Some airport lounge
Can’t remember this photo fully but it’s in Canada because I see CP24 . Ah, the work-remotely-from-airport-lounges days…

How to Convince Work to Continue Working Remotely After Covid / Coronavirus


I started travelling 2012 and right then I knew this was somewhat a necessity for the things I want to do. Ever since, I tried different strategies to make this work then good ol’ beautiful 2020 rolls in and suddenly it’s mandatory.

Well, I did get to travel while working remotely so NYA HA HA! Kidding, anyways this article is meant to help you gather up your case to continue or start working post-covid. Surely it’s not something that will come easy (bonus if it is). It is still going to be a conversation with your superior. That’s never comfortable, but hey, let’s see if I can help:

Disclaimer: At the time of writing, I am still working from home due to the pandemic. We’re not back and not forced to be back in the office yet. Prior to the pandemic, I have a comfortable some-some days of working remotely already. I actually prefer this currently so I don’t have any reason to convince my boss to work/continue working remotely (I have it already). BUT if I didn’t have this privilege yet, these items below are the things I would do/use

Reasons Why Your Boss Should Allow You to Work Remotely

Health and Safety

‘Nuff said. Just bring up “2020” and surely this will be an easy point.


No, not presidents. Precedent: usually used in law, basically a past (valid) example that reflects similarly with your current situation. You then bring up the logic of: “if that worked, this should work too”.

Previously the problem was the lack of…good sample sizes to choose from. “He gets to work remotely because his profession is X”, “Her work culture allows her to do Y”, “Unlike you, they are/can Z”. The problem was it’s hard to reference someone, a situation where it exactly reflects your situation. Now post-covid, everyone has been forced to work from home, everyone now has “work remotely experience” and now you can reference so many people, so many situations!

Boss’s discomfort of “will it work”

The other realistic and practical concern most conventional bosses have is the “will it work”; commonly known as “Mmm, I don’t know. I’m losing too much control, I can hover over you. You’re going to have too much freedom than what conventional workplaces provide”.

So let’s assume you have a nice and true leader of a boss who cares about results not how many hours s/he sees you on your seat. If that’s the case, there is the practical concern they have. They have never seen you interact and do business with them by working remotely and you know how humans feel on things they don’t know (fearful). You may be experienced but if they haven’t dealt with you like this before, that’s irrelevant. That’s why I brought up “precedents” above; to ease it and use as a good stable measure for them.

Hopefully you’ve been forced to work remotely due to the pandemic and that you have continued to excel and deliver good work to your boss/employer (this is important). Because if that’s the case, all you have to say is: “you need proof? I’ve been doing it for months”. Well, phrase that in a more professional way.

If this is not your case and you’re just starting a new job or something and then you have to bring it up from scratch, what I would do is:

  • Be sure you’ve reviewed the starter questionnaire when it comes to working remotely
  • Set a high, yet realistic, bar in terms of quality, personality, and professionalism for yourself.
  • Slowly ease the topic in the conversation after months and see how they’ve dealt with the workplace during the pandemic (you’re looking for situations were people worked remotely. You are looking for your precedents)
  • If none, perhaps slide in and subtly ask about acquaintances or personal connections of the person you’re trying to convince if they’ve worked remotely (you want him/her to bring it up and see their reaction. You want to know how they feel about working remotely)
  • Assuming it’s a favourable situation for you, you can then slowly pull out the distance/visibility in the equation. What do I mean? Continue to deliver good work while you’re literally, physically getting farther and farther from the person you’re trying to convince. Maybe work in the kitchen, then conference room, later on when you have a minor illness still do great work (but of course don’t be a pushover that your boss forms an expectation for when you’re sick), then yeah do it farther, for longer duration, etc. You see what I’m trying to suggest here right? Similar to the frog in a slow-burning water. This is a blog in itself. I’ll write about this later.

“It’s not a culture in our office/company”

So this excuse falls flat now faster than a wabbit. I don’t even think you have to do anything any more since most if not all companies INTERNATIONALLY have been forced to work remotely. Thus, it has been forced to their office/company culture already. This assumes everyone was forced to work remotely due to the pandemic.

I don’t even know how or why I should elaborate on this. I know I’m stating employer concerns here and how it differs now, but this should be n/a now to the point that if your employer brings this up, it’s just a massive turn off that people might start pulling up Indeed right away.

However, I will add some exceptions to this. For example, there really are just some professions where you can’t work remotely like surgeons or construction workers even if your employer wanted to. In this case you’re just asking for pigs to fly.

In addition to this, there are companies who are really that closed-minded and just not up with the times. Sometimes it’s also systemic (e.g.: your boss is cool with it but he won’t allow it because no one above him or even important people in other departments have/exercise this perks). I’m not saying give up, but if you’re in this scenario, I feel like even at your best mood, presentation, convincing, and dialogues, I feel like best case scenario is you do that big swing only to make a tiny dent in convincing them.

You can do this on and on, but by the time you’ve rendered those blood, sweat, tears, and time, I think you would’ve been better off if you just switched.

Remote Work is not just for fun and games

If working remotely is a big factor for you, I highly suggest do not do this long route and just shop. Again at best, you’ll just be helping the next guy, which is nice, but I’m looking out for you.
I know a lot of commendable and awesome people who would actually prefer to work remotely NOT because of travelling. They prefer to work remotely because she’s taking care of a kid though this does not make her result/quality any less. I also know of a male friend who welcomes work remotely opportunities since he followed the love of his life in another country. I’m telling you this because if you are/will be an employer, remember that not all people who request remote work are just out for fun. Some are doing it to make our world and their world better, some are doing it for necessity.

Wrap Up

I think those are the usual concerns and luckily for us (just in this work remotely context), the pandemic has definitely helped us. There are of course varying concerns for each of us and of your bosses. Ultimately what you want and what you’re trying to do here is to alleviate risk, stress, and concerns for them. So if you have concerns not listed here, I would suggest finding a way to get all your boss’s concerns , and then show evidence that they are / will not be an issue in the future. It helps to have previous experience and things to show.

Once you’ve removed all the risk, stress, and concerns of that supervisor and you’ve continually provided awesome work, I think you’ll get a favourable answer after that. If after all the facts have been presented and your supervisor is not providing you with a reasonable, rational, understandable excuse, well then you know who you’re dealing with. You’ll know what to do.