I am going to share my personal experience on how I negotiated with my boss to get approval to telework. This is based on my experience and it will also depend on your line of work. In my case, I work for one of the top IT companies in the industry as an Engineer. I was hired and started my career in the office sitting inside a 4 x 4 cubicle with no windows.

How did the idea of telework start?

A coworker, introduced me to Timothy Ferriss’s book called the 4 Hour Work Week. He let me burrow the book for a week, but I only read the introduction and quickly lost interest. Personally I do not like to read topics I am not interested in, however I do like to listen. I went online and downloaded the audio version. I listened to it during my commute to/from work, this seems to be the best time for me since I have less distractions. It wasn’t until later in the chapter when my interest was drawn, yes the chapter about teleworking. I listened to that chapter at least five times until I came up with a game plan.

The game plan


It all depends on your work situation, your relationship with key management, and how you are perceived by others. For me, I did it the good ol’ fashion way, through hard work. I worked my behind to get noticed by my peers and more importantly by several managers. I took on difficult projects that my peers would shy away from. Once you take on those project, you shine. You make it known that you know what you are doing and that other team members can rely you. When issues come up and you are the go to person, then you know you have earned your spot a one of elite performers or in the IT world we call it SME ( Subject Matter Expert ). However it took time to get to this level, it definitely did not happen overnight.  About two years of hard dedicated work.

Once I became a SME, that’s when I knew I had the leverage. When you become a SME, it is harder for the company to get rid of you because they depend on your knowledge and experience. They basically trust you. When you have earned their trust, it is like an open door for negotiation. That’s exactly what I did, I waited until a major project was successfully completed then I scheduled a meeting with my boss. My exact lines were “I love working on this project, I like my peers. The management is very supportive. However, I am planning to move to ( fill in the blank ) but I would like to remain on this project. ” If they really like you, they will consider your request or at least help you find another position within the company at your new location. For me, thankfully it worked out, I have been teleworking for almost 4 years. It has allowed me to focus on my business and life. It is a Blessing.

Now it’s your turn to give it a try. The worst that can happen is they say no and you get to keep your job.

Reference Links:

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    1. captainbluff Post author

      We need to work otherwise we’ll end up like the humans in the movie Wall-E…haha. Unfortunately there are jobs that cannot be done remotely, but nowadays many jobs can be done remotely with the help of technology.

  1. Zeus69

    @captainbluff, I work for the City of Cape Town and we just recently implemented what is called a travel demand strategy which includes a work from home option, it works extremely well and staff are very happy. One of the other options is to work from a remote site close to home.
    Thanks for your interesting article.
    Mark (Zeus69)