How to Convince Your Boss to Let You Work Remotely

While pitching your boss on work-related ideas and projects is part of your daily job, it can be hard - even daunting - to convince your boss to allow a remote work arrangement. Whether you are looking to join YonderWork and travel the world, relocate and keep the same job, or just work from home, working remotely is a great option. So to master the diplomacy of establishing a remote work arrangement, we’ve outlined a few strategies to help you deliver a smooth and successful pitch:

Coworking | Bali | Hubud | YonderWork

Do Your Homework: Knowing what you want is the first step: doing your homework will really show your passion and commitment. Know what resources and technologies are available to support your remote work, how you will communicate, and how you will demonstrate productivity. If you have coworkers who have made the transition to remote working, reach out to them for lessons learned. If you are prepared, you will have a much greater chance of success. 

Put Yourself in Your Boss’s Shoes: Try to put yourself in your boss’s shoes and frame the conversation around the benefits for your employer. (psst: you can read our post here to find out more about the benefits of working remotely) Also, anticipate your boss’s reaction and proactively think through counter-arguments. 

Tie Remote Working to Your Scope of Work or Professional Development Goals: If you are looking to travel or relocate abroad, offer to work with customers or colleagues in your time zone. Think about how time saved by not commuting could be directed towards continued learning or how working from a coworking space or participating in YonderWork would strengthen your professional skills. 

Develop a Written Proposal: After you’ve done your research, it’s important to come up with a written proposal to prove your ability to work remotely. Try to be as detailed as possible; not only will this show that you are 100% committed, but will also show that you are extremely organized and will not let things fall to the wayside once you’re remote. This proposal will set expectations from the get-go and also allow your boss to envision how you can successfully work remotely.

Be Confident and Prepared for Questions: You are ready to make the pitch to your boss . The way you present yourself and your proposed remote work arrangement will have a significant impact on their decision. If you seem nervous or unsure, your boss might deem you unfit for this type of arrangement. Be prepared to answer a lot of questions and to address potential concerns. 

Be Flexible: Remember that this is a negotiation and that you should be prepared to accept a “trial” run before s/he signs off. Balancing confidence with preparedness and flexibility will ensure you have the best chance of reaching your dreams of working remotely.

By Arielle Crane @aricrane

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