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July 14, 2026

Open Enrollment Done Right: Four Strategies to Drive Engagement and Reduce Regret

Six months from now, will your workers be satisfied with their employee benefits elections? Or will they be frustrated with the options and regretful of their selections? Open enrollment plays a critical role in employee satisfaction and the perceived value of your benefits program. The steps that you take over the next few months will determine the outcome of your open enrollment.

Five Common Open Enrollment Pitfalls

The concept of open enrollment is simple. Every year, employees are given a chance to review their benefit options and select the benefits that best fit their needs. In theory, it should be a positive experience for employees… but that’s not how it always plays out.

Here are five ways open enrollment can go wrong.

  • Rushed Timelines. The open enrollment period usually lasts for two to four weeks. While that may seem like plenty of time, it can end up feeling rushed. The process often takes place in October or November, so it may overlap with the Thanksgiving holiday break, when workers are preoccupied with family and food and may not be thinking about work. If your open enrollment also overlaps with a busy time at your company, the entire process can end up feeling rushed.
  • Missed Deadlines. Even if your workers have ample time, missed deadlines are possible. When people have plenty of time, they tend to procrastinate. As a result, a long open enrollment period may increase the risk of missed deadlines if there aren’t enough reminders.
  • Uninformed Elections. Selecting your benefits is a high-stakes decision, so it deserves a person’s full attention. However, according to HR Dive, a study from PlanSource found that employees spend an average of just 18 minutes on the process. This is probably not enough time to read over plan details.
  • Constant Confusion. Research from Businessolver found that 85% of employees struggle to understand their benefits. Confusion can make the open enrollment period a source of stress, and employees who don’t understand their benefits may make selections they later regret.
  • Lackluster Enthusiasm. If employees don’t like their benefit options, they’re unlikely to get excited about making their selections, and employers may not see a positive return on their benefits program as a result. Rising premiums are particularly likely to put a damper on the experience, and employees may view it as a pay cut.

Strategies for Open Enrollment Success

The challenges are real, but employers and HR professionals who start preparing early can help drive engagement and reduce regret.

  1. Build a benefits program that employees will value.

Ultimately, open enrollment is all about the benefits. If the benefit options don’t meet your workers’ needs, no amount of employee education or engagement will change that.

  • For diverse workforces, consider offering two or more health plan options. Workers who don’t expect to have significant healthcare costs may prefer a high-deductible health plan, while workers who expect to have higher healthcare costs may want to pay more in premiums for a more robust health plan.
  • Consider offering additional voluntary benefits. Vision, dental, life and disability insurance are often offered as voluntary benefits. Employers may want to add extra options, such as identity theft protection and pet insurance, to appeal to a wider range of worker needs.
  • Leverage data-driven insights. You may think your benefit offerings are great, but what do your workers think? Satisfaction surveys, participation rates and benchmarking can help you assess your benefits fairly, so you can focus on options that support your business goals.
  • Be mindful of the out-of-pocket costs. If premiums, co-pays and other out-of-pocket expenses are too high, enrollment and plan utilization will go down.
  1. Create a comprehensive enrollment timeline.

An open enrollment schedule should consist of more than just the start and end dates.

First, it’s important to plan the open enrollment period for a good time. Consider conflicts with holidays, busy periods and other potential issues. Some overlap may be unavoidable, but there should be enough time for everyone to give their enrollment the attention it deserves.

Second, plan out all the notices, events, meetings and reminders that will occur before and during open enrollment. The goal is to ensure that open enrollment stays top of mind, so no one misses the deadline.

  1. Make benefits education accessible to all employees.

Most workers need help understanding their benefits. If your education efforts only reach some of your workforce, you may end up with a lot of workers who struggle.

  • Appeal to different types of workers. In-person events can be great… for in-office workers. If you have remote and hybrid workers, you’ll need some remote options, too. If your company has satellite offices or graveyard shifts, make sure those workers receive help, too. And if you have workers on leave or receiving COBRA coverage, don’t forget about them.
  • Appeal to different types of learners. Graphics for your visual learners, meetings for your collaborative learners, online tutorials for your kinesthetic learners – there should be something for everyone.
  1. Build in time for verification and improvement.

Mistakes happen. Even if you prepare everything as well as possible, some problems may arise.

  • Give yourself time to review employee elections. This allows you to verify that everything is correct and fix problems before it’s too late.
  • Consider how to improve next year’s enrollment. Reflect on what went well and what could have gone better, and conduct surveys to elicit feedback from employees. This should be done immediately to ensure that everything is fresh in your mind.

A successful open enrollment begins long before enrollment materials are distributed. Heffernan Insurance Brokers can help your company design a competitive benefits program and increase engagement throughout the enrollment process. In addition to helping you develop a benefits package that meets your company’s goals, we can act as an extension of your HR team and provide ongoing support. Learn more about our benefits and advisory services.

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