I would suggest you start by educating your administration. Whoever is going to administer your benefits, payroll, taxes, etc, must be educated on this subject to keep you compliant. For example, the question comes up regarding 1099 employees. If you feel that you will use what could be a W-2 employee as an independent contractor, and issue a 1099 to avoid getting caught up in the entire Obamacare dilemma, please proceed with caution.

I would like to refer you to the IRS’s website for definitions of self-employed or employee status. I would suggest that if there is any doubt in the eyes of the judge, you may be considered an employer. Therefore, I would play it safe and at least offer the coverage and allow this person to accept or waive.