How to Negotiate a Remote Work Agreement

How to Negotiate a Remote Work Agreement

How to negotiate a remote work agreement with your company / boss / employer/job.

  • If living the digital nomad life is your goal, this may be the quickest way to do that – quicker than starting your own small business.
  • Rather than sticking it out then just quitting your job, it’s possible to do your current job, just remotely.

I’ve met several people who work for companies remotely, and every year I feel like I meet more and more. I met a guy at the Nomad Summit 2019 who negotiated a multi-month remote work agreement at a large cable network company in Toronto. I also interviewed Brendy who did the same with her company in Amsterdam.

Here are some tips I gathered from talking to remote workers over my 5 years as a full-time digital nomad!

A shot of one of my many remote work setups in Bali, Indonesia, a remote worker hotspot. I typically work from cafes & coworking spaces.


  • It comes down the relationship with your manager/supervisor/boss
    • How good of terms you are on
    • Get on good terms with them
    • Perform well, so they like you
    • Meet deadlines, so they don’t worry about you
    • They must be confident in you
  • When the time is right, bring it up in a casual way
    • By the water cooler
    • At lunch
    • Or bring it up in their office after another good conversation
    • Ideally, bring it up after a great conversation
  • Start Leaving Clues first
    • Bring up working from “Home Office” first
    • “… you know speaking of that, I’m actually quite productive at home…  do people ever ask you about working from home a couple of days a week?”
    • “ … you know, I actually did most of this work at home… I’ve found that I actually get more done in my home office .. fewer distractions, etc…”
    • “… yeah on that note, I tell you what, if you let me work from home a few days a week, I promise I’ll get have all the same done, and be at all necessary meetings…”
    • “… how about a 1 day a week trial, and we see how it goes? I promise it will be a win-win. Easier for you, easier for me. Sound reasonable?”
  • Make a Proposal
    • Outline the proposal in detail
    • Have a Plan A and Plan B
    • Plan A might be a 6-month remote work agreement
    • Plan B might be 2-months
    • Offer to take on a bit extra work to compensate & make them happy
    • Prepare a full-blown stats sheet on the studies that show why remote work is great for companies (see articles)
      • Including cost savings, increased productivity, employee morale, and flexible schedule
    • Example intro: “I would like to explore the possibility of performing my duties as a web developer from my home office for three days a week. I propose that we can do a three-month trial telecommuting arrangement starting on March 1st and then evaluate continuing that work arrangement based on my productivity and quality of work.”
    • Ensure that your clients won’t have a bad experience with this
  • Find out about your company’s existing remote work policies and work that into the pitch.
    • Has/does anyone in your company worked remotely? If so, this is HUGE! Use that example to your advantage and work it into your proposal.

Tips from Brendy:

  • Choose the most openminded manager to talk to!
  • Talk to your colleagues and ask for advice.
    • Ask how to best deal with the manager if they know him/her better
    • Have them vouch for you
  • The pitch: have a plan laid out
    • If your plan is to work from Bali or Chiang Mai or Southeast Asia, explain why.
      • It’s a remote work hub
      • Cost of living allows you to save twice as much for your investment portfolio
      • Coworking spaces are world-class
      • Surrounded with other remote workers with various skills that you can pick up on / collab with
      • The tropical weather keeps you happy, which raises productivity.
    • Pitch a set timeframe as a trial period.
      • e.g. 3 countries, 3 months
      • Tell them we will evaluate after this trial period, and keep doing it if all parties are benefitting.
    • Ensure that you can attend all life calls remotely, if necessary
    • Ensure that you can reply to messages promptly, but let them know about the timezone differences – e.g. you will reply to messages every morning and evening.
    • At the same time, be real about your work-life balance goals. Life should be a balance!
      • “I love my job, I really want to continue to do well here, I just need a change of scenery” 
      • Explain that it’s NOT for a holiday. 
    • Give the hint that if they don’t let you, another company will!
  • Frame it as how it will benefit the company
    • E.g. it’s looking for business opportunities abroad (if it actually is)
    • An opportunity for you to grow your skills
    • You will grow as a person
    • Show studies that show that most Professionals who return from a ‘sabbatical’ are happier and improved.
  • Frame working from home as a productivity increase.
    • Share data/stories about how you are more productive working from home.
    • Explain that you are happier out of the office, and when you are happier = more productive. 
    • Share studies that show that a high percentage of employees are more productive working from home.
  • Get that courage! 
    • You just gotta ASK!
    • Come from a place of truth – don’t try to bluff or try to hide something. Come from the heart.
    • They might think you’re crazy!
    • You must choose for yourself.  It’s your life. 
  • To your parents / friends / colleges / boss:
    • Some will think you are crazy and discourage you
    • Simply ask for their support, and they will! “Please support me. I’m asking for your support. Because I’m going to do what I want anyway”
  • The Transition to Entrepreneurship: Work your Side Hustle on the Side:
    • The ultimate goal is to be your own boss!
    • Register yourself as an Entrepreneur at your local Chamber of Commerce (it’s an easy simple first step to take your entrepreneurial career seriously).
    • Nights and weekends, Brendy worked on getting clients for her career consulting business on LinkedIn, and sent out 100 cold emails a day.
    • Learn from other entrepreneurs online

In summary, working remote can be a great opportunity to be more productive, have more time to work on your business, or to start living the digital nomad life in Bali. It can be done!

Every company and situation is different, but long story short, get on good terms with your manager and make a compelling case to allow you to work remotely! If it ends up being a win-win-win for you, the company, and the clients, then why not?! Everything is GREAT! We live in an AMAZING time in that we are even able to work remotely, so take advantage of technology to live your best life!

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