How to Ask Your Boss to Work From Home

work from home, remote work

Working from home sure has its advantages, you don’t need to tell me. This morning I had to commute all the way from the bedroom to the couch to write this article. I love that about my job. After all, for me the best time to work is right in the morning. I often get an hour of good work done before I’ve even had breakfast.

Even better, I can work for my boss or for my personal company when I need to, instead of at a certain time of day.

That’s great, because it means that I can be far more productive and can deal with urgent things as soon as they arise. If you want to do the same, however, you’ll need to convince your boss.

How to Ask Your Boss to Work From Home 

How can you do that? Here are some things that you need to consider.

You Have to Have the Right Reputation

Remote work means that your boss is giving you a lot of trust. Therefore, you need to first demonstrate that you can be an incredibly trustworthy person. I suggest that you make sure that you really focus on hitting every deadline and completing a whole lot of projects to perfection.

Only when you’ve done that for a while should you make the approach. Then the boss will think back:
“can I trust this person?” And a whole list of memories where you were highly trustworthy will occur to them.

Can Your Job Be Done Remotely?

The first thing that you’ll need to think about is whether your job can be done remotely. Some jobs simply don’t allow it. For other jobs, it can be difficult. That said, far more jobs can be done remotely than most people are aware of.

If you think that your job can be done remotely, then you need to start working on the arguments. Find the arguments for working remotely and make sure you’ve got them down. More importantly, find the main arguments against you working remotely and make sure that you’ve got your counter arguments for them ready as well. The best way to find out what the arguments against you working remotely is to ask other people. They might see things that you yourself hadn’t thought about.

In that way, when the discussion does come up, you won’t be blindsided and you’ll be ready with the right tools at hand.

Ask Other People Who Have Similar Positions and Work Remotely What the Opportunities and Obstacles Are

You might have a certain idea of what it would be like to work remotely in your mind. That does not mean, however, that this is how things will actually be. There is a good chance that the reality will be quite different.

The best way to make sure that doesn’t happen is to talk to other people who’ve gone through similar experiences. They will tell you how these things actually go. Then you can make sure that you understand the pitfalls and that you are as prepared for them as you can be.

Have a Formal Plan

Sure, some of us are great at bringing things up in casual conversations and then winning over people to our side. If you’re one of those people, go ahead and do that. If you’re like the vast majority, however, it might be a better idea to first formulate a plan. Don’t just do it in your head, either, but do it on paper.

In this way, you’ll have much better control of the arguments orally and can also simply hand off the document itself if your boss doesn’t want to talk about it. Then they’ll have an eloquently worded argument that they can read comfortably when they have time to do so.

Get a New Boss

Of course, your boss might still say no after all of those ideas. In that case, you should be ready to consider finding a new boss where the opportunities are more in line with your thinking. If there is a lot of resistance from up on high to your idea of working from home, then it might be time to start looking for other opportunities.

The great thing is that this can both give you a new place to work where working remotely isn’t a problem, or – when your bosses find out that they’re about to lose you and that you’re dedicated to this strategy – a re-think on whether they can let you work remotely or not. In that case you’ll be in the enviable position of choosing which option suits you better. So what are you waiting for? 

Realize That This Might Take Some Time

Yes, you might get lucky. You might have a boss who immediately agrees to your request and lets you work remotely – part time or otherwise. But it doesn’t always happen that way. Sometimes bosses need time to be convinced. You’ll need to have a conversation. You’ll need to approach the topic several times to deal with the concerns they have.

In these cases, don’t get frustrated. Bide your time. Though you want to be firm, you don’t want to make your boss feel like you’re driving them into a corner. That will create resentment and might very well backfire on you.

So if you want to work from home by a certain date, possibly because you’re moving or because you want to be there for your children, make sure that you start this process sufficiently early. That way, there is time built in to give all sides time to get comfortable with these new ideas and so that you can all thrash out the new arrangement.

Last Words

And once you can work from home, make sure that you don’t disappoint. You can rest assured that in the beginning, particularly if your company isn’t used to this kind of an arrangement, people will be watching you very closely. Don’t give them anything to complain about.

The best way to do that is to make sure that you can be as productive at home as you can be at work. For that reason, have an office, don’t break your routine and use all the other tricks of the trade to maintain your productivity. For once you’ve got the right habits, they’re easy to maintain – while if you develop bad ones you’ll have to go through all the effort of breaking them.

Posted in ,

Sylvia Giltner

Silvia Giltner is an HR manager and freelance writer at Studyclerk. She helps people to write the perfect resume and land a desirable job. She is also an active guest contributor. Sylvia’s writing has been featured on Forbes, Next Avenue, TLNT, and more.

Reader Interactions


  1. Henry @ ISL says

    Great post Sylvia, I’m very much in the same camp as yourself, I have a boss and I also work for myself.
    So how about we spin this around and say find a boss who encourages you to work from home.
    Without doubt the future for most of us at least.

  2. KovalD says

    I totally agree with you because I also prefer working from home. You don`t need to stay in the traffic jam or queues , spend 2 hours just to get to working place. After I started to work as a freelance writer in one of top UK dissertatation writing services , I can use my free time as I want.


Pin It on Pinterest