regards.’ Right?

As we talk through these steps, you’ll come to realise some take a lot more time and thinking to build out, while others are really little bursts that help you along the way. Step 1 here is low-hanging fruit, easy to implement but can be done so a lot of the time… well in my opinion, incorrectly.

Picking the right date

Every company will have a calendar to some sort of annual cycle, and paying attention to it will increase your chances of an approval for the request more than you think. We’re talking reoccurring milestones like annual shutdown periods, performance review periods, and typically busy periods for that field (eg. close to end of financial year for accounting, or summer months for construction).

Picking the right date maximises your chances of a yes if you are able to command your employer or manager’s full and undivided attention. So for example:

• Don’t ask them when they are busy settling the financial results for the year.
  → Instead, wait for an off peak period.
• Don’t ask them leading up to Christmas when they are trying to close out end of year deadlines.
  → Instead, ask a couple of weeks after the break when things are running at normal speed.
• And don’t ask them when they are simultaneously reviewing your performance.
  → Instead, ask when you don’t want to divide their attention between how you are performing vs your request, both of which are important.

Picking the right time

Now that you’ve got the week locked in, and checked off all the no-go’s that would affect your asking power from a bigger picture perspective, we dive even deeper with time.

This will depend on your work schedule, but most office roles tend to favour Tuesdays to Thursdays, to avoid the busy Monday or the relaxed Friday to bring up the discussion. I find the best time is mid-morning (around 9am to 11am), where they are more likely going to have fresh energy to speak to you about it. Ultimately, time is up to you, but I would very much discourage setting this meeting for the end of the day.

With the duration, this can vary. Setting it for one hour allows for a full discussion, which I recommend for several reasons that I’ll explain in the next section. If you want an initial discussion to float the idea, 30 minutes is probably enough. Just make sure (where possible), that they don’t have a following meeting because that sets an unnecessary amount of stress to reach a conclusion without margin for run-overs.

Wording for the invite

My biggest tip here: An invite doesn’t have to tell all.

In fact, I think there is power in holding some of the cards in your own hands until you have the opportunity to discuss everything in full (which is likely during that meeting). You essentially want to drive that conversation your way by taking away their time to prepare a response before you have made your case, but doing so without a full blindside.

I would word my invite like this:

Hi [Manager],

I would love to set up some time, as included in the details of this calendar invite, to discuss some career related adjustments that I would like to propose.

Given the items I want to cover, I thought it would be best to do this over an in-person catchup rather than over emails.

I look forward to us having that discussion.

Kind regards, [You]

This rounds it all off by setting your ideal time and date, and provides enough context so that they are heading in with some idea, but not with everything.

Step 2: Frame your reason (And make it personal)

Now that you are in there, the floor is yours… But where do you start?

My personal opinion is that you need to start with your reasons. What is the motivation behind this request? Is it to care for family, or reunite with a relationship? Maybe learning a new culture or language that matters to you, or wanting to improve your work skills in an overseas setting?

A lot of us forget, our managers and employers are people too at the end of the day. They have the power to either make the decision, or at least throw support for the decision once you step away from this meeting. And the way they make these decisions can be either financial (which is something you cannot change), or human (where you tap into their empathy and understanding of your reasons).

Make it personal. Tell the story of why this matters to you on a human level.

Because eventually we will go through the more logistical and practical steps of this all, but it needs to be clear what your intentions are for the rest to make sense. And if you can weave in how this links to your career still continuing to develop, that makes an even stronger case.

For example, don’t say:

• I want to work remotely so I can travel around and experience new things.
  → Instead, I want to work remote so that I can travel around to learn new skills for my role that I wouldn’t otherwise gain staying in this country.
• I want to work remotely so I can be with a long-distance partner.
  → Instead, I want to work remotely because I value both career development and personal relationships, and I want us to find a way to foster both for a healthy work-life balance.
• I want to work remotely because I’m sick of the office hours and routine.
  → Instead, I want to work remotely as I know this ensures my future here is sustainable, as new experiences challenges me in my career and makes me resilient against burnout.

Step 3: Build your work structure

Say you’ve got them with your reason, they love and support it! But how is it going to work?

Well now is the time for you to be crystal clear on three simple things:

1. What will working remote actually look like?
2. What are the changes about your role?
3. How long will it be for?

Work out your overlap hours

Chances are if you are working remotely to be able to do digital nomading, time difference will be a big obstacle. By mapping it out beforehand, you can go into the conversation proactively with purpose of communicating what you see as a feasible arrangement.

This can be easily checked on a time zone converter site, allowing you to add multiple countries and set the date of your actual working period*.

For example, if your destination country is 8 hours behind (which was the case between my Australian office and my European destinations), you will quickly realise that starting work at 9am with the rest of your colleagues is near impossible, given that it will be 1am where you are!

Highlight the cross-over that is possible. This will help you build out the options later on, and shape what your work day will look like relative to the rest of the office back at home.

*Be aware of daylight saving changes, not only in your destination country but back in your home country.

Complete a task audit for your position

When it comes to your position, most likely you will have some roles and responsibilities assigned to it. This is a good place to start, but you could also jot down your repeated daily tasks that are important to your job.

We need to audit and categorise these so they are clear. They should fall in three different categories – can be done remotely, needs someone to cover, or will be put on pause until your return.

If the list is robust and many fall into the can be done remotely category, this becomes a huge selling point in proving that you can carry out that position without much of a problem. If that is not the case, then still bring it up through the perspective of having thought about that. Acknowledging these limitations is better than ignoring them, and redefine the role for the duration of your arrangement.

Present your options

I’ve said this before, but I’ll shout it for those in the back because it is so important: Give your company flexibility to negotiate, because giving them not only options, but the choice and agency to make a decision is truly the most powerful way to get a proposal across the line.

If you’ve completed the above two sections within Step 3, you will be able to put this together quickly and concisely for your discussions.

For example, if you are a marketing manager and you’ve identified that you can only have maximum of 4 hours of crossover time, but 90% of your work can be completed remotely because you can still communicate effectively with your team and your clients through video calls, you can lay out the following two options.

What makes Option A feasible is that having half cross over with clients still does not hinder the majority of your work in this example. Option B is enticing because it allows full access to clients and your internal team if your company wants a 100% crossover, as long as you are happy with the salary sacrifice.

There are many ways to lay out your options, to tinker with those categories until you both agree to the right fit for the role, but this is your ultimate weapon that makes it hard to say no to.

Step 4: Elaborate on the benefits and opportunities

There are many benefits that can be gained from an experience like this, and now is the time to tell them all about it. This is your sell section.

So sell it – what are the unique opportunities that benefit both yourself and the company that makes this all worthwhile? Be creative, but realistic. Expand on these sections and talk your manager through this – they likely haven’t thought about it in this way yet!

Let’s have a look at four different case studies (non-tech roles of course) for what is available, and how you can tackle this section.

• Accountant: Overnight reporting and fast turn-arounds, no need for replacement hires in busy season, client files can stay with one person to avoid breaching confidentiality.
• Lawyer: Billable work keeps moving without pause, clients keep their lawyer which is a relationship built on trust, unique position to observe how contracts and law is carried out in a different part of the world.
• Teacher: More time to spend on refining teaching resources, keeping an experienced teacher which is hard to find, opportunity to develop material for the classroom influenced by overseas teaching styles, opens up more time to do tutoring or after school classes.
• Project manager: Intricate details of live projects do not need to be briefed to someone else, certain phases get full focus due to lack of on site distractions, ability to provide updates and answers to questions outside of construction hours.

Step 5: Tackle the concerns

Ok this is a scary one – nobody wants to highlight the things that potentially don’t work.

But having a think about these before and handling them in a proactive way where you are not only addressing it, but also provide potential solutions?

When you think about your list, consider examples that address these employer concerns which show up consistently across most industries:

• Cost, how can you ensure this arrangement is not too expensive for your employer?
• Capacity, how can you ensure that the overall capacity for your team to carry out your work isn’t jeopradised?
• Practicality, what is the evidence that suggests you can practically carry out your role?
• Inefficiency, how can you prevent significant loss in efficiency or productivity?
• Taxes, how will you stay compliant?

Make it as specific as you can to your industry, and a good way to show proof is to have some form of evidence.

This could be showcasing a good track record with how much profit or contribution you’ve made while away from the office, like periods of working from home (hitting the practicality and inefficiency aspect). Or maybe highlighting the costs of recruitment to hire someone to replace your position, when having you work remote is likely no more costly than having you in the office (hitting the cost aspect).

That is a gold mine. I mean think about it: If you’ve already done the thinking for them, doesn’t it make it easier to say yes?

Step 6: Follow it up and get it in writing

The last step… Just one more push and you could be on your way to an amazing opportunity.

This is the post discussion action, you’ve done all you can to explain, persuade, and lay it all out there. And Step 6 is all about holding them accountable for a response.

Follow Up Email

You may have spent weeks researching and planning your proposal, you know it inside out I’m sure. But your manager will need something to review to take your request. Everything you explained to them needs to be summarised in a written form very clearly so that they understand: You are serious about this, not just some overnight request on a whim.

To help you with your written proposal, sign up below and you’ll instantly get sent a free copy of the proposal that got me the yes. I’ve given you the exact wording to show real life proof that it works, and will help you quickly build your document without the fuss.

Finalise a Contract Variation

Once they agree to your proposal, get a formal adjustment to your contract.

This variation protects you because it is a legal document that binds you and your company to that agreement, showing important aspects like your updated salary, roles and responsibilities, and the end date of your agreement.

Then it’s pen to paper, one beautiful signature later, welcome to the start of an incredible chapter to your career.

Top Areas Where People Go Wrong

• Only offering one option of how this works. This makes it go from a negotiation, to a yes/no. Which human psychology has proven many times over, is usually a no unless it’s a clear yes. So to avoid this, give them some choice and options to work with.
• Talking only of the benefits to themselves. A company has very limited interest in entertaining a proposal if you cannot point out why it is also a benefit to them too.
• Ignoring the concerns. If it’s not you pointing them out, they will eventually get to it. Not only are you then unprepared for the answers because you haven’t thought of it beforehand, you also lose the advantage of appearing proactive about this.
• Not following up. Completely understandable why you might forget, you’ve just gone into battle and have talked relentlessly about your proposal! But without the follow up, there is nothing to hold them accountable for actioning it.
• Underestimating the pace of digital nomading. This is a lifestyle where routine is difficult to come by, and people in your community will come and go very quickly. This means you spend a lot of energy dealing with life things, so be careful not to overreach and overpromise on work things.

Frequently Asked Questions (FAQs)

What kind of jobs do digital nomads have that allow remote working?

A whole variety, and much more expansive than you think!

I have personally done this as a structural engineer, but there are also various examples of roles that can make this work: Teachers, lawyers, consultants, project managers, digital marketers and graphic designers are amongst the many examples.

How do you manage time zones when working remotely?

You need be clear on what your work hours are and set boundaries in both your home and destination country, in a way that allows you to interact with your home office or clients to carry out your role.

Communicating your boundaries in advance will help everybody be across when it is appropriate to contact you or expect you to deliver a piece of work to reasonable expectations.

Is it better to carry out the negotiation as a formal setting, or casual?

Either one is fine, but if you choose to have a casual coffee to launch the idea, always follow up with a formal meeting to discuss the details of the proposal. This ensures both parties are clear in a professional capacity what is being agreed upon.

In both of these, always try to do them in person. A video call unfortunately does not create the sense of human trust and empathy that is required to get a proposal like this across the line.

How should I treat taxes when working overseas?

Taxes are very specific to both your home and destination country, so you must do this check as part of your preparation.

Broadly speaking, you will be continuing to pay tax in the country that has employed you. However, staying in a country for over 183 days will likely trigger tax obligations in that country. There are special agreements that prevent double taxation (DTA) so do confirm if these are applicable for you.

What do I do if they say ‘no’ to my working remote or digital nomad proposal?

Unfortunately with negotiations, we have to be prepared for a ‘No.’

However, do not let this be the end of the conversation. There is always an appropriate response to an objection, either through clarifying or reframing so it’s more agreeable. Or maybe it is not the most appropriate time to ask, and therefore you can always request a follow up conversation in the future.

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