• Krissy Weekley

6 Tips On How to Talk to Your Boss About Working Remotely

Updated: Sep 28, 2019


Many people think that you have to be a developer or a designer to work remotely, when in reality you can find remote work in almost every field. The ability to work remotely comes down to a simple conversation with your boss.


The key is to present the idea of you working remotely in a way that benefits both the company, and you as an employee.


Here are some tips on how to do that:


1) Figure out how often you need to be in the office.


To do this, ask yourself these questions:

  • How many meetings do you have each week?

  • How involved are you in each of these meetings?

  • Can they be done over video conference?

If your time in meetings is minimal, or can be done through video conferences, share that with your boss.


2) Figure out how much work you get done from your computer.


How much of your work is done strictly from your computer? If it takes up the majority of your time, that’s good. You could say something like this to your boss:


“I spend [percentage] of work hours on a computer doing tasks such as emailing, coordinating, organizing, etc. As long as I have good wifi—which I will—I could do my job from anywhere.


3) Figure out your daily tasks.


You will need to evaluate who you work with and what type of communication needs to continue with them to get your job done. Ask these people if they are okay with video conferences, or messages if you were to be away for awhile. If they are—after you’ve talked to your boss—reassure them that being remote will not affect the frequency and quality of your conversations.


When you talk to your boss, tell them something like:


“I’ve written out a list of people I communicate with to get my job done. I’ve mentioned the idea of communicating with them via video calls and messaging if I were to be out of town. They seem to have no problem with the idea of communicating this way.”


4) Evaluate your performance with your boss.


Ask yourself: what have I done for this company? If you get all your tasks done on time, have a good relationship with your coworkers, and show ownership in your role, you’re in a good spot.


Really emphasize to your boss how you’ve contributed to your company. This will reassure them of your value. Then, tell them that you will continue to do so while you’re working remotely.


5) Get your boss to empathize with you.


What could you say to your boss to help them see why working remotely is a good opportunity for you? Maybe say something like:


“Have you ever wished you could live in another country for a month while still being dedicated to the work you enjoy? Well, now is a time in my life where I have few commitments, including my job. I have the opportunity to meet new people who also value work and play while experiencing new cultures. Wouldn’t you take an opportunity like that if you could?”


6) Assess whether your boss is more formal or informal.


Next, you will need to figure out how to present all these points mentioned above to your boss. If your boss is informal, schedule some in-person time with them to have an honest, open conversation. If they are formal, you should consider creating some type of presentation that you can present to them in person. Here are a couple of ways you could present your case:

  • A written proposal.

  • A slide deck/powerpoint presentation.

Whether you choose a written proposal, or a slide deck, all the previous points should be included in the presentation.


Working remotely is possible. Pump yourself up; you can do this.


If you’ve applied to Monthly Roamers, we’ll help you have those conversations with your boss.



Haven’t applied to Monthly Roamers yet?


Click here to fill out an application.

83 views