How to convince your boss to let you work remotely

How to convince your boss to let you work remotely

If you’re reading this, I don’t need to sell you on the perks of working remotely. Remote work lets you avoid long commutes and irritating office distractions. Frankly, it rocks. You aren’t the person who needs convincing of the benefits of working remotely. Your boss is. Here are some tips that will help you convince your boss to let you work remotely!

Preparation is key

Before you have the conversation with your boss about working remotely, you’ve got a lot of preparing to do. Firstly for a week or two, jot down any ideas that you have to improve the company or make existing projects work more efficiently. Keep this list on hand for the future.
Regarding your performance, the weeks leading up to the conversation with your boss remote work need to be very good ones. You want to be a model employee in your boss’s eyes. This isn’t the time to be caught surfing the web on company time or coming into work late.
Finally there are a few key areas your boss will likely have questions about when you bring up the idea of working remotely – productivity, accountability, security, and logistical. Here’s how I would suggest working on those:


Some bosses have a picture of remote workers sitting around in their pajamas, getting paid to watch Jeopardy reruns and doing no work at all. This is a largely unfounded fear. In fact, many people are way more productive while working at home. Here are a few great resources to show your boss on why remote workers are more productive:


Your boss will worry that by letting you work from home they’ll no longer be able to track your productivity. The simplest solution is to have boss install tracking software on your work computer. This is fine if you’d be working from a computer owned by the company and used only for work.

If you’d be working from a personal computer then I would advise against letting the boss track its every move. Instead, I would suggest emailing them status updates a few times a day with quantifiable progress you’re making so they feel needed and in the loop. These updates should include what you’re working on for the day, happen three or four times a day, and will put your boss at ease.


Companies are worried about the security of their information. While most cloud storage and virtual work systems are secure, you should be able to provide data giving them peace of mind that the company’s information and trade secrets are safe. Here are a few great articles explaining how to address your boss’s security concerns:


Make a list of all your job duties, and list out all the reasons why you can do those remotely. Just about any job duty that doesn’t involve face-to-face interaction can be done out of the office but you should have a detailed list ready to go. Here are some awesome resources:

Optional sick day maneuver

If your job is already set up so that you can do some of your work remotely, something you can try is calling in sick and working from home that day. If you are able to do this, make your sick work from home day an incredibly productive one. You’ll show that you work more efficiently when not in the office even while sick and that being sick will no longer impact how much you are able to work.

Having the conversation

Set a meeting with your boss a few days in advance to discuss your request. This will give you time to get your final presentation ready without giving your boss too much time to form any objection. When you have this meeting, start by requesting to work remotely just one day a week. Give the boss the option to end the experiment any time they like, which should give them a feeling of control over the situation. It’ll likely be much easier to get the boss to agree to one day a week than a complete remote arrangement right off the bat. It is possible your boss will have a few questions, concerns, and objections which is why you did your homework before the meeting. You have a ton of resources and your own track record which should make a pretty convincing case.

Your first few days working remotely

Make the day each week you spend not working in the office your most productive ever. Additionally, be sure to keep your boss in the loop at all times and exceed any targets you’ve been given. Hey, remember that list of great ideas I had you write down? This is the time to present them. You should give your boss your best money saving and revenue producing ideas on your remote days. The better results you can show, the more likely it is you can negotiate for additional days working from home until you’ve gotten as much remote work flexibility as you need.

What not to do

We’ve spent a lot of time talking about what you need to do to convince your boss to let you work remotely. Just as important as what you should do is what you should avoid doing. Here is what to avoid:

  • Push the idea really aggressively. Everyone will be happier if the boss believes this is their idea. It’s unlikely you’ll get the work arrangement you’re after if you try and bully your boss into it.
  • Slack off. Your first few days and weeks of remote work should be your most productive ever. If your productivity goes down, kiss your remote work goodbye.
  • Brag. The last thing you want to do is have your coworkers complaining how jealous they are of you. If everyone in the office demands to work remotely for fairness, your boss might pull the plug on the whole thing to keep the peace.

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