Let's be honest here. With the recent COVID-19 going around, your chances couldn't be better to finally make the step and start working remotely.
Perhaps your company already has offered you to work from home temporarily until things get better. So now all you have to do is shine so bright and be so good at working remotely that you just keep doing it, even when COVID-19 isn't even a thing anymore.
But virus aside, what can you do to convince your boss to work remotely?
Let’s look at the challenges of working remotely. There are always three parties involved. It's you, your boss and the team you work with. They all have to somewhat agree this is a good idea.
Usually, when the boss is against working remotely, it isn't so much that they are against it because of you, but because it would mean a significant change for the entire team. If your boss allows you to work remotely, they probably have to allow everyone to work remotely — which is why most companies either decide completely against it or open it up for everyone.
Making exceptions for just a few employees only creates bad blood, with those employees' coworkers to thinking they've been cheated.
So if your company isn't really open to working remotely, there are like many reasons why.
But let’s see what we can do about it.
Step 1: Start small and simple
You're trying to convince your boss of something that goes against their ground rules. You need to first prove yourself. Instead of asking to work fully remote, ask if you can work just Fridays from home. Just one day of the week, what can go wrong?
If you still don't get approval, negotiate even further. What else could make your boss change their mind? Could you accept a temporary pay-cut for the chance to work from wherever you want? Could you promise to work some extra time as an experiment?
Essentially, you want to give your boss such a great offer they can't decline. And remember, that offer is just temporary. Say something like "Hey, I'd love to work from home every Friday. Let’s make it an experiment for only 2 months and I will also do XYZ."
Chances are your boss will be into it.
Step 2: Overdeliver and prove yourself
Once you've been approved to work from home every Friday for two months, take it as seriously as you can. You're now trying to remove any doubt for your boss and the team you work with. Don't chill at home. Work hard, overdeliver on the work you do and be as present as you can. We've collected some remote working tips right here and here that may help.
For the next two months, your Fridays have to be completely flawless. Even one colleague who complains that you weren't answering in a timely fashion will ruin your entire deal. Your boss is waiting to say, "See, I told you, it just doesn't work." Prove them wrong. Don't treat it like "working from home" but as a chance to make an impression.
Step 3: Re-negotiate
Let's assume you've completed your 2-month trial with flying colors. There was not a single complaint and people didn't even notice that you weren't in the office (that's really what you want to aim for). Now it's time to renegotiate your deal.
Go back to your boss. Don't start by asking for something else, but rather ask for feedback. "Hey, how do you think everything is going? Anything I can improve with my remote work? We got so much done the last two months, but I want to make this even better and more efficient.” Your boss is going to love you for your proactive attitude and eagerness to get better. They may give you some feedback, but you already know they can't say much because you've been incredibly good at everything.
Now you hit them. "Hey, what do you think we do another trial for two months? I'll also work from home on Wednesdays, so it will be Wednesdays and Fridays. Monday, Tuesday and Thursday I'm still in the office, no one will even notice."
Chances are, your boss will approve. So you repeat the entire process.
Step 4: Keep re-negotiating
The beauty of this process is that the better you get at working remotely, the easier it will be to renegotiate your deal. You've already built up trust with your boss. At some point, your team will appreciate how happy and productive you are when working remotely, so they won't question your petition to work remotely more often. And at that point, once your boss sees how successful this remote working trial was (thanks to you), chances are this eventually becomes an option for the whole team.
There are usually two mistakes people make when trying to work remotely:
1. They ask for too much upfront. Keep it simple, keep it small. Make bite-sized requests and enjoy the process of convincing your boss and team.
2. They're not good at working remotely. As I explain in this article here, not everyone works well remotely. Being good at it needs to be a requirement. Otherwise you won’t be able to get approval, or you'll lose the opportunity fast if you do.
Now, good luck with working remotely! I personally believe it is the future, but I also know that not everyone even wants to work remotely. Decide for yourself if you're the person who's right for it, and if you are, I hope the advice above helps you to make it happen.
Hi, I'm Tobias, a German designer living in New York. I'm the founder of DESK, nice to meet you!