Convincing Your Boss To Let You Work Remotely

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Looking to end the daily commute or relocate abroad? Here’s how I convinced my company to re-evaluate remote work.
The first part in a series of articles on working remotely.

I started working remotely in early 2017. At the time I was employed as a developer for an e-commerce company in the UK, in a small team with about 4 other developers.

This is how I convinced my company to let me work remotely.

My Motivation

My girlfriend wasn’t from the UK, we were in a long-distance relationship, one of us needed to leave their home country for the two of us to be together. We decided that I’d come to her country in Asia.

In the past, I had managed to secure a couple of short sprints where I’d worked remotely for a day or two in the UK.

My company CEO was sceptical that a developer could offer the same level of productivity from outside the office.

The day when I’d ask to work remotely long term was coming, so I knuckled down and worked my ass off, not wanting to give the boss any excuse to deny my future request.

At this time I was working a couple of days remotely per month. A great chance to exceed expectations.

Being Productive

Working remotely isn’t like working from an office. The extra freedom to manage your day isn’t a free ticket to mess about.

Talk More

Slack, Hangouts, Skype or whatever your company uses. You need to try harder than normal to be part of the team, especially if you’re the only one based remotely.

For me, communication with the dev team went fantastically via slack. Daily stand-ups made sure everyone knew what the hell they were doing in relation to each other.

Communication with other departments was another matter. Since some teams in the business didn’t have access, or any prior requirement for an instant messaging app. Sometimes I had to pick up the phone and call people.

If I didn’t understand something, I’d schedule a very quick meeting to run through the points.

For those one or two days a month I worked remote, I was the only one in the company outside of the office. It was my responsibility to make sure that it didn’t negatively impact the team.


Some people are not well suited to working remotely. There are stories of people struggling to concentrate while working from home.

From day one I made sure that I had a quiet & comfortable space in the house. A good office chair and desk are a must-have.

I knew from day one that you need self-decline to succeed in a home office. Which means staying off social media, YouTube or any other procrastination friendly service.

Sure, you can have a break, but try and take a timed break away from your desk and be back to work at the promised time.

The Result

My work output actually increased by quite a bit while away from the office. I owe this to self-discipline and the removal of office-based distractions such as colleagues coming over for a chat.

I was quite happy to use some of the time I’d normally use for commuting, to prep for work. Read through email’s and review open work items while having my morning coffee.

The Request

Nobody in the history of the company had been allowed to work away from the office for more than a day or two. Myself included, yet I was going to ask for permission to work remotely long term in a different time zone.

My company CEO was known for being old fashioned, without a development background he was uneasy about having workers that he couldn’t check-up on in-person. This is something I hear a lot from companies who are uneasy about remote workers, the best solution is to show them how we use tools like git, which can be used to track the amount of work submitted by a developer.

The fact that my productivity had been higher than normal while out of the office was ammunition for my proposal.

One day I approached my boss with the request to work remotely. My boss had to pass the request to the CEO for approval. I thought this would be a hard sell, but I’d built up a level of trust with my boss and the CEO so my request to work remotely was granted.

The First Day Remote

I’d done it.

Booked my flight and took my belongings and a company issued laptop to a small country in SE Asia a few weeks later.

Working in a completely different time zone and a new country brought its own challenges. Something I’ll cover in a later entry in this series.

More Reading

Article Categories: # remote-working
Date Published: Jul 16, 2019


A tech blog by Andy P. I talk about coding, enterprise software development, tech, games design & other things that interest me.

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