Checklist: Enrollment Time Doesn’t Have to be Hard

For the small business owner, the annual benefits enrollment process can be complex, especially since employees want to be educated about benefits and any changes that result from federal and state reforms. They will be looking to you, their employer, to provide this knowledge.

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 planning their vacation than reviewing insurance elections and their needs. Employees who choose the wrong benefits for their needs end up wasting up to $750 annually.

There can be penalties for employees who do not sign up for a benefit plan, whether it be through a company sponsored-plan or the federal marketplace.

Enrollment doesn’t have to be a monumental feat. Here, we boil down the “must dos” to get you ready for an efficient enrollment process.


  • Review your past year’s benefit offerings and consider what worked, and where you fell short. Are there any benefits that your employees would love to see? Have you even asked them?
  • 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 employees) in terms of copays and deductibles.
  • Enrollment time is confusing for employees, research shows that the majority of employees—almost three quarters—do not understand annual changes to policies and these changes will impact them.  Make sure you thoughtfully plan your communications to employees about any changes.
  • Meet with your employees to go over planned options, as well as to answer any preliminary questions about the upcoming enrollment period. At this time, it’s also best to make it clear what the open enrollment period is going to look like and how you plan to communicate information.
  • Now is also the time to share information on the broker you plan to use for this project – you should have already fleshed it out with them in terms of how they want you to handle the process and what types of additional support will be made available to you during the process. Some are better than others, so be sure to thoroughly vet your agent and make sure they are a good fit for your company.
  • As a side note, if you’re running the show, you’re going to need to keep an eye on deadlines. This year, the enrollment period for the federal marketplace in most states is very much condensed, running for just six weeks between November 1 and December 15. For a full list of state deadlines, click here.

During enrollment:

As long as you’ve done your prep work in the run-up to enrollment, the actual process should be fairly straightforward. However, it’s never without an occasional hiccup. With that in mind, make sure your employees have all the tools they will need for successful enrollment. This should include:

  • An enrollment schedule
  • Clear communication of deadlines
  • A statement of current coverage
  • Summaries for all the current plan offerings and their associated price breakdowns
  • An open enrollment booklet
  • All paperwork
  • Reminders for how and when to contact your broker
  • Remember, during this process, you must make yourself as available as possible – workers are going to have questions about the process and it’s up to you to figure out the answer or put them in touch with someone that can. Yes, you can call the broker, but this is a busy time for them too, so you need to do what you can on your end to answer questions before moving it up the ranks.
  • As a business owner, you also will need to play the role of enforcer. It’s going to be up to you to ensure that your employees are participating in the process, adhering to deadlines and staying on top of things. We recommend that you send out deadline reminders at regularly scheduled intervals, as well as host small employee meetings to address any questions and concerns across the enrollment period.
  • And finally, it’s also going to fall to you to collect all the paperwork, as well as figure out payment set up.


  • Once again, the responsibility of paperwork completion will fall to you. Here’s what you need to do:
    • Check everyone has turned in the correct forms
    • Check that everyone qualifies for the plan that they are trying to enroll in
    • Make sure they’ve filled them out completely AND correctly
    • Submit the paperwork to your new best friend: your broker.
  • A few weeks later, you will once again be called upon to follow up, this time that everyone has received their ID cards and that they are successfully enrolled in the plan that they wanted.
  • And a few days after that, once the dust settles just a bit, again you should start meeting with employees (again!) to make sure they understand how to use their plans and have no lingering questions or concerns.

And that’s it – you’re done… until the next enrollment season. A Professional Employer Organization (PEO) can help with the entire process, ensuring your peace of mind.