How to convince your boss to make your job remote

So, you want to work remotely.

You certainly aren’t alone. The concept of telecommuting is becoming more popular on a global scale. Not so long ago, most people thought of work as going to an office, sitting in a cubicle, and staying there from 9 to 5. Technology is changing that concept. In 2018, a study by Switzerland-based company IWG concluded that 70 percent of global professionals work remotely at least once per week. If you are trying to convince your boss to make your job remote, statistics are on your side.


If you are going to win your boss over to your way of thinking, you will need to think about more than just how working remotely will benefit you, exploring how it will benefit your performance, the company you work for, and their bottom line.

Start by focusing on technology, the big factor that spurred the growth in remote work in the first place.

Technology and Telecommuting: Why Remote Work Is on the Rise 

High-speed internet access, innovative apps, high-quality voice and video chat options, and the ability to stay connected at all times are all things that have made telecommuting remarkably easy in many industries. Why work in an office when your iPhone can effectively shrink the distance between your living room and the boardroom to nothing?

Even the entities that built the gig economy -- disruptors like Uber, Lyft, Airbnb, Postmates, and Etsy -- are in large part tech companies. Their business models work because of apps, websites, and social media. And their disruptions have been successful: at this point, roughly 36 percent of the American workforce is part of the gig economy.

If you want your boss to let you telecommute, focus on the technologies that are going to allow you to do your work effectively from a distance. Talk about how you will be able to videoconference in for meetings easily, or about how chat apps like Slack can bottle an entire company’s communications and collaboration in a single program.

Think about your day-to-day routine and workflow. What assets do you use at the office and how can you access them remotely? Who do you collaborate with and how will you maintain a productive connection with them if you aren’t in the office? Having answers to these questions ready to go will help you satisfy the queries that your boss is sure to ask when you raise the subject of taking your job remote.

Productivity and Responsibility 

Even if technology makes working remotely feasible in your situation, that doesn’t necessarily make it a good idea, nor does it mean your boss will go for it. A bigger concern than technology might be your own productivity.

Some employees feed off the atmosphere of the traditional workplace and need to be in the office to lock into a productive routine. If you are someone who tends to get distracted easily when you try to work from home, a remote job arrangement might not be for you. Propose a remote work trial period to your boss, so you can both track your performance and see how it compares to your in-office work record.

With that point made, there are a fair number of studies that show that telecommuting can indeed benefit productivity. This study found that 77 percent of remote workers say that they are more productive working remotely than they would be in the office. This report revealed how remote work often leads to lower stress, greater wellbeing and emotional stability, and better job satisfaction.

So, Your Boss Said No: Finding Your Dream Remote Job 

Some employers just aren’t ready to embrace remote work yet. You can present them with pages upon pages on how remote work is good for productivity and can reduce employer operating costs, or how telecommuting is the future of work. In the end, if your boss says no, there isn’t much you can do to change her mind.

If you are serious about finding a remote job, know that there are plenty of them out there. For every employer that is reluctant to embrace the rise of the gig economy and remote work, there are others that are diving in headfirst. Especially in younger generations, a lot of job seekers are looking for remote jobs, so know that you aren’t alone in searching for this kind of employment.

A good place to start your remote job search is on sites that focus specifically on freelance jobs. Top options include FlexJobs, Jobspresso, HubStaff Talent, and While you can find remote job listings on more popular job boards like Monster or LinkedIn, they aren’t usually the first place to look for this kind of work. You might also look for sites dedicated to the specific type of remote work you are looking to do. For instance, you can find a whole slew of sites built specifically around freelance writing jobs or contract graphic design work. One other option: pursue a side gig that will allow you to test your aptitude for remote work.

As you search, treat the process like you are applying for traditional jobs. Have updated resumes and cover letters ready to go in case you need them. Know which work samples you want to use to spotlight your skills. Call up a few references to see if they are willing to speak on your behalf. Be ready to undergo background checks, which are becoming increasingly common even for freelance or temporary contract work.

Finally, be ready to hustle! Many remote jobs are freelance-based, which means you might not find a full-time remote opportunity right away. If you’re willing to work hard and prove yourself, those opportunities might come later. Alternatively, you can build up a consistent stable of freelance clients that can match or exceed the money that you were making in your old job.

Image Credit: Rawpixel / Shutterstock

Michael Klazema is Chief Marketing Technologist at and has over two decades of experience in digital consulting, online product management, and technology innovation. He is the lead author and editor for Dallas-based with a focus on human resource and employment screening developments.

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