Actually – the work of a personal assistant should NOT be issued a 1099. The work they perform is that of an employee, and not a contractor. Misclassifying them as such can result in steep fines from the IRS, who are cracking down on this behavior (businesses trying to save money by not being a accountable for their workers and properly giving them a W-2. If you can’t afford to offer a W-2, then maybe you can’t afford an assistant.
Having worked remotely for my whole career (25 years) I found this to be a great read. I certainly agree with the elements as provided. It does take a certain personality to be able to stay focused and committed without the boss watching. wink wink. The biggest challenge I find is actually separating from work. With the advent of PDA this is really the norm rather then the exception. 

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Virtual collaboration offers a profound way to cater to employees with diverse working styles. For example, detailed-driven workers tend to excel in virtual environments. They typically have no trouble planning their workday and accomplishing daily tasks. Emotionally driven individuals may prefer to speak directly over the phone or face-to-face in a video conference, because they typically read social cues very well and prefer verbal communication. Idea-driven workers thrive when facilitating change and usually prefer a lead role in brainstorming solutions, so you should consider giving them more responsibility when strategizing in the virtual setting. Data-driven workers are highly adept at solving complex problems. They don’t typically need an extra push to stay on topic or on budget, but they may prefer to work alone quietly rather than lead a virtual group discussion.
Virtual team is an emerging new-age trend with followers across business sectors. Just like any other new trend, virtual team also has to undergo strict scrutiny of researchers to weigh its advantages and disadvantages before being accepted by the professionals. The advantages and disadvantages of virtual teams can be looked upon from three levels - individual, organizational and societal as a whole. This article summarizes different perspectives on the advantages and disadvantages of the virtual team and serves as ready reference guide to our readers.
Cost savings - The biggest advantage of virtual team enjoyed by an organization is the associated cost savings. The organization can do away with huge expenses on real estate, office spaces, utilities bills such as gas, electricity, water etc. and executives’ travel. Many organizations outsource their operations to the low-cost regions. Thus production cost also decreases with the reduced raw material cost, operational costs and lower wages of the employees in these geographic locations.
Establish an onboarding process. Be sure that every employee who collaborates virtually has the same onboarding experience. They should be given access to the same communication systems and handbooks that explain the company processes. Everyone should be given the same advice and tools for success as they’re brought on board. If possible, it can even be very valuable to have an initial onboarding done face-to-face in an office location.

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