Enrollment Time is Your Worst Enemy. Here’s How to Defeat It.

Next to tax season, there are few periods during the year that small business owners dread more than open enrollment time. Benefits selection can be confusing and frustrating for employees, who are far from experts in the field. And you know there are always the employees who wait until the last possible second to decide.

Majority of employees (77 percent) spend 60 minutes or less preparing for and selecting benefits, and nearly half (46 percent) spend 30 minutes or less deciding; the majority (90 percent) just take what they had last year, according to Aflac, an insurance provider who did a study about the issue. Generally, employees spend way more time selecting and planning their vacation than insurance elections. Employees who choose the wrong benefits for their needs end up wasting up to $750 annually.

Employees want to be educated about their benefits and any changes that result from federal and state reforms and they look to their employer to provide this education. A Professional Employer Organization (PEO) can help with the process.

However, enrollment doesn’t have to be a colossal struggle each time. Here, we boil down the “must dos” to get you – and your company – prepped for a streamlined enrollment season.


  • Be prepared to answer questions from your staff about health care reform legislation and how it may impact their insurance offerings for 2019.
  • Survey your staff on what they would like to see in terms of new or exciting benefits offerings.
  • Determine what health, dental and vision plans are available to you and how much it is going to cost both you (the employer) and them (your workers) in terms of copays and deductibles.
  • Keep a log of employee questions, comments and concerns about the enrollment period, as well as information on their preferred communication methods and even preferred enrollment method. Tracking questions will help ensure they are all answered and help you anticipate needs next year.
  • Make sure you spread the word about coverage options and any changes for the new calendar year. Research shows that the majority of employees—almost three quarters—do not understand annual changes to policies and these changes will impact them. Hold meetings, have workers log on to webinars, distribute mailers, and post a frequently asked questions info sheet around the office – the more modes of communication, the more likely they are to pay attention.
  • Communicate essential enrollment information such as changes in cost, deductible sizes, out-of-pocket maximums and employer’s contributions.
  • Share helpful phone numbers, websites, and contact numbers with workers looking for additional support to get their individual questions answered.

During enrollment:

  • Make sure your employees have all the tools to handle the process, including an open enrollment schedule with deadlines clearly spelled out, statement of current coverage, plan specific summaries that include information on any changes to offerings or price changes, an open-enrollment booklet and forms, and contact information for your plan administrator.
  • Encourage workers to come to you with any questions – no matter how big or small – and make sure that you are working to find the answer, either on your own or by engaging with your broker/agent as needed.
  • Provide frequent reminders about upcoming deadlines – we recommend at least one-week warning, as well as one at about two days prior to the scheduled deadline. This is one time more frequent reminders are not a bad thing.
  • Determine how enrollment will be collected, whether it be through online member self-service, HR input, or paper forms and make sure it is clearly and frequently communicated to all.


  • Make sure you have received new enrollments, including qualifying life events.
  • Check employee forms for any missing information or any portions that are incorrectly or incompletely filled out.
  • Submit all enrollment forms to your broker.
  • Follow up to ensure all employees have received their ID cards and other necessary documentation to prove that they are successfully enrolled in the correct plan.
  • Follow up (yet again!) to make sure that employees understand their benefits, how to use them and have no lingering questions or concerns.
  • Breathe a huge sigh of relief – you made it through open enrollment season!

And finally, just a quick reminder of a few key dates for those using the Marketplace:

November 1: Open enrollment for 2019 individual market coverage begins November 1. This applies to plans purchased both in the exchange and off the exchange
December 15: Open enrollment for these plans ends (and yes, we realize its only six weeks long this year, versus the usual 12 weeks!) This means that employees cannot make changes after this period unless they live in California and Washington, D.C. (which both offer an extended season) or if that employee has a “qualifying event,” such as the adoption or birth of a child or a loss of coverage.

A PEO can help you make smart benefit decisions for your company while making the enrollment process less painful with step-by-step assistance. A PEO has much greater buying power when it comes to comprehensive and affordable benefits. That means it can offer excellent benefits at affordable rates, which boosts employee morale and retention, and reduces the expense and disruption of turnover.