How Do I Convince My Employer To Let Me Work Remotely?

Remote work relies very heavily on trust and communication. I’ve just returned to a remote-first culture, so while there was never a need to sell the idea, there is still the ongoing need to ensure that I maintain the trust and open communication. Remember that, even in a job setting, you are in community with others.

If you’ve demonstrated the ability to deliver without issue, you will probably have an easier time convincing an employer. If they still are resisting the idea, perhaps working into it slowly could help ease any fears about the change in your physical presence.

Do a trial run domestically, if you haven’t already, to understand the impact to everyone in the organization. This could just be working from home, although I’d suggest trying a few different locations to understand where you work best. A sample progression may look like this:

• Phase 1: Working remotely within your current city
• Phase 2: Working remotely from another city within your state (or neighboring state)
• Phase 3: Working remotely from a different timezone within your home country
• Phase 4: Working remotely from a neighboring country

Remember, that it’s not just about your bosses. There might be some unforeseen leaks in communication with your colleagues as well. Review periodically, address any that you find and proceed, extending the distance.

A progressive move also gives you an opportunity to workout logistical issues, from internet connections to what you pack. If you are attempting a trip, take note of:

• the things you forgot,
• things that you could easily pick up in the new destination and,
• things that you couldn’t easily find. These will most likely be must pack travel items when you’re abroad.

I’m a huge fan of Mexico as the first destination for North Americans in Phase 4. The change isn’t as disruptive as say moving to Southeast Asia. If too many variables change (language, culture, time zone, disruption of your daily routine), it can really affect your performance at work

In terms of working from another country, you’ll definitely want to make sure that tax and employment law issues are not an obstacle. They impact both you and your employer, so it’s best to know what those issues are upfront.

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