3 Steps to Negotiating a Remote Work Arrangement at Your Current Job

You want to travel the world…

You want to experience other cultures, see new places, eat new food, and meet new people.

And you definitely want to stop living in a grey, lifeless cubicle everyday.

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Problem is, you can’t just up-and-quit your job – you have bills to pay, a family to support, and dignity to maintain.

What if, though, you could live your cubicle-less dreams without quitting your job and risking it all?

What if you could go travel the world and keep the job you have?

Meanwhile, you could build new streams of income on the side (it’s far easier to build other streams of income with a remote gig than with an in-house gig).

Well, you can.

And here’s how you can negotiate remote working conditions with your boss (assuming that your current job just requires a computer and WiFi).

Step #1: Make yourself irreplaceable…

The more valuable you are to the company you work for, the easier it’ll be to negotiate remote work conditions…

But, gauging how valuable you are to your company isn’t always easy. I talk to people all the time who have TONS of leverage but don’t see it and people who have NO leverage but think they do.

To clear the water, ask yourself this question:

If you weren’t at work for a week and no one was there to replace you, what would happen? – Imagine that you quit out of nowhere without any notice. You just left. What would happen? Would processes be damaged beyond repair? Would the company be scrambling to find someone to replace you? Or would they find someone else effortlessly? The more damage done by you leaving without notice, the more valuable you are to the company.

Once you have a general gauge of your current value, you’ll be in one of two positions…

  1. The company would have a hard time replacing you.
  2. The company would have little problem replacing you.

In the case of the first, move on to Step #2. In the case of the second, find ways to increase your value at the company…

What things can you learn to do that would make you more difficult to replace? Are there any skillsets you could learn, processes you could create, or results you could drive that would make replacing you more of a headache?

Brainstorm ideas and then start pushing your way into company-critical processes and tasks. The more you do this, the more valuable you’ll be. Hit me in the comments if you want help brainstorming ideas.

Step #2: Pretend to be sick for a few days…

Choose one or two days to fake sick…

But, during those days, offer to work from your laptop at home rather than simply taking sick time. Explain to your boss that you have some stuff you’d really like to get done and that the tasks can just be done from home.

Ideally, take a sick day on Tuesday, Wednesday, or Thursday to avoid the suspiciousness of trying to get a 3-day weekend.

During the day working from home, double or even triple your productivity. Keep records of the work you finished – even if it’s just on a sheet of paper and make sure that you get more done than normal.

At the end of the sick day(s), email your boss with something like,

Hey [name],

I’m starting to a feel a bit better, fortunately. And I wanted to send you an end-of-day report with everything I got finished since I was out of the office.

[Impressive list of things you got done].

To be honest, this experience was a bit enlightening for me. Working from home, I felt much more productive than working in the office since I was able to give my entire focus to one task at a time.

In fact, I’d like to propose a test: for the next two weeks, I work from home on Tuesday and Thursday – you can veto this at any time if you feel it isn’t working out.

But it’s something I’d like to try if you’re willing.

Does that seem reasonable?

Best,

[Name]

Most bosses will have some objections after your first email.

When they do, simply answer the objection by offering a piece of software or process-iteration as a solution…

Then ask for the close again…

“So, is this something you’d be willing to test?”

Once the experiment gets approved, move on to Step #3…

Step #3: Double your productivity and make a final ask…

During the trial period, focus on increasing your productivity on the days when you work from home.

The more productive you are during these times, the better chance that your boss will opt to make your position entirely remote. Your goal is to prove to your boss that remote work conditions will benefit the company more than in-house work conditions.

To increase your boss’ confidence that you’re working efficiently during those days, send an impressive review of all the work you got finished at the end of each working day at home.

Use any leftover time to tackle extra projects and further impress your boss.

Then, at the end of the two week test, send your boss an email like this…

Hey [Name],

The two week test is finished and I feel that my productivity has increased significantly by working at home. I would like to try another experiment to increase my productivity even further if you’d be open to it.

For two more weeks, I’d like to try working completely from home. This would also just be a test so you could veto it at any point. If, though, my productivity continues to increase and you’re satisfied with my results, then I’d like to consider turning my position into a full-time remote job.

Would you be willing to try this?

Best,

[Name]

One you get this proposal accepted, continue to increase your productivity and prove to your boss that this remote-work thing is a good idea.

Also, continue to send updates at the end of each day with impressive reviews of everything you got finished.

By the end of this two week test, send an email like this…

Hey [Name]

Again, I felt that this experiment proved how much more productive I am outside the office verses inside the office. For that reason (and since it gives me more time with my family) I’d like to consider making this position permanently remote.

What do you think?

Best,

[Name]

A disclaimer…

There’s no guarantee that this process is going to land you full-time remote working conditions. It partly depends on how flexible your boss is and it partly depends on how much decision-making power they have over your position.

Here’s the thing, though…

Even if you don’t achieve full-time remote work conditions, wouldn’t it be worth it if you got 2 or 3 days a week to work from home?

Then, you’d increase work flexibility and be able to focus more on creating other streams of income during your free time.

In other words, results vary.

But even one day off of remote work every week will push you in the right direction…

Toward creating other supporting streams of income…

Toward spending more time with your family…

And eventually, toward traveling the world…

It might take some time, but here’s a quote to keep you inspired…

time will pass


 

cuteness
Baby Andie smiling at the camera with a breath-taking view of Taormina, Sicily behind her

 

2 thoughts on “3 Steps to Negotiating a Remote Work Arrangement at Your Current Job

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