Micro-Management: Legal Handling of Your Scattered Employees

You may not have any employees at all. However, from time to time you may find it necessary to bring in some extra help. When you do, you have two choices: hire an employee, or enlist a contractor. Both of these methods have different tax concerns—and because they are far less complicated for contractual help, most virtual corporations choose to outsource the services they can’t provide themselves.
Employee Tax Issues: Any business owner knows an employee is an investment. If you’re running a virtual corporation, in the beginning stages it’s almost always better to outsource extra work. However, as you grow you may want to consider
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hiring someone who will work with you on a long-term basis and know your company almost as well as you.
In regards to taxes, as an employer you must pay Social Security, Medicare and unemployment tax for any permanent employee. One concern related to the virtual office is the physical location of your employee. You may choose to hire a telecommuter—someone else who works from home. If your employee(s) live in another state, you must file a W-2 (standard income tax form for employees) with that state. This costs an additional fee, but usually no more than $10 annually.
Regardless of where your employees live, you must provide all regular employees with a W-2 at the end of each tax year.
Contractor Tax Issues: The independent contractor is responsible for all of his or her own taxes. Therefore, most virtual corporations prefer to work with contractors, or as they are often called, freelancers. As a virtual business owner, your only tax responsibility for freelancers is to provide them with a Form 1099 at the end of the tax year, provided you paid them more than $600 in the year. You must keep track of any outsourced work you purchased so you can report it on your own tax forms.
NOTE: If you’re not sure whether a person who has done work for you is an employee or a contractor, the IRS provides a set of 20 questions to help you
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make that determination. Basically, if you directly control the way the work is done (you are in direct supervision of the person working for you), you should treat them as an employee. If you simply assign a task and do not control how it is done, but rather receive a finished piece of work after a specified time period (such as web copy writing, site design, or outside bookkeeping services); the person handling the work is considered a contractor.