Your manager is the first person you have to convince, and they probably have some reservations about letting you work remotely. Make it easy for them to say yes by addressing some of their basic concerns.
Be trustworthy. The most convincing argument that you will do a good job remotely is to do a good job in the office. Build your manager’s trust by performing well. Show them your history of dependable performance and make it clear you will continue that stable performance remotely.
Define performance metrics. Make a plan for assessing how well you are doing once you start working remotely. Ask for extra performance reviews during the first six months. Make it clear that you intend to show tangible results when working from home.
Make a travel schedule. Have a plan for how often you will return to the office after making the transition. If there are any upcoming events that require you to be there in person, plan for them ahead of time.
Talk about your job, and show your manager how you will do your job remotely. Are there times when you need to physically touch hardware? Do you spend a lot of time in face-to-face meetings? Create a plan for how you will accomplish each part of your current job remotely.
Talk about collaboration. You need to communicate well with your team and your boss needs to understand how you are planning to do that after you leave the office. Detail any new tools you want to use with your team. Will the rest of the team need to do anything differently to collaborate with you remotely? The communication part later in this book discusses the issues of communicating with a distributed team.
Have your coworkers speak on your behalf. They are the ones who will need to collaborate with you and having them believe it will work is a big part of the argument.
Give your boss an escape clause. There are many good reasons to work remotely, but it can be difficult to get final approval. Your boss might worry they can’t bring you back once you start. This is especially true if you are moving to a different city. Ease their fears by reviewing what will happen if working remotely doesn’t work out, or doing it for a trial period before you finally commit.