If your going-remote plan includes the need to convince your boss, then the first step is to complete the “Are You Ready to Work Remotely?” questionnaire just preceding (if you haven’t done so already). This is because the ammunition you’ll need for convincing your boss will come from your written-out YES answers to the various questions; those answers will demonstrate you’ve got what it takes to make your remote venture a success. (Ideally you’ll have very few items—if any—remaining in your NOT YET camp before you broach the subject with your boss.)
To begin your boss-convincing plan, let’s turn again to the Meghan M. Biro comment quoted earlier, this time in full:
When my role is to be a virtual team member, I need to be self-motivated, focused, curious, flexible, and, above all, collaborative. When my role is to be an entrepreneur managing virtual teams, I need to be empathetic, emotionally intelligent, sensitive to what others need, and willing and able to provide whatever tools are necessary for success. In either role, I must … be self-aware—in tune with my skills, capabilities, strengths, and weaknesses.1
Consider this description in light of your manager. Do you think she or he is “empathetic, emotionally intelligent, sensitive to what others need, and willing and able to provide whatever tools are necessary for success”? Perhaps that’s too much to know the answer to right away, but keep it in mind as you proceed.
Regardless of how well ...