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.
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.