There are pros and cons of working from home. Every organization is unique — what may work for one may not work for another — but society is advancing in a way that’s leading to more virtual teams and opportunities to work remotely. Once a company decides to implement work from home policies, it’s wise to consider the possible roadblocks to success.
Keep in mind that if you pay someone more than $600 per calendar year, the IRS has pretty strict guidelines about making sure you issue a 1099. Of course, that means the assistant has to pay taxes on the earned income, which dents his bottom line. So you can always make the choice to pay an assistant under the table. What you do is up to you, but let me repeat: Always keep in mind what tax laws dictate, and make smart choices based on that.