Important Medicare Planning Questions if Working Past Age 65 1. Does your employer have 20 or more full-time workers? 2. Is your current health coverage working for you? 3. Is your employer's drug coverage as good as Medicare Part D? 4. Are you currently receiving Social Security? 5. Do you want to keep adding to a Health Savings Account? 6. Are you and/or your spouse high-income earners? 7. Are you covered by your spouse's plan or the other way around?